Getting Nailed, Complete

Getting Nailed, by J. Birdman

This story is not intended for children and if you are not old enough to read sexually explicit material, go away. This story features some elements of female domination (femdom), cross-dressing (CD), mild bondage, Trangender (TG) and a few other fantasies of mine. I hope you find it entertaining, but if you might be offended, stop reading and do something else. The author retains all rights to this story. You may re- post the story unchanged, provided there is no intent to profit from this story (it is not nice to make money from someone else's work).

Chapter 1, The Bet

Sarah and Jack

We have been married for several years and we both were experiencing very active professional lives. Our jobs are quite demanding, requiring us to work long hours and consuming most of our creative energy. This daily grind had the same effect on us as most other couples in the 90s. Our love life was shrinking down to one or two times on weekends without a great deal of inspiration. We both longed for our early days of our relationship when sex was very regular and was our first choice in recreation activity.

One thing I missed a lot was Sarah's long fingernails. Sarah is a great looking woman, a complete package of brains and beauty. She is almost 6 feet tall, has light red hair and green eyes. I have always thought she has the perfect figure with great breasts and a butt to match.

Sarah used to keep her nails long and manicured. Her work requires her to use a computer most of the day and she found the long nails to be problem. Little by little her nails got shorter, until today they are just about the same length as mine.

I still get a little rush when I think back to those long nails and how she would use them to tease me sexually. Taking the edge of her shaped nail and running it along the veins in my cock and around the head. I think she could keep me on the edge of orgasm for days if she wanted to with her fingernail tricks. Then she would take my dick into that perfect pussy and while she rode me she would lightly rake my chest with her nails. Not quite breaking the skin, just enough pressure to drive me crazy with lust. Sarah could take the edge of those nails around my nipples bringing the little nubs to rock hard points and then when she reached orgasm she would pinch my little nubs as we pounded our bodies together and I was cumming like a mad man.

Always the next day the warm shower would bring little red lines on my chest to a visible state and when I was shaving seeing the marks in the mirror made me stiff again.

Friday Night: The Actual Bet

"Your late Jack and now I don't want to go out for dinner this late. Here we go again, a Friday night finally gets here and we are stuck with nowhere to go and nothing to do."

"I'm sorry Sarah, but I had to get my budget input completed for the consulting proposal we worked on all week. If I didn't stay until it was done, I would have to go in tomorrow. If I went in to the office, I would have been sucked-in to help finish other parts of the proposal for Monday and I didn't feel like blowing my weekend because others didn't get done today."

"Your trying to make me feel better by telling me it could have been worse?"

"No, I'm only trying to explain why I ended up working late. How does a movie sound? You said you wanted to go to see some chick-flick that's out now"

"What a great way to ask me out for a date, asking me if I want to see some chick-flick you can't even remember the title of, Jack. Why bother, just forget about it. You can run over to the video store and check out a rental movie and I will make us a chef salad."

"Are you sure? I asked lamely"

"Yes Jack, and knock off the puppy dog look. Open that bottle of wine in the refrigerator and pour me a glass. By the time you get back, I will be chilled out."

"Sarah, this is starting to sound like a good plan."

I ran over to the video store and picked up a couple of movies that might be interesting. I was hoping that one of them might be sexy enough to give us a libido boost, as we were way overdue for some good sex (any sex even bad sex). I also picked up some dark chocolate and some fresh strawberries. If the movie failed to get a spark started with Sarah, the chocolate and strawberries were pretty surefire.

When I got back, Sarah had finished the salad and had set up a "picnic" on the den floor. She had some nice candles burning and pillows available for getting comfortable. This was much better than going to see that "chick-flick".

I threw in one of the movies and we started to enjoy the good food and wine. The movie was not that good, but as we were more involved in our various appetites, so it didn't seem to matter. By the time we finished the salad and were snacking on the strawberries and chocolate the videotape had been stopped.

Sex was on our mind and we had all evening to share our lust for each other. We had not had sex for days and I wanted to take some time. Abstinence has different effects on Sarah and me. Sarah takes much longer to orgasm and I take much less time. As we indulged in foreplay, I kept reminding myself to slowdown and put the energy into making Sarah as hot as I could.

I was so horny that my dick hurt in my pants. I needed more room and getting Sarah and me out of our cloths became my focus. As I undressed Sarah, I kissed every inch of skin I could find. Sarah's neck is glorious and is a highly erotic zone for her. She can almost orgasm from my kissing and stroking of her neck. I began working my way down from her neck, slowly unbuttoning her blouse, and kissing her warm flesh as inch new area is exposed. By the time I am down to her bellybutton, she is pulling my shirt off with no regard to my personal safety. I have to stop what I am doing and give better access or I might get strangled in the process. We are back to kissing and I am working on getting her lace bra off. I could unhook it and get it off in a few seconds if I wanted it that way, but I wanted to make this as sensual as possible. After what seemed to be forever but had to be a minute or two, I had Sarah's bra off and her beautiful breasts were now the center of my universe. After kissing all of the soft skin of her breasts, I took one then the other nipple into my mouth. Running my tongue around and over her nipples brought them to a very hard state. Sarah is starting to move into that special zone where her whole body becomes sexually charged. Her body starts to tremble and her eyes are a pool of lust.

Being so close to orgasm without quite getting over the top was frustrating Sarah. She grabs at my belt and urgently drags my pants down over my briefs and hard cock. I know that as hot as we both are, I would explode very quickly if I entered her wonderful pussy. I quickly shuck Sarah's shorts and lace panty. Kissing my way down her belly, I start teasing her pussy. Sarah has the best tasting pussy in the world and giving her head is a great joy for me. I lightly stroke her outer lips as she spreads her legs. Sarah is very close to going over the edge, but I want to drag her orgasm out as long as possible. I slide down further to give Sarah's pussy the tongue-lashing I so enjoy providing. Sarah wants me to shift around to a 69 position so she can return the oral stimulation, but I refuse. I don't want to change positions and lose my concentration. When Sarah gets into this zone, she is having small orgasm after small orgasm and keeps building to a large crashing climax. My world is Sarah's pussy by this point. I keep working Sarah closer and closer to the edge by licking and sucking her clit then going back to licking her pussy lips. The only part of my body Sarah can reach is my head and she has her fingers twisted into my hair and she is pulling my mouth into the pussy. Her body starts to quiver and suddenly she goes stiff for a moment and then begins to shudder. I move my hand from Sarah's butt and insert a finger into her pussy. Taking the wet finger around to her asshole, I start finger fucking her rear entrance. That finishes her and takes her over the edge. A major orgasm starts and goes on for several minutes, drenching my face with her lovely nectar. Sarah has these major over the top orgasms most of the time when we make love, but when we have gone without sex for a while, the result is unbelievable. Her pussy juice is flowing so hard that I can't even lap it all up, her body rocks and convulses so hard that she gets cramps in her legs and toes and Sarah moans for so long that she completely runs out of breath.

It is over, and Sarah has collapsed into a limp pile. Sarah's clit is ultra- sensitive now and she can't stand to have any more additional stimulation. I slide up next to her and hug her as she comes down from the climax. She starts licking her juice off my face and crushes me against her breasts. Sarah says that she goes completely out-of-body when she has these powerful climaxes and I am both amazed and jealous of her orgasm. My dick is still throbbing in my briefs and I almost came myself without being touched. I slide my briefs off and put my erection between Sarah's legs, but not in her pussy. As Sarah clamps her legs together my dick is trapped against her clit and her pussy juice is flowing over my cock. She rocks her hips slowly to rub her clit against the top of my dick as she comes down some more.

After several minutes Sarah can talk again and begins to relax her legs and arms so I can move again. Now it is my turn, but Sarah is a little pissed that I teased her so long before taking her over the edge. Figuring that what is good for the goose is good for the gander; she starts to tease me. I tell Sarah that I am already hot as can be and just want to fuck. No way is Sarah going to let me off that easy and she starts tweaking my nipples and asking me questions.

"Jack, why are you so cruel to me when I am ready to climax and want your hard dick in me"?

I explain that it is so rewarding to me when I take her over the edge like that and if we are fucking my orgasm might occur too quickly for her major orgasm. This is especially true when we have not had sex for a while.

"Besides Sarah, you are not so innocent of sexually teasing. Remember how you used to tie me up and tease me with your fingernails for hours? You would make me beg to come and make me eat you to orgasm after orgasm. Then you would leave the bedroom for a while, come back when my erection was starting to droop and start all over again."

Sarah got this evil look on her face and started to tease me about my fascination with her long nails.

"Well Jack, I think you have a little bit of a fetish when it comes to long fingernails."

"If I do, it is because you taught me to respond to your nails with your sexual teasing."

"I think you have a little too much interest in my having long fingernails."

I was starting to feel defensive and tried to push back on Sarah.

"I really can't remember your long nails that well, since you have kept them chopped off for so long." "I mostly remember the great sex we had back then and how often you put some real energy into pleasing me."

I had hit a little below the belt with that remark and Sarah looked hurt.

"Are you trying to say I don't put energy into sex anymore, huh Jack"?

"Not exactly, but you used to keep your nails long for me and now you don't" "This is one example of how we let our work lives interfere with our sex lives."

I thought by using the "our" sex lives line, that Sarah would get back to our love making and forget about this budding argument. I wasn't quite that lucky.

"Jack, you are so full of shit." "Do you have any idea how hard it is to keep long nails?"

"I watched you take care of them, and I don't think it was that big a deal Sarah."

"It isn't the time it takes to do your nails, it is the extra time routine activities take when you have the long nails."

I should have just agreed, but I had to have the last word.

"I think you are exaggerating how hard it is to have long nails."

"You want to bet, buddy?"

Now I was really stupid.

"You got a bet Sarah!"

I had no idea what I had just got myself into, but my male ego just walked me into a bold statement with implications that I had not considered.

"OK Jack, you are going to have to prove to me that it is no big deal to have long nails."

"You're on!"

Sarah went on to set the terms of our bet, then we put it in writing and both signed it.

Nail Bet Between Jack and Sarah

1. Sarah will put long nails and polish on Jack.2) Jack will wear the nails until he gives up or any of the following conditions are met. 2a) 24 hours pass with Jack successfully wearing the nails. 2b) Some emergency occurs; in which case the bet will be suspended to a future time. 2c) Sarah agrees that Jack has proven that wearing long nails is "no big deal". 3) The loserr of the bet will be the sex slave to the winner for 2 weekends.

There, it was done. It was time to put up or shut up. After all the times I had wined to Sarah about not having long nails, I was about to find out what the wearing of long nails was like.

I had lost my erection by now, but I was horny as could be. Sarah had a major orgasm, but I was still without for over a week. The earlier activities had given me a case of "blue-balls" and all I really wanted to do was get my dick into Sarah's hot pussy. Sarah had other plans. She took me into the bedroom and sat my naked butt at the dressing table. She had an antique armchair at her dressing table with a padded seat and back but ornate carved arms. She sat me down in the chair and took several silk scarves out of the dresser. Sarah started tying each of my arms to the chair.

"Hey, what is that for?" I asked.

"I don't want you to try and back out after I get started."

Sarah sat in my lap and started kissing me. Running her hands over my face and down my chest, she kept it up until I regained my erection. Grabbing my dick, Sarah starts masturbating me, kissing me and rubbing her breasts against me. Her tempo starts building and she is getting me closer to orgasm, then simply stops.

"Hey, don't leave me like this!"

Sarah just laughs as she dances into her walk-in closet. I can see in the mirror that she is looking for something and then changes. When she walks out of the closet, she is wearing the short silk robe and matching panties that I bought her for Valentine's day. She looks unbelievable with her figure accented by the drape of silk. Sarah goes about collecting various items she is planning to use. She keeps moving from side to side as she gathers and discards items. I know she is doing this to set a physiological edge to our bet. Somehow, the whole show Sarah is putting on keeps me fully erect without any direct stimulation.

"I see that you find getting your nails done exciting?!"

"That is not fare Sarah, you know how good that silk makes you look, and besides I am the one with blue balls."

Sarah just smiles and plops down in my lap. She sets her tools down on the table and starts dressing my nails. She shapes my cuticles, trims and files each nail just the way she likes it. All this time, she keeps rubbing her beautiful ass against my erection. As she works, I try to look over her shoulder, but she keeps shifting around to block my view and rub my cock. This was making me even more excited and that didn't seem possible.

"Now to put on your nails!"

Sarah looks in her fingernail kit and finds her glue is dry.

"I guess you are going to have to wait here while I go get some more glue."

"Sarah, please don't leave me like this." "Can't we finish having sex and then go get some glue?"

"Poor baby, are you getting that desperate?" "Maybe I can find some more glue around the house and won't have to go out."

Sarah turned around in the chair and started kissing me again. She slid off her panties and is sliding her cunt up and down the bottom of my cock. Sarah grinds her hips against my cock, trying to crush my cock with her clit. I am at the edge of ejaculation when Sarah jumps off my lap, gives my hair a quick toss and jumps out of the room to look for glue. I can't believe it, my dick looks purple. It is twitching and throbbing but she stopped just short of my orgasm. If she keeps this up, I will be a complete drooling idiot. An erection with a body existing to provide nourishment, all other life events forgotten as the controlling erection seeks orgasm.

"Looks like I don't have to go out after all!"

"Hold on there a minute, that's super glue" "You can't take that stuff off, can you?"

"I'm not sure Jack, I never put nails on with super glue and I think they make some kind of remover, but I guess we will just have to find out."

"No way Sarah, please don't use that glue?"

"Beg me!"

"What."

"You heard me Jack, beg me or else, I am going to use super glue for your new nails!"

I started begging Sarah like crazy. She sat on my lap facing me again and started rubbing her tits on my face and pressing my dick against my stomach with her sopping wet cunt. I could not concentrate and before long I was begging her to let me cum and I forget all about the super glue.

"Please let me cum Sarah!?" I begged.

"You can't cum until we finish your nails Jack."

"Please hurry up then, your driving me crazy!"

"I have to go to the store and get some more glue and that could take an hour with traffic and all."

"OK, OK use the supper glue!" "Please, just hurry"

Sarah just stopped and laughed at my predicament. She was getting turned on to the whole scene and was so excited herself that her nipples were hard as rocks and her cunt lips were glistening in the soft bedroom lights.

Turning around, Sarah bends my cock down and sits in my lap. She squirms around until my cock is nestled in the folds of her cunt lips and she can rub her hard clit along the top of my shaft. She rocks back and forth giving herself direct stimulation and driving me to greater and greater lust. Suddenly Sarah stops rocking and a small shudder shakes her body and she lets all the air out of her lungs as she climaxes.

"What about me?" I begged.

"I told you Jack, that you can't cum until we finish your nails!" "Besides, that was only a little orgasm for me."

As Sarah goes to work on my nails she keeps rocking her hips randomly so that my erection keeps pressing up into her clit. Her nectar is flowing down over my cock and I can feel the wetness leaking over my balls. I am sure some of the wetness is pre-cum from my dick, but I can't see my erection.

I can't stand the frustration and simply close my eyes and concentrate on breathing. I think I was just about to pass out and it took all of my concentration just to force air into my lungs. I started thinking, and realized that I had been on the verge of my orgasm for about 2 hours now. I don't think I can survive much longer in this state of arousal.

"There, all done!"

I looked down as Sarah got off my lap. I didn't look at my nails yet, because I had to look at my cock. It was twitching and throbbing, was red in spots and had a purple cast to its coloration. It was covered with pre-cum and pussy juice and it seemed to belong to itself. Sort of a symbiotic relationship. The cock existed for one purpose, orgasm. The body existed to provide nourishment to the cock and in return got to experience the orgasm with the cock. I never understood why men gave nicknames to their cocks until now. It was a life-force of it's own.

"Well Jack, what do you think?"

I saw my nails for the first time and almost fainted. Sarah had put on the longest nails in her kit. The longest nails must have been 1.5" to 1.75" and even the nails on my little fingers are 1" long. Sarah has painted them a color I would call candy-apple-red if it were on a car. I can't believe what I am seeing and my cock starts to jerk up and down. Sarah realizes my cock is about to erupt and grabs my balls. Squeezing them to the point of pain, Sarah breaks the stimulation path and halts my orgasm. Reaching over the wine bucket, she grabs a handful of ice, starts rubbing my cock and balls. I think death must be near and then a split second later I come down to earth. My cock is still purple and fully erect, but my balls have shriveled up into my abdomen.

"Sarah please let me cum?!"

"All in good time Jack, all in good time."

I made my eyes focus on my nails and I couldn't believe what I was seeing. My fingers moved and if I just looked at the hands below the scarves tying me to the chair, you could believe that the hands belonged to a woman. My hands are very small in comparison to my body and the effect was unbelievable. I was mesmerized as I drummed the nails on the arm of the chair.

"Well what do you think Jack?"

"They are beautiful!"

"I know, even though I don't have time to keep my nails done up this way, I still am a bit of an artist." "Don't you agree?"

I had to admit that Sarah was unbelievably good at doing nails if she could make my hands look like this.

"Great, now can you let me out of this chair, please?!"

"Just a minute Jack, let's go over our bet first." "Remember, you have to prove that you can cope with the nails to win the bet!"

"Yeah yeah yeah, please untie me!" "My legs are falling asleep and my dick needs relief!"

"Well Jack, I think you need to get used to your new nails doing some routine tasks before jumping into heavy sex." "If you break your nails in a moment of passion, you would lose the bet, so I think it would be wise to get used to them for a while first."

"What do you mean, I lose the bet if I break a nail?"

"Of course Jack, if I am at work and break a nail just before the big client presentation I am screwed." "Can you imagine the horror a woman feels pointing to visual aids with a broken nail?" "You think it is easy or at least no big deal to have nails, so you have to prove you can do typical things without breaking your nails or anything else!"

I had to admit Sarah had a point, but I didn't think I could stand to not cum.

"OK Sarah, you win, but can't you give me some relief sexually without me risking my nails?" "Maybe a blowjob or something?"

"Would you like to get that dick into my pussy?"

"Yes, please I can't go on without some relief."

"OK Jack, but to protect your new nails, I am going to have to keep you tied up."

"OK Sarah, please I am desperate for relief!"

Sarah went into the closet and got out our box of sex toys. I hadn't seen the box in over a year but knew what she was after. Sarah pulled out the sex cuffs that were padded and could be worn for hours without any risk to your arms or legs. Sarah released me from the chair and pulled my by my cock over to bed. She pulled back the covers and had me lay down in the middle of the bed. Taking a cuff, she attached each of my arms and then legs to the corners of the bed. I am now tied spread-eagle and even more helpless to resist any new torture Sarah can come up with.

Sarah gets between my legs and starts to nibble on my cock. I never get quite enough stimulation from having my cock sucked on, but little love bites can drive me completely crazy. Sarah gets me near explosion again and then takes my cock into her mouth and slowly sucks and bobs on my cock. I can't cum, but the wet oral stimulation keeps my right on the edge. Again I beg for relief.

"Please Sarah, I am desperate for relief"

"That is your problem Jack, I have already had a couple of good orgasms tonight and frankly I am getting tired. I think we should finish tomorrow morning. After all, you have over 23 hours to go on our bet!"

"Sarah, you said I could get my dick into your pussy if I let you tie me up on the bed!"

"Well, I guess a promise is a promise, so I will have to let you in my pussy if you still want to."

"Thank you, thank you!"

Sarah jumped off the bed and ran into the bathroom. She came back with several condoms and started putting one on my dick.

"Hey, we don't use condoms anymore, what is that for?"

"You are just too hot and I am tired." "If we are going to have sex, I don't want you to cum before I get relief and this will slow you down."

Sarah proceeded to roll two more condoms on my cock. She rolled each condom past the ring on the prior condom and they were having the effect of a cock ring. I was now 3 layers away from the velvet sensation of Sarah's pussy. She slid up my chest and sat her pussy on my face. I was so horny that I just went crazy licking her pussy and when her juice was flowing fully, she moved down and impaled herself on my dick. The warmth was immediate, but I could not quite feel her movement. It was just a whisper in the night. I knew it was happening, but could not realize the full effect. As Sarah rode up and down faster and faster she began to talk.

"Your nails really turn me on, you know?" "I have always has a little bit of a lesbian fantasy but no interest in actually having sex with a woman." "I think to prove that you can handle the long nails, you need to do everything a woman would have to do!" "Don't you agree?"

I didn't care anymore, I would agree to anything to get relief. If she asked me to commit murder at that moment, I am sure I would agree!

"Yes, yes, yes!" "Anything you say, just let me cum!"

Sarah exploded in her third big orgasm of the night and collapsed on my chest. I was twitching inside her cunt but still no climax. Sarah rolled off and started kissing and stroking my face. I was out of body just watching the scene. The cock was the center of my universe and the rest of the room was just spinning slowly around the cock. I say the cock, because it was in charge and I was just a slave to it.

"To prove you can make love as a woman, I am going to let you masturbate a real cock!" "How does that sound?"

"What do you mean, a real cock?"

"I am going to release your hand and you are going to masturbate your cock with your new nails, just like a woman would have to if she was in a car on a date!" "What do you say?"

I quickly agreed. Anything to get relief. Sarah released my left hand from the cuff and it flew to my cock. I was right handed, and with the long nails, it was very clumsy, but I was desperate to cum. Grabbing my cock, I started to pump it up and down, only to find the three condoms in the way.

"Please Sarah, take off the condoms?!"

"If I take them off, you lose the bet"

This was impossible, I didn't think I could get the three tight condoms off and giving up on the bet was not an option. My long denied orgasm was driving me crazy and I had to stop reacting to my cock and concentrate. Slowly I explored getting the outer condom started up. My new nails kept me from grabbing it and rolling it back off over the bands of the other condoms was not going well. Sarah climbed up on the bed and adjusted a pillow so that she was sitting at the foot of the bed facing me. She started masturbating in my plain view as I struggled with the condoms. I felt like I was spending as much energy working on that condom as I would in a basketball game. Suddenly I got the outer condom to roll over the band of the other two using my fingertips and keeping the nails out of the way. The next condom was much easier and I was finally able to remove the condoms.

Sarah told me to just use the edge of the nails on my cock head to get it sensitive. I did as instructed, after all she wasn't asking me to kill anybody yet and I knew even that was possible right now.

Sarah tells me to start pumping my cock, but to keep all 5 nails in contact with my cock flesh as my hand flies up and down. Sarah stuffs more pillows under my head to insure that I am looking at my cock. I am racing toward orgasm and close my eyes.

"Open your eyes Jack!"

I open my eyes and see a beautifully manicured hand flying up and down a rockhard shaft. My out of body experience ends and I collapse back into my body. I can't help myself and just explode. I am thrashing about on the bed and spewing sperm high in the air. Sarah has been rubbing her breasts with one hand while fingering her clit with the other and explodes in orgasm herself.

This is the closest I have ever come to having the unbelievable over-the- top orgasm like Sarah has. I am drained and my body tingles all over. Then I hear Sarah's voice.

"What a mess you made, I didn't think you could possibly have that much sperm in you!" "You better clean up your mess Jack!"

"I can't, I am all tied up except for my left hand and I can't reach the other cuffs."

"You have to do it like a woman would, and clean it up with your hands and tongue!"

"Come on Sarah, that is not part of our bet!"

"Are you admitting that you lose the bet Jack?" "Then get to work, if I was making love to you and you exploded, I would clean you up with my hands and mouth, so get to work!"

I looked down at my hand with the beautiful nails soaked with my sperm. Slowly I brought my hand to my mouth and as the sperm dripped off the tip of a nail into my mouth, I had a second orgasm. Not a large orgasm with sperm flying, but my whole body was climaxing over and over again. I could not believe it, I was slurping my sperm off my own fingers, and shaking in multiple orgasm after orgasm. My hand was flying back down to my dick, scraping up any sperm I could find and back to my mouth. Over and over again until I could not find any sperm on my dick, stomach or chest.

I was coming down finally when I saw a bright flash. Sarah had gotten off the bed and was taking pictures with our Polaroid. The look of horror on my face stopped Sarah from taking pictures and then she started laughing at my predicament. I looked around the bed and saw what must have been a dozen pictures taken of me from every possible angle. Fingers dripping with sperm jammed in my mouth, clearly my own hand with painted nails covered with sperm being sucked clean and nothing but lust on my face.

I was speechless and then Sarah collected the pictures and left the room. When she came back I asked what she did with the pictures.

"I hid them for those nights when you are on a business trip and I need to masturbate to get to sleep." "I am going to take them out of their hiding place and remember this night again and again!" "This is probably the most exciting sex I have ever had and Jack, I plan to relive it whenever I get the chance!"

I was in shock, on one hand I knew she was right, this was the only time in my life that I had been able to keep climaxing like a woman's multiple orgasm. On the other hand, if anybody else saw those pictures, I was ruined in my mind.

"We need to get some sleep now, because you are going to have a long day tomorrow"

Sarah started untie me while explaining that I was to clean up, go to the bathroom and comeback and lie down again. She was going to put me back in the cuffs to protect my nails during the night. Sarah explained that I wasn't used to the nails and if I tossed and turned during the night they might get caught in the covers, come off and I would lose the bet.

I was so exhausted, I didn't even argue. I simply got up, went to the bathroom, cleaned up a few stray drops of sperm, emptied my bladder and came back to bed. Sarah put me back into the bondage and pulled the covers up for sleep. Sarah kissed me gently and played with my cock until she drifted off to sleep.

I went over my situation in my mind as I was nodding off myself. I had on super glue nails that were obscenely long, my dick was hard again in my sleeping wife's hand and I had a full day ahead to win or lose the bet. I was afraid and excited at the same time, what a night.

As I dropped off to sleep, I could hardly wait for morning and the start of day 2 ........

Chapter 2, The Start of a Long Day

I couldn't believe what Sarah did to me to wake me up on Saturday. She released my right hand from the cuff and tickled my nose with a feather. When I went to reach my nose to scratch the tickle some beast with deadly talons and a terrible cackling screech attacked me. As I came rushing to full consciousness, I realized that the terrible beast scratching my face was my right hand and the cackling screech was just Sarah laughing hysterically.

It was a good thing that Sarah still had me tied down on three corners, or I would have killed her.

"Good morning sleepy head."

"You are such a bitch when you want to be Sarah!"

"Now, Now Jack, don't get pissed off so soon, you are going to have enough frustration today getting things done with your new nails." "Don't waste your energy on this little event."

"What do you think happens to me when I scratch my face during the night and I have long nails on?" "Are you ready to give up already?"

I wasn't and besides, I needed to get out of bed and take a piss.

"OK, just let me up so I can go to the bathroom."

"I am going to go to the store and pick up a few things and you can get cleaned up for the day." "Take a shower, shave and anything else you need and I will be back in a few minutes."

As Sarah was took the cuff off my other hand and as she headed for the door she reminded me that I better be ready when she got back.

Getting my other hand free enabled me to sit up and if I leaned way over, I could just reach the cuff on one of my legs at a time. I had to work at it long enough that I thought I would have to wet the bed if I didn't get it off soon. I felt a great sense of accomplishment just getting it unbuckled. The second leg cuff was a piece of cake and I ran for the bathroom as my bladder was starting to relax.

The shower was next and I could hardly hold the bar of soap. It kept slipping out of my hand and then I had a devil of time picking it up off the floor. Giving up, I got out a washcloth and took my shower that way. I had not used a washcloth since I was a little boy and found it very odd to see my body being washed by a beautifully manicured feminine hand holding a washcloth while I was alone in the shower. Next was the shampoo and after struggling with the lid, I got it done without any severe damage to my scalp. The nails kept getting caught in my longish hair (for a man) and it took twice as long to complete this simple task.

After the shower, it was shaving and brushing my teeth. I was starting to get the feel for the nails by now and could do simple tasks by extending my fingers out straight and working the fingertips. This angle kept the nails from digging in.

I was blowing my hair dry when I heard Sarah in the bedroom.

"Come on Jack, I have been gone an hour and you are still getting cleaned up!"

This was shocking, I had spent three times as long getting cleaned up as normal, but at least I still had on all 10 nails.

"Hey, I am beginning to get the hang of these nails, they aren't so bad once you get a little practice!"

"Glad to hear it Jack, because now is you time for the next challenge."

I stopped breathing and fear rushed over me. I could not believe how terrified and excited her words made me as Sarah handed me a package of pantyhose.

"Put them on Jack."

"You have got to be kidding!?"

"No Jack, I have to do this every day and it is not that easy." "If you are going to prove your point and win the bet, you are going to have to show me!"

I was stuck and Sarah knew it. Sitting down on the bed, I started opening the package. Using my teeth, the bag was not much of a challenge, but the next step was very unfamiliar. I had watched Sarah do this many times and had a clue but not much else. Working my feet into the hose, I started smoothing them up my leg. The nails kept getting caught and the hair on my legs was being bent backwards, but with patience I got them up over my knees.

"Hurry up boy, I would be late to work everyday if I took this long to put on my pantyhose!"

Standing up, I started pulling and tugging the hose up over my thighs. It wasn't working anymore. The new hose were just not long enough, but I kept working the material higher and higher. Just about had the hose up to my crotch when it happened.

The hose ripped, one of my nails went sailing across the bedroom and a run shot down my leg.

"You lose, you lose, you lose!"

Sarah was gloating and I was so embarrassed that I turned red.

"That's not fair Sarah!" "You run nylons all the time and you don't have long nails anymore and you lost a nail before and and .... !"

"Jack, you lose!" "You said it was easy and this proves I won the bet!"

I was frantic, I didn't want to lose the bet (male ego I guess) and had to get a second chance. I proposed to Sarah that one single incident wasn't enough and that we needed a point system to determine who won the bet. It took a while but Sarah finally agreed, provided I did something else in return.

"Jack, I want you to shave your legs and under arms."

By now, I was willing to go along with Sarah on just about any condition. While Sarah glued my lost nail back on and touched up the polish, I kept trying to talk Sarah out of the shave, but she insisted. I went back into the shower and started shaving my legs and under arms. After 20 minutes and 3 razors, I was about done when Sarah came in to take a peek. Sarah reached into the shower and started rubbing cream on me and said it would soothe the razor burn. She was taking great care to rub my dick and chest and even worked it into my ass cheeks. I was starting to build for orgasm as she worked a finger up and down my crack and found my asshole. Then Sarah stopped and said I had enough "help" and I needed to rinse off.

After I got out of the shower, Sarah was helping me dry off when she told me to look in the mirror. I could not believe the picture looking back at me. She had used a hair remover and I was completely bald from my neck down to my toes. I was not very hairy to begin with, but this was shocking. My hardon looked even bigger without any hair on my pubic area. I wanted to protest, but Sarah was rubbing my dick and telling me how much fun this bet was working out to be.

Handing me a new package of pantyhose, Sarah told me to put them on and come down to the kitchen. With the new smoothness of my shaved legs and experience from my first attempt, I was successful this time getting the pantyhose all the way on. The sensation of hose on my legs was great. I always liked Sarah to rub her nylon-covered legs against mine when we made love and this was almost as good. The only draw back was all this sensation was giving me a hardon. The result of my erection was kind of comical when I looked at my profile in the mirror. I was interrupted from my state by Sarah's voice.

"Jack, are you done yet?"

Going down to the kitchen, I was strutting like a proud peacock. I was thrusting my hips a little forward to make sure Sarah couldn't miss my erection when I made my "grand" entrance. Sarah wrapped me in her arms and kissed me deeply. Rubbing my erection through my pantyhose she whispered in my ear.

"I see you like dressing up in women's underwear as much as you like wearing long fingernails."

I pulled away and again turned red with embarrassment and humiliation. Sarah calmly pulled me back to her and told me how much this was turning her on as well. I relaxed again as she continued to rub me through the pantyhose, bringing me close to orgasm again. Then she stopped her stimulation and returned to a very business like manor.

"Jack, I have revised our agreement and you need to review it and sign the new bet"

Revised Nail Bet Between Jack and Sarah

1. Sarah will put long nails and polish on Jack. 2) Jack will wear the nails until he gives up or any of the following conditions are met. 2a) 24 hours pass with Jack successfully wearing the nails. - 2 points for each nail damage event. - 1 point for each failed activity (including damage to any article). 2b) Jack fails if he earns 10 or more points. 2c) Some emergency occurs, in which case the bet will be suspended to a future time. 2d) Sarah agrees that Jack has proven that wearing long nails is "no big deal". 3) The loserr of the bet will be the sex slave to the winner for 2 weekends.

I was down 3 points already, but if I didn't agree to this change to the bet I would already lose. With not much of an option, I signed.

"OK Jack, you get to make me brunch now."

"I didn't lose this bet yet, how come you are already treating me like a slave?"

"Silly boy, this is just the next test." "You need to prove that you can cook with long nails, or else you are saying that the nails do interfere with real life."

I had to work very hard on this bet and Sarah was getting treated like a queen. Somehow, she was winning even if she lost the bet. Sarah always was a clever woman.

Sarah wanted me to make omelets for brunch and I didn't like this idea. I would have to chop a lot of items to make omelets and it was a lot of work without the long nails. She had chosen wisely. I started to go back to the bedroom and get dressed, but Sarah had other ideas.

"Jack, I like the way you look, just put on an apron."

Sarah got out her most frilly apron. It was handmade by her aunt, pink and white checks with stiff lace sewn onto the apron for feminine decoration. The sleeves were ruffled and it was the least masculine apron in the house. I blushed again as Sarah tied it tightly around me.

Getting to work, I chopped the meat and vegetables for the omelet and it only took a little longer than normal. After making the coffee and juice, the griddle work started. It was a real trip working the spatula, but I managed. Sarah made me do the whole drill, set the table and serve her. I make omelets one at a time, so I went back to work on mine after serving Sarah.

When I sat down, Sarah was already done and as I ate she started teasing me about how sexy I was in the pantyhose and apron. She described how much it turned her on to watch me working in the kitchen with my legs and butt highlighted by the hose. To her, my apron was "adorable" and made her think about her lesbian fantasy. I wasn't sure where she was going with this conversation, but as she talked my erection returned and was making my apron peak up. The tightness of the hose was causing some discomfort but, the nylon was also rubbing my dick to a point of extreme sensitivity. As I was finishing brunch, Sarah came around the table and started rubbing my chest under the apron and working her hands down to my dick.

"You really like being dressed up like a little horny housewife, don't you Jack?"

"That's not exactly right Sarah, you keep making everything we do sexual and that is what turns me on." "It's you, not the apron and hose!"

It was a lie, this whole scene was making me hot, not just the feminine clothes and not just Sarah. She knew this and worked her point a little more.

"Then how come you had a hardon when you came out of the bedroom in your pantyhose?"

"I guess you are right, being made to wear forbidden cloths is a bit of a rush"

Sarah slid down in my lap and started kissing me and feeling me up everywhere her hands could reach.

"Jack, make love to me like a woman!" "Just use your hands and mouth, OK?" "Your hands are very sexy with the long nails!"

I started kissing Sarah back and getting turned on big time. This was not a great position for making love, so I started to stand and pick up Sarah.

"No Jack, a woman would not carry me to bed!" "Take my hand and gently take me to bed or the couch on the sun porch."

I tried it Sarah's way and led her to the sun porch. This was one of Sarah's favorite rooms to make love in, but I didn't like the furniture for good old fashioned fucking. This wicker stuff was good sitting but not for a good pounding of my dick into Sarah's wet pussy. Sitting down on the love seat, we kissed and stroked each other's face. I gently unbuttoned Sarah blouse and tried to act like the extra time the nails made me take was part of a slow seduction. Finally I got the blouse unbuttoned and began to caress her breasts through her bra. As her nipples stiffened, she took a deep breath.

"Take my bra off Jack!"

Her words made a chill run up my spine. I had enough trouble getting her bra off without nails, and I realized that this bra was Sarah's tightest. I started working on the clasp, but I could not get enough slack in the material to open the little catches. Sarah was rubbing my dick through the hose and would slide the hose up and down my erection. The material has a grain to it and it began to rub my dick a little raw.

"Come on Jack, I am so horny, get my bra off!"

I couldn't do it, her bra was so tight I could not get my fingers to pull up on the fabric to get some slack.

"If you can't do it Jack, give up the bet and I will do it."

That did it, I redoubled my effort and dug the bra away from her back with the nails. I got the 3 little catches to release and the bra came free. Pulling her blouse free of her shorts, I soon had her topless.

"Jack, use you nails on my breasts!"

I went to work on her breasts using the nails. It was so sexy gently raking the nails along the sides of her breasts and tweaking her nipples. I remembered how Sarah had done this to me when she had her long nails and I tried to repeat her motions. She was breathing heavy and her eyes were glazed over as she kissed me again and again. Her rubbing of my dick was erratic and the unpredictability kept me completely off stride in my response. The stimulation was causing me to leak pre-cum on the panty hose but was not going to give me any relief.

"Finish undressing me Jack!"

The shorts were a little tight, but I was able to work the zipper pretty quickly. Pulling her shorts off with her panties I was shocked by the wetness leaking out of her pussy. I was drawn to her pussy by the nectar and knelt down to taste her pussy. Licking at her cunt lips I can feel her building to a climax. I part her lips with my fingers and accidentally scraped Sarah with the edge of my long nail. She shuddered and grabbed my hair, pulling me up to the seat again.

"Use you nails on my cunt!"

I start rubbing the tips of my fingernails along the edge of her pussy. I remember how Sarah used to drive me crazy by scrapping her nails along my dick and tried to copy her technique. With my other hand I pulled Sarah around so that her back is against my chest. Now I could reach her breasts with one hand while using the other on her wet pussy. Sarah was trembling all over and her breathing is short and fast. Looking down, I can see my wife's beautiful body being made love to by two hands that should be on another woman. It is like watching a porn movie where two women are performing mutual masturbation. Sarah's is smashing my dick against my body and I can feel it throbbing in my pantyhose.

"Open your eyes Sarah and look at my hands on your body!"

Sarah looks down and can see what I have been watching. Two hands with long red nails massaging her breast and cunt. Faster and faster I finger her cunt as she races to orgasm. Watching the whole scene is overwhelming to me, so Sarah must be close to one of her out-of-body orgasms. I take first one finger and slide it into her cunt. I start finger fucking her and take a nipple in the tips of my nails like a pair of needle- nose pliers. Now I have 2 fingers in her cunt and am working them in and out as fast as I can in this position. Pumping and pumping my hand Sarah is having multiple small orgasms, but is not quite over the top. I pull my hand out to the tip and run the edge of my nail around her rock hard clit and quickly jam 3 fingers in her cunt. She is starting to stiffen her whole body when I do it again, twice more quickly. She reaches her peak and has the big orgasm. I keep rubbing my nails along her breast and outer cunt lips as she orgasms for what seemed like several minutes until she completely collapsed.

I hold her and rock her for several minutes as she comes down.

"Now you can make me come like I am your lesbian lover Sarah."

Sarah spun around and asked me if that was what I wanted. I said it sure was.

"OK Jack, but first you need an enema"

"What?"

"I am going to fuck you with our vibrator and you need to be clean before I use it on you!"

Our vibrator was bigger than my dick and was one of the models shaped like a real cock with a harder plastic vibrator in the center. Sarah says it feels very real when I use it on her (and when she uses it herself because I am out of town).

"I don't think that is such a good idea, I can't take that up my butt!"

"Yes you can, you just don't know it yet." "I will work you up to it and you can stop me anytime you want Jack." "I won't force this one as a condition of the bet, just trust me."

I had never been so sexually charged in my life and I really did trust Sarah with my life, so what was my asshole compared to that?

"Ok, you can do it."

Sarah led me to the bedroom stroking my pre-cum soaked dick trough my pantyhose all the way.

"Before we start, lets review the score Jack." "You chipped your polish on one nail on the left hand and one nail is almost completely off on your right."

I looked down and she was right. In the middle of our lovemaking, I had done some serious damage to my new nails.

"You also scratched my back taking my bra off, so you scored a total of 5 points plus your prior 3 to bring your score to 8!"

I was shocked to see my points pilling up so fast and it wasn't even noon yet.

"That's not right Sarah, I damaged my nails doing one task, the fact that I damaged 2 nails counts the same as 1 nail or 10 nails as long as it happens during the same activity."

"Well Jack, since we didn't clearly state the rules regarding this per event vs. per nail rule, I am going to let you have it your way." "Let's see, that makes your score 6." "Your not going to make it Jack, want to give up now?"

"No, I am only a little over halfway there on score and about the same amount of time has gone by." "I think I still have a great chance to win the bet!"

Sarah just smiled and sat me down to fix my nails again. She replaced the severely damaged nail using a lot of super glue, removed all my polish and redid my 10 nails. They looked wonderful again. I could see what time and effort Sarah had put into her nails based on the last 13 or so hours to agree that it was not easy, but I didn't want to lose the bet so I kept my mouth shut.

Sarah told me to sit still and let my nails dry before we moved on. She slid around behind me and again started rubbing my cock through the pantyhose. You can't imagine how good something can feel and still hurt until someone masturbates you with pre-cum soaked nylons. I think it is like a little "Scotch" pad rubbing away layers of skin cells, stimulating you while hurting enough to hold you short of orgasm.

"Don't go away, I have to go potty." "And whatever you do, don't touch anything with your wet nails, it will smear the polish and I will be pissed if you make me redo them!"

She did it again, bringing me to the edge of orgasm and then stopped in the nick of time so that I am getting a second case of "blue-balls" in as many days. I close my eyes and relax in Sarah's armchair at her dressing table. I don't know how long I waited, but when I opened my eyes again, Sarah was taking Polaroid pictures again. She was dropping them on the floor and had taken good six or seven pictures of me sitting at her dressing table wearing a very frilly apron and pantyhose. These pictures were more humiliating (if that was possible) than the first. Before, I was clearly tied up and could at least argue that I was under the control of someone else. This time I was sitting there untied in an apron wearing pantyhose and I had a huge bulge in my apron where my dick was sticking out.

"Hey, no pictures!" "You can't keep those, give them to me!"

"Jack, I am not going to share these with anybody!" "I just want to be able to take them out when we are old and have kids around keeping us from playing sex games like this on a Saturday." "Nobody will ever see these pictures but us, I promise!"

"We will talk about it later, but for now I guess you can keep them."

"Good, now sit still and I will show them to you!"

Sarah flew into my lap and sat down on my dick. After I yelped in pain, she pulled up my apron and sat down so that her cunt was on top of my dick and we were front to back. Sarah kept wiggling her but as she showed me the pictures, she was going to make sure that I didn't lose my erection as she showed me the pictures.

"See how sexy you look in your apron and hose Jack?"

"If you say so Sarah."

"Oh I do and besides, if you grow your hair out a little longer, you can let me give you a hair-do to go with your nails" "Wouldn't that be sexy?"

"I don't know anymore Sarah, this is already way beyond what I thought my limits were in sexual matters!"

"You look great in pink Jack and I think I am going to have to dress you up more often!" "It is sort of like playing Barbie with a life size doll, doing makeup with a girlfriend and having great sex with your husband all in one."

I didn't know about the first two, but I knew that this was the best sex we have had in a long time.

"I guess so, but playing like this will take a little getting used to."

After a few more minutes, Sarah said my nails were dry and we needed to move on to our "girl-on-girl" sex. Taking me into the bathroom, she got out the enema bag. I have a very sensitive asshole, and the idea of getting an enema was not high on my list of activities. Sarah went about getting things ready and filled the bag up with a lot of warm soapy water.

"That looks like a lot of water Sarah!"

"Don't worry Jack, you can take it." "Yea, take it like a man!"

I didn't like her little joke, but my hardon and blue-balls kept me cooperative. Sarah bent me over just so on my knees, pulled down my pantyhose and started working some KY jelly into my ass. Soon she was finger fucking me and I was moaning in pleasure. Now she was fucking me with longer strokes and I was really starting to like this feeling. Sarah, stopped moving in and out of my ass and I felt the pressure. She had been fucking my ass with the enema nozzle.

The warm water was rushing in very fast, and I let out a "Sarah!" to let her know I didn't like this. She slowed down the water and let me get used to the pressure. Before I got completely use to the pressure, she was done. Sarah quickly popped the nozzle out of my ass and pulled up my pantyhose. Standing upright again, I looked down at the bulge in my front, it could not have been any bigger. My guts were full beyond belief and Sarah was rubbing her tits against my back and rubbing her hands on my stomach.

"Do you think being pregnant will feel like being full like this Jack?"

"How would I know, I have never been pregnant and never will be."

"I know Jack, but close you eyes and imagine being pregnant." "When I was in highschool, one of the girls got pregnant, and a couple of us gave each other enema's and tried to imagine what it felt like to be pregnant."

This was the first time Sarah had ever mentioned doing anything like this with other girls and I wondered if this was the basis of her lesbian fantasy.

"Jack, telephone!"

I had not heard the phone ring as I stood there thinking about Sarah's words, but I went into the bedroom to see what was going on.

"It's your Mother and she wants to say hi!"

I pick up the phone and said hi to my Mom.

"I didn't hear the phone ring Mom, but thanks for calling."

"Sarah called and said we hadn't talked in a while so she was going to make sure her husband kept in contact with his mother." "Wasn't that nice of her!"

The cramps in my gut hit about the time my mom got to the part about how nice Sarah was.

"Yes Mom, Sarah is special that way"

I very quickly reached the point of agony and had to get off the phone. Sarah was sitting across the room grinning ear to ear over my predicament.

"Can I call you back tomorrow Mom, I was just going out the door to help a buddy with his car and I want to get going so I can get done and back home to Sarah." "Sarah is being a little trouble maker, calling you as I was going out the door."

My Mom thought that this was extremely funny and she would be happy to get my call tomorrow. I hung up the phone and ran to the bathroom. Getting the panty hose down was a lot easier than putting them on, but it was still difficult when you are about to blow. Somehow I made it and sat down on the toilet.

"Sarah you can be such a bitch at times!"

She had put the toilet seat up and I had sat down in the cold water. I don't know how, but I managed to pick up my butt, put the seat down and sit back down before the worst could happen.

It was a major league sensation as the water rushed out of me. I had never had an enema even as a child and this was overwhelming. As I was coming to my senses again, I saw the flash of the camera again. I was numb, and only looked at Sarah as she recorded my current humiliating position. She stopped and showed me the pictures. There I was with pantyhose pulled down, in a pink and white apron, and my manicured hands resting on my nylon covered thighs. The hose were black and the red polish was clearly visible. My face had a strangely satisfied look and you could easily believe I was very happy to be sitting on the toilet like a woman in nails, hose and apron.

Sarah darted off to put away her new treasure. When she returned, she told me to take my time and when I was ready, take off the apron and hose and shower up again. She wanted me clean inside and out.

It took a few more minutes before I was ready, and I reached for the toilet paper and froze. I could not image how to wipe my butt with these nails. Sarah had been hiding just around the corner and she poked her head in when I froze.

"If I have to wipe your butt, you lose Jack!"

I made up my mind to not lose after all I had been through. Working carefully, I managed to complete my paper work (pun intended). Getting into the shower was a perfect idea and I slipped into the warm water. After a few minutes, I looked around for some soap and the only thing in the shower was one of those nylon net body washers and liquid soap.

"Sarah, bring me some soap, please."

"Just use the liquid soap, we are out of your bar soap."

I soaped up the body washer and washed up. The texture of the net against my hairless skin was very erotic. I was getting quite aroused again when it hit me how much this soap smelled. Sarah had put her strongest perfume soap in the shower. I was going to smell like no man I had ever been around after this.

When I got out of the shower, Sarah was again ready to dry my off. She worked the towel against my skin until my skin was pink all over. Sarah grabbed me by my hard dick and led me into the bedroom. Turning me around she put her naked body against me and started kissing me. I tried to kiss back, but she stopped me.

"Not that way Jack, remember you are going to let me make love to you like a woman."

I relaxed and let Sarah take the lead. She kissed me and caressed my very smooth and soft skin (at least for me). Every time I tried to move Sarah along, she told me to relax and let the sensations come to me. I was hard as a rock and reaching the point that I didn't care what Sarah did next, I just wanted to feel everything she could make me feel. Then she stopped.

"Time to get dressed Jack."

Sarah drew my attention to the bed and I saw what she was pointing to. On the bed was a pair of very shear stocking, a garter belt, pink silk panties and a matching pink silk camisole. I was hesitating and then Sarah simply said "Please, for Me." and I was putty in her hands.

Sarah helped me this time with each article of clothes as she got me dressed just so. When she was done she showed me my reflection in the mirror. I almost exploded in my panties, but she pinched my nipples very hard through the camisole to bring me back to earth.

"Get on your knees, on the bed and put your hands at the corners."

Sarah put my hands in the cuffs again and started kissing me all over my face and neck. She slid up and down my body, got on the bed under me and was truly making every inch of my sensitive skin tingle. The feel of the silk sliding over my hairless body was a new and wonderful sensation. Sarah worked around behind me and started sliding my panties down in the back. The front couldn't clear my dick, so they would only come down enough for Sarah to reach my asshole but not my balls. She had hidden some lubricant and started working it into my hole.

"I am going to treat you ass as if it was your cunt." "I will take my time opening you up like the virgin you are, so tell me if I am going faster than you like."

"Why did you have to tie my hands for this?"

"You get to control how fast and what limits you have, but I get to decide what happens!" "Don't you think that is fair?"

I didn't, but at this point her finger was starting to feel quite good in my ass, I mean cunt. As Sarah worked my new cunt, she told me that many women can't orgasm with just stimulation of the vagina, and needed to have their clit stimulated also. She kept asking me if my clit needed stimulation to reach orgasm or could I experience a "vaginal" orgasm like her. I had no idea, but I was willing to keep going. Sarah pushed in some more lubricant and started working two fingers in and out of my "cunt".

I was moaning now and knew that trusting Sarah was going to get me well satisfied. I was feeling a little fuller now as Sarah worked three fingers into my "cunt". I adjusted quickly now and started rocking back against her hand. Sarah had converted me, I knew that having my ass fucked, finger fucked, vibrator fucked was now well within my limits.

I looked back over my shoulder as Sarah let out a little moan. She had the dildo/vibrator in her own pussy and was working it in and out slowly.

"I am warming it up for you, I don't want you to lose your virginity to a cold phallus."

How kind of Sarah, worrying about my "de-flowering" and wanting it to feel as good as possible, even if she had to get some pleasure in the process. Sarah worked some more lubricant into my "cunt" and put the tip of the dildo against my anus. With the stretching she had done, it went in right away. She started working the dildo in and out and each time the thrust went a little deeper. I was being fucked and liking it. As she worked the dildo I rocked my hips back to meet each thrust. Then Sarah stopped fucking me, turned on the vibrator and started kissing me on my ears and neck.

"Don't stop!"

"Beg me Jack!"

"What!"

"You heard me Jack, beg me." "Beg me to fuck you until you cum!"

I begged, oh how I begged!

"Please fuck me Sarah, please!" "I'm so horny and need you to keep fucking my ass!" "Make me cum with your fucking!"

Sarah kept me begging for several minutes while she teased me and then she suddenly got off the bed. When she returned, she had put on a strap- on harness. I had forgotten we even had the darn thing. Someone had given it to Sarah as a gag at her bachelorette party and it had gotten tossed in the closet and forgotten. The dick was even bigger than the vibrator up my ass and looked very real.

"That is bigger than I can take, don't, please don't!"

"You get to control how fast we go Jack, not what we do, remember!" "If it starts hurting, I will wait until you are ready for more."

Sarah got up on the bed behind me and started working the head of the dildo into my "cunt". As she pressed forward, I felt the head slide in. I let my breath out and Sarah waited for a minute. As I adjusted, she started working it in and out slowly. Very quickly it was going in halfway and I was moaning again in pleasure. As I started rocking to meet her thrusts, she pushed further in each time until I felt her pubic hairs against my ass. I was hooked. She was picking up the pace and I was rocking back in complete synchronization. She had taken me past a new limit and I didn't even care. With each thrust she reached the hilt and I let out a moan when she buried the dildo in me. The dildo harness setup had a clit stimulator built into it and Sarah was getting worked up herself. I don't know how long she kept rocking into my ass and running her hands over my silk covered body, it could have been all day as far as I was concerned. I was almost out of body with sensation and I was for certain out of my mind with lust.

Sarah started to climax, her body shaking strongly as she reached orgasm again. I was still rocking, but she wanted to hold still for a moment. When she relaxed again, she reached up and unbuckled my hand.

"You must need to have your clit stimulated to reach orgasm."

My hand flew to my dick and I drug my pre-cum soaked panties over the head of my dick and started stroking.

"Slow down, and set a rhythm on your clit to keep pace with my fucking of your cunt!"

Sarah started rocking into me again and I matched her thrusts with my manicured hand on my own dick.

"Just use the tips of the nails and get your dick ultra-sensitive."

Sarah had me in a place I had never been and I liked it a lot. As she pumped my ass with that big dildo, I used my nails to rake up and down my own cock. I closed my eyes and imagined what Sarah must feel like to get fucked and it was wonderful. Faster and faster she worked the dildo in and out of my ass until she let out her breath and started to orgasm again.

I went over the top, and started spewing all over my hand as she was slamming into my "cunt" and climaxing herself. I think I had the longest orgasm of my life as she reamed me good.

"Time to clean up your mess Jack."

I knew what she wanted and started licking my hand clean and Sarah kept reaming my ass as I licked up my own sperm. I felt total humiliation over being a cum-eater cross-dresser and total exhilaration with all my new sexual sensations. My hand would go down to my dick and grab all the sperm I could find and flash back to my mouth to be licked clean again. The sperm dripping off the long nails was so erotic and totally humiliating. Like the night before, I kept having small orgasms, one after the other for a good five minutes (as time goes during orgasm). Finally I just collapsed on the bed and Sarah fell forward driving her dick into my ass. She just lay on my back whispering into my ears about how good it was for her and how much I must have enjoyed my first fucking. I could not believe how many new sexual experiences we had enjoyed since last night and did not want it to end.

After a little more rest, Sarah got up and pulled the dildo out of my ass and I hated the empty feeling.

"I will never be the same after that."

"I know just how you feel, loosing your virginity is almost always a life- changing event Jack." "You truly will never be the same."

"This is the second time I lost my virginity and it is more memorable than the first!" "I didn't know what I was doing then and I was so excited that is was over almost before it started." "This was one of the best orgasms I have ever had and that isn't true about my first straight sex experience."

Sarah undid the other cuff and we cuddled up and took a nap.

Chapter 3, End of a Long Day

I heard Sarah's voice calling me back to real time and slowly woke up.

"Jack, wake up." "I am not going to let you win the bet by doing nothing this afternoon!"

The sun was down a bit and we must have slept for 2 hours. Sarah was draining me with all this stimulation. It was exquisite to feel like this. I looked at my body as Sarah was rubbing my silk covered chest.

"Where did you get this silk stuff Sarah?"

"When I went out this morning, I ran over to Sally's Boutique and picked it up." "She always has some really nice items like this in the store."

"This isn't your size, so who did she thing they were for?!"

"Don't worry Jack, I told her that I had to rush to a bridal shower for a girl at work and hadn't been able to get off from work in time to shop."

I was relieved and amazed at how fast Sarah had put all these sex scenes together in such a short time.

"Sarah, if I didn't know better, I would say you had been planning this for weeks."

"Jack, I was so excited last night I woke up after a couple hours of sleep and just had sex thoughts running through my mind." "I tried to masturbate myself back to sleep and planned this out as I fantasized about you."

This was high stakes sex and Sarah just kept taking me a little further past my limits. Once I had a new barrier in my head, Sarah shattered it.

"Time for nail inspection!"

Checking my nails out, Sarah found one of them chipped badly. I must have done it when I pulled my panties down to get at my hardon. I had almost ripped the panties tugging on them and I hadn't even tried to avoid putting pressure on the nails.

"That is two more points Jack, you are up to 8!" "Are you ready to give up?"

"Not a chance Sarah, you have to earn the last 2 points before I will admit you win."

"OK, have it your way." "Get up and let me fix you up again."

Sarah took one look at my cum and lubricant stained panties, then chastised me on my poor hygiene and upkeep. She took the lead and pulled off the soiled panties and surprised me with a second pair of matching pink silk panties.

"I girl has to plan for accidents Jack or maybe I should start calling you Jacquelyn." "You can put on your new panties after we clean you up!" "You will also have to hand wash these items to keep them nice."

I shot her a dirty look as Sarah sat me back down in the armchair and repaired my nails again.

"Jacquelyn, since you seem to be leaking so much, I think you need to put in your tampon!"

"What are you talking about Sarah?"

"Well Jack, you cunt is full of pussy juice after fucking and you don't want it to run out and ruin you new panties do you?" "Besides, this will be your next test." "One thing I never liked was putting in a tampon when I had long nails." "If you want to win the bet, prove you can do this task I have to do each month."

My repaired nails were dry, so I followed Sarah back into our bathroom. She got out a couple of tampons and showed me how the applicator system worked with one and handed me the second.

"Sit down on the toilet and put it in your "cunt" to absorb the discharge Jack, then wipe your bottom and you'll be all done"

Listening to Sarah talk like that was spinning my head again. I think she has been thinking about this stuff a lot longer than last night while I slept. Putting the applicator against my "cunt", I pressed it in. The thing slipped right in with the lubrication and stretching I already had. Step 2 was to press the applicator and I was stuck. How do you hold the damn thing with the nails getting in the way and still make it work? The more I worked at it, the more the lubricant made it hard to hold. Sarah flashed a picture just as I got it to slide home and a smile broke out on my face. I had to laugh a little bit as Sarah was so excited to snap the picture at just the right time. When she showed me the picture, you could see me sitting on the toilet, dressed in silk and hose, playing with my own ass and smiling like an idiot. If anybody ever saw these pictures I was dead.

"Now don't forget to wipe Jacquelyn"

I did as told and got up, put on the new pair of panties and let Sarah lead me by my hand to our bed.

"Jacquelyn, now it is your turn to fuck me like a lesbian!"

"How am I going to do that Sarah, I have a real dick and not a dildo in a harness?"

"Well, I have an idea or two." "Just start making love to me like we have been practicing and I will show what I have in mind."

I was sitting on the edge of the bed with my naked wife, dressed in silk boudoir wear and had a tampon up my new "cunt". If all the kinky sex we had ever done was an 8 on a scale of 10, we were now over 20 on the 10-point scale.

My horniness was no longer at a peak with all the sex we had since starting this bet, so it was pretty easy to keep myself from racing toward fucking. Kissing Sarah could be an event not just foreplay. We kissed each other a very long time and slowly my dick/clit began to stiffen. Sarah was gently stroking my face and letting me hold her as we frenched each other. A passion was building, but not with my usual urgency. Sarah moved my hands to her breasts and whispered in my ear that she was ready for me to use my nails on her. I thought that having long manicured nails scraped against your flesh was my fantasy, but Sarah was turned on by the sensations as much as me. My nail fetish was her nail fetish.

As I traced my nails along her breast I was mesmerized by the look of the nails against her skin. Candy apple red and long, highlighted by the milky white flesh of her breasts. I was fully erect now. My second pair of silk panties was a "tap pants" style and had a lot more room for a hardon, so I was not terribly uncomfortable. Sarah would lightly brush my dick through the silk to add to my sensation. Sarah leaned back on the bed and pulled me down with her. Her breathing was getting deeper and her eyes had that lust in them again as we continued our kissing and breast play.

"Use your nails on my pussy Jacquelyn!"

I kind of had the idea now what I could do to play with Sarah's pussy using my nails. Lightly scraping her pussy lips as we kissed was getting her very excited. I took just one nail and ran the edge along her moistness and gently scraped her clit with it. Insert one or two fingers in her pussy, then keep working the sharp edge of my nails on her sensitive spots. My erection was stretching out my panties but Sarah had drained me so much that I couldn't see any pre-cum stains on the pink silk. We went on like this for a long time and Sarah had several small orgasms. Kissing stroking and pinching her nipples while using my nails on her pussy was a lot of stimulation, but not enough to take Sarah over the top and a major orgasm.

"Time for my dildo fucking Jacquelyn!"

"You want me to fuck you with the dildo now?"

"Not exactly, we have done that lots of times, what I want is for you to simulate what I did to you with the big dildo and harness!" "Let me show you what I mean!"

Sarah pushed me flat on the bed, pulled my silk panties down and took my dick in her mouth. She was bobbing her head up and down aggressively and this always takes me very close without letting me cum. When she had me as hard as she liked, she reached over to the nightstand and got a little bag of stuff. I watched as Sarah took out a roll of gauze. I was amazed as she started wrapping the gauze tightly around my dick. She started at the base and worked up to the tip. Back down again, around behind my balls in a tight band, a third smooth layer wrapped on my dick. Sarah repeated this process until the whole roll of gauze was wrapped tightly around my dick. The effect was amazing. The gauze was holding my erection like a cock-ring and would insure my erection was not going to go down anytime soon, while the layers of gauze made my dick much thicker. Next Sarah took out a condom and rolled it down my shaft. It was very tight, but she managed to get it on over the layers of gauze.

"One size fits all you know!"

With a smile and her sexiest look, Sarah started masturbating my dick. Nothing, I could not feel a thing, except the pulling and pushing of my dick as she went up and down. She had turned my own dick into a dildo.

"Fuck me Jacquelyn, start from the rear"

Sarah got up on the bed on her hands and knees and I stood in the floor behind her as I pushed my dildo/dick into her pussy. Her pussy was very wet and I had no trouble sliding in.

"Ah, that feels so good Jacquelyn!" "It is so much thicker than my husband's dick, fuck me!" "I need a thick dick up my pussy to get this horny!" "You're fucking my brains out Jacquelyn, fuck me deeper!"

I knew Sarah was saying these things to humiliate me and excite me, and I was responding. I was a little pissed off and was really trying to pound into Sarah's pussy. I was pounding away for all I was worth and all I could feel was a 2 direction tugging of my dick. I wondered if that was what Sarah felt when she fucked me in the ass today... I decided not, she at least had the clit stimulator on her dildo harness and I wasn't getting the tip of my dick rubbed by anything. She was the winner of this comparison as well. Sarah was climaxing again and again as I held her hips and pounded her pussy.

After a while I was a little board with the lack of stimulation for my body and started watching the action in the mirror to get some visual stimulation. I was shocked my what I saw! If I ignored my face and lack of tits, my wife was getting the dildo reaming of her life on our bed by a "woman" in beautiful silk bedroom wear tightly gripping her hips with hands tipped in the longest nails I had ever seen.

"Don't stop Jacquelyn, my husband never fucks me long enough!" "You make me cum again and again!"

It was true, I never could last this long when we fucked. Sarah could orgasm for days if I could keep up with her. Even on my best days she always wanted more than I could give. She said no man could fuck her as long as she liked. I wondered if she had been dildo fucked by a woman before? Maybe when she did the enema play in highschool?

Sarah had a big orgasm and clamped her cunt down on my dick. I could feel the vice like pressure and stopped fucking her as she collapsed on the bed. I kept my dick buried in her pussy, fell forward with her and gently stroked her neck and face as she came down. After she relaxed slightly, she asked me to lie down on the bed. I lay on my back and she straddled my dick. Sliding down she wiggled until I was completely buried in her pussy. Rocking back and forth, she started talking.

"Jacquelyn, you are a fantastic lesbian lover!" "My husband is a wonderful lover, but he can't make me cum like this!" "As much as I like it when he cums in my pussy, it is never enough!" "He rushes as his climax approaches and I love it but it ends way to soon!" "He has a nice dick, but your dick is much thicker and it gets me so horny!"

As she talked she started working her pussy up my pole and down to the hilt. I told her to open her eyes and look in the mirror. Sarah broke out in a great smile as she watched herself ridding up and down on my dick/dildo.

"Put your hands on my tits and use your nails Jacquelyn!"

I didn't like her calling me Jacquelyn, but this was her trip and I was not going to argue as she fucked herself to death on my dick/dildo. Up and down she went as I worked my hands along her breasts and pinched he nipples lightly with the tips of my nails. She was flowing so heavily, that it was dripping down my balls and soaking the sheets. When she finally climaxed this time, she fell forward against my chest and was kind of flopping like a fish as her whole body was racked with her climax. I held her tight so she would not rip my dick off my body with her convulsions.

Sarah was sobbing lightly as I held her. She had never had a climax like that before and I was again jealous of her.

"Why are you crying?"

"I can't explain, it was just more than I could take."

I held her for a good 15 minutes as she came back to normal. Slowly she got enough strength to pull herself off my dick/dildo.

"Jacquelyn, that was unbelievable!" "I have always wanted to make love like this, but didn't know how to do it and not hurt Jack." "Now I know what it feels like to be fucked with a big fat cock and I was faithful to my husband at the same time!"

We lay in each other's arms (me in the wet spot) for several minutes when Sarah sat up and looked at my dick.

"Poor baby, we better get you some air!"

Sarah pulled the rubber off and started unwinding my dick. As the gauze came off, I could see how purple my dick was. If she had left this on much longer, I sure it would not have been safe. As she pulled more and more gauze off, my dick spun around like a little crank and fresh blood came rushing in as she went. I groaned in mild pain coupled with the sexual stimulation.

"Did it hurt?"

I told Sarah that it did not until she pulled off the gauze, but now it was returning to normal. She held me for a few minutes more and then got up and pulled me up off the bed. She spun me around and checked to see if my tampon was still in place and after tugging on the string, she seemed satisfied.

"Pull you panties up, go make us a little snack and I am going to put on some cloths"

"That was amazing Sarah, I kind of wish you had some pictures of making love like this." "I am sure you would think that they were better than all the pictures you have taken so far!"

Sarah just smiled and pointed to the closet. She had left the closet door open slightly and on the tripod was our video camera.

"I got the whole thing on tape!"

I couldn't even breathe when Sarah told me she had made the video! I pulled up my panties and headed for the kitchen.

Fifteen minutes later Sarah joined me in the Kitchen. She was dressed in tight black jeans, simple white T-shirt and her black boots with heels that make her taller than me. She didn't have a bra on and her breasts were beautiful in the tight white shirt. We sat down to the little snack of soup and fruit, while sipping a glass of wine in blissful silence.

"Time for nail inspection!"

Sarah inspected my nails for a long time, but could find no new damage.

"You are still at 8 points Jack, maybe you have got a chance after all."

I was starting to get a cocky little smile on my face when she scared me to death!

"One last test, time to go out of the house!"

I was not going to agree to this, now way, no how!

"Forget it Sarah, I am not going out of this house with these nails and that's final!"

"Come on Jack, I think you have enjoyed this bet as much as I have and you know I won't do anything to hurt you or publicly embarrass you!"

Her words were calming me down, but I still thought the risk was more than I wanted to take.

"Sarah, I have not been sexually stimulated and satisfied like this since we were first in love or maybe ever, but I just don't think I can do this."

"OK Jack, let me fix you up the way I want and you can look at yourself in the mirror and tell me if anybody will know you are wearing nails." "If you can tell, I won't make you do it." "If you can't tell in the mirror from any angle, then we go."

I agreed, because there was no way Sarah was going to cover this up and take me out in public. She then went about collecting some items and before I knew it she was back with her treasures. I did not see anyway that the items she had with her would do the trick, so I told he as much. Sarah just laughed and said that time would tell.

Last summer I had taken an old pair of jeans and made some cut-offs. Sarah had gotten the bottom of the legs from these old jeans out of the ragbag, one of my belts and some twine from the garage. She started poking a series of holes in the jeans legs, then Sarah slid each jeans leg up one of my legs. She then put the belt around my waist and threaded the twine through the holes she punched. By fiddling with the twine, Sarah could adjust the old pants legs so they reached the tops of my feet as well as a tailor.

Sarah had me stand up and she checked that the jeans legs came to the tops of my feet. She spent a great deal of time checking her adjustments until completely satisfied. Next Sarah picked up a top outfit she got from her closet. It was one of those "layered" knit things with the different colors. The outer layer was a black sweater thing, and the inner layer was a white knit turtleneck. Sarah separated the two parts and she had a turtle knit thing that would come down to the tops of her breasts and had no sleeves. They used to sell something like this in men's stores and we called it a "dickey". She pulled the "dickey" over my head and adjusted it just the way she liked it. Next she had me put on my running shoes and stand back up. I took a look in the hall mirror and was not going anywhere like this. I saw the silk camisole with matching panties, stockings and garter, and these incomplete articles of clothing. It was worse than being naked. Now Sarah picked up my "London Fog" trench coat that I wore over my dress cloths and zipped out the liner. She helped me on with the coat, buttoned it up, tied the coat belt and told me to put my hands in the pockets. Sarah pushed me down the hall to get a good look in the mirror.

"I think we are going out Jack!"

I was shocked, there was not any way you could tell that I was in silk and wearing nails. Sarah had covered my so that anybody who saw me would think I was dressed for a cool fall evening, nothing more. I turned every way I could and there was nothing that gave away my humiliating state of dress. I would be in public and in mental bondage if we went out that door and no one would know but Sarah and me.

"I don't know about this Sarah, I looks OK, but in the bright outdoors, who knows."

"That works out fine Jack, I want to go to the movies and that is very dark!" "Remember that chick flick I wanted to see, well we are going to see it together."

My head was spinning, I didn't have any reason not to do what Sarah wanted, except my fear.

"Remember what we agreed, If you could not tell, we would go!"

I was trapped and Sarah knew it.

"Don't go away, I will be right back."

Sarah was back in a flash. She had put on my old leather motorcycle style jacket and she looked great. It was a bit of a gender reversal, her in tight jeans, T-shirt, leather and a little taller than me, while I was in silk, hose, garter belt, and wearing my long manicured nails.

Sarah put her arm in mine and led me to the garage. She opened the passenger door for me and got in to drive. My heart was pounding all the way to the theater. I might as well been handcuffed, the mental bondage kept my hands buried deep in my pockets. I was alternating from blushing to chills as we drove past our familiar landmarks. I was so relieved when we got to the theater without having a wreck, that I took my first deep breath since she started the car. Sarah put her arm in mine and we walked up to the ticket window.

"Let me get it Jack, I have more cash than I like to carry on me."

Sarah turned just a little, so I could see her T-shirt wrapped breasts jiggle in the open jacket as she wiggled her hands into the tight jeans and got her money. Paying for our tickets, we headed into the theater. The ticket taker was very disinterested and I could have been naked without him noticing a thing. Sarah grabbed my arm and drug me to the concession counter as she got a big drink and some popcorn. This was the early show and the movie had been out for a few weeks, so we had no trouble finding some secluded seats.

"I told you no would know how you are dressed Jack."

I didn't care, I was so nervous that I can't remember anything about the movie, except that it started and ended. Sarah kept me in a constant state of arousal throughout the show. She would slide her hand in my coat and rub my dick through my silk panties until I was about to cum and then take a sip of cola and eat some popcorn. She would stick the straw in my mouth and hold the coke in place until I took a drink. She stuck the straw in my mouth so much that I must have drank well over half of the coke.

Finally, the credits started to roll.

"Lets go home and fuck some more." I whispered in Sarah's ear.

Sarah took my arm and we headed out the exit to our car.

"Jack, my eyes are hurting and I need for you to drive home."

Sarah was quick when she wanted to be and she just darted ahead and jumped in the passenger seat and locked the doors again.

"Sarah, let me in the car!"

"You know the code Jack, let yourself in!"

We had a touch pad on the driver's door of the car and if you pushed in the right code, it unlocked the door.

"I can't Sarah, people will see my nails!"

"If you don't get in here, people will think you are trying to attack me in the parking lot and then you will really have a problem!"

I don't think anybody was paying any attention, but Sarah had created the image in my head and I was convinced everyone was looking at me.

"Sarah, open up now!"

Sarah just smiled at me and shook her head. I was getting frantic, all the coke Sarah made me drink was making me have to pee! I was shuddering and holding back my flow for all I was worth and Sarah was getting the biggest kick out of my predicament.

"Please Sarah, open the door!"

"Not a chance Jack, if you want to go home, get in yourself." "If you don't get in soon, I am going to leave you here!"

I was frantic, the cool air was blowing up my coat and my full bladder was protesting. I was not going to take these hands out of my pocket for any earthly reason. The longer I stood there the more desperate I got. Taking my hand out of my pocket, I started poking in the digital code that would give me safety. I was so nervous that I hit the wrong keys several times and still could not gain access.

"Remember Jack, If you enter the code wrong 4 times, you have to wait 5 minutes before it will work again!"

I was shaking so bad that I didn't think I could do it correctly. I had entered it wrong at least 3 times and if it didn't open this time I would have to wait the 5 minutes. With all my concentration, I entered the code and my whole world changed when the door lock popped up.

"You are such a bitch at times Sarah!"

Sarah just smiled as she handed me the keys.

"I can't drive, I don't have my license and I can't let anybody see my nails!"

"Well, I am not going to drive tonight and as far as I am concerned we can sit here all night."

My bladder was about to bust, so I slowly reached for the keys and started the car. I drove with my hands at the bottom of the wheel and made sure that I obeyed all traffic rules as we headed for the house. Sarah had her hands back under my coat stroking my silk covered cock all the way. My head was spinning, my heart was pounding and my dick was throbbing.

At last, the house was just ahead and I was beginning to feel safe, when Sarah reached over and honked the horn and waved at our neighbors Lori and Frank out taking a walk. My heart stopped for several beats as they stopped at our driveway for a friendly chat. Sarah jumped out of the car and headed down the drive. It took a few seconds longer for me to get out of the car with my hardon sticking out in front. The humiliation of the situation was helping my erection shrink, but I still needed time to compose myself.

"Come on Jack, come say Hi!"

I gave a big wave while I was still standing in the shadow of the garage, stuffed my hands back in my pockets and walked down the drive. I could feel my face blushing and my heart was pounding.

"Jack, are you feeling OK?" Lori asked.

"I think I may be coming down with something, I feel very flushed."

"You better get to bed and try to get rested before Monday, or you could be sick for the big presentation!"

Sarah and Lori talked a lot, and she knew our proposal was going forward Monday and I was expected to make the customer presentation.

"I think your right Lori, I am going to take Jack straight to bed."

We said our good-byes and headed into the house.

"Sarah, you can be such a bitch when you want to be!"

I grabbed Sarah, sat down in a chair and pulled her across my knee. I just started spanking her ass as hard as I could with my bare hand. It was hurting my hand after about 20 swats, so I stopped and got her pants pulled down to her knees. I really laid into her panty-covered ass now. I could see her skin turning red through her shear panties. Sarah was wiggling around, and I realized she was grinding her cunt against my leg. I didn't know Sarah liked getting spanked, but after all the other things we tried in the last 24 hours, I wasn't surprised. Her pussy juice was leaking through her panties onto my nylon-covered leg. The faster and harder I went, the more she would grind her cunt into my leg. I spanked each ass cheek over every inch of skin and when she spread her legs, I spanked her between her asshole and her pussy. I finally gave up, my arm was worn out and she wasn't phased in the least by my spanking. I pulled Sarah off my lap and stood up. No one said a word, but we both headed for the bedroom.

As we went down the hall, Sarah was dragging my cloths off, getting the twine lose and pulling my 1/2 pants off. She seamed desperate to have me back down to just silk and hose. I got her naked just as fast as I could, pulling cloths off as we stumbled into the bedroom. I literally threw Sarah on the bed, pulled my panties down and drove my cock into her wet pussy. I have never been able to enter Sarah without foreplay, but the spanking had her nectar flowing freely. With both of us so sexually charged, we didn't last long. After only a few thrusts, Sarah started climaxing and her body was soon shaking. Then I exploded into her pussy, trying to punch through to the other side. Then I was spent and so much energy went out of me I think I blacked out for a moment.

When I recovered, Sarah was lightly stroking my face and telling me how much she loved me.

"I know Sarah, and I have never felt closer to you than right now!"

"Jack, we have done so many things, acted out all these different fantasies, I was afraid it was more than our relationship could take!" "I can't believe the sex and passion we have shared."

"Just rest Sarah, we can talk about it later." "Right now I just want to hold you and melt into the feelings."

We lay together for several minutes until my bladder started protesting again.

"Sarah, I have to get up and take a piss, be right back."

When I went into the bathroom, I was reminded how I was dressed by the image in the mirror. I was a mess, but I still had on the silk camisole, hose and garter belt. I took a good look at myself as I emptied my bladder. It was weird, I had never thought about silk and hose for me, but I had so much fun in my outfit, I knew we would play this way again. I was done and flushed the toilet.

"Jack, time for nail inspection!"

I had forgotten about our bet. But Sarah was going to make sure we both knew who won and lost the bet. I was kind of afraid to look so I just went in to let Sarah do her inspection. Before she even looked at my nails, she inspected my pink camisole, adjusted the garter belt, looked for runs in the hose and finally checked to see if my tampon was in place.

"Well Jack, you have not been very careful with your delicate silk items, but I think they will be OK after being hand washed." "Let me see your nails."

I presented my hands, nails up for inspection. It didn't take long for Sarah to find 3 damaged nails.

"I have good news and bad news Jack!" "The good news is we are going to have a lot more fun next weekend, the bad news is you have ruined 3 of your nails and you lose the bet with 14 points!" "I also don't know if I can get the super glued nails off without filing them off!"

I looked at the nails for the first time in hours, and they were pretty beat up. I don't know if I did it trying to punch in the code on the car, when I was spanking Sarah or when I was pulling off her cloths. It didn't matter, I lost fair and square.

"I don't care if I lost or won Sarah." "I lost the bet and will be you sex slave for 2 weekends, but I would volunteer right now to do it without a bet!" "I didn't think I could do half the things we did in the last 24 hours, but I have become addicted to this wild side sex!"

We held each other and kissed warmly for several minutes while we chatted about some of our sexier moments. I had never been happier in our relationship and told Sarah so.

"Do you mean that Jack?"

"Yes, not a doubt in my mind!"

"Jack, I have always wanted to do these things with someone, but I needed to trust them completely to have enough confidence to actually do them."

"I am hooked Sarah, we can play anytime you want."

She knew I meant it and she was grinning ear to ear.

"Do you want to play now Jack?"

Laying in bed with my beautiful naked wife, dressed in my pink silk camisole, wearing stockings held up by my garter belt and with a tampon up my ass/cunt, I could only give one answer as my dick started to harden......... Yes!

"Then clean my pussy, after all you made the mess and I didn't say you could cum and from now on you are going to recycle all the sperm you shoot and I hear it makes you cum eating sissy men horny to eat your sperm and you are going to pay for spanking me, I liked it and you can spank me anytime you want, but you are still going to pay because I am going to use a switch on your ass tomorrow and you will not be able to sit down Monday at work and maybe I will have you wear your silk panties under your suit and when I have the girls over next month I may have you serve us in your pink apron and panty hose and that way they can see your nails and you need to beg me to let you suck your sperm out of my pussy, say 'Please let Sissy Jacquelyn lick her sperm from Sarah's sweet pussy, Sissy Jacquelyn has to eat sperm because it makes her horny.' and I don't want to ever see any body hair on you again and I think you will look good with lipstick that matches you nail polish and you need to learn how to cum when I fuck you in your ass/cunt because it may be the only way I will let you cum for a while and I think we will need a bigger dildo for fucking your ass/cunt and I want you to grow your hair longer so I can style it and Lori says she hates to give Frank head because he is so big and since you like sperm so much I may loan you to Lori when Frank wants a blowjob or Lori can come over after Frank fucks her and you can beg her to let Sissy Jacquelyn suck Frank's sperm from her pussy and if we get your nipples pierced, we can use weights on them to make them bigger and ........ !"

Chapter 4, Sunday Brunch

I hate waking up to bright sunlight and the sudden glare in my face from opening drapes was agony. I tried to cover my face, but Sarah had bound me to the bed in my sleep. With my eyes tightly closed against the unwelcome light, I couldn't see Sarah running to jump on my stomach. If I was prepared, it would be no big deal, but I thought I was going to die from a burst bladder as she landed in my midsection.

"Good morning Jacquelyn, are you ready to get up?"

"Yes, and get off me! I am going to wet the bed if you keep bouncing up and down on my gut!"

"Not so fast Jacquelyn, do you remember our discussion last night?"

It all came back in a rush of excitement. How could I forget eating my sperm from Sarah's well-fucked pussy as she promised to make me into her cum eating sissy slave? I knew that eating Frank's sperm was not going to happen, but the rest of her plan was making my dick harder.

"You said you want to play sissy Jacquelyn whenever I want and you lost the bet, so you are my slave for 2 weeks!"

"Sarah, the bet payoff does not start until next weekend."

"I know Jacquelyn, but you have a problem. You see you have on long nails they won't come off without some help from me! You are going to have to do everything I say, or I will not take them off for you!"

I could see by the smile on Sarah's face that she was planning to drag out my situation as long as she could today.

"If you don't want my help, you can drive yourself down to the hardware store and get some super glue remover and take the nails off yourself!"

I was stuck; I needed these nails off before tomorrow, when my presentation was going to be given to the Client. If Sarah didn't take them off for me, I was going to have to go out in public and buy something in a store. There was no way I was going to do that and show my nails in public.

"OK Sarah, I am your slave for the rest of the weekend, just take these nails off and let me up to take a piss!"

Sarah had no plans to let me up just yet. She reached back and started stroking my cock.

"I don't think a sissy like you should have such a big clit. It will get in the way of all the pretty silk clothes Sissy Jacquelyn will get to wear. You are going to have to learn to control this thing or I will have to control it for you"

I didn't like the sound of that, but I needed to get to the bathroom.

"If you quit playing with my dick Sarah and let me take a piss, it will not be so big."

"Ok Jacquelyn, I will let you up if you promise to quit calling your clit a dick and do exactly what I say."

I agreed immediately and Sarah then laid out my first activities of the day: 1) I was to go to the bathroom and relieve my self by sitting like a sissy girl on the toilet and removing my tampon from by bottom. 2) I was to shave my face twice to get off my entire beard. 3) I was required to cover my entire body below my neck with hair removal cream for 20 minutes and let it remove any trace of my body hair. 4) I would then take a scented bath to soften my skin and after soaking for 15 minutes I had to rub my whole body down with her scented lotion. 5) After all that, I was to get dressed in whatever she lay out on the bed and then fix brunch for Mistress Sarah.

I quickly agreed and Sarah let up to get started. A little over an hour later, I returned to the bedroom and saw Sarah sitting naked on the bed stroking her pussy slowly.

"Get dressed Jacquelyn."

I was not sure I wanted to wear what Sarah had set out for me. There was a butt plug on the bed that I had never seen. It was way too big to go up my ass and it was going to hurt like hell to get it in.

"Sarah I can't put that thing up my ass!"

"Does Sissy Jacquelyn want me to help her prepare for her new friend?"

"No, please don't make me take that thing up my ass!"

"Well Jacquelyn, beg me to stretch you out so you can take you new friend in your sissy cunt. Besides, that plug is not as big as Frank's dick, so you better get used to it before Frank has his way with your sissy ass!"

I was stuck; begging Sarah for anal stretching would cost me now but save me pain later. It would also move me further toward the humiliation of having Frank stick his dick into some part of my body if Sarah was serious.

"Please Sarah, help Sissy Jacquelyn get her bottom stretched out for Frank's big dick."

Sarah made me beg for several minutes before she finally agreed to "help" me. She had me get up on the side of the bed and reach back and grab my ankles. Sarah then put the cuffs on my wrists and ankles so she could hook them together. The next thing I felt was Sarah working her fingers into my ass and loading lubricant into my sissy cunt. I was grateful for the lube, but could not take my mind off the plug she was planning to plant in my ass.

"Beg me to fuck your cunt Jacquelyn"

I begged like there was no tomorrow.

"Please fuck my cunt Sarah, Sissy Jacquelyn needs to have you stretch out her cunt for Frank's big dick"

Sarah soon obliged me and put on the strap-on harness with the dildo and started working it in and out of my ass. Sarah was already horny from playing with herself and it didn't take her long to work up to fucking my ass long and hard. I could hear her breathing hard and nearing an orgasm as my ass/cunt began to loosen up. As she worked her pelvis back in forth, the backside of the dildo was putting pressure on her clit and my bottom was starting to like the feeling of fullness. Back and forth she went slamming into my ass. My dick was getting hard as a steel rod and Sarah would reach around and stroke it once in a while.

"I want Sissy Jacquelyn to come for me when I fuck her bottom! If you don't come this way, I am not going to let you come at all!"

Sarah's words were driving me crazy. I had come so many times the last 2 days, there was not much chance of my getting off this way, but the more she worked that dildo in and out of my ass, the more I began to think I could come from ass fucking. Then I herd Sarah's orgasm and she collapsed on me driving in the dildo in deeper than I thought it would ever go and driving my hard dick into the bed. After a Sarah recovered from her thrashing of my bottom, she pulled out of me.

"Now Sissy Jacquelyn that is the biggest dildo we have now, so you are going to have to relax if I am going to get this plug into your cunt."

I tried to prepare my self for the plug, but I began to complain as she started working it into my ass.

"Now you better shut up Sissy Jacquelyn, or I am going to call Frank up right now and have him come over and open you up himself!"

I bit my lip, and pushed my face into the bed as my ass was stretched beyond anything I thought possible and them suddenly the plug slipped in.

"See, I knew that your sissy cunt would take the plug"

The shot of pain had taken my erection away and my balls just shriveled up inside me! Then I felt something very cool as Sarah rubbed alcohol on my dick, balls and the rest of my crotch.

"I told you I didn't want your clit sticking out so unladylike. You obviously can't control that thing, so I am going to help you learn control."

Sarah took a 3 inch roll of flesh colored surgical tape and cut off a six inch piece. My dick and balls had shriveled up from the pain and cold and Sarah quite easily pulled everything back and up into me with one hand and pressed the tape in place with the other. After a few minutes of effort my dick and balls were pushed up in my belly, Sarah had the effect she wanted and released the cuffs.

I looked down, and my sex was gone! Sarah had pressed the flesh colored tape in place so that my groin was smooth and flat. I didn't look like a man and I didn't look like a woman. I was more or less sexless!

"I like the new look! You need to quit relating to your clit as your sexual identity and learn to think of your cunt as your sexual organ! Then and only then will you get any sexual relief"

I didn't know what to say, but the only accessible area that could receive sexual stimulation was my asshole.

"Now you need to finish getting dressed Sissy Jacquelyn"

I looked at the rest of what Sarah had out for me to put on. It wasn't much, but it was all black, silky and sexy. I put on the hose quickly, pulled up the silk thong panties and added the garter belt. These were Sarah's best fancy hose with lace tops and seams up the back. I always got a hard-on watching Sarah put them on and the thought of Sarah's sexy legs in these very hose make my dick try and stiffen. There was no room for it to get hard and it just caused me pain. I took my mind off the silk and hose and my dick settled down a little. Next Sarah handed me a matching black silk camisole and held out her hand with a tube of lipstick.

"Sissy Jacquelyn needs to learn to put on her lipstick now." Sarah informed me.

I was starting to get into character by now and I just followed her over to the dressing table as she taught me how to put on the lipstick to make my lips look their sexiest. It took me about 10 tries to get it on to her satisfaction, but I finally got it.

"Ok Sissy Jacquelyn, quit primping and get to the kitchen to make brunch. Oh, don't forget to put on your shoes to keep from ruining your hose."

Sarah was holding a pair of black high-heeled bedroom slippers with a big poofy ball of lace on the arch strap. Sarah had picked them up at a garage sale a few weeks ago and I had told her at the time that they went out of style in the 50s and were not going to fit her feet. Now I remembered the smile on her face as she told me not to worry, that they would not got to waste.

I took the two slippers from her like they were dog turds.

"Hurry up Sissy Jacquelyn, I am very hungry and you need to get going on brunch."

I put on the slippers and tried walking to the kitchen. It took me several minutes to get the feel of walking in the high-heeled slippers and by then my arches and calf muscles started hurting. It took me a good 40 minutes to get our brunch fixed with me walking around on the heels and with the intruder up my bottom. The whole time Sarah sat reading the paper and sipping the coffee with that impish grin on her face. I started to set the table when Sarah made her dining preference known.

"Take it out to the sun porch Jacquelyn"

I was horrified, the sun porch was floor to ceiling windows and any neighbor who tried very hard could look in on us on the sun porch and if they had binoculars they would get quite a show.

"Please don't make me serve brunch on the sun porch!"

"Now stop complaining Sissy Jacquelyn, nobody is going to pay any attention to you so just get going"

Brunch was moved out to the sun porch and served. I was in a constant state of panic as we ate and only caught about half of Sarah's conversation. She was getting angry with this and told me to pay attention to her or I was going to regret it later.

She took the longest time eating and chatting about all the sales in the Sunday paper. Every sale she brought up was for lingerie. An hour of talking about sexy silk clothes was more than I could take, but Sarah did not let me see the sports page and always changed the conversation back to lingerie.

Finally we finished and she set me to cleaning up the food and dishes while she read the paper some more. I was told to report back to her when I was done in the kitchen.

"I am done in the kitchen Mistress Sarah." I said when I reported back.

"Good, now I want you to take down those two large hanging planters Jacquelyn."

I didn't know what she had in mind, but I was guessing that she planned to hang something else from the planter hooks. When I had them down and set where she wanted them, she sent me back to the bedroom to get the padded cuffs. When I returned Sarah pulled my hands up high with the cuffs and then pulled my legs well apart by tying them to the two heavy planters. I was tied spread-eagle with very little slack. My legs and feet were already sore from making brunch in the heels and they started hurting a lot more as I could only shift my weight a little bit.

"Sarah, please let me out of these heels!"

"No Sissy Jacquelyn, you need to learn to spend the entire day in heels. Those heels are not that high and when women go to work, they have to stay in their heels all day. How are you going to learn to be a good sissy without practice?"

I tried to quit complaining, but as I stood there watching her read the paper and sip her coffee, I started up again.

"My legs are killing me, please Mistress Sarah can you take off my heels?"

Sarah didn't say a word, just got up and left the sun porch. When she returned she had some things that were not going to make me any more comfortable.

"Open wide Sissy Jacquelyn. You might as well practice sucking on a cock while you practice standing on your heels."

When I hesitated, Sarah pinched my nose until I opened up to accept the dildo from her harness. It was bigger around than my cock and it made me open my mouth so far that it stretched my lips. Then Sarah took a long ribbon and wrapped it tightly around the base of the artificial cock several times, took the ends around my neck, crossed them behind me and then tied the ends off in front of my neck like a choker. I was now unable to complain about my position. Next Sarah took out her silk boudoir eye cover and tied it over my eyes to blind me.

"Now Sissy Jacquelyn can concentrate on learning to be on her feet all day in heels and practice her cock sucking at the same time!"

The next thing I felt was Sarah putting headphones on my head. She then started playing a tape recorded from a porno movie where a female voice begged to have her cunt filled with a big cock and then when I could hear the sounds of heavy fucking the woman started begging for a big cock for her mouth. After a while all I heard on the tape was the sounds of fucking, sucking and orgasm after orgasm.

In this state of deprived sensory input, I lost track of time. The tape went on and on with begging for big cocks and the sounds of fucking leading to screaming orgasm after orgasm. Then it would start over again. Suddenly I was startled to feel someone touch my skin. I was so sensitive to touch with all my hair removed and having been deprived of sight, the touch made me shudder all over. It was almost like an orgasm, but no one could even touch my imprisoned cock.

When I quite shaking, the hands started touching my body all over. Light touches and the feel of a ribbon being pulled around different parts of my body. It took a while for me to realize that the hands were taking my measurements. That was when someone started kissing my face and neck and rubbing my tits through the silk camisole.

There were two sets of hands on my body and I tried to scream, but the cock in my mouth kept me quite. I only got out muffled sounds and then I could hear giggling in the distance over the fucking sounds in the earphones.

The hands started rubbing me all over, stroking and rubbing. The measurements were all taken, but the hands kept me on edge while the tape played on. Then suddenly they left me and shut off the tape. I could hear their feet walking around me and to the front door. The door opened and shut and then footsteps back to the sun porch.

Sarah removed the earphones and blindfold and after a few seconds I quite blinking, I could see Sarah's beautiful face in the bright light on the porch.

"I let you figure out that someone else knows about Sissy Jacquelyn so later when I have you serve as my maid around visitors you will not resist. You have already been 'outed' and it is only a question of who I trust to share Sissy Jacquelyn with."

I must have looked like I had been shot.

"Do you understand Sissy Jacquelyn?"

I nodded my head yes.

"Now one more thing before I let you down and take off you nails. Last night when you spanked me, I had such a powerful climax that I want to return the favor to Sissy Jacquelyn. I am not as strong as you are, so I am going to use a switch on you instead of my hand. It is only fair that you receive the same level of spanking that I did."

I looked with shock as Sarah took a long switch she had cut from our willow tree. It was about 4 feet long and was as big as my finger at the base, tapering to fine tip at the end. I tried to say something in protest, but with the cock in my mouth I only got out grunts.

Sarah walked around my body flicking my legs, back and crotch with her switch. After about 3 trips around me she stopped and released my garters to pull down my panties. Then she refastened the garters.

"The garters form a perfect frame for your spanking. The top of the picture frame is the garter belt, the bottom is the top of your hose and the pulled down panties and the garter straps make up the sides of the frame. I am going to color in the white space inside the frame like a coloring book! Won't that be fun and artistic at the same time?!"

Sarah started on by hairless ass with the switch. I tried to scream out when the first blow landed, but the cock in my mouth kept me from making much of a noise. I think she gave that first swing her all. I could hear the switch whistling through the air as Sarah swung it against my bare ass. It was like an electric shock ran through my body. Then just about the time I could take a breath, the next blow came down. This time I think she backed off a little or else my skin was already in overload and the second blow did not have the same effect.

Then the switch began to strike every inch of my bare ass. First Sarah went from side to side as each arm tired and laid parallel lines across my ass. After a while, she switched to a bit of an angle to cover in the little white spaces between the red marks. I had long forgot about the pain in my legs and feet from the heels. Now my whole world was focused on my flaming hot ass.

"I do think your ass is a thing of beauty. I have colored in the whole area now and it is a wonderful shade of red. In fact, it is very close to the color of your lipstick! The only problem is the vertical white stripe in the middle."

Sarah then took the switch and struck me between my ass cheeks over and over until she was satisfied with the color of the flesh in my crack. The cock in my mouth kept me from scaring the neighbors. I have never felt a hot pain like that. The flesh in my ass crack was very thin and her blows with the switch were unbearable.

"Now your cunt lips are as red and pink as a real slut, don't you think Jacquelyn!"

I had no idea what my ass looked like but I knew how it felt! It was on fire! My face was streaked with tears from my switching. Sarah came around in front and started kissing my tears away as she rubbed her body against mine. She let her silk robe fall open and pressed her breasts against my chest, kissing me and rubbing me seductively. As she kissed me all over she started rubbing my tits and pinching my nipples. The camisole had ties for shoulder straps and she untied them and let the silk slide down to my waste. Now she started sucking and lightly biting my nipples. I don't know how long she worked on my nipples, but they were getting quite sensitive to her touch. Then she stopped and went behind me again. I now realized that my dick was throbbing under the tape. It could not get hard and was the tape made it painful, but I hadn't notice before because my ass was hurt so bad.

Sarah's hands reached around me and as she pushed her naked chest against my back, she pinched my right nipple to make it very hard. Then she placed a clothespin right on the tip of my nipple. The pain ran through me like a jolt and I started shaking again. My body was convulsing and twitching and I could feel my prostrate spasm. Then Sarah started pinching my left nipple and as she put a cloths pin on it she bit my neck and sucked hard to make a hickey. I had not had a hickey since I was a teenager, but I was getting the biggest hickey ever. Sarah was sucking on my neck like a vampire. Again my body was racked with spasms and my whole groin was twitching with sexual energy. My dick was trying to get hard, but the tape held tight and everything was kept pulled up into my abdomen. I was sexually charged and denied at the same time.

Sarah moved around in front and started removing the ribbon from my neck.

"I want to kiss you and feel your lipstick coated lips against mine!"

Sarah removed the cock from my mouth and after a few seconds I could close my mouth again.

"Pucker up Sissy Jacquelyn"

I had no resistance left and put my lips together for her to apply a fresh coat of lipstick. When she was satisfied, she stepped back and plucked the cloths pins off my nipples. A pain shot through my chest as the blood and feeling returned and as I opened my mouth to groan Sarah slammed her mouth against mine. She kissed me as though she was raping my mouth. I lost track of time as she kissed me and rubbed her tits against mine. I closed my eyes and floated into a trance.

"Owe!" I groaned into her mouth when she grabbed my red ass. As Sarah kissed me deeply, she began to rub her hands over my abused flesh. Over and over she stroked me until my hips started bucking and my body twitched all over. I nearly passed out from sensory overload and then Sarah stopped.

"I think you are close to learning how to climax without anybody touching your clit!"

Sarah was right, my dick was still trapped up inside of me and I had not even been able to get an erection. Yet, I had had several body convulsions that were stronger than the orgasms I enjoyed when Sarah and I fucked. I felt like my whole body was one sexual organ.

"Beg me to fuck you ass Sissy Jacquelyn!"

I was over the top and I started to beg to be fucked like the porno tape Sarah made me listen to.

"Please fuck Sissy Jacquelyn with your big cock! I need to be fucked, fuck me like the sissy slut I am!"

As I begged, Sarah moved around behind me and gave the butt plug a pull. The pain of removal was short and I was left with the feeling of an empty hole.

"Please fill up my ass, I need your cock in me. Make me cum with your big dick. Sissy Jacquelyn needs to be fucked like the slut she is!"

Sarah pushed the dildo in with one quick thrust. I was held tight by the ropes and when her loins pressed against my raw ass I thought I was going to die. Sarah had her way with me, as she was quite horny herself by now. She was rocking back and forth against a much-reduced resistance because of the stretching from the plug.

"Keep begging for a fucking and moan like the sluts on the tape!"

I began to beg again. "Please fuck me with your big dick, I need to be fucked! Slam that monster in me and make me scream"

I was begging and moaning for all I was worth when I started shaking again. I don't know how loud I was, but I was begging and moaning for all I was worth.

"Yes, yes, yes, fuck me with your big dick!"

Then Sarah reached her orgasm and started shaking. She rammed her cock into me as hard as she could 3 times and then twisted her arms and legs around mine so both of us were supported on my abused legs. Sarah hung on my back with the dildo as deep as she can push it as her body continues to shudder and twitch. Every twitch makes the dildo twitch and it rubs me deep inside and I convulsed in my body. I think Sarah kept jamming her fake cock into my ass for at least 5 minutes as she kept both our bodies racking with sexual release.

"That was a fantastic fuck you slut Jacquelyn! I don't think I have ever had a better piece of ass in all my life!"

I didn't know how many times Sarah had put on a dildo harness and ridden someone to satisfaction, but I knew I had never been fucked like that!

"I think you deserve a reward for being such a good fuck Jacquelyn. I am going to release your clit and give you one more fucking before I stop and take off your nails! Won't that be fun?"

"Please fuck me again with your big dick Mistress Sarah!"

Sarah released my hands and I all most fell over, but she steadied me before I fell. Next she moved my hands behind my back and hooked the cuff together. She removed the cuffs from my legs and pulled my panties all the way off and hooked the garters back. Sarah had me spread my legs and she gave the tape a hard tug to free my trapped dick and balls. My abused dick quickly gained an erection.

"Sissy Jacquelyn has leaked pussy juice, what a slut to leak pussy juice all over your clit!"

Sarah rubbed the pre-cum off my dick and had me suck her fingers clean.

"You are going to look so pretty with those red lips wrapped around a real cock. I wish Frank was here right now, but I guess we will have to improvise."

Sarah led me over to the ottoman and had me lay on my stomach with my head down by the floor. She put a pillow on the floor and had me slide forward a little more. I have always been flexible, but I was surprised how much I was able to keep curling up as Sarah pushed my head and shoulders toward my ass and kept pulling my ass to my head. Then Sarah got behind me and pushed my legs as far apart as she could. When Sarah pulled the ottoman out, I was suspended by my feet spread very wide and by my neck and shoulders on the pillow. The most amazing thing was that I was looking right at my hard dick just inches from my face.

"I am going to fuck your cunt until you cum Sissy Jacquelyn! You can just come from the fucking or you can help yourself along by using your mouth! Which ever way you cum, I am not going to stop before you cum and you will lick up every drop!"

Sarah started working her cock in to my ass again. This time, her pushing on my ass caused me to curl a little more and then my dick was bouncing against my nose and lips. I could not help myself and when my body curled a little more, I opened my mouth and sucked the head of my dick in.

"You look perfect with your red lips wrapped around a real cock Jacquelyn!" I bet you can't wait for Frank to let you taste his big dick!"

I could wait forever to suck a dick; I was not a cocksucker I thought as my own dick was in my mouth. As Sarah worked her dick into my ass, my dick would push in a little further and when she pulled back, I could keep it in my mouth by sucking hard. We built a steady rhythm and pretty soon I was building to my orgasm. Faster and harder Sarah thrust her dick into my ass and the harder and longer I sucked on my own dick.

I shuddered to my biggest orgasm of the day from the double sensation of my ass fucking and the self provided blowjob. My cock started spurting and my ass was having spasms every time my dick spurt into my mouth. Sarah felt the spasm and started pushing her dick in sync with my spurts. I think Sarah was able to pump at least a dozen or spurts out of my dick directly into my mouth. I sucked each spurt down and swallowed every drop.

Sarah pulled out and helped me onto my side to take the pressure off my neck and shoulders.

"You looked fantastic with your lips wrapped around a dick! Beg me to get you a real dick to suck, so you can give a real blowjob to a big dick, not your own little dick!"

I knew my dick was not little, but to have Sarah taunt me like that was humiliating and exciting at the same time.

"Please bring Sissy Jacquelyn a real dick to suck on! I need to suck on a real cock, not some overgrown sissy clit like mine!"

I was over the edge again and I was slipping further into the mental state of a sissy slut! I could not believe how far I had come in just 2 1/2 days. Here I was begging Sarah to bring me a real cock to suck and I had never had any interest in sex with a man!

"Soon enough I will let you suck a real cock, don't worry your little head! I know you will like sucking Frank's cock and it will help Lori out since she can't take the big thing in her mouth!"

After I rested a few minutes, Sarah helped me up and helped me back to the bedroom. She sat me down at her dressing table and I jumped back up!

"Owe, my ass is way to sore to sit on it!"

"Ok, Sissy Jacquelyn, you can kneel down and let me work on taking your nails off."

It took Sarah over an hour to get the nails off. First she removed all the polish and them she started working super glue remover under the edges of the fake nails. After she was done, she used a polishing compound on a battery powered little tool and buffed up the nail surface to finish the cleanup.

"The natural shine will last a few days and people will almost think you have clear nail polish on!"

I didn't care, I was just glad to have my normal looking hands back even if nothing else was normal anymore.

"We can't play anymore today, tomorrow is a big day and you need to relax and get ready for your presentation to the Client."

I agreed and I started to get out of the silk things. As we put out toys away and washed up the lingerie, Sarah and I both grinned as we handled each item. It had been an amazing weekend with the best sex we had ever had.

I looked at my ass in the mirror and it was going to be sore for several days. Sarah had done a number on it with the switch and it was red as the lipstick Sarah had used on my lips!

We had a light dinner and went to bed early (I slept on my stomach).

I could hardly wait for next weekend to get here and as I drifted off to sleep, I kept seeing the image of a big dick between my lips!

Chapter 5, First Week of Service

Monday morning came too soon. I was excited about the big Client presentation and could not sleep the night before. It didn't help that every time I started to drift off to sleep, the kinky sex weekend started playing like a movie in my head and I would panic when I got to the point that someone out there knew about Sissy Jacquelyn.

I was happy to hear the Monday morning alarm and I could get started on what would be the biggest event ever for our project team at work. I was humming to myself in the shower when I turned and the hot water hit my raw ass. I made so much noise that Sarah thought I had fallen and broken my neck!

"Are you alright Jack?"

"Yes, but you did a real number on my ass yesterday, the hot water made me think my ass was on fire!"

I could not believe that Sarah thought it was funny. I finished my shower and took a good look at my ass in the mirror. It was still quite red and had deep red streaks where each blow of the switch had landed. I was going to have a terrible time sitting today.

When I finished shaving and came out to get dressed, Sarah was waiting to give me her helpful hints.

"Jack, by the looks of your ass, you are not going to be able to wear your regular underwear. I think you are going to have to wear the lightest and softest underwear possible or your not going to get through your presentation!"

Sarah was holding up the pink silk tap panties that we had carefully hand washed yesterday.

It didn't take me long to realize that the silk was going to be a lot more comfortable than my regular "guy" briefs. Sarah knelt down and sucked my dick in her mouth as she had me lift each leg and step into the silk panties. As my dick stiffened, she let it slide out of her mouth and she slid the panties up my hairless legs. By the time she had them pulled up to my waist, my dick was fully erect and she kept rubbing it through the silk panties.

"Jack, you are not going to be able to finish getting dressed if your clit keeps sticking out so lewdly! Do I have to get out my tape and make you flat again?"

"Sarah, quite playing with my dick and let me get dressed! You're going to make me late!"

Sarah released ma and I put on my undershirt and dress shirt while I let my dick go down. By the time I had on my socks, shirt and tie on, I was down to normal and could put on my pants. I headed to the kitchen for breakfast while Sarah finished getting dressed.

We headed in to the office, but I had to have Sarah drive so I could sit on my hip instead of on my butt cheeks. The Client presentation went very well, and I just stood up to address the Client team as we went through our materials. They were impressed with the work our team produced and we won the project.

The senior managers planned to take the team out for a quick celebration after work, so I could not cut out early. All day I could not sit still because my ass was so raw. When people asked me why I was stirring around like a cat on a hot tin roof, I just said that I was excited by the big win on our Client proposal.

When we got to the bar for post work celebration, I just kept on my feet and made my rounds to all the team members, congratulating each one. As the project team started home, I looked around for Sarah, but she was no where to be found.

"Oh Jack, Sarah went ahead. Her friend Lori came and picked her up 30 minutes ago and she asked me to tell you to just come home when thing wound down here." our friend Pat told me.

A few minutes later I was on the road home and it was the most uncomfortable drive of my life. If a cop had seen me twitching around in the car seat I am sure I would have been stopped. Luckily I made it home without incidence.

"Sarah I'm home, where are you?"

"I'm back in the bedroom Jack, come on back I have a surprise for you."

I went back to the bedroom and on the bed was over a dozen silk panties and just as many silk tank tops.

"I got rid of all your ugly old rough underwear and got you new things! Aren't your excited!"

I was excited all right, but I was also terrified at the same time.

"I can't go around in that stuff all the time Sarah! It is OK when we are home, but I can't change in a locker room or go to the doctor in that stuff!"

"Not to worry Jack, I got you a few pair of men's silk boxers and you can wear them when you have to do some manly ting!"

Sarah had covered all the bases in her mind. I was not sure whether I was more excited or scared by the new cloths.

"Come on Jack, get out of your suit and into your robe so we can eat dinner and relax."

I got out of my suit but left the panties on. When I went for my terry robe it was gone and a new silk robe was in its place.

"Sarah, where is my robe?"

"I got you a new one Jack, besides the old one was worn out."

I slipped on the robe and went out to eat. Sarah had candles light and a nice light dinner all set on the table. As she handed me a glass of wine she made a toast.

"Welcome to the world, Sissy Jacquelyn!"

We toasted and sat down to eat. Or at least Sarah sat, I kept shifting around to try and find a spot that didn't hurt on my bottom. After we finished eating and cleaning up, we went back to the bedroom to relax and watch a little TV and share the rest of the wine. We enjoyed an old movie together and when it was over it was time for sleep.

"Jack, I want you to save all your sperm for this weekend, so I need to keep you from playing with yourself before Friday. I am going to put you in the cuffs each night this week to make sure that by the weekend you have a full load for me and I purchased a new chastity trainer for you."

Sarah had me stand and she took out a strange looking leather belt. She had me take off my panties and step through the leg straps. As she pulled it up I could see how it worked. It was like a jock strap, that had a flat leather front with a hole and a steel ring where my dick was located. She pulled it up and pulled my flaccid dick and balls through the ring, and then she pulled the center strap back between my legs. After buckling the wide belt tightly around my waist, she was ready to hook the divider strap in the back.

"I almost forgot the best part Jack, bend over and grab your ankles!"

Sarah worked some lube into my ass and started pushing a plug in. It slipped in much easier after the workout yesterday and she pulled the divider strap tight to hold it in place. When I stood again, Sarah hooked each wrist cuff to a D ring on the side of the belt.

"Now you can't play with yourself, and I can stretch your cunt all night! I have a whole set of plugs to work you up to Frank's dick size. Very soon, you will be able to take a good ass fucking like a true sissy slut!"

Sarah had me lie down with her and she kissed me, played with my nipples and rubbed my cock until it was hard. The steel ring was sized so that my dick could harden, but the blood was now partly trapped in my erection by the steel ring. I was at Sarah's mercy. Plug up my bottom, dick trapped in a steel cock ring and Sarah making me horny.

"You are so hot Jacquelyn, I have to fuck you!"

Sarah put me on my back and sat on my face. I was desperate for relief, and I ate her cunt like a madman. Sarah rode my face to 3 orgasms and then collapsed on my chest. After she got her breath back, she got out 3 condoms and rolled them on my hard dick. She had picked the size of the steel ring perfectly. It helped trap blood in my dick to keep my erection very full, but it was not so small that my dick was turning purple. I could wear the belt for hours without damage to my cock!

"I need to get my cunt filled up Sissy Jacquelyn, but your don't have a real cock to do the job, so I am going to have to use your fake cock for my pleasure! I don't like the feel of plastic or latex in my cunt as much as real cock flesh, but this is the best we can do for now!"

Sarah slid her wet cunt on my pole, but with all the condoms on I could not get enough stimulation for any pleasure of my own. Sarah rode me till she had a huge explosion after many small orgasms. As she fucked herself crazy on my "numb" cock, she was forcing my raw ass down on the bed and each time she pushed it down, I tried to push my ass off the bed just as hard, the result was the hardest fucking Sarah had ever received. I had no idea how many times she climaxed, but I could feel her cunt juice running out of her and all over by legs. I sure hoped the leather chastity trainer was of very good quality if it was going to handle all this wetness.

When Sarah was done, she took off the condoms and inspected them for cum.

"Good, you did not lose a load! You are going to be good and horny by the weekend!"

As Sarah curled up and lay her head on my shoulder, I drifted off to sleep with no hope of getting at my dick to masturbate.

The rest of the week went much the same, I dressed in my new silk things each day and slept in my chastity trainer at night. Sarah had me eat her cunt to several orgasms each night and if her cunt was not sore, rode my latex covered dick to her biggest orgasms. She was completely satisfied each night and I was hopelessly horny! Each night she put in a bigger plug in my new cunt and said I was getting close to being a real fuck slut. It no longer pained me to receive the plug and it even felt strange to not be filled up during the day at work.

Thursday night Sarah had me do the hair removal cream again so I would be very smooth for the weekend. Friday morning I was getting dressed when Sarah held up a pair of fine silk hose.

"You need to start wearing hose under you slacks for work Jacquelyn." Sarah informed me.

"How am I going to hold them up all day Sarah?"

It didn't even occur to me that I should refuse, I was molding more each day into Sarah's sex slave and it was only a question of how to comply, not if I would comply!

"Well Jacquelyn, I thought about having you wear a garter belt under you suit, but the straps might show. I don't thing you are ready for that much exposure in real life, so I came up with plan B. I have some special double sided adhesive tape that we are going to stick on your thighs at just the write height and when you pull up your stockings, they will hold tight."

With Sarah's help, we found the right location for the tape and put 4 2 in. by 3-in. pieces of the double sided tape on each leg. The stocking tops were rolled over the tape and pressed firmly in place. I was holding very tight and was still going to be invisible under my suit.

"If you get cold feet and try to take off the hose Jacquelyn, the tape will not re-stick and I will know! You better come home with the hose stuck tight tonight!"

Off to work we went on Friday with me in silk and hose under my suit. All day when I moved, I thought about sex and wanted to masturbate. There was no escaping from my chastity at work and I was getting desperate for release! At least my ass was no longer sore and I could sit comfortably during the day.

Friday night Sarah put me in the chastity trainer again and used the largest plug to fill up my cunt for the night.

"Well Sissy Jacquelyn that is my biggest training plug. The wide part is supposed to be as wide as Frank's dick, but the training width is a little less once it slides in all the way."

The widest part had been hard to slide in, but it didn't make me feel like the thing was going to rip me apart. If Frank's dick was that big, I think I could make it through the ass fucking. What was I thinking, I was not a "queer" and yet I was resolved to taking Frank's dick up my ass when Sarah wanted to make it happen. Sarah had me eat her to orgasm several times, but she didn't ride my latex covered dick so she would not get sore before the weekend.

I woke up Saturday morning more horny I have ever been before. Sarah had used me and teased me unmercifully all week and given me no release.

"Well Sissy Jacquelyn, now you are mine for the next two days to do what I will. You are to do everything I ask per the terms of our bet or you will get switched again. You will get switched as many times as necessary to keep you in line and following instructions without question! Is that perfectly clear Jacquelyn?"

"Yes Mistress Sarah, Sissy Jacquelyn understands."

"We are going to have a series of events today and tomorrow that will test your limits Jacquelyn, but you will not be hurt physically or professionally. Just follow instructions and all will be fine."

I trusted Sarah completely and started following her directions. First I got my shower with Sarah watching to make sure I didn't masturbate and then I shaved twice. Sarah cleaned my cock and balls with the cold alcohol and using the surgical tape, she flattened my sex into the body recess again. I was now a sexless being with only my mouth and ass/cunt for sexual pleasure. It hurt a bit getting my balls shoved up into my abdomen, since Sarah had been giving be the blue balls chastity treatment all week, but she was satisfied with the flat look when she finished. Next she had me put on the pink silk panties and matching camisole, garter belt and hose and when that was all finished, she had me sit at the dressing table and put on bright red lipstick to her satisfaction.

Sarah put mouse in my hair, which was getting a bit long for work since I had not been able to get it cut with my busy schedule, then she combed it and blow-dried it into a sweeping feminine style. I looked into the mirror and wondered how much sexier Sarah could make a man look!?

Sarah helped me into the bedroom slippers and had me put on my silk robe.

"We are going over to Frank and Lori's house to get something very special Lori made for you".

"I can't let them see me like this, please don't humiliate me like this!"

"You do not have any choice and Lori is very excited to meet Sissy Jacquelyn and if you don't get moving, I am going to get my switch".

The switch was not even a possible choice for me so I got up and followed Sarah out our back door. Our back lots were connected and we had put a gate in the fence so we could go back and forth without walking around the block. The patio door was open and we let ourselves in.

"Lori, where are you?"

"I am in the bedroom Sarah, bring Sissy Jacquelyn back to meet me!"

Sarah took my hand and pulled me to Frank and Lori's bedroom. I knew Frank was not home, because I had cancelled out of our golf round and he had teased me all week about being "pussy whipped" for staying home with Sarah. Frank and Lori both had a very tough childhood. Lori was born is South Korea to a poor young Korean woman and an American GI. When she was about 8, Lori and her mom moved to the states with the help of an uncle. By the time she was 10 her mom had died in a car wreck. Her aunt and uncle raised her after that. As we got to know Lori (she goes by Lori because it sounds a lot like her Korean name) she told how her uncle has sexually abused her and threatened her with being sent back to Korea as an orphan if she complained. She had to work in his clothing sweat shop everyday sewing and he kept her around till late when he could use her for his sexual needs. As soon as she graduated from High School she took off and went to college with scholarships and work- study. She has never gone back to her uncle's house again and talks with her aunt rarely.

Frank was born to a Mexican girl and a Black kid who took off and never saw his son. Frank got beat up constantly growing up and his mothers family called him a "half-breed" until he got so tough that nobody wanted to tangle with him. By the time he was 16, he was sent to the juvenile home for boys who had run out of options. He never told me what he did to get sent there, but he said he was a real bad ass for a 16-year-old. When he was in juvenile lockup, he connected with a teacher who convinced him that he could turn his life around if he wanted to. With the teacher's help, Frank got his HS diploma and was admitted to college by the time he turned 18 and left juvenile. The teacher kept in touch with him and encouraged him to stay away from his old life and stay clean. Frank never looked back and cut off all contact to his alcoholic mother and the rest of his family. He said he never missed them and could not think of a reason to see them.

Frank and Lori met in college and because of their backgrounds, felt like soul mates from the start. They fell in love and got married their senior year. Now we were there only "Family" and Lori and Sarah were like sisters. Frank was very macho at times and he didn't let himself get very close to anybody besides Lori, but I was as close to Frank as anyone could be. Lori tells Sarah everything and she told Sarah that her uncle made her give him blowjobs at the factory. She learned to hate it and even though she loved Frank in made her sick to go down on Frank's big dick. I had seen his cock in the locker room and it was bigger flaccid than my dick was hard. I had no idea how big, but Lori had described it to Sarah as a real monster.

"Come closer Sissy Jacquelyn and let me see you."

Lori looked beautiful with her face framed by her long dark hair on the satin pillowcase. Frank and Lori were both gorgeous. They had that mixed race exotic look and I swear they had the best features of all the mixed race genes in their background. When they were in college, them both did some modeling to earn money.

"Don't be shy Sissy Jacquelyn, Lori has already seen you."

Now I knew who owned the other hands.

"I have a present for Sissy Jacquelyn." Lori told me.

"Thank you I muttered"

Lori handled me a wrapped package that was too nice to open.

I just stood there in shame and humiliation till Sarah spoke and told me to open it. I worked the wrapping off carefully and when I got past all the layers of tissue I found a very fancy corset. It was made of silk, had heavy boning and had been hand made. The corset had half cups for tits and ended with garters to hold up a pair of hose.

"You better thank Lori for such a fine handmade gift."

I made my best effort to thank Lori for the corset, but when I finished Sarah said that it was not good enough and that words alone could not show my appreciation.

"Why don't you offer Lori something special in return for such a fine gift?" Sara prodded me.

I had nothing to give Lori and I did not know what she could possibly want in return.

"Lori, thank you very much for such a sweet gift and if there is something I can do in return I would be more than happy to try giving you something as wonderful."

"Well Sissy Jacquelyn there is something you can give me that would be just as nice a gift. You see Frank does not like to go down on me and lick my clit because in the world he grew up in that was just the nastiest thing. We are quite a pair, I can't stand to give Frank head and he can't stand eating pussy. Sarah says you are an expert at cunt licking and she has promised that I can borrow Sissy Jacquelyn for cunt eating when she knows about it. So, would you give me my first real cunt licking Jacquelyn?"

I looked at Sarah and she nodded her approval and left the room. I was standing there holding a corset and being asked to eat the pussy of one of the most beautiful women I know.

"Yes Lori, I would be happy to eat you pussy. I don't think it is as nice a gift as your gift, but if that is what you want from me I will be happy to give it to you."

Lori pulled the sheets back and I saw her naked form under an expensive silk and lace bedroom gown. She slowly pulled up the gown until I could see her pubic hair peaking out. I could not take my eyes off her pussy as she slid her hips to the edge of the bed.

"Kneel down and make me happy with your mouth, but just your mouth. You can not touch me with any other part of your body." Lori told me.

I was on my knees in a flash and as I leaned forward I saw her cunt up close. It was strange looking and seemed to have an unusual odor. I started kissing her feet and legs on my way to her pussy and as I got closer I was looking right into her cunt. Then it hit me, Frank had just fucked her before we came over and she had been laying in bed with his sperm in her pussy just for my humiliation. I looked up and Lori just smiled.

"Sarah says that Sissy Jacquelyn loves to eat sperm so I saved you some. I told Frank all week that my stomach was upset and that I didn't feel well enough for sex. It was a hard week for Frank because I never made him go without for more than 2 days before. I have 5 days of sperm in me and Frank came twice before he quite. Now beg me like Sarah says you do!"

I started begging for Lori to let me suck Frank's cum from her pussy.

"Please Mistress Lori, let me lick your sweat pussy and clean Frank's sperm from your cunt."

I must have learned to beg well, because Lori grabbed my hair and pulled my mouth to her cunt. It was a mess. Frank's big dick had left her hole wide open and it was full of his sperm. The more I licked it up, the more excited Lori got and the more her cunt flowed with her pussy juice. As she responded to my tongue, her clit was swelling with excitement. Her clit is the biggest I have ever seen. It poked out from her pussy lips like a miniature cock. The end of her clit was like the tip of my little finger. Sarah's clit is only a small little nub, but this clit was big enough to suck into my mouth like a tiny cock. I sucked her clit between my lips and ran my tongue over the tip until her body went rigid with orgasm. I went back to licking her pussy lips but I could not clean her up fast enough and the combined love juices were running out of her cunt and down her ass.

"Lay on your back on the floor!" Lori told me.

Lori got up and sat her gaping hole right down on my mouth. I just had to swallow as Frank's sperm and Lori's pussy juice fell out and into my mouth. A big glob of Frank's cum slid down my throat and made me gag. I managed to keep from throwing up and Lori was starting to rock her pussy back and forth on my face. Her wide-open cunt was smearing slime from the tip of my chin to the tip of my nose. I could only make brief contact with her clit as it slid up my face and again when it came back down to my chin. She kept up her pelvis motions for several minutes while she built for a grand orgasm. When she came, I thought she was going to break my jaw and nose. As she came down I gently licked her pussy lips and avoided her very sensitive clit. She slowly relaxed her leg muscles and pulled herself off my face and crawled back into bed. I couldn't quit thinking about the girl's clits, very different in size but both are very sensitive.

"How did you like Sissy Jacquelyn's tongue Lori?"

I looked at Sarah to see that she had been recording a video of the whole thing.

"It was fantastic, Frank will never eat me out. All he will do is kiss me lightly on my pussy mound and no more! I know you told me how good Jacquelyn can eat pussy, but that was fantastic, almost as good as fucking Frank's big dick."

"Thank Lori for letting you eat Frank's sperm from her pussy Sissy Jacquelyn!"

"Thank you for feeding Frank's sperm to me, eating sperm makes a sissy slut like me horny! Thank you for letting me taste you pretty pussy Mistress Lori it was very sweet!"

It was true, eating a strange pussy and being made to eat another man's sperm was making my dick hurt in its surgical tape prison. There was no room for me to get an erection, but my dick was trying as hard as it could. My crotch was throbbing and twitching and it had no stimulation at all.

"Time to try on your new corset Jacquelyn!" Sarah informed us.

Sarah and Lori led the way to the family room with the beams and vaulted ceiling. Sarah quickly put the cuffs on me and hoisted my up tight using one of the beams in the middle of the room. I was still in the high heel slippers and knew I was going to get uncomfortable quickly. Next, them put the cuffs on my ankles and pulled my legs out a bit and tied me to the furniture. I was again stretched tight and could only shift slightly.

"You are going to love having this corset on when you see how nice it makes you look Jacquelyn!"

Them started by unhooking the front of the corset. It took them several minutes because there were so many hooks.

"Lori wanted your corset to lay very flat, so she sewed in all the front hooks with no gaps. Isn't she a special friend to make your corset so well Sissy Jacquelyn?"

"Thank you Mistress Lori for making such a special corset for Sissy Jacquelyn!"

It too several more minutes to hook the front closed again. This thing fit me like a second skin. Lori could sew anything after working in the factory and she had taken my measurements for an exact fit.

"Now we can lace it up for you Sissy Jacquelyn! You may beg us to lace you into your silk and lace corset."

"Please Mistress Sarah and Mistress Lori, lace me into my corset and make me look like a real sissy slut!"

They started working the laces. It took 30 minutes to get me down in the waist like Sarah wanted. It hurt like hell as them pulled the laces tighter each time I let out my breath. By the time they were done, I must have lost 2 or 3 inches off my waist and it made my hips look bigger.

"It looks good, but it is missing something Sarah." Lori proclaimed.

"Not to worry, I have just the perfect items to complete the look."

Sarah went to her bag and brought out 2 breast forms that looked like perfect breasts.

"I got you a C cup Sissy Jacquelyn, I know a slut like you wants breasts as big as a cow, but Lori and I don't want to get jealous of your new tits!"

Lori placed each one in the empty cups, checked the fit and them took them back out.

"It is a perfect fit, but I want you to experience the feel of breasts attached to your chest, so I am going to attach them to you with a special liquid adhesive. It is made so women with mastectomies can go swimming without the breast form slipping out of the suit. It holds strong and is water proof!"

Sarah coated the back of each breast form with the glue and placed it back in the half cups of my corset. She positioned the artificial breasts carefully and made sure they were in balance. The glue felt cold, but quickly dried and set.

"These are the very best breast forms I could buy and they will jiggle and bounce just like real ones. The nipple is molded in the breast form and I selected your new tits with the largest erect nipple available. Mistress Lori made the cups on your corset to support your new tits but leave your nipples exposed. I want you to look hot and slutty all the time and these are perfect tits for Sissy Jacquelyn.

When they were convinced that the glue was completely dry, they released me from my suspension. It hurt like hell to lower my arms and put more pressure on my stomach. I walked around a few steps to get the kinks out of my legs and suddenly I saw myself in the mirror. I was shocked with the image with naturally jiggling breasts. I really had a woman's shape with the breasts and tightly laced waist. The heels made my legs look great and my hair was shaped quite nicely. My face was a mess.

Lori has smeared her and Frank's cum all over my face and my lipstick was smeared just as much. It made me look like a big whore who had fucked the whole navy. I was appalled with my face.

"Please can Sissy Jacquelyn clean her face so she doesn't look like such a whore?" I begged.

"Why yes Jacquelyn, I am glad to see you taking more of an interest in your appearance."

When I came back to the family room, they both looked like the cat that ate the canary.

"We have to go now Sissy Jacquelyn, so tell Lori ta-ta for now."

"Goodbye Mistress Lori and thank you for my pretty corset and for letting me eat Frank's sperm from you pussy. It made me very horny."

Sarah took me home and I almost fell over trying to keep up. When we got home, Sarah took me back to the bedroom and told me to finish dressing. She had out a simple nylon-jogging suit for me and after I got it on, you had to do a double take to tell if I was a man or woman.

"Don't worry, after we get you in makeup you will have no problem passing as a girl!"

I didn't want to pass as a girl, it was a lot of fun playing sex games with Sarah and Lori, but I did not want to go anywhere that required me to pass as a girl.

"Time to go, you don't want to miss your appointment do you Sissy Jacquelyn?"

"What appointment, I don't have any plans to go anywhere!"

"I got you a beauty appointment and lets go before you are late!"

I started to argue, but remembered the switch. Lori grabbed her purse and went to the garage with me close behind. Fifteen minutes later, we were in a beauty shop. It was still early and no other clients were there.

"To make you more comfortable in your first trip, I got Pauline to open early."

I took my first look at Pauline and after a few seconds I realized that Pauline was a very female looking guy.

"Yes darling, I am a sissy just like you and your lovely lady asked me to help you look your best for tonight." Pauline said in a rich low voice that gave just a hint of her gender.

I could think of nothing as Sarah and Pauline guided me into the chair. The two of them talked and discussed options, made their decisions and got started. My ears were pierced, my eyebrows were thinned a bit, and my hair was clipped and styled perfectly and then the nail girl came in and started working on my nails. She had her instructions and she got started putting on her longest nails with bright red polish. I thought Sarah did my nails great last week but this was even better. I was just amazed by the look she achieved, longer redder, brighter and perfectly shaped. I think there were 5 layers of polish and 3 layers of a shiny topcoat. I am sure any movement of my fingers would catch the eye of someone a mile away. This was exciting and humiliating at the same time. My heart was pounding and my poor abused waist was restricting my breathing.

Pauline came back to do my makeup and just finished as other customers started to come in. I didn't talk to anyone, but I could tell from the looks that they were impressed and not sure if I was a tall woman or one of Pauline's transgender friends. I looked at myself in the mirror and knew that if I didn't talk, nobody could tell for sure. Sarah was grinning ear to ear as we drove away.

"I knew Pauline would be perfect for you Sissy Jacquelyn! What do you have to say for yourself?"

"Thank you mistress Sarah, you have made me look very pretty and I am so horny being made to be your sissy slut!"

It was true, my whole body was charged with an energy like never before. I was driving around town looking like a good-looking woman out with her good-looking friend. We turned quite a few heads as we drove home. When we got home, Sarah fixed us a bite of lunch took off my tape so I could pee and told me that we were going to relax the rest of the afternoon and keep my pretty new look for tonight. When I asked why, she said that it was a surprise and I just had to wait.

Now that my dick was free again, I was able to get an erection again and my tits and look kept me hard and aroused in my panties all afternoon. Sarah got out a romance movie and gave me some lingerie catalogs to look at as she relaxed and I stayed charged with sexual tension. It was early evening when Sarah said we needed to eat a bite of soup to keep our stomachs from growling, but not spoil my appetite for later. I didn't know what she was saying but went along as requested. We had a little chicken soup and cleaned up the kitchen.

"Jacquelyn, I am going to ask your permission to do something later tonight and I want you to say yes, but if you don't want me to do this thing I am not going to. It will disappoint me greatly not to get to have this experience, but I will understand if you say no. One other thing you should keep in mind before you answer, I do not think we well play Sissy Jacquelyn again if you refuse me my pleasure."

"Ask me anything Mistress Sarah, I can deny you no pleasure after all the pleasure you have given me when we play Sissy Jacquelyn sex games!"

I knew I meant what I said, but in the back of my mind I still wondered what she could want that I might refuse her. Sarah asked me to come back to the bedroom while she got dressed. She told me that my dick was free and she didn't trust me to keep from masturbating as soon as she left. Sarah had me strip down to silk and hose then draw her a bath. She had me hand her items as she shaved her legs, trimmed her pubic hair and got dressed into silk and hose just like mine. I didn't know she had purchased matching sets for us. Next she changed my earrings to large gold hoops and put the small training studs away. Then she did her nails to match mine, but at her natural length. She styled her hair as much as she could like mine and put on the same shade of lipstick. I could see that she was making us up to be "twins" if that was possible. We had on identical items including matching lipstick, perfume and jewelry. Sarah went to the closet and got out two shoeboxes. In each one were matching black heels with sexy ankle straps. She helped me on with mine, because with these nails, I could never close the little buckles. She had me walk around the bedroom to practice on my new heels as she finished up her own preparation.

When Sarah was finished she looked great. I wanted to grab her and fuck her, but I knew not to push my ideas while I was serving as her sissy slave. She went to the closet and got out two dresses. They were long silk dresses with high necks and tight skirts with leg slits that you see geisha girls wearing in the movies. Sarah slid mine on for me and zipped me in tightly. I could hardly move as she had me walk around the room again while she put on her own dress. I tried to ask questions, but Sarah cut me off each time I asked. I was about to burst when the doorbell rang.

Chapter 6, First Week of Service

"Please Sarah, don't make me answer the door in my dress!"

"I told you Sissy Jacquelyn, you are to do as you are commanded or I will find my switch!"

I did as I was told and tried not to worry about it because I thought I might pass as long as I didn't speak. When I opened the door, I was shocked to see a shorter version of me looking me back in the face. Lori was standing there in the same silk dress and Frank was right behind her.

"Don't just stand blocking the door Sarah, let us in. This fall air is getting cold and we don't have coats on".

Frank didn't realize that I was not Sarah as I let them in the house. Frank was having a running conversation with no one in particular when Sarah walked into the room. Frank stopped in mid-sentence.

"Well if you are Sarah, who in the hell is that standing with Lori?"

"It is our new friend Jacquelyn. Frank, this is Jacquelyn and Jacquelyn this is Frank. You will have to excuse Jacquelyn; she was at a football game last night and lost her voice shouting. How do you like our silk dresses that Lori made? We are thinking about dressing up for Halloween as Geisha girls."

Frank stuck out his hand and I gave my hand as lady like as I could. My long nails were all he could see as he shook my hand and he did not take a good look at my face.

"I don't know when I have been with three such sexy women. You would be the hit of any Halloween party in those sexy dresses. I am getting horny just standing here in the middle of you all!"

"Well, that is the idea Frank to drive all you macho men crazy with lust so we can wrap you around our little fingers and have our way with you!"

"Where is Jack, isn't he ready yet. He better get out here before I claim all you ladies for myself!"

Frank was a very good-looking man and he had developed quite a reputation with the ladies before he settled down with Lori. He could still flirt with the best of the woman chasers and he liked to play at flirting when he could get away with it.

"Jack got called for special duty tonight with his top Client and he may not show at all. You are just going to have to let all of us Geisha girls take care of you and only you."

Sarah had me sit as she and Lori served sake and prepared sushi. Frank kept staring at my tits in the tight silk dress and my long nails as I laid my hands in my lap to make sure he didn't see a bulge. The erect nipples of my breast forms were sticking straight out and Frank didn't know that they were always hard. The girls flirted back at Frank and almost all the conversation had a sexual connotation.

Every one was starting to get a little tipsy from all the sake and Frank was getting very horny with all the sexy attention Sarah and Lori were showing him. The tight skirts kept their steps short and they had to bend at the knees and almost sit down to serve Frank his drinks. It was a very sexy having the two of them act like Geisha girls and they lost no opportunity to seductively touch Frank.

"If Jack does not get back soon, I am just going to have to take care of all three of you by myself!" Frank bragged.

"Jack does not exist tonight as far as I am concerned. He can't bother to make an appearance when we need a real man around, so forget him."

I knew Sarah was baiting me to speak up and let Frank know who I was, but I could not make myself.

"Frank, I have told Sarah and Jacquelyn that they could see your dick sometime because I am tired of them saying that I am lying about how big it is." Lori blurted out.

"What! You are kidding aren't you Lori?"

"No Frank, and I have had enough of this sake tonight to have you show them."

"Well good for them, but what is in it for me, I am not some freak show! It is my dick and I don't go around giving free looks just to satisfy someone's curiosity!"

"I think you have a point Frank. I tell you what, I will let one of the girls give you a hand job and one of the girls can take you back to the bedroom for a private inspection of your dick if you let them see it hard. What do you say Honey?"

"You must be drunk, because you have never let me act like this in our entire marriage."

"I am tired of being accused of lying and my pussy is very sore from fucking this morning and you are still very horny after not having sex all week and you were a good sport about it all week and you deserve a reward of some kind. This is your chance tonight, take it or leave it, I may never again be drunk enough to let them see your cock."

"Ok, I will show them, but I get to pick who does what! I want a hand job from Jacquelyn with those long nails and I always had a fantasy about getting into Sarah's pants so those are my conditions!"

Frank fell right in line with Sarah's plan. She obviously had worked the situation around to have Frank pick perfectly!

"I want to see that dick myself, but I don't know if Jack would ever forgive me if I let you take me to bed! Sarah stated.

Looking right at me, "Jacquelyn, I must be drunk, but do you think Jack would forgive me for what I am thinking about doing?"

I hesitated for several seconds, turned several shades of red and then just nodded my head yes. This was what Sarah had meant when she said I would have to give my approval for her pleasure. Sarah wanted to cuckold me with Frank!

"Then it is settled. Jacquelyn come over here and get my dick hard with those fantastic nails of yours and make me hard so you girls can see a real man sized cock!"

I know I blushed as Frank grinned at me lewdly. I got up nervously and walked over to Frank. I could hardly move in the tight skirt and my emotions were running wild with the fear of discovery, humiliation and lust as I knelt between Frank's legs. After several tries I was able to get his belt off and his fly open. He lifted his hips off the couch as I slid his pants down and took off his shoes and socks (It was a good thing that he had slip-on shoes). I came back up and slid my hands into the waist of his boxer shorts. As I pulled them down they got stuck on his dick and balls, but after a tug or two the base of his cock came into view. As I got his boxers all the way off, Lori spoke up.

"I told you he was bigger soft than most man are hard. He is a lot bigger than my uncle and cousins who I saw growing up and he is bigger than a lot of the men in porno movies!"

I had to agree, I was impressed and I had not even touched it yet. I reached out and touched it lightly with my hands and jerked back as soon as I touched it. I was doing something a "queer" would do and I was not a queer!

"It won't hurt you girl, run those nails around the head of my cock and you will make it nice and hard!'

I did as suggested I lifted his big shaft in one hand and started running the edge of my nails around the head of Frank's dick. The monster started to harden in my hands and I almost snapped out of my Sissy Jacquelyn role and ran.

"Go for it Jacquelyn, don't be nervous. I want to see you handle that monster cock!" Sarah told me when she sensed my fear.

Frank's balls were at least twice as big as my balls are. If my balls were the size of walnuts, then his were the size of key limes. I started concentrating on my stroking and as I slid one hand up and down the shaft, I traced the edge of Frank's cock head with the other. It was getting full and hard when I took the five nails on one hand and started lightly scraping just the head of his cock like I was trying to pick up an ice cube. As I was doing that, I started running my other hand back and forth on his shaft, twisting my hand as I stroked and letting my nails drag a little as I went. Every few strokes, I used my nails to scrape Frank's ball sack. Starting under his balls and in front of his asshole, I would lightly scratch with 4 nails to the bottom of his sack. Then it was back to stroking his shaft with one hand as I worked on the head with the other. I could see the look on Frank's face and I knew I was driving him crazy. I knew just what to do because I had handled my own dick and masturbated a thousand times before. I began to smile as I controlled my pressure and tempo to bring him to maximum arousal without letting him cum! I was learning to be a cock tease and I kept Frank on the edge of climax for several minutes!

"Let's take a measurement girls!"

Sarah held out a dress makers cloth measuring tape. I took the tape and measured Frank's length along the top of his shaft and with amazement told the girls that he was 10.5 inches long, base to tip. His dick was almost twice as long as my dick is when it is hard. Next I slid the tape around his dick near the base and took a measurement of his thickness. His dick was 6.5 inches around at the base, that was almost 2 inches more than my dick and he was as big around as I was long. I measured around his cock right behind the head and it was 6 inches at that point. I know that my dick hard is about average, 6.5 inches and 4.75 inches around, but I never felt like less of a man. I was kneeling in front of a magnificent cock and balls in real life and this was no porno movie. In a porno movie, you can discount the big cocks because it is a "movie" and they use all those special effects to make movies. But this was real and I had been the one to make it hard with my own hands. I was repulsed, humiliated and sexually charged.

"I told you he was that big, now you know I was telling the truth!" Lori bragged.

"It is a good thing Jack isn't here, he would feel so inadequate in the presence of a real cock like Frank's! Make that big dick dance Jacquelyn!" Sarah said for my humiliation.

"Come on Jacquelyn, don't leave me hanging. Make my dick happy!" Frank whined.

I went back to work on Frank's dick and I was getting turned on to the experience of handling a dick dressed as a sissy slut, my head was spinning and my dick ached with lust. I kept pumping his shaft with one hand while flicking the head of his monster with the nails of my other hand. I could feel Frank's dick start to twitch as I picked up the pace and I knew he was going to shoot his load very soon. Frank was moaning and he was rocking his hips against my hands.

"Don't let him cum on your dress Jacquelyn, it will ruin the silk!"

I looked up at Sarah and saw her grinning about my dilemma. Frank was going to cum in a fraction of a second and there was no way to avoid a mess. I could not move quickly enough in this dress to avoid his sperm flying around.

"Quick Jacquelyn, catch it in your mouth!"

Without thinking, I leaned forward just in time and opened my lips. Frank pushed my head down hard with his hands, but my jaw wasn't prepared for that monster. I could only get the head of it in when Frank started bucking his hips and as his dick spasms in my hands. I had no choice but to swallow his load directly from his dick. I was eating another man's sperm directly from the source. I had a cock in my mouth just like a queer cocksucker, a cock, and a huge cock at that. My lips were stretched tight and his hands held me on his cock as he pumped his load down my throat, not a drop could escape my tightly sealed lips as he moaned loudly. I kept both hands on his cock, trying to stop him from forcing more of his cock in my mouth. I don't know how long he pumped his load in my mouth, but this was the third time today he climaxed and he was still producing a lot of sperm. Finally Frank relaxed and fell back into the cushions of the chair.

I carefully pulled my head off his dick when he relaxed his grip on my head and made sure I didn't dribble on my dress as I sat back on my heels.

"That was fantastic Jacquelyn, Lori does not like to put my dick in her mouth because it is so big and she doesn't ever let me cum in her mouth! You are fantastic with those red nails and red lips! I have never had such a good hand job; it was like you knew exactly where to touch my dick! You slurped down my cum like an old pro, you must be a good cocksucker!"

I did know where to touch his dick, because I had practiced on my own many times. I carefully got up and moved to a chair well away from him so that Frank would not see the bulge in the front of my dress.

"Jacquelyn, I bet that load of cream will help your voice recover!" Frank bragged.

Sarah and Lori served some more sake and sushi as Frank recovered. They kept talking with amazement about how good a job I did making Frank cum and how big his cock was. I was full of conflicting emotions. I had been having lots of sex all week and yet to have a climax of my own. I had just acted like a queer and given a man a hand job. I had slurped down a man's sperm directly from his dick. What was I becoming, a queer, bisexual or was I a sissy slut like Sarah said. I was so confused and horny!

Frank recovered and said it was getting late and if he and Sarah were really going get it on, they better get started before Jack showed up. Sarah looked at Lori and me and asked if we were sure she could do this and not ruin her friendship with Lori and her marriage to Jack. Lori told her to go for it, she was sore from this morning and she wanted to share Frank's cock with Sarah so she could see for herself what it was like to be fucked with a real cock. It was agreed then that Sarah and Frank would go to our bedroom and cuckold Jack in his own bed. As Frank and Sarah got up to leave, Sarah had one more suggestion.

"Lori, since Frank is getting a little strange pussy tonight, maybe you should take Jacquelyn to the guest room and let her make love to you!"

Frank had a shocked look on his face.

"Frank, can't you tell Jacquelyn is bisexual, she swings both ways. Didn't you notice how she kept checking Lori and me out as we served food and drinks? Why she is as turned on by our sexy dresses as you are!"

"Now that you point it out, it is obvious. She is so turned on that her nipples have been hard all night and she hasn't been staring at me!"

I guess Sarah was right, I was swinging both ways these days, but not the way Frank was suggesting.

"Go for it Lori, you said your pussy was sore and couldn't take anymore fucking tonight! I would like to watch, but I am going to be busy with Sarah."

Off we went to the bedrooms. Frank to my bed to fuck Sarah with his big cock and me to the guestroom to lick Lori's pussy. When we got to the bedroom Lori told me to undress her and make love to her with my mouth and hands.

"Sarah told me how much fun it will be to get teased and stroked by your long nails, to have you make lesbian love to me and to keep Sissy Jacquelyn frustrated all night!"

"What about me, I need to cum so bad?" I begged.

"Sarah told me to tell you that you could have a climax if you could manage without my help. That means I can not touch your little dick and I am not to help you out of your dress. If you can climax while eating my pussy, then go for it. Otherwise, you are going to stay horny."

It had taken me several minutes to get Lori's dress unhooked at the collar and to slide the long zipper down the back of her skin tight dress and over her butt with these dam long nails on my hands! There was no way I could unzip my own dress. The bottom of my dress was very tight above the knees and I could not pull up the dress more than a few inches. I was in a silk cocoon and I would stay in it until Sarah wanted to let me out!

Lori just held still and had me kiss each inch of her body as I remove her silk lingerie. I explored each new section of flesh with my lips as I exposed it and lightly drug my nails across the flesh to make it more sensitive. It must have taken me 15 or 20 minutes to get her down to her silk panties. Lori sat on the edge of the bed and told me to make love to her breasts with my nails and lips. Her breasts were unbelievable. Her breasts are large for an Asian woman and very high and tight. Lori could make a dead man horny with her exotic looks and beautiful body. I did as she asked and as Sarah had taught me, making lesbian love to Lori's breasts. Lori was starting to moan softly and she pushed down on me. As I kept kissing her breasts, I slid her panties off her legs. I traced my nails along the front of her legs and worked slowly back to her pussy. Lori parted her legs and I started stroking her pussy lips with my Nails.

Lori pushed me away and kneeled on the bed with her butt pointing toward me. As she slid her legs wide apart and pressed her body low on the bed, her ass cheeks spread wide.

"Make love to my ass Jacquelyn, lick my asshole and make me cum!"

As I knelt before her ass, I leaned forward and kissed her rosebud. I felt so flushed that I was sure that I was going to pass out. I started licking her asshole and stroking her ass cheeks with my long nails. She was moaning softly and as her hole relaxed I started pushing my tongue in as far as I could. I was tongue fucking her rosebud and making her groan. I reached under her and started stroking her pussy lips again with my nails. I could feel her asshole spasm as she had several small orgasms. Lori was so turned on that she had her hands twisted into the sheets and was close to coming hard when I heard a low moan. It was Sarah moaning in my bed. I could hear her moaning loudly as Frank fucked her. My dick was twitching in my silk panties from all the sexual images running through my head. My wife getting the fucking of her life and making me a cuckold at the same time. Serving as Lori's lesbian sex slave and eating her asshole like my tongue was my dick. Dressed head to toe in fine silk and looking like a woman. I really thought I was about to come when Lori let out a long moan and fell forward on the bed.

"That was fantastic Sissy Jacquelyn! I am afraid to let Frank play with my asshole because he will want to fuck it. There is no way he will get that big dick of his up my ass!"

I could hear Sarah in my bed making so much noise that I feared the neighbors would hear her and call the cops! She had been moaning and begging Frank to fuck her harder for several minutes now and I could not imagine that he could fuck for so long. I know he had just cum in my mouth, but I never lasted so long when I was in Sarah's sweet pussy. Sarah always wanted me to go much longer than I could last and she was often frustrated when I came quickly. I felt completely humiliated by Frank, his dick and the pleasure he was giving my wife. It was something I could never achieve. I would never have a big dick like Frank and I never lasted long once I got my little dick in Sarah's sweet pussy.

"Back to work Sissy Jacquelyn!" Lori said to bring me back from my image of Frank's dick ruining Sarah's pussy for my small dick.

Lori was sitting on the edge of the bed and she spread her legs and pointed to her pussy. I leaned forward and placed my lips on her pussy. As I licked I was trying to determine if her pussy had recovered from fucking Frank this morning. I was scared that her pussy was always stretched out and that now Sarah would not even be able to feel my dick when I fucked her. I was sure that Frank had made Sarah his slut by ruining her pussy for my little dick.

"Listen to Sarah beg for Frank's dick Sissy Jacquelyn. You should feel lucky that Mistress Sarah can receive such pleasure from a real dick! She will never be completely satisfied with a small dick like yours now! Sarah never was able to get completely satisfied with your dick and now she will see for herself what a real cock feels like!"

I was completely humiliated my Sarah's obvious pleasure and by Lori's words. Lori had a tight hold of my hair and was rocking her cunt against my face as I licked her sweet pussy for all I was worth. It tasted much better without Frank's sperm leaking out of it. Her clit was pushing out hard as I licked her pussy. It occurred to me that Lori was rocking in rhythm to Frank and Sarah's fucking. We all had a sex beat going and Frank, Sarah and Lori were all rushing to orgasm together. I was just the cuckold sissy husband. The image of Sarah fucking Frank's big cock in my bed was the worst humiliation of my life. I could not even satisfy my own wife and she had to get a real dick in her pussy for this kind of pleasure.

Frank let out a loud moan and Sarah had one last scream and then Lori started shaking all over and pulled my face into her cunt as hard as she could. It was all over in a few seconds, but I kept gently licking Lori's pussy after she fell back on the bed after her orgasm. They had all climaxed at the same time, in 2 different rooms.

Lori had me stop licking her pussy after she rested a few minutes and I helped her get dressed again. She told me that Frank never did anything like this to her, because Frank thought that real men didn't lick pussy. That is why she and Sarah wanted this swap of husbands to happen, my tongue for Frank's dick.

"It was very nice Jack, but I will never get enough of Frank's dick. I would have the perfect lover if I could have your tongue and Frank's dick!"

By the time Lori and I got to the living room, Frank was waiting without Sarah.

"Sarah said she is to sore to move and that Lori and I should go on home and that Jacquelyn would help her get cleaned up."

As they left and said goodnight, I wondered what I would find in my bed. I took a deep breath and went back. In the light from the candles Sarah had lit, I could see Sarah's sex splayed wide open and there were globs of Frank's sperm visible across the room.

"Time for cleanup Sissy Jacquelyn. As you lick my pussy clean and I tell you about Frank fucking me, think about which way you like to eat Frank's sperm. Is it best from Lori's pussy, my pussy or direct from the tap?"

I knelt down and started licking her cum covered pussy. Sarah's pussy was wide open and raw looking. I could taste Frank's sperm and Sarah's pussy juice and as I thought about it, I began to recognize the difference in taste from Lori's pussy and from the direct source. It was like Sarah was teaching me to taste sperm like a wine taster!

"Lay on your back on the bed Sissy Jacquelyn so you can get the rest of Frank's cum out of my pussy!"

I lay down as instructed and Sarah laid her robe across my chest to protect my silk dress from the flow of sperm and pussy juice and sat on my mouth. Frank's sperm and Sarah's juice ran down hill into my waiting mouth and I swallowed every drop. I gently liked Sarah to two more orgasms as she told me how Frank's big dick made her feel and how she didn't think that fucking my little dick could ever satisfy her like that. Just like Lori, she said that if she could have Frank's dick and my tongue she would have the perfect lover.

When she had enough, she helped my up and out of my dress. As she undressed me, she said how lovely I looked and that she was going to leave on my corset the rest of the weekend except when I was in the shower. After she had me stripped of everything but my new corset, she got out the chastity Trainer.

"What about me Sarah, I am so horny I could die! Please Mistress Sarah can I please have an orgasm, please I am desperate!"

"Not tonight Jacquelyn, I am tired and besides your goal is to give me pleasure. If you get any pleasure this weekend it should be from serving me, not having your own dick pleasured."

She got me back into the belt and when she cuffed my hands she got out the biggest plug and told me she had been wrong, this was still not big enough to break me in for Frank's big cock. Sarah told me not to worry, that she loved me only, but that I could never fuck her as good as Frank and that I never fucked long enough to really get her off. I just came faster than she liked and my dick had always felt small to her. Now that she had been fucked with a real cock, she was not going to be satisfied with letting me fuck her with my little cock. She said that since I was a sissy slut, I must want to be fucked by Frank just like her. If I was real good to her and Lori she might let me fuck Frank someday, so I should not be jealous of her.

I could not sleep. I had to lay on my back with the fake tits on my chest and my horny body kept me on edge. Every time I started to drift off, I would wake with a start as the image of Frank's dick in Sarah's pussy came into my mind.

The next morning I woke up with a start as Sarah was measuring my dick with a morning erection.

"Your dick is only half of Frank's, you can't ever give me a fucking like that, can you Sissy Jacquelyn? Did you get a good look at his Balls? They were huge; can you imagine how much sex juice a set of balls like that produce? No wonder Frank can fuck so many times and still spew sperm like a horse!"

I admitted that my dick was not as good as Frank's and that I am happy she had the experience of a real dick like Frank's in her pussy. Sarah got horny talking about it and sat on my face for a "wake-up-orgasm". As I licked I noticed that her cunt lips were still swollen and that she was still opened up from Frank's fucking! I couldn't help but think that Frank had stretched her out and ruined her pussy for my dick. She had made me a cuckold in my own bed and had even had my blessing to do it. My cock was throbbing and I was so horny that I would have fucked anything to get off.

When Sarah was satisfied, she took me out of the corset and trainer for my shower. She got in the shower with me and she played with my glued on tits and soaped my cock until I thought I would cum, but Sarah knew when to stop. My new tits were so realistic that Sarah claimed she could not tell them from her real ones if she kept her eyes closed. The glue she used was made for swimming and exercise, so they didn't come loose in the shower. After we dried up, she put me back into the corset and re- tightened the laces. I was starting to get used to the feeling. Sarah used ice on my groin to shrink my dick and balls and then pushed my dick and balls up into my abdomen so she could tape it flat again. Then she had me put on silk panties, hose and the high-heel slippers. Sarah told me she was sore from her Frank fucking last night and that she was going to rest all day. I was to put on my lipstick, fix her breakfast in bed and after cleaning up, I was to do all the weekend household choirs and wait on her.

I went about doing my chore list with dedication and hope that if I did very well, Sarah would fuck me tonight. All day long, Sarah would call me back to her bed and tell me that she had gotten horny thinking about fucking Frank and she needed me to take care of her "itch". I would lick her cunt till she was satisfied and then she would dismiss me to touch up my lipstick and do more of my choirs. By the end of the day, Sarah had made me lick her to orgasm at least 10 times. Her cunt was very sensitive and it remained swollen all day. It may have been imagination, but I was sure her cunt was still open from Frank's dick.

I made a candle light dinner and served Sarah in my frilly apron. After dinner Sarah watched a movie and had me lick her pussy the whole time. I don't think she could possibly pay that much attention to a movie with my head between her legs, but by the time the movie was over my jaw was numb and my tongue was sore. I did not know your tongue could get sore, but mine was. It was time for bed and I still had not had an orgasm. Sarah was driving me crazy with lust.

"Sissy Jacquelyn, you have tried very hard to please me this weekend. You even gave your blessing to my fucking Frank. You have pleased me more than I expected."

I was blushing with pride as Sarah talked about my performance.

"I had planned to let you fuck me tonight, but my pussy is still sore from Frank's dick. Even if I let you fuck me, I don't think I could feel it after his big dick stretched me so much. I know his dick is not as big as a baby, but a woman can't have sex for 6 weeks after a baby and they say her pussy is never as tight again. I don't think your little dick could even fill me up now. Since it is my pleasure that counts this weekend and since it wouldn't give me any pleasure to put your small dick in my pussy, I have decided not to let you put your little dick in my stretched pussy."

I was completely humiliated my Sarah's words, but it was turning me on at the same time. My dick was trying to get hard under the tape. Sarah had let me out several times today for bio-breaks, but she had taped me back up each time.

"So, I am going to give you a chance for an orgasm. I am going to let you fuck yourself on a dildo for 5 minutes and if you can cum from that you get your orgasm. If you don't, I am going to put back in the chastity trainer and go to sleep."

I stood staring as Sarah waited for my answer.

"Well, does Sissy Jacquelyn want to fuck herself?"

"Please let Sissy Jacquelyn fuck herself on a dildo and have an orgasm!"

Sarah had me bend over and she lubed up my ass/cunt and set a large fake cock on the floor. It was almost as big as Frank's dick and had molded balls in the base that helped it sit on the floor. Sarah put me back in the chastity trainer, but left off the dick cover/ring and ass divider strap. After she had my hands cuffed to the belt, she started playing with my dick and had it hard in no time. She then rolled a condom on my cock and told me to get going because 5 minutes was not long.

I moved over to the fake cock and knelt down over it but as I lowered my ass down I knocked it over. Sarah was giggling at my efforts. I was so desperate for an orgasm; I spun around and picked up the dick with my mouth and set it upright. This time I got my asshole over he tip of my plastic lover. It took a good 40 seconds of wiggling to slide it into my ass/cunt, but once it started in I was able to impale myself in one stroke due to all the stretching Sarah had done. Sarah called out 4 minutes as I started fucking myself wantonly on the fake cock. Faster and faster I went as Saran called out the time every 30 seconds. When she had counted me down to 30 seconds, I was pumping myself up and down like a rabid animal. I shoved my ass down fast and hard on the fake dick, trying to get off before Sarah called time! She counted down the last 10 seconds like a NASA rocket launch. When she reached 0, blastoff I climaxed. I was bucking wildly as my dick shot spurt after spurt of cum into the condom. Sarah had denied my release for a week and had kept my sexually stimulated at the same time. It was the biggest load I had ever produced. When I came down from my sexual high Sarah told me to hold the cock in my pussy and crawl over to her so she could put on the rest of the trainer. She had a very difficult time putting my dick through the steel ring of the front cover. Sarah gave my balls a hard squeeze and the pain made my dick shrink enough that by using strong force she was able to get my poor dick and swollen balls through the ring. Then she pulled the divider strap tight and trapped the fake dick in my ass.

"Open your mouth wide and stick out your tongue as far as you can Sissy Jacquelyn."

I followed her commands without question by now.

"Do not close you mouth until I tell you to, no matter what!"

Sarah rolled the condom half way up my dick and then pinching it tightly; she slid it off my dick with all my sperm inside. She then put the opening of the condom on my tongue and slid it on as far as it would go.

"Close your lips and teeth on your tongue and hold the condom in place with your tongue sticking out."

Sarah took several pictures of me holding a very full condom in my mouth with bright red lipstick on my lips. When she was finished, she had me lay down on my back and gave me my final instructions before turning off the light and going to sleep.

"Sissy Jacquelyn, I want you to enjoy your sperm for hours, so you are to suck all of the sperm out of the condom before you fall asleep. Keep the condom in you mouth all night and in the morning, I will inspect it to see if you got it clean. If you get it clean, I will take off your nails and tits so you can go to work next week. If you don't I will switch your ass and make you stay as Sissy Jacquelyn all day Monday."

As Sarah drifted off to sleep, I was sucking the sperm out of my condom with complete dedication.

This is the end of Chapter 6 (of 7), of the story "Getting Nailed".

Chapter 7, A New Life, Paid in Full

I woke up before Sarah on Sunday morning and as my memories came back to me, I remembered that I was expected to have the condom in my mouth. Sometime during the night it had fallen out of my mouth or maybe I swallowed it! I was in a panic. If Sarah kept me in my corset and breast forms, I would have to call in sick and that would be a big problem. I had meetings scheduled to jump start the project we just won and nothing could happen if I was absent! I could see all that I had worked for the last several months going up in smoke.

I started trying to locate the condom without waking Sarah. It was still rather dark in the bedroom and my hands were locked in the chastity trainer. By rolling left and right slightly, I was able to feel the condom lying on the side of my neck. It had dried out in that spot and was holding tight. If my hands were free, I could have pulled it right off. I was screwed!

After a few seconds of panic, I decided to get it back in mouth or die trying. I gently rolled off the bed and knelt on the floor. I worked my way over to a small lamp table and carefully scraped the condom free on the corner of the table. When it fell free it bounced under the table and I had to crawl on my belly to get my head under the table so I could suck it back into my mouth. It was pretty nasty. Sarah had told me to get it clean, but I don't think you can actually suck sperm completely out of a used condom using just your mouth! I had been eating my own sperm for over an hour last night and was still not done getting it all sucked out of the condom when I must have dozed off. The nasty thing now had lint and small gritty particles on it. I started trying to wash it in my mouth. I rolled it around and probed it with my tongue, I sucked and swallowed and repeated the process until I felt like it was coming pretty clean. I can not explain why I would perform such a perverted act and why it excited me so.

Sarah stirred and called out for me, "Where are you Sissy Jacquelyn?"

"I am sorry Mistress Sarah. I fell out of bed and it must have woke you."

I was hoping that my line made enough sense to Sarah while she was in a groggy state of consciousness and that she would believe me! She did, and after she made sure that I was OK, remembered to check the condom.

"Jacquelyn, place your condom in my hand and it better be clean!" she threatened.

After placing the nasty condom in her hand with my lips I waited breathlessly as Sarah turned on the lamp and made her inspection.

"It is not perfectly clean Sissy Jacquelyn, but you did good enough for the first time."

I was so excited that I had not completely disappointed Mistress Sarah. Sara went on to explain that since it wasn't a perfect job, I would have to be punished, but she would let me remove my nails and tits for work on Monday.

"Thank me for letting you cum and for letting you eat your own sperm!"

"Thank you Mistress Sarah, I so enjoyed fucking myself on the dildo and it was so generous of you to let me have a climax and thank you for letting me eat my sperm, it makes a sissy slut like me so horny to eat sperm!"

I went on until Mistress Sarah was convinced of my sincerity. Sarah said I could kneel and lick her pussy to start the day right. She was sitting on the edge of the bed and as she spread her legs, I could see that her pussy hole was still "open" from Frank's fucking. She probably would never let me fuck her again after having Frank properly fuck her with a real man's dick.

While licking Mistress Sarah to 2 powerful orgasms she told me how big Frank's dick was and how good it felt to be fucked with a real dick and could I tell how much it stretched her tight pussy to fuck Frank.

She let me get up to go to the bathroom after I satisfied her itchy pussy. When I returned, she said she was ready to start my punishment for failing to eat all of my sperm. She removed the divider strap from my chastity trainer and took the dildo from my ass. Sarah explained that this particular dildo was part of a set of sexual aid products that used a locking system to attach items to belts and other accessories. One of the bases provided in the set was a large suction cup. Sarah had me lick the suction cup to get it wet and she pressed it firmly to the full-length mirror on the closet door. Next she placed the just removed dick on the base so that it was sticking straight out from the mirror at a normal crotch height. After putting fresh lipstick on me, Sarah gave me my instructions.

"Sissy Jacquelyn, you did not pay enough attention to cleaning up your sperm and because of that, you are going to be given a motivation to do better in the future. You are to spend the next hour worshiping the cock that I just removed from your ass. You are to lick it completely clean in that hour and I am going to drink my coffee and read the paper in bed while keeping an eye on your efforts. You are to watch yourself worship the cock in the mirror. You are to observe how sexy your red lips look wrapped around the cock and how full it makes your cheeks look as you work your mouth on it. I know it is not quite as big as Frank's cock, but you need a little practice before you take on that monster with your mouth and lips! Think about how turned on you are from licking a cock and how exciting it is for you to lick sperm directly from a real cock. I will be inspecting it when the hour is up and you will receive a much more severe punishment if it is not completely clean."

My hands were still cuffed to the side of the belt and I was still wearing the sexy silk corset with garters holding up my hose and breast forms. As I moved over to the dildo, I could not believe what I was about to do. I knelt down and took the nasty thing in my mouth and slid my lips over the head. I was gagging, but managed not to throw-up. I did as instructed and began to clean the surface of the fake dick with my lips and tongue and as revolting as this was, I never lost my erection. My cock was dripping pre-cum from all of my excitement.

I was mesmerized by the image in the mirror. It was like watching myself perform in a porno movie and I could see the movement of my red lips as I obscenely made love to a fake cock. It was much bigger than my little dick, but still not as big as Frank's. I could not swallow it deep enough to clean it by sliding it back and forth in my mouth, so I had to lick up and down the shaft and work the surface with my tongue to clean it. I was completely humiliated but I could not stop staring at the lewd sexual display. I looked down at my own inadequate dick and wished that my cock were at least as big as the fake cock in my mouth. But the whole time, I was hard and leaking.

When the hour was up my jaw ached. Sarah inspected the dildo carefully and proclaimed that I was indeed learning to be a good dick-licker.

"I have one more surprise for Sissy Jacquelyn to help her become the biggest sissy slut of all time. It is a device that will help you learn control of your big sissy clit. I am going to have you wear a device called a Kali's Teeth Bracelet or KTB for short."

The device was going to help me keep my erection from ruining the look of my silk dress when I was dressed up. Sarah described it as a positive feedback device. When she showed it to me, I was shocked by the cruel simplicity of the device. It was a steel ring that locked onto a flaccid dick and was lined with hundreds of very sharp points. Once I was locked into the KTB device any attempt to gain an erection would cause extreme discomfort.

Sarah went to the kitchen and returned with an ice pack to apply to my groin. Very quickly, my dick was flaccid and Sarah quickly locked my dick up for training. It is a very well designed device and once locked on properly, there was no to remove it without Sarah's help.

"The goal is for you to concentrate on my pleasure and not on your own little dick. This will help you pay attention to me and not to your own desire."

Sarah released me from the chastity trainer and lay on the bed and told me to give her a rub down to relax her and when she was ready for it, I was to lick her ass as long as it took to please her. I worked her muscles from her neck down to her toes and back several times. When Sarah was ready for ass worship, she slid a pillow under her pussy and told me to begin. As she lay there relaxed I started kissing her ass cheeks and eventually was licking her cleft and getting closer to her rosebud. Sarah was making little moaning sound and I began to tongue fuck her asshole. She was soon squirming on the bed and grinding her pussy into the pillow. I was getting very excited, but each time my dick tried to harden, the sharp teeth of the Kali's bracelet dug in and caused me to shrink again. When Sarah was satisfied, she rolled over and told me to give her a front side massage and when she was ready I could lick her pussy till she was satisfied.

It took over and hour before Sarah decided that she had enough. I lost track of how many orgasms she received from my hands and mouth. It was so sexy to watch my beautiful nails tracing Sarah's nipples and it was having a torturous effect on my dick. The whole time my dick wanted to harden, but could not because of the KTB device.

Sarah had me do my lipstick and made me up, dressed me in fresh silk panties and sexy hose attached to the garters of the corset and gave me a list of chores to perform. I worked off my list all day and whenever Sarah got to feeling horny again, I was commanded to lick her pussy or ass again while she talked about Frank's ability to satisfy her pussy. I was getting a supper workout sexually, but was unable to achieve an erection. Sarah was very satisfied and I was completely frustrated.

Late Sunday afternoon, Lori called and said she was ready for us to come over. I got dressed in my sweets and we went through the gate. Frank had just left to go to the gym and play basketball. The second we got to the bedroom, I knew Frank had just fucked Lori. After removing my sweets, Lori wanted a detailed inspection of the KTB device and a demonstration of it working. I made love to Lori and licked Frank's sperm from her pussy for an hour and not once did I even want to get hard due to the pain it caused my poor little dick.

"That little dick of yours is worthless now Sissy Jacquelyn! You can't even fuck Sarah if she gave you permission. If you were a real man, you would get hard from eating all this gorgeous pussy today and you have not had a single erection!"

We left before Frank got back and went back to our bedroom where I licked Sarah's ass and pussy to several orgasms. I was sent to make dinner and when I was done cleaning up after dinner, Sarah put me in the chastity trainer and removed the KTB.

"I can't leave it on at night, because you might get a sleep erection and hurt you little dickey. The purpose is to help you learn complete mental control of erections, not cause you damage."

I was put to bed for the night after licking Sarah to one more orgasm to see if I had learned control. I failed and gained an erection without permission. Sarah told me not to worry; it was my first day using the KTB. She said that I would soon be completely impotent without her permission to have an erection and that the only pleasure I was going to receive was from having my ass/cunt fucked. I thanked Mistress Sarah for the KTB gift and for all the training I had received this weekend!

Monday morning Sarah removed my corset and spent over 30 minutes removing my nails. When we finished Sarah took me to the bathroom to apply a special solvent and removed the breast forms from my chest. It felt weird to lose the weight from my chest after 2 days. I was getting quite used to having them on and their absence was a bit unsettling to my balance.

After getting showered under Sarah's supervision, I dressed in the silk panties selected for the day and put on a new pair of hose that Sarah gave me that had a lace top that was elastic and would hold themselves up. On the outside my business suit maintained my appearance. I was to wear panties and hose under my suit from now on and I had to have the Kali's Teeth Bracelet locked on my dick every day to keep me from getting an erection and masturbating at work. Sarah let me take out my earrings at work, but at night, I always put on earrings to keep my piercing open.

My weekly routine had me living two completely different existences. At work I was viewed as a professional man and at home I was a sissy slut. I was not sure anymore which was my natural state and which was role- playing.

This weekend was Frank and Lori's Halloween party, and all week Sarah talked about the surprise costume I would be wearing. I was afraid to guess what Sarah and Lori was cooking up. Sarah took every opportunity to tease me sexually and not only denied me release, she had denied me erections. My dick not only was inadequate compared to Frank's but it was now useless to me or Sarah locked in the KTB device. Each time my dick tried to harden, the KTB caused me so much pain that I quickly lost the erection.

Friday night came and Sarah told me how pleased she was about my training and she was going to put me in the chastity-training belt and release my dick from the KTB to see if I was ready to take control of my clit. To monitor my dick, Sarah took out a strip of 1-cent postage stamps and glued the stamps around my dick in a tight circle. If I became erect the stamp ring would tear and give proof positive that I had failed to control my dick. Sarah promised me an orgasm if I could remain in control of my little dick. I licked Sarah's rosebud and worshiped her ass for several small orgasms and one big climax. When she checked my dick the stamps were not broken and so far I had kept from becoming erect. Next Sarah sat on the edge of the bed and had me kneel between her legs and start to worship her pussy. I licked her to several strong orgasms and I knew I was doing OK on controlling my little dick. Then Sarah started talking about fucking Frank and how good it felt to be filled up with a real dick. She talked about how tight her pussy was when he stuck it in her and how I could never satisfy her pussy with my little dick again. She said the best thing was when Frank had finished splitting her pussy wide open, I had licked his sperm right up like it was honey. I must be a real sissy slut to eat sperm so willingly!

When Sarah grabbed my hair and pulled my face into her pussy and locked her legs around my head and shuddered to a major climax I felt the delicate stamps tear. I was going to be frustrated sexually again tonight. Sarah encouraged me by saying that it had only been 1 week of training in the KTB and that I had made good progress. She concluded that I would need a lot more practice in the future to finally solve my dick control problem.

When Saturday morning arrived, Sarah had me remove all my body hair again, locked my dick in the KTB and let me know we were going to visit Lori to pick up my costume for the Halloween party tonight. We also had an appointment to have my hair, nails and makeup done at the beauty shop.

Lori put on my breast forms with the glue and laced me tightly in the corset. I went over to Lori's alone and she was waiting in bed with her legs up keeping her pussy filled with Frank's sperm. She gave me a gift- wrapped box for tonight and told me not to open until Sarah gave me permission.

I knelt between Lori's legs and cleaned Frank's sperm from her abused pussy. Her pussy was stretched more than ever and Lori told me that Frank had fucked her twice this morning. Frank got very excited by Lori recounting how I had tongue fucked her asshole last weekend and after he came the first time, he just kept fucking her as she talked about my oral service. The load was huge and it took me quite a well to lick it all up. When Lori was satisfied, I cleaned up my face and put on my lipstick before returning to Sarah.

This time my appointment was during regular hours and the shop was very busy with girls getting fixed up for parties tonight. Sarah had dressed me in a simple silk blouse that showed my nipples very well and a very short and tight skirt. I had to be careful not to let the skirt rise and show my stocking tops and garter. As I walked on my heels into the salon, all the women gave me dirty looks. Was I a she-male friend of the shop owner or was I just a slut. With all the people getting worked on it took till 1:00 for me to get my hair, nails and makeup finished. The women working on me put me in a chair in the front window and positioned me so that people looking in the shop from the street could see my panties, garters and hose. I kept trying to pull the tiny skirt down, but with my nails being worked on, it was impossible to avoid the humiliation of strangers staring up my skirt. When I was done, Sarah took me home and had me relax until it was time to get ready for Frank and Lori's party. About an hour before the party, Sarah gave me permission to open my costume package.

Inside was a black silk French Maid outfit including several stiff taffeta petticoats. Saran applied some makeup to the area where my breast forms were glued to my chest so I would have better appearance with the low neckline and started helping me get into costume.

First, she slid on crotch-less panties that were a black silk with stiff red lace sewn on them. Next I put on black hose and attached them to the garters on my corset. Then the very stiff taffeta petticoats and finally the very short maid dress. It was so tight that it took Sarah about 5 minutes to get it zipped up. With all the stiff petticoats, the very short skirt didn't even cover my whole ass. If I bent over, my asshole, dick and balls would be visible through the slit of the crotch-less panties. For the final effect, Sarah gave me permission to get hard and she licked my dick a few times. I was so horny that I got a full erection almost instantly. Sarah took out a satin hair ribbon and tied a snug bow around my dick and balls.

Sarah had me lift my skirt up and turn around in front of the mirror. My erect dick and balls stuck lewdly out from my body and the stiff taffeta petticoat was the only thing keeping my erection from view. The ribbon was going to keep the blood trapped in my cock and I was very horny from the sexual denial this week.

Sarah put me in black high-heels and had me walk around to practice before we left for Frank and Lori's. The costume had a nasty surprise for me. As I walked, my dick swung back and forth rubbing the head in the folds of the stiff taffeta petticoats. I was getting my dick rubbed for the first time in almost 2 weeks and it would keep me hard all night. Sarah smiled as I recognized that this was part of her and Lori's plan.

"One last touch for your costume Sissy Jacquelyn!"

Sarah rolled a bright red condom on my dick and told me that it was to keep me from dripping pre-cum all over Lori's house as I walked around. If I sat down or bent over during the evening, the whole party would notice my red erection bobbing around.

Sarah went to change into the long silk Geisha Girl dress and when she was ready, we went over to join the party.

There was no pretext of hiding my identity tonight. Lori and Sarah drug me around to everyone to meet and they even told people to call me Jacquelyn tonight. The men made jokes about what a wimp I was to let the girls play "Barbie" with me. The women told me how much fun it must be for me to get to wear such a sexy costume. As people got a little drunk, I was also getting groped my men and women. Lori asked me to help her serve drinks and handed me a big tray with wineglasses on it. I had to go around the room and serve the wine in my French Maid outfit to people sitting in the low furniture. If I bent down, my ass would hang out completely, so I just kept my back straight and lowered myself by bending at my knees.

The word got out among the women that I was somewhat naked in my petticoats and they started brushing up to my erection at every opportunity. One good friend of Lori's who had just gotten divorced reached under my skirt and stroked my dick as I held the tray of wineglasses for her. Nobody but me knew that she was stroking my dick under my skirt. The whole time that she was playing with my dick, she was looking me in the eye and telling me how much I must like being a French Maid, because it was obviously very sexy for me. She said that she was just going to ask Sarah to loan me to her the next time she needed to "entertain". After that, many of the women found a way to give my cock a squeeze and make some humiliating remark. I was terribly horny and all the stimulation of my dick was driving me crazy with lust.

At last the party was over and I had won the best costume prize, a "Victoria's Secrets" gift certificate. Frank said that since I was a French Maid, I could clean up the party mess while he and the girls relaxed. When I finished picking up, I came back to Sarah's side.

"Jacquelyn we have been telling Frank a little about your costume and how much sexual teasing you have gotten lately. I also told Frank that you obviously know he fucked my pussy last weekend since we outed you as Jacquelyn tonight and that Lori and I felt that you should get to fuck his wife in fairness. Frank refused, because he said Lori's pussy is for him only. Besides after fucking Frank so many times, your much smaller dick would not give Lori much pleasure if any. Anyway, Lori suggested that since she has never had anal sex and never could with Frank, that perhaps she could let you fuck her in the ass.

I stood there open mouthed as they chatted on about all the options they had considered that would be fair and acceptable to all. Frank had a couple of additional requests. First, he wanted to see me make lesbian love to Lori like last weekend and second, If I got to take Lori's anal virginity and if I was going to enjoy something that he never would, he wanted an equivalent gift from me. He wanted to take me in the ass, since with his big dick he had not had anal sex with anyone since he left the juvenile reform prison. Lori then said that she wasn't going to be left out of our orgy and that if Frank got hard again watching me make love to Lori, she wanted me to ask him use his big cock on her pussy again.

It was up to me they said. But with one catch. Sarah said that if I wanted to cum tonight, it was going to be in Lori's ass, take it or leave it. I was so horny that I had no choice. I accepted the terms and we got started.

"Get your sissy ass over here and make my dick hard again with your lips and those sexy nails." Frank commanded.

I did as ordered and removed Franks pants and knelt down to start playing with his cock and balls. He was very excited by the scene and I had him erect in a matter of seconds.

"You better get my dick very wet or I might rip your ass bad when I fuck you Jacquelyn!"

I was sure that Sarah would let me use lubricant, but the threat insured that I used my mouth well to lick Frank's huge shaft and prepare him for fucking my ass. Sarah had opened my up a lot with the dildo training, but Frank's cock was going to hurt a lot if I didn't have plenty of lube!

Frank said he was ready to take me in the ass and Sarah helped me remove my maid dress and petticoats. I was still in my corset; hose and crotch-less panties as Sarah helped me get ready for my first real dick. Lori and Sarah had already gotten out of their dresses and were stroking their pussies through their panties as they prepared to watch the show. After lubing my asshole and Frank's dick I got on my knees for Frank.

"He will probably make a lot of noise, so we need to find a way to keep him quit!"

It was decided that I would kneel between Sarah's legs and eat her pussy while Frank took my anal cherry. That way if I made any sound it would get MUFFLED. (They all laughed at Sarah's pun.)

I got into position and as I licked Sarah's pussy, Frank pressed the head of his dick against my asshole. I could not believe how hard he was pushing and the head of his dick was not going in. Lori sat on my back and pulled my ass cheeks apart and Frank started pushing again. This time the head popped in and I screamed into Sarah's pussy. When I screamed, Sarah shook with a small orgasm. Lori slapped her hand down hard on my ass and told me to be quite. Frank started rocking back and forth to open me up and soon I was sure that I would die from his monster cock. Each time I made a loud sound, Lori spanked my ass and Sarah pulled my face tighter into her pussy. Frank started rocking back and forward a little faster and each time he pushed his dick into me, my mouth pushed into Sarah's pussy. In about 5 minutes, Frank had me opened up enough to get 1/2 of his cock in me. I was in major pain and almost sobbing as he had his way with my ass.

"Spank his ass Lori if he doesn't shut up his blubbering!" Frank commanded.

We settled into a rhythm, Frank slowly stroking in me deeper each time, shoving my mouth into Sarah's pussy and Lori spanking my ass in time to Frank's withdrawal. I was completely humiliated and turned on at the same time. I was licking Sarah's pretty pussy and getting fucked like a queer at the same time. When I felt Frank bury himself to the hilt for the first time, I moaned loudly and Sarah's body was shaking with orgasm after orgasm. Then the fucking started in earnest. Frank was pounding away faster and faster, Lori was spanking my ass as hard as she could and Sarah was coming so much that I could not lick up all her pussy juice. Very quickly Frank moaned and started bucking his hips and coming up my ass.

"Oh God, your ass is so tight, Oh God, it feels so good on my dick, Oh..."

Frank shoved in as hard as he could and held his dick in as he came down from his orgasm. We were locked up like a pair of dogs. My ass was clamping tight on his dick after the abuse and as soon as he quit working his dick in and out, we locked up. It took several minutes for some of the blood to leave his dick and as he shrunk slightly he pulled out of my. I was so open, that my asshole would not close completely when he withdrew. I was very turned on. My dick was throbbing, but the pain had been too much for me to cum.

"That was fantastic Jacquelyn! What a tight fuck you are!"

I was sent to the bathroom to clean up my ass and to bring back a damp cloth to clean up Frank's dick. I sat on the toilet and let Frank's cum run out of my ass. My asshole was still wide open and it took several minutes of clinching my ass muscles to get it to close again. At least Frank had not broken my ass permanently with his big cock.

I returned to clean Frank's dick up and was grateful that Sarah didn't make me lick it clean. When I was done, Sarah had me kiss Frank's dick and thank him for fucking my ass.

"Thank you Master Frank for fucking my ass, my ass never felt so full and you made me so horny by fucking my sissy ass with your big dick!"

Frank grinned and told me that there was plenty of his cock for my ass and he was sure that I would get to try it again in the future.

"My turn!" Lori demanded.

"First, Sissy Jacquelyn needs to put on fresh lipstick!" Sarah suggested.

I started undressing Lori and kissing her skin as I went. I used my nails to pinch and scrape her body as it came into view. When I had her bra off, I licked her nipples to get them hard and then I raked my nails along the sides of her breast to her nipples and gently pinched the hard nubs. Lori was getting unsteady on her feet, so she had me pull off her panties and kneel before her pussy. She grabbed my hair to steady her legs and had me lick her to a couple of small orgasms. I loved to lick Lori's long clit. It was so different than Sarah's and I could use my lips on it directly as my tongue flicked the end. Lori sat back on a chair and pulled my mouth to her pussy again. As I licked her to a large orgasm Frank was making comments about what a sissy I was to eat pussy like that. When Lori was finally satisfied, Sarah told me to beg Frank to let me put my little dick in Lori's asshole.

"Please Master Frank may I please put my little dick in Lori's pretty ass. I am so horny and I really need to cum. Please may I have my orgasm in Mistress Lori's bottom?"

"Well, Sissy Jacquelyn, show me how much you want to cum! I want you to lick my dick and suck on the head of my big dick to show me how grateful you are!"

I was on Frank's dick in a flash and I licked his shaft up and down as I worked his heavy balls with my nails. As he got fully erect, I pushed my lips down his shaft until I felt his dick pressing on the back of my throat. His dick was so big around that my teeth were in contact with the shaft and my mouth was wide open. I sucked on his shaft for several minutes until Lori said that she was getting pissed and that I better get my little dick up her ass now or I could forget having an orgasm!

Frank told me to kiss the head of his dick again and thank him for Lori's anal cherry!

I was willing to do anything to have a climax so I kissed Frank's cock head and begged for Lori's asshole.

"Please Master Frank, may I climax in Lori's ass. I am just a sissy slut, but you promised me that I could cum if I was good and I licked your dick as you asked. Please let me cum Master Frank!"

Frank gave his permission so I positioned Lori over the back of a low overstuffed chair. Her feet barely touched the ground as she spread her legs wide. Her rosebud was very exposed, as her ass-cheeks were wide open in this position.

Sarah sat on Frank's lap front to back, so that her cunt was lying on top of Frank's hard dick and her legs were over the arms of the chair. Her pussy was stretched wide by the position and Frank could slide his dick against Sarah's clit without entering her pussy. Frank was playing with Sarah's tits and tweaking her nipples as I started making love to Lori's ass. I knelt between Lori's legs and started licking her ass. As I tongue fucked Lori's asshole, Frank and Sarah made remarks about what a sissy slut I was to lick Lori's ass like that. The remarks were humiliating me as much as they excited me. I was raking my long nails along Lori's legs as she moaned into the cushions. With the long nails on, I could drive Lori crazy by moving the hard edge of my nails along her swollen pussy lips. I licked her asshole until I felt her legs tense and she climaxed on my tongue. I gently kissed her ass and stroked her pussy lips as she came down from her climax.

"Fuck me now with your little sissy dick!"

I used the lubricant to prepare her ass and worked plenty on my condom- covered dick. The end of the condom had already collected my pre-cum and it was making a noticeable bulge in the tip of the condom. I started working the lube into Lori's asshole with my fingers. It is very hard to work a finger into an asshole with long nails, but I gently opened her up. As soon as I thought she was ready, I put the tip of my dick against her opening. After having my own ass reamed out by Frank, I knew how not to take an anal cherry. Very gently I pressed my hard dick into her bottom a fraction of an inch at a time. I kept working my nails on her ass-cheeks while she got used to my dick in her hole. When I felt her tight hole relax, I worked a little more in. In very short time, I had the head of my dick in. I started slowly working in and out and Lori was moaning as I had 1/2 of my dick working into her ass. The next time I pushed in, my dick went to the hilt. Lori let out a loud moan and her whole body shook with a strong climax.

I heard Sarah moaning and looked up to see her rubbing her clit along the top of Frank's hard cock as he played with her tits and pinched her nipples.

"Fuck me Sissy Jacquelyn!"

I started rocking my dick back and forth gently in Lori's ass to get her loose. When she relaxed her asshole on my dick, I started fucking her faster. Lori was morning and her asshole was having a constant series of spasms on my dick. I reached around her hips and dug my nails into the sensitive skin next to her pubic hair and pulled her back to meet the thrusts of my dick. My climax had been denied all week and I was starting to twitch with excitement. It had been a long time since I had cum and Lori's virgin ass was so tight and hot on my horny dick and soon I was slamming in and out for all I was worth. Then I came! I was absolutely bucking and shaking as my dick shoot my biggest load in Lori's ass. Lori was having body shakes as my orgasm drove her body over the edge to a major orgasm of her own. Her asshole had many strong spasms on my dick, giving me more pleasure than a sissy slut deserved. I rocked into Lori hard and fast as a long moan escaped my lips. I had cum after all the teasing, all the denial and all the stimulation. When I was spent, I collapsed on Lori's back.

Sarah let me rest for a moment and then she called me back to earth.

"Pull yourself out of Mistress Lori's ass and keep your condom on your dick as you come out of her ass. Then you need to thank Mistress Lori for letting you cum in her ass."

My dick was still pretty hard with the ribbon tied around my cock and balls holding in most of the blood and the extreme excitement Sarah had put me through to get an orgasm. Once I was out, I knelt down and kissed Mistress Lori on the ass and licked her rosebud to help bring her down from her climax. When Lori's asshole quit quivering I thanked her.

"Thank you Mistress Lori for letting me cum in your beautiful ass. It was very exciting to fuck your asshole and it made me very horny to be the one to take your anal cherry!"

"Come over to Frank and I will give Sissy Jacquelyn a reward for your efforts to fuck Mistress Lori well!"

When I reached Sarah, she carefully removed the condom from my dick. It was the biggest load of sperm I have ever shot. It looked like several ounces of cum were held in the end of the condom. Sarah got up off of Frank's hard dick and carefully emptied the contents of my condom on Frank's cock.

"Clean up your mess Sissy Jacquelyn!" Sarah commanded.

My horniness was reduced to at least normal and the thought of eating sperm was gross to me. To have to eat my own sperm was bad enough, but to see my fresh sperm coating Frank's dick was very strange and sick. As I knelt to lick up my sperm I had to fight the urge to gag. Frank grabbed my head and shoved his dick into my mouth as far as it would go. As he face fucked me, I sucked down my own cum. The humiliation was unbearable but with the humiliation I felt an equal lust. My dick was fully erect and it was twitching wildly in the air as I gave Frank's cock oral stimulation.

"Lick up your sperm mess from his shaft Sissy Jacquelyn before it drips off and makes a mess!" Sarah directed.

Frank released his grip on my head and I pulled my lips off his cock head. I licked my sissy cum off along the top of Frank's dick and swallowed it all down before it could drip off. As I worked my tongue and lips along Frank's shaft, he moaned his approval. When I had his dick cleaned off Sarah let me stop and thank Frank and Lori for my treat. She also said that I should beg Frank to fuck her pussy so he could get rid of his erection that I caused by being such a cock-tease.

"Thank you Master Frank for letting me fuck Mistress Lori in the ass. It was very nice to be able to cum in her tight ass and thank you Master Frank for letting me lick my own sperm from your big dick; it makes sissy sluts like me very horny to eat sperm. Please Master Frank would you fuck Mistress Sarah's sweet pussy with your big dick. It gives her great pleasure to have your big dick in her pussy and my small dick can't make her feel as good!"

Frank lay on the carpet and told Sarah to sit on his dick. I was in a trance watching Sarah lower her pussy on the head of Frank's dick. At first she could not get the head in, but her weight opened her pussy up and she slid down a few inches. It took Sarah a good 5 minutes to slide completely down Frank's big dick. She was squirming and moaning as she started pushing off and dropping down. It was very obscene to watch that big dick splitting my wife's pussy and I knew that Sarah would be unable to have that same kind of satisfaction with my little dick. Frank was playing roughly with Sarah's nipples as she tried to bounce up and down on his shaft. Sarah was starting to have many small orgasms and her pussy was driving Frank crazy with lust as her tight pussy clamped uncontrollably on his hard cock. I was so envious of Frank at that moment. He was giving Sarah the fucking she always wanted and deserved. It was something that I was inadequate to provide.

Sarah was screaming out to Frank to fuck her with his big dick and claim her pussy forever. The lust was intense in Frank's face as Sarah had one of her over-the-top orgasms that leave her body limp. Frank was not done with his climax, so he sat up and picked Sarah up while his big cock was still buried deep in her pussy. He carried Sarah over to a chair and sat her in the seat. Frank was between Sarah's legs on his knees and he started banging Sarah's pussy fast and hard. Lori was sitting on the couch playing with her pussy as Frank fucked my wife and she motioned for me to kneel between her legs and eat her pussy. Sarah came back to life quickly and locked her legs around Frank's back. As Frank pulled out Sarah dug her heals into his ass to spur him on. Sarah's pussy had to be tearing open, but she just begged for more of Frank's big dick. I think Frank fucked her like that for about ten minutes as he built toward his own climax. When he came, he slammed his cock in very hard 6 or 7 times as he roared like a bull elk. They lay in each other's arms as they relaxed and recovered from fucking. Frank slowly pulled out of Sarah's gaping pussy.

"My pussy hurts Sissy Jacquelyn, kiss it and make it feel better!"

I assumed my position between Sarah's legs and started licking up their combined sex juice. Globs of Frank's fresh, hot sperm slid down my throat and Sarah was still flowing pussy juice hard, which washed Frank's sperm out of her pussy and into my mouth all the faster. Sarah's pussy was wide open from the fucking from Frank's cock. Her pussy was even more open than the last time he fucked her and made me a cuckold the first time.

"What a perverted sissy slut you are to eat my sperm from your own wife's pussy!" Frank said with cockiness in his voice.

When Sarah was satisfied with my cleanup of her pussy she sent me to get cleaned up and dressed again in my French Maid uniform. Lori came along to help me get dressed and get my lipstick on right. Lori sat on the counter in the bathroom and made me lick her pussy again so she could have one more orgasm (she said that Sarah had interrupted my pussy licking and left her hanging). We returned when my French Maid dress was back on and my makeup was restored.

When I came back to the living room, Sarah had me sit in a wooden chair in the center of the room. She placed the cuffs on my hands and ankles so that I was tied to the chair. Sarah lifted my skirt and licked my small dick until I was hard again. Lori switched places with Sarah and gently stroked my dick with the stiff taffeta petticoats to tease me. Sarah sat in Frank's lap and played with his dick as she started talking.

"Sissy Jacquelyn, we have some things to tell you. You do not know the whole story about your new life and it is time for you to know our plan. If you are going to understand our plan, you are going to need for me to start my explanation 2 months ago."

"Lori called me crying about a fight she had with Frank. He was upset with her because she would not give him oral sex and her pussy got very sore from Frank's big cock. He was only getting about 1/2 the sex he needed and he didn't like having to masturbate 3 or 4 times a week. His balls are huge and he needs a lot more sex than most men do. Lori told me again how her uncle had made her give him blowjobs and hand-jobs as a girl and how it makes her sick to have to do that with Frank or any man."

"As I tried to talk Lori into giving oral sex a try again, she started crying again and said it hurt her mouth a lot when Frank tried to stick his dick between her lips. He liked to grab her head and fuck her face, but his dick was to big for her mouth. I didn't believe her at first, but the more she talked about Frank's big dick, the more I had to see for myself. I soaked my panties as she talked about his size, because I have always fantasized about being fucked with a big cock. I had an old boyfriend before I knew you who had a big cock, maybe 8 inches, but nothing like Frank's. Your little cock never made me feel as good as my old boyfriend and the more Lori talked, the more I had to try Frank's big dick. I was convinced that if we took things step by step, we could solve her sex problems with Frank before things got out of hand in the relationship, give me a chance at Frank's cock and so I convinced Lori to let me help her and Frank."

Sarah went on and told me the whole 2-month story. The first thing Sarah had Lori do was to get Frank hard and take accurate measurements of his cock. When Sarah saw the size of Frank's dick measurements, she was skeptical, but Lori convinced her that after all the years working in her uncle's factory sewing, that she knew how to use a measuring tape. Sarah had Lori open he mouth as wide as she could and Sarah found out by measuring that with Lori's Korean background and small features, her mouth was just too small to accommodate Frank's dick. On a hunch, Lori measured Sarah's mouth and Frank's cock was to big for her mouth also. Sarah was getting jealous of Lori and she wanted to get a chance to see Frank's cock for herself.

Sarah dug deeper about why Frank wanted a blowjob so much, when his cock was that big and would not fit in Lori's mouth. Lori told Sarah about Frank's time in Juvenile and his secret sex life. Frank's first steady "girlfriend" was a sissy boy in juvenile and that was where Frank learned to enjoy blowjobs. He was very popular with a couple of "girls" because he had a big cock and they used to fight over who would get to give Frank his blowjobs. Frank never mentions his sissy sex to anybody, because he thinks someone might think of him as a queer. By the time he left Juvenile, he had a string of sissy sluts that were giving him blowjobs and letting Frank fuck them in the ass, he never considered himself homosexual, because he didn't touch the sissy boys himself and he has a big hang-up about homosexuality.

Frank left the sissy boy/girls behind when he started college and was fucking his way through the coed population. When he met the shy Lori in class he changed his wanton ways. They fell in love quickly and Frank left his old sex life far behind. Besides, AIDS was getting to be a big problem and Frank sure didn't want to go back to having risky sex with sissy boys and getting sick from HIV or even giving Lori AIDS. There was no way that Frank was going to get his kicks with anybody but Lori, out of love for her and to be safe.

"It suddenly occurred to me that Lori had more cock than she could use and I didn't have enough cock", Sarah explained.

The more Sarah and Lori talked about Frank's and Lori's sex problems, the more Sarah shared about our sex live. She told Lori about how much I enjoyed eating her pussy, almost as much as I liked fucking and if I were very horny I would even tongue fuck her asshole. Lori was amazed, because Frank said that he couldn't eat pussy and that in his neighborhood eating pussy was considered nasty. Frank never went down on Lori and he said he would get over his hang-up on eating pussy when Lori got over her hang-up on blowjobs. There was no way Frank would put his tongue in Lori's asshole if he wouldn't even eat pussy!

One problem was that Sarah had to overcome was her decision that she could not fuck Frank or anybody else behind my back. If she was going to do Frank, I was going to have to know about it and give my blessing. The girls worked out details of fairness, if Sarah was going to help take care of Frank's cock I was going to get to do Lori in return. After working on ideas for 2 weeks, they sat Frank down and explained the plan to him. Frank didn't believe his ears, but he saw no harm in talking about the idea because it was making him horny. He didn't think that there was any way that he could imagine a real man who would let his wife fuck somebody else. No "real" man would allow himself to become a cuckold. He also knew that he was not going to share Lori's pussy with any man! Frank told Sarah that if she had sex with him on a regular basis, a normal cock would never satisfy her pussy again and she should be warned that all his old girlfriends claimed they were ruined for normal dicks.

The girls kept working on ideas and Frank agreed to go along with them as long as his rules were not violated. He was the only one to fuck Lori's pussy, that he would not do anything a queer would do and I was his best friend so it had to be my choice to do this. His last condition was that nobody outside of the four of us could be involved in actual sex, because of safety.

It took them over an hour to lay out the story and remind me of everything that they did to get me to this point. Lori had continued to play with my dick and keep me close to orgasm, but always stopped before I could cum. Frank's dick was hard and sticking out directly in front of my face. I could not forget for a second how inadequate my dick was while Sarah played with a real man's cock. Sarah explained that if I would agree to the following rules, then we would go on having kinky sex and if I refused we would go back to the way it was before.

1. Frank would fuck both Lori's and Sarah's pussy on a regular basis.

2. I would not be able to fuck Lori's or Sarah's pussy, because Frank would not share Lori's pussy with anybody and Sarah could not get satisfaction from my little dick once Frank broke her pussy in.

3. I would be Sarah's and Lori's pussy slave and Lori would in exchange, quit asking Frank to eat her pussy. I would eat Sarah's pussy anytime she wanted me to, and I would get to eat Lori's pussy when Sarah gave me permission. I was to eagerly eat their pussies after Frank was done fucking them and was to clean up any sperm Frank or I shot when the girls commanded.

4. I was to keep Sarah's and Lori's asshole sensitive by oral worship and train them to orgasm from my tongue fucking. (This is important for rule 5 below they explained.)

5. My only option for fucking was to be penetration of Sarah or Lori in the ass. Frank could not have anal sex with the girls because of his big dick and in return for ruining Sarah's pussy for my small dick, I could fuck Lori in the ass with Frank's permission. It was fair they said, because Frank got both pussies and I got both assholes. Each of got what we could use best with our individual cocks.

5a) Frank would receive several blowjobs from me each month with Sarah's permission and in return, I would be allowed to cum in Sarah's ass an equal number of times. I would not get to climax more times than Sarah felt appropriate to maintain my motivation to serve as their sexual slave.

5b) Frank would have anal intercourse with me about once a month. That would give my ass time to recover and thus, maintain the tightness of my asshole for his pleasure. I would be encouraged to learn to cum from having my ass fucked by Frank as a second form of sexual release. In return for taking Frank's dick in my ass, I would get to fuck Lori in her ass an equal number of times. However, if I came from Frank fucking me in the ass, I would forfeit my penetration of Lori's ass (Frank's idea).

1. Frank was not homosexual and he would not touch me sexually in anyway, but if I liked being a sissy slut, he would go along with my humiliation.

2. To keep me motivated as a sex slave, I would continue my chastity training under Sarah's control. I would be kept sexually stimulated every day and denied sexual relief without permission. I would be given some sexual relief, but not enough to blunt my desire to serve as Sarah's sissy slave. My dick would be kept in the KTB device when I was out of Sarah's direct control and in the chastity trainer at night.

The discussion had my mind spinning as Lori kept teasing my little dick in my petticoats. I would have balls to maintain my sex drive and be denied my cock to obtain release. If the sultans had removed dicks instead of balls, their harem eunuchs would have gone mad, female pussy everywhere with an intact desire for sex and no chance for release without a cock. That was what they were purposing for me. I would become a dickless eunuch for Frank's pussy harem and my balls would keep me in a constant state of sexual frustration. Sarah would drive me mad with desire, use me as her pussy slave, cuckold me with Frank's big cock, end forever my fucking of a woman's pussy and give me a life of sexual humiliation with Frank and Lori's help.

Sarah again explained that if I said no, then none of us would ever speak about the agreement again.

"I think that the three of you get more out of this than I do!" I pointed out.

"You may be right, but I think we each get our needs met by this agreement. Lori gets oral sex and a gentle lover on top of Frank's big dick that she loves but wears her out. I get to fuck the big cock I always wanted and still get to have you perform oral sex on my pussy and asshole as much as I like. I like having you as my sissy sex slave. Frank gets enough pussy to satisfy his sexual overdrive and an occasional blowjob or anal sex from a sissy slut just like when he was in juvenile prison. Sissy Jacquelyn gets what she wants deep down. I have watched you the last 16 days since our bet and you are perfect for this life. You get off on being forced to wear sissy clothes and you are completely turned on by the humiliation. You can almost cum from licking my pussy after Frank fucks my pussy and his cum slides past your lips. When I make you eat your own sperm after you cum, your cock stays hard and the look of lust on your face when I made you lick your own sperm off Frank's cock was priceless. You are into being Sissy Jacquelyn more that I thought possible, I believe it is your sexual destiny."

"If you end this tonight Jack, you will always know in your heart that you made a mistake. My pussy will recover a lot in a few weeks and I will be able to feel your little dick again, but you will have denied me the pleasure I need sexually. I was never completely satisfied with your little cock before and now I could never be satisfied with you after having a real man's cock like Frank's in my pussy. Your little dick is just that, little. It may be average compared to other men, but to me it is just inadequate and Frank has made it impossible for me to enjoy fucking you. Lori and Frank will go on having sex problems to the point that it could easily ruin their marriage and you can help save their marriage. You will have an itch that you can't reach if you kill Sissy Jacquelyn tonight and deny yourself a life as my sissy slut. Take it or leave it, but tonight you have to make your choice, Jack or Sissy Jacquelyn!"

After a few seconds I gave my answer...

Epilogue

I made my decision that night to live as Sissy Jacquelyn. It was a very hard decision for me to give up my wife's pussy to Frank's cock. I would never have normal sex with a woman again if we stayed with this relationship. My little dick was never going to be wrapped in warm, wet pussy again. I can almost cry if I think about it, so I don't unless Sarah makes me remember as part of keeping me sexually tense.

"Does Sissy Jacquelyn want to stick her little dick in my pussy? I bet you wish my pussy wasn't so stretched out and that you were still man enough to fuck your own wife! My pussy gets more dick than it needs from Frank's monster and I don't miss your little dick at all. I do miss the look of ecstasy you used to get when you slid your little cock into my hot pussy. Maybe I will let you have sex again someday, but I don't think it will be with me. I could bring home one of the divorced girls from work who won't know cock size any better than a teenager and let them have fun with your little dick. They would be happy for the attention and you would get to put your dick in a warm pussy again. No, that would never workout, you might decide to try going back to living as a man and I would not get to fuck Frank's dick anymore. I guess your little dick will just be a big clit on a sissy slut."

Sarah drives me crazy with lust when she talks about getting my dick into a warm wet pussy. I miss that feeling terribly and think about pussy constantly. I long for the feeling of my dick sliding in and out of Sarah's pussy, but don't want to give up serving as Sarah's sex slave just to get pussy. I have more sex than ever and I am kept constantly horny and respond to Sarah's sexual needs instantly. I lick her pussy as much as Sarah wants and that serves to make me desire her all the more. The sexual frustration builds for days and then I have the best orgasms of my life when I finally get to cum.

I can not cheat on Sarah even if I wanted too, she keeps my cock locked up all the time. The chastity trainer at night and the Kali's Teeth Bracelet (KTB) at work. If I start to get horny, the KTB devise painfully grips my cock and prevents me from obtaining an erection. I have a permanent case of "blue-balls" and I live to give sexual pleasure in the hope of obtaining my own climax. You can not imagine how crazy with lust you can get until your mistress takes away your cock. Sarah controls my erections and uses her sexual power to keep me focused on her pleasure. The silk cloths and forced feminization treatment by Sarah and Lori coupled with spending so much time licking pussy makes my sexual fulfillment the driving force in my life. Sarah makes sure that I always want more and that I remain motivated to serve.

Lori has made me several lacing corsets now and Sarah has decided to add diet and targeted exercises to my life. With Lori's tighter corsets and Sarah's diet and exercise plan, my body is taking on a more female shape. The have kept me in the corset so much that my stomach muscles are starting to lose strength and I feel a strain when I am out of the tight corset. They have my waist down nearly 4 inches now and Sarah thinks I will get down 1 or 2 more inches. I will soon have to start wearing a corset without breast cups under my business suit and male clothes for support.

Sarah had me purchase two small plungers for sinks (plumber's helpers) and remove the handles. She will make wear the suction cups on my tits for over an hour to stretch them out. Just before I remove the plungers, Sarah wraps twine tightly around the base of each pulled out tit so that they will protrude for several hours. When she has me take off the plungers, I have nice "A" cup breasts. The plungers leave a red ring around my little tits that won't fade for a day or more. The treatment makes my little nipples very hard and tender. The twine helps keeps my "tits" swelled out, but is not tight enough to cause damage. When Sarah finishes giving my tits a workout and removes the twine, my body will shake from the stimulation of the renewed blood flow.

A few weeks ago Sarah added suction tubes from an old snake bite kit. The small tubes have an opening about the size of a fingertip. I have spent hours with the devices attached to my nipples so they will stretch out for Sarah's amusement. Now my breasts and nipples are quite sensitive and I can hardly stand having to wear a starched dress shirt even with a silk undershirt.

Sarah wants me to be embarrassed to go without a shirt because of my developing tits and nipples, but does not want me to have hormone treatment. She wants my hormones to be 100% male so that my sexual frustration will be max. I have both nipples pierced and Sarah likes to play with the rings in my nipples to torture them along with the suction cup treatment. My nipples have grown enough that the nipple rings have been replaced 2 times.

Lori will lock my hands behind my back with the cuffs and remove the KTB from my dick so that it can get hard. Lori then licks and sucks my nipples until they are starting to get very sensitive. While she sucks on one nipple, she gently rolls and pulls the other nipple with her fingers. I get so turned on that I try to hump my dick against the air to find some direct stimulation and obtain some relief. Lori says that it is her goal to make me cum by just sucking my nipples. I think that she will soon reach her goal. When Lori is done sucking my nipples, she likes to hang a small bell from each nipple ring so that she can keep track of me when I am at her house.

Sarah is planning to have my dick tattooed with the words "Sarah's Slave" and "Sissy Jacquelyn" along the sides of my erect cock. She will take me to the tattoo parlor, put me in a cock ring so I can't get limp again and get me hard. She will have the words added to my dick so that I will always know my place as Sarah's sissy slave. It will show very nicely when I am erect, but will be unreadable when my little dick is flaccid. With the KTB device installed, nobody will read my tattoo without Sarah's permission, but anytime I am able to get an erection, everyone will know who owns me. Sarah is also thinking about having my dick pierced horizontally through the head. She will have a D-ring installed so she can attach a leash to the head of my dick. She thinks it would be great fun to cuff my hands behind my back and leash me to the foot of the bed while she fucks Frank. She can also pull my dick back between my legs and tie it to my corset when she want's a smooth line in my panties. It should be much faster than using the tape to hide my little dick. She thinks that such a piercing will take months to develop enough that she can use it with a leash.

The girls like to play "Barbie" with me and dress me up in all kinds of clothes. I have been made into everything from a pre-teen girl in short skirt and knee socks to a slut streetwalker who has on whorish makeup. I now do my own nails and makeup except for special occasions when Sarah takes me to Pauline's. Sarah likes to make me beg to lick her pussy after Frank fucks her and Lori likes me to lick her pussy before Frank fucks her and tongue fuck her ass after he has cum in her pussy and I have cleaned up that mess. I lick up every load of sperm Frank gives up when he fucks Sarah and about half of his loads deposited in Lori and I always eat every drop of sperm that I produce. Most of the time I am so horny that eating the sperm is just part of the experience. But, when I have just climaxed, having to eat Frank's sperm still makes me queasy. I have given up all my hobbies and spend all my non-work time being a sissy slut sex slave for Sarah, Frank and Lori.

Frank has gotten into humiliating me more than the girls do. It is now over five months since I became Sissy Jacquelyn permanently and I have not put my little dick into Lori's ass once in that time. Since I only get to fuck Lori when Frank fucks my ass and without me having a climax from his fucking, he has been able toy with me sexually. Frank's big dick has made me cum each time before he climaxes and I must wait the next 3 or 4 weeks before I get my next chance at Lori's ass. His big cock fills my ass completely and my prostate is stimulated to a point that I can't hold back my orgasm. He gets very excited making me beg to give him a blowjob so that I can earn a climax in Sarah's asshole. It is always humiliating, but I am kept in such a state of excitement that I beg for the humiliation with little prompting.

Frank tortures me for a week in advance of my ass reaming by not letting me give him a blowjob no matter how much I beg. He comes over to our house and fucks Sarah in my bed. I have to get Sarah ready for his big cock by licking her to several orgasms and then Frank has me suck his dick to prepare him for fucking Sarah. I beg Frank for a taste of his cock and I promise to make his dick feel good with my lips and long nails. I am very horny and I know if I can make Frank cum in my mouth, I get to fuck Sarah in the ass. Frank lets me bring him close and then he pulls out of my mouth.

"I can't believe how bad you are at sucking cock! If you were any good at giving blowjobs, you would make me cum in your mouth. Everybody knows that real men like blowjobs as much or better than pussy and you can't even make me cum in your mouth. I guess you just don't want to cum bad enough. Perhaps if you learned to give better blowjobs you would get to cum more often. I just can't pass up Sarah's sweet pussy for your poor effort at sucking my cock!"

My whole body was sexually charged and I get no release again that night. Frank then takes Sarah with his huge cock and has her describe for me how good it feels to have a real cock in her pussy. He cuckolds me in my own bed with me watching on my knees, hands cuffed behind my back and wishing I could suck cock better. When Frank finishes he gives one more chance to make him cum with my lips as I clean his sperm and Lori's pussy juice from his shaft. Frank pulls out of my mouth before he can get fully hard and tells me to do better in the future if I ever want to put my little dick in Sarah's bottom again. Frank goes home to fuck Lori and I spend the next hour or so licking Sarah's pussy and asshole. Sarah never lets me quit until there is no trace of Frank's sperm in her pussy. The whole time my dick remains flaccid in the KTB device.

Sarah's says that her pussy is ruined for small cocks like mine and her pussy is so stretched out that she has quit using tampons during her period. A few weeks ago, Sarah had me suck Frank to get him hard and then she had me make a mold of his big cock with this fast setting compound. Then she sent the mold off to a small plastic shop that makes sex toys as one of their product lines. Sarah has received back an assortment of dildos, which are perfect replicas of Frank's cock. The various versions of Frank's dick are a constant reminder to me of how much difference there is between our cocks. Sarah loves to hold the dildo up next to my dick when I am hard and ask me if I can deny her the pleasure of a real cock.

The one I hate the most is part of a mouth gag. One end is the head of Frank's cock and slips into my mouth. The part in my mouth is about 1/2 as long as Frank's real dick, but just as big around. The short end is held in my mouth and fastened like a ball-gag with a leather strap. The other end juts out from my lips with a complete replica of Frank's hard dick, all 10 or so inches. Sarah will make me fuck her pussy with this gag in my mouth. I give her pleasure as she talks about how small my own dick is and that it just won't fill her pussy up enough to give her pleasure. Now with my mouth dick I get to fuck her all night and practice licking Frank's dick at the same time to please Sarah. I feel this terrible humiliation without end and my sexual needs builds a frenzied desire to give Sarah satisfaction. The smell of her pussy is all over my face as her juice flows out. She loves to have me lie down and she slides her pussy up and down until her pussy can't take anymore stimulation. When she is finished her pussy juice has run down the shaft of the fake dick and into my mouth and nose. I am overwhelmed with her pussy and I have not even been able to directly touch it. When she is satisfied, Sarah has me clean the dick gag with my mouth and put it away for my next humiliation.

The night of my ass reaming by Frank arrives after he has denied me sexual release for over a week. I report to Frank after giving myself enemas until my ass is perfectly clean. Only then can I go over to Frank and Lori's bedroom and serve as their sex slave. Frank has me use my mouth to get Lori ready and his dick hard. He then fucks Lori to a big climax with me watching while I kneel at the foot of the bed. When he pulls out, I must beg to clean his dick and get it hard for my ass fucking.

"Please Master Frank, let Sissy Jacquelyn lick your dick and make it hard so you can fuck my sissy cunt! Sissy Jacquelyn needs your cock in her ass badly because she is so horny! Please let me make your big dick hard again!"

After Frank thinks I have humiliated myself enough to earn his dick, he lets me use my mouth to clean his sperm off his cock.

When Frank is ready to go again, he gives me Sarah's key and lets me removes my KTB device. I get an erection immediately and put a condom on my small, hard dick to catch my sperm. I kneel between Lori's legs so I can lick her pussy while Frank fills my asshole with his cock. Frank's cum is running out of Lori's wide-open pussy and Frank is working my ass for all he is worth. After several days of having no release, I eat Lori's pussy like a madman. Frank's cum is draining out of her pussy very fast, but I drink it down like nectar.

I am now stretched to the point that Frank has only minor trouble getting his dick into my sissy asshole. Frank has denied me climax for over a week while he and the girls have sexually tormented me. Frank has just cum in Lori's pussy and he has a very unfair advantage in our perverted race to see who will cum first. While Frank pumps his big dick into my ass, I rhythmically squeeze my asshole to give his dick the best ride I can. I am desperate to fuck Lori, but Frank seems determined to deny my access to Lori's asshole. It is not much of a contest and Frank makes me cum very quickly with his big cock. During my ass fucking, Frank taunts me about being such a big sissy slut. When I start to cum, my asshole spasms wildly on Frank's cock and he picks up his pace to fuck my faster, which makes my dick spurt more sperm into the condom. Frank isn't done and he continues to fuck me for several minutes until he has his second climax. I continue to lick Lori's pussy as she pulls my mouth tightly to her pussy. By the time Frank is done, my asshole is ruined for several days and I won't be able to sit down comfortably for a week. Frank points out that I prefer to have my ass reamed over getting to fuck the lovely Lori.

"I can't believe you like to have your ass fucked so much that you can't wait long enough for your orgasm to earn a chance to put your little dick in Lori's beautiful ass. Lori was looking forward to having you fuck her, but you are undisciplined!"

When Frank is done, he pulls out of me and has me put a butt plug in my ass to hold his sperm in to show Sarah later. My hole is stretched out so much from his fucking that the plug slides in easily. Frank has Lori lay over the back of the armchair and then I am instructed to empty my full condom on her ass. I am instructed to pour it out at the top of her crack and let it run down to her asshole. Frank makes me spread my sperm over Lori's entire butt with just the tip of my tongue. When Frank is satisfied that my sperm is covering both butt cheeks and her asshole adequately, he tells me to clean up my mess. I make love to Lori's ass and tongue fuck her asshole to give her another orgasm. Frank makes me keep licking Lori's ass until he is convinced that I have cleaned up every drop of my own sperm.

When I get home, I am forced tell Sarah about my night and I have to lick her to several orgasms. When she is satisfied, I am allowed to remove my butt plug and clean up. I am put back into my chastity trainer and we go to bed. Tomorrow Frank will make me beg to suck his dick again.

I have learned to love my perverted life as Sissy Jacquelyn. Sarah keeps me sexually aroused each day and by denying me climax keeps me in a constant state of sexual frustration. This keeps me motivated to serve her well as a sissy slave. Sarah has never had so many orgasms and she loves her role as my mistress. She is always looking for new ways to tease me sexually and continue my denial. I must make Frank cum with my lips or my ass/cunt to earn any relief. Frank makes me beg to have his dick in my mouth or asshole and he takes it as a challenge to keep me from having my turn with Lori's ass.

The girls have great fun dressing me up in various costumes and then making me beg to lick their pussies. I have gotten very good at tongue fucking the girl's assholes and they are now very sensitive to my anal worship. Lori says that she likes me to lick her ass as much as her pussy. She says it gives her a sense of power and helps make up for all the times her uncle made her lick his cock.

The girls make me dress in the French Maids uniform and serve their girlfriends at showers and other "girl's night" get-togethers. At most parties, the Girls compete for a prize of having Sissy Jacquelyn lick them to orgasm. I am blindfolded and my wrists are cuffed to my ankles. Sarah sets me in my kneeling position in front of a large armchair in the guest bedroom and I wait for the winner to sit down in front of my face for tongue worship. The winning woman gets to have their pussy or ass licked to orgasm for up to an hour. Sarah never tells me whom won or who I got to lick. For a couple of baby showers, I licked the pregnant women who had cut out intercourse during the last trimester of the pregnancy (I could tell who it was those times). One of the mothers-to-be said that she now knew that she had never had a real orgasm before my oral worship. Sarah told her that after the baby was born, I would be available to teach her how to orgasm every time she had sex. Sarah was very proud of me that night and let me fuck her in the ass without first making Frank cum with my lips. The girls don't tell Frank that they make me lick these women's pussies and assholes. Sarah is trying to get the other women to take charge of their own husbands and I serve as a living example of what can be accomplished when a woman takes charge of a man.

Some of the women in this small group are starting to seriously consider feminizing their own husbands. There is a lot of discussion of technique and Sarah uses me as a model for demonstrations. I have been teased to the point of orgasm by several different hands during a "Girls" night, but never allowed to climax (it would defeat the purpose of the demonstration). Sarah assures the girls that a man who is sexually frustrated will do most anything to get an orgasm.

It is a crazy perverted life, but I chose this life of my own free will. I get more and better sex than I got before becoming Sissy Jacquelyn. By my mental calculations, I have a few more orgasms over a month and I have constant sexual stimulation driving me crazy for more sex. I don't get to have a sperm-shooting climax as often, but I have a more satisfying orgasm when I finally earn my release. During my sexual service, I often have many small orgasms without ejaculations or even erections. They are nice, but do not give me the release my body demands. I am a drug addict and my drug is being allowed to orgasm. The satin and silk provided by Sarah and Lori keep my hairless skin stimulated each waking moment of my day. If I think about eating Frank's cock, it revolts me, but it also excites me more than straight sex does. I know that I am not a true bisexual, but a sex slave to Sarah and I get off on being forced to perform on Frank. If Sarah didn't "make me", I would never suck Frank's cock!

I do not wish to go back to a normal male life and Lori, Frank and Sarah tell me that they have never been happier than now. As Sarah predicted, we all get what we want and need from having Sissy Jacquelyn in our lives! I am Sissy Jacquelyn forever!

I am starting my 6th month of sexual slavery for Mistress Sarah and she has given me unexpected news. Both Sarah and Lori have decided that Frank is not living up to his obligations in the relationship. He is, in their mind "abusing" Sissy Jacquelyn. Sarah feels very strongly that a Master or Mistress must give back to the slave equally for what they receive. It is not just a matter of taking pleasure from the slave; it is a big responsibility to "Top" a slave without abusing the dynamics of the relationship. I have not complained about Frank, but Sarah's comments make a lot of sense.

"Lori and I have decided to take Frank's dick away from him until he learns to be a more responsible Master. He is using his position to maximize his pleasure without regard for the sacrifice that you make to the master slave relationship. Until Frank knows what it is like to be the bottom in a Domination/Submission relationship, he will fail to be a good Master."

I didn't know where this was going, but I liked the sound of things to come.

"Tonight when Frank is sleeping, Lori will place a KTB on Frank's dick. During the night, he will try to get an erection and the pain will wake him. Lori will not remove the KTB until Frank is installed in a Chastity Trainer like yours. Lori will keep him locked up until he is willing to serve as a slave."

"Whose Slave?" I asked.

"I would say he must learn to serve as your slave. You are my slave and now Frank is beneath you. You have earned the privilege of being the head slave and Frank is just starting to learn his place."

My world was spinning around me again. I had gotten used to my new life as Sissy Jacquelyn and now the whole dynamic was changing again. Frank was going to learn to serve as a slave if he was going to be a master again.

"Frank will be given the choice of becoming your slave and earning his way back to being a Master or the current relationship ends forever. Frank likes having 2 pussies to fuck and a sissy slave to give him blowjobs, so he has a lot to lose. I just could not let him take advantage of you any longer."

Sarah had me kneel between her legs and start licking her pussy as she explained the situation to me.

"I want Frank to beg to serve you. He must be willing to suck your dick if he expects you to suck his dick. He must learn to give pleasure as well as taking his own pleasure. He thinks that having a big dick is good enough and that we all should be grateful for just being allowed to enjoy his cock during sex. He has gotten lazy and mean spirited. This can not be tolerated."

The plan was for Lori and Sarah to cut Frank off from orgasms and have him earn a climax by first learning to lick Lori's pussy. After he becomes a good pussy eater with my coaching, I would next teach him to tongue fuck Lori's asshole. It would be my job to demonstrate technique and criticize his tongue work until he can give Lori pleasure with just his mouth. Each time Lori is satisfied with Frank's progress, he earns an orgasm, he will be allowed 3 minutes out of the Chastity Trainer or KTB device to masturbate. If he doesn't cum in the allotted time, he will remain frustrated and start over to earn a climax.

During the next phase, Frank would have to learn to eat the sperm he shoots. Lori will have him wear a condom to masturbate and then give Frank the choice to cleaning up his sperm right away or saving it in the refrigerator till later. Under no circumstances, will he get his next orgasm without eating the sperm he has already produced. I will be given the job of helping Frank spread his sperm over Lori's ass with his tongue and then licking it back off just as Frank supervised me. The goal is to learn that eating sperm leads to his ultimate pleasure.

Eventually, Sarah intended to have Frank begging to suck my dick. If he could not learn to serve me, he could not expect to be served.

"Frank is not naturally a "Sub" and it will not be easy for him to accept being the bottom in a D/S relationship. Once he has learned his lesson, he will naturally return to being a Master. Sissy Jacquelyn you are a natural Sub and you will always enjoy that role more than the more dominant one. You are going to have to learn how to be the Top with Frank without making the same mistakes he made toward you."

I was excited by the idea of having Frank beg to suck my dick. I wanted to see the look of humiliation on his face when he first took my dick between his lips. It would be a great payback for the humiliation he forced on me without compassion or understanding. I was going to have to try hard not to gloat!

"My goal is to have both men in a 69 cock sucking race to see who can make the other cum first. You will have your hands tied to your ankles and will have to get the silk panties off the other slave's dick with your mouth. Once the slave frees the dick, they must use their lips and tongue to make the opponent cum first. The winner gets to have his way with the wife of the other slave and the loserr gets to clean up the pussy (if Frank wins) or asshole (when I win) after the winner cums in his wife."

I can clearly see Frank licking my sperm from Lori's asshole as I continue to lick Sarah to a third or forth orgasm. I don't know what Frank will choose, but I sure hope he decides to stick with our 2 couple relationship. He is hooked on having 2 pussies to fuck and he likes getting the blowjobs a lot. He will think with his dick and very soon he will be addicted to orgasm. He will do things he never dreamed possible just to get his dick back long enough to cum. Frank will beg to suck my dick in a month or less. Well that is my prediction for his future and I can hardly wait.

----------------------- The end ------------------------------------

This is the end of the epilogue, of the story "Getting Nailed"

I tried to add some good suggestions from reader feedback on the posted 7 chapters. If you have suggestions or other feedback, please respond to me by e-mail << j_birdman@hotmail.com >>. I only have one more adventure for Jack and Sarah in my head and your feedback might be just the catalyst to get me going on that story or a new suggested adventure.

J. Birdman