The Apartment Where It Happened.
(Authoress Note: All disclaimers regarding characters, age appropriateness etc. are in effect. I really advise anyone under 21 do not read my stories. It takes a certain degree of maturity to enjoy this story. Don't write a review if you don't like the theme of the story. That's just childish. But criticism is always good and helps me.
Chapter 1: Who Am I
When does one know they are a sissy? I'm not talking gay. I'm talking submissive sissy.
It began at a young age. I was staying at my uncle's house and one of my cousins was a girl about 3 years older than me. I was 11. When everyone was out one day I went into her room and rummaged through her drawers. I found a pair of white satin panties. Touching them filled my senses. I tried them on. It was such a sexy feeling.
Of course, I put them back in the drawer and no I didn't masturbate. But the thought of those panties never left me.
When I was 13 in 8th grade there were three tough boys who had been left back twice so they were 15 years old. These were some bad boys and somehow, I was attracted to them. I ended up in the park with them one day and the leader told me to open my mouth. He spat into my mouth and told me to swallow. I did and they laughed.
We all graduated two weeks later so I never saw them again. But I've often thought about what happened over the years.
I went to an all-boys Catholic high school and went to the dances with the girls schools. Those years I tried to not think about my earlier feelings. And so, I graduated and went on to college.
My best friend and I lived in an apartment building on different floors. We didn't go to college together. We both had girlfriends on an off. One day I was in his bedroom talking and he said something like, "if you suck my cock I'll suck yours."
I wasn't thinking of myself as a sissy then but more of a curiosity. Before I said yes I had him promise he wouldn't cum in my mouth. Of course, he did and reflexively I spit it out. He apologized. And after spitting his cum out I wasn't turned on then, so he didn't reciprocate.
John was bigger and stronger than me. I think he was 6'2". Dark brown hair with eyes of dark coffee and topaz mixed together. Back then he probably weighed 185 lbs. and was quite ripped since he worked out at the gym three days a week.
Over the next few years between girlfriends several things happened. This was back when there were porno parlors where you'd go to watch porn, buy porn magazines etc. The old New York 42nd Street. Not the Disneyland of today.
John loved going down there and I more or less tagged along. Turns out I began to watch tranny porn and would get excited beating off when I was home alone.
We had this business together and so we got an apartment together and this started the next stage.
To submit I needed something which I felt would exonerate my behavior. That turned out to be strip poker. The loser would have to do whatever the winner wanted for some period decided beforehand.
The first time I tried to win but I lost. Subsequently I would lose on purpose. I'd throw away good cards to create a terrible hand. This went on for about a month until John got a girlfriend and moved out.
I got a girlfriend shortly after and then everything changed.
After living with my girlfriend for the past six month she had just left a week ago for a model job in Europe which would last for the next two months.
John came over since his girlfriend was away for the weekend. And we decided instead of playing Strip Poker we would simply draw a card. High Card wins. One piece of clothing would come off. First one naked was the sub for the next 24 hours and had to do anything the winner asked.
We drew a few cards, and we had both won and lost. I had lost my shirt and socks. He had lost a bit more. It looked like I'd be the winner till the next card I lost and he said, "take off your underwear." Which would mean I'd be naked and thus lose.
When I said he had to pick my belt first he reminded me we hadn't said which layer had to come off. So, I lost and was naked.
Then John asked if Janet had left any of her clothes and I said yes. I was a skinny 5'6" and she was 5'7". I weighed in at around 145 and Janet fluctuated between 135 and 140.
Without taking forever to explain this he told me to put on an entire outfit. Bra, panties, skirt, blouse, stockings. Lipstick. Perfume. And even a pair of heels. As weird as it seems I fit her shoes. Janet and I used to laugh about that. Janet's skirt was beige and about four inches above the knee. I was amazed it fit but Janet was a full girl, and I was a skinny guy. The stockings were nude color, and the blouse was a simple frilly white. The bra and panties were black as were the heels. I'm sure I looked ridiculous but I couldn't see the outfit I could only feel the panties and bra. I knew I was wearing a skirt.
John asked if there was nail polish. I said yes. And he said to do my fingers and toes. The only color she had was a bright red like her lipstick.
I was so nervous when I stepped out dressed up. John said for the next 24 hours I would be his girlfriend, Lauren. John had a beard. I was clean shaven. The stockings covered the slight amount of hair on my legs and my arms were never hairy. And my hair was a very light platinum blond so you wouldn't really even notice. Janet, a brunette, was a bit jealous. She said a girl with hair like mine would shine in makeup.
At that time in my life my hair was long but not cut as a girl but John had me turn around and parted my hair in the middle and created two sort of pigtails he tied with some pink ribbon. I have no idea where he found that.
He told me to sit down next to him. I did. He put his arm around me and pulled me close. His eyes focused like a lion on his prey.
It was strange seeing my fingernails painted red. My toenails were also but they were hidden under the stockings and heels I wore. John said I should act and try to sound like a girl. I was looking right in his those commanding eyes...sitting there....knowing I was getting an erection when he suddenly and forcefully not only kissed me but stuck his tongue in my mouth.
I nearly fainted. His tongue probed my mouth licking the roof, my tongue and my lips. His saliva dripping into my throat. Captured prey.
He said, as his girlfriend to put my hand on his crotch. Which I did. I kidded myself it was because I had lost the bet, but it was the submissive me taking center stage.
His cock felt hard and warm through the pants.
"Lauren, unzip me and suck my cock like a good girl," John commanded.
My fingers unzipped his fly and pulled his cock through the hole in his underwear. He was a good 8 inches hard. I knew this from before. When I'm hard I'm about 5 inches though I like to think I'm 5 ½ ". He is also thicker than I am.
His hand went to the back of my head, and he slowly move my mouth towards his erection. I could see some glistening at the tip of his cock.
"Lauren, you will not only suck my cock, but I will cum your mouth, and you will swallow it like a good girl."
I was in a state of shock as my mouth surrounded his engorged cock and I, now Lauren, was giving a blow job.
When he came I realized his load was much thicker and more copious then my own. As he took his hand off the back of my head he said, "Show me your cum filled mouth Lauren."
Embarrassed, shaking, feeling things I wasn't sure of I lifted my head, opened my mouth so he could look at his seed coating my tongue.
"Now swallow and lick you lips."
As I swallowed, I thought of his cum filling my body.
"Make me a gin and tonic and get yourself a little girly drink. And don't touch yourself. If you do, you'll get a spanking."
In the background from a mix tape was Roberta Flack singing "Killing me Softly."
From the little bar I mixed his drink and made one of Janet's drinks, a Cosmopolitan (vodka, triple sec, cranberry juice and a lime). I even put a little umbrella in it as I would for Janet.
I returned to the sofa with both drinks and went to hand John his.
"No, Lauren. Go back and put your drink down. Put mine on a tray with a napkin. Bring it over here. Bend down and offer it to me."
Submission was like an aphrodisiac.
With his drink on a tray, I returned. Bent at the waist one of John's hands swept behind me to feel my ass and the other picked up his drink.
"Put on a fresh coat of lipstick and then come sit next to me."
When I finally sat next to him with my Cosmo he told me to drink it in sips. I saw my lipstick on the rim. John had his hand on my thigh with a couple of fingers under my skirt.
John pulled a joint from his shirt pocket, handed me the lighter and I knew he expected me to light it for him. I did.
It was very strong pot. The liquor and the pot. Me as a girl. But whatever it was my mind was swooning.
"The next 24 hours you will be my docile girlfriend. You'll make dinner. You'll clean up. We will sleep together and tomorrow at 5pm you can turn back into David."
"Remember, if you touch your penis, I will spank you. If you forget to act like the submissive girl, you are, I'll spank you. You will freshen you makeup as necessary and not wear any of Janet's pants. Now thank me in your girly voice for cumming in your mouth."
I was both horrified and excited by the thoughts of the next 23 hours.
John finished his drink and had me get him another while I slowly sipped mine. His hand inched up under my skirt and he began rubbing my panties as if I had a pussy under my panties and not an erect cock.
Just as I was feeling I might cum, John took an ice cube from his drink and dropped it inside my panties. My cock deflated.
"No matter what I do you will not cum until I give you permission. Do you understand?"
"Yes."
It's "Yes Sir," John stated.
I accidently lisped "Yeth Sir."
"I like the lisp. Use it every time you talk. And don't talk unless given permission. I don't care what the reason is. Even if you need to use the bathroom. Understood?"
"Yeth Sir," I squeaked.
I was too far gone to do anything but obey. I was Lauren. There was no David.
I made a simple dinner. Grilled Chicken breast, Pasta and a Salad.
After I served John, I was going to get a plate for myself, but John said he'd tell me when I could eat. I couldn't believe the dynamic but I was Lauren till 5pm the next day.
"Go take a bath and if Janet has some bubble bath use that. Shave you legs, arms, armpits and face. Also use Janet's curler to curl your hair. You can straighten it later.
Although I thought about objecting I was also thinking about my cousin's panties as well as the porn videos I had seen. First I ran a shower as I shaved my legs, arms, armpits etc. I had seen Janet do it so I figured I knew what to do. Janet had an electric razor. I think it was Schick, but I don't remember.
"And shave your pussy leaving just a landing strip," John called out.
I have blond pubic hair lighter than the hair on my head and I didn't have a large bush so it was fairly easy to do except for the landing strip. By the time I was done I don't think it was ¾ of an inch wide and an inch long since I had made several mistakes.
I must have been nearly an hour in the bathroom when John came to the door and said, `I've laid out what I want you to wear on the bed."
When I dried off, I went into the bedroom. John had put Janet's little black dress which flared at the waist. There was also clip on earrings, a necklace of fake pearls since Janet had taken the good set with her. The tube of fuck me red lipstick was next to the black bra and panties I had left when I went to the bathroom.
"Try to do your eyes and makeup," John said.
What he didn't know was I knew how to apply makeup since I had been in the drama club at college.
Finally dressed, hungry, horny and looking very girly I came out to the living room. John was nearly naked. Only wearing a white pair of cotton jockeys.
I felt my cock twitch and remember having swallowed his cum just a few hours ago. I reached down to move my cock and John said, "I told you. Now come here for a spanking."
Now you may be wondering how were getting here this fast, but you need to remember we had been going to porn parlors for a while, playing strip poker, masturbating each other and a few times I had given him a blow job but I always spit his cum out.
Once he pulled out and splattered my face with his cum. It was so icky and his loads were thick and plenty.
Walking over to him he patted his knee and apprehensively I lay down.
He spanked me hard but only about 10 strokes saying, "Only I can touch your clit."
I can't explain my feelings exactly but in a way I must have wanted to be spanked since I had a few more spankings over the course of 24 hours.
After spanking me, I rubbed my ass but John again said, "No, never touch. It is suppose to sting as a reminder of your place."
We danced to Etta James singing "At Last." Pulling me close he French tongued me again. His palms encasing my ass cheeks as his cock, through his shorts, ground into my black satin covered belly. My arms were around his neck like Janet would do when we slowed dance. My aroma was all feminine his was all testosterone. I wasn't sure who I was. I didn't feel gay. But at the same time, I didn't feel the same way my girlfriend usually was. For me the eroticism lasted as if someone had rubbed a kilo of erotic cocaine on me. Janet wanted to cuddle after sex and usually talk.
But John didn't want to talk, and I couldn't talk unless he gave permission. And even if I could I think I would have only been able to stammer and mumble.
When the dance ended, we sat down on the sofa. His cock was so big the head poked out of the elastic band. My blue eyes were transfixed. We kissed and I rubbed his cock with my hand.
"Lauren, you have one hole. It's both a pussy and an asshole. You have a nice clit. From now on you will orgasm like a girl by having your clit palmed and rubbed. No hand around it. You will always refer to your hole as your pussy unless instructed otherwise. And you will always think of your clit as only a clit."
His hands probed my body. At one point he put his thumb and forefinger around my nipple and played with it till it turned hard. I was amazed by the feeling.
Later, when I was making him coffee I had to pee so badly I was rubbing my legs together. John looked at me amused but before I had an accident he asked, "Do you need to pee?"
I answered, "Yeth Sir."
John instructed me to say, "Lauren pee-pee Daddy, pwease?" And to use a girly singing voice ending with an upscale pleading on pwease.
I used the toilet like a girl, pulling down my panties my red nails a reminder I was not a man, hiking up my dress and sitting with my clit tight between my legs. John watched. He was really enjoying his dominance. I wondered if he was like this with Cecilia his girlfriend.
"Always wipe front to back Lauren," John said. As we smoked more dope, I was feeling the urge for munchies but John seemed not to care nor offered me a chance to ask.
At around 11pm we ended up in the bedroom. John pushed me down on the bed, hiked my skirt, pulled down the back of my panties leaving my clit still covered. Then he lowered his jockeys and after lubing me he fucked me hard. As he thrusted in and out of me, I rubbed back and forth on the bed, my clit hard. John spanked my ass several times and I came in my panties just as John filled my hole (my pussy) with a hot load of his jism.
After he pulled out he spanked my ass a couple of times and then pulled up the back my panties. He had me remove my dress and climb into bed. (Guess he forgot a girl needs to take her makeup off.) There I was pussy/asshole filled with cum wearing my cum in the crotch of my panties. But it didn't matter since I fell asleep so quickly. As I found out later, he had put clonazepam in my glass of water and had me drink up before we came to the bedroom.
Not sure what he did but early the next morning John, who was lying in bed with me, said he need a morning BJ. He said he loved a morning piss erection. I rolled over wearing my bra and panties, makeup smeared, gave him a blow job and he shot another big load in my mouth. His cum was the first thing I tasted that morning. I showed him his cum and then swallowed obediently. That reminded me my asshole was filled with his jizz from last night. And the crotch of my panties had my small, caked load.
John seemed to be able to get hard and fuck without cumming for what seemed like hours or he could shoot a load whenever he pleased. As if his body was made cum instantly. I was good for one or two orgasms in a day.
The rest of the day was pretty tame at this point. One more load up my chute and two down my throat. Oh, and two spankings one for cumming without permission and the other because John wanted to.
When John left that afternoon, I was exhausted and mesmerized. I was back in the skirt and blouse I had worn earlier last evening. The dress would need to be dry cleaned.
My ass was so sore I waddled as I walked. I had been fucked `royally.'
Two big things happened over the next week and one more three weeks later. First, Janet said she wasn't coming back. She had met this wealthy guy and was living with him. I asked what to do with her stuff. She said, "give it to charity, I don't need it."
The second thing was my realization I was glad she wasn't coming back but I had no idea what I was going to do. John was tight with Cecilia, and I was pretty sure he would marry her.
The third thing happened three weeks later. John called and said Cecilia had to go home. Her dad was in the hospital and she would have to help him for the next six weeks. Her dad lived nearly a thousand miles away. And back then there were no cell phones. There were long distance charges on out-of-state phone calls so people tended to make a time when they would call.
We had split up our business nearly half a year ago. John bought me out and I used the funds to help me establish my career in writing. John kept the small construction company, and I was making money writing short stories, product manuals, etc. It's not like I was rich, but I had enough to make do.
John had ruminated he would probably marry Cecilia and move upstate moving the business with him but that was a few months away and with Cecilia far away, John's idea was I would be his submissive slut girlfriend for the next month or two until Cecilia returned. No more strip poker. I would be his to do with as he pleased. And, as you probably guessed I agreed.
Back then there were some stores catering to transgendered clothing. John found one using the "yellow pages." He also found a store specializing in selling B&D stuff. Both were downtown on the lower East side.
We went together and first stopped at the TG clothing store. John instructed the salesgirl how he wanted me to look, what clothes to wear etc. The salesgirl loved the whole idea, and she called some friends. And before you could say `bat shit.' I had a wardrobe; my hair had been styled and colored (was fine with me since I did my work at home with a typewriter) and I really didn't care about the neighbors since the owner of the brownstone was gay. The other tenant was old and nearly blind.
The girl who styled my hair, Ellen, took a look at my landing strip and decided she would style it and color it pink. She also gave me depilatory creams to rub over my body.
"Not your face darling," she instructed.
I also got a proper Mani/Pedi with the red nail polish at the salon next door where they did my hair. My hair was styled in an edgy short blond look.
By the time I left the TG store etc. I was wearing a sundress. My bra was stuffed with something they sold for women who had breast surgery. A pair of open toed espadrilles with the strap wrapping up on my calf. One of the women spray some perfume on me. I was walking around as a woman/girl. Probably everyone knew or perhaps they didn't, but I didn't care. John would grab my ass as we walked one block to the B&D store. John had parked his car between the two stores.
At the B&D store John knew what he wanted and just gave the list to the salesman who went and got everything. He wrapped it up in brown paper. We put everything into John's car and drove to my place. Besides lugging everything up into the apartment John also had brought an old 8mm projector and whole box of porn films. (There was no streaming back then.).
Yes, we spent some money, but you'd be surprised. It wasn't outrageous and we both pitched in to pay.
What John didn't know was I had been tanning in one of Janet's bikinis on the roof top so I now had tan lines. With Janet out of my life I had embellished what had happened a month ago but only as a soloist. Now a new chapter was beginning. At least for the next six weeks or so.
John had told Cecilia he was going to be staying with me since he was bored home alone and the decided to talk every Wednesday at 7pm.
"Lauren, I don't want you to swish only the lisp and I'd like you to call me Daddy. Be a woman this next month. One who obeys her man. Is told when and what to eat. When to use the bathroom. Cooks, cleans and pleases her man whenever he wants."
Here I was, a long way from those white satin panties. Now 23 not 11