My name is Dani and I am a 30 year old cross dresser and I wanted to share the greatest experience of my life. For background I am 5' 7", weigh in at 145 pounds and maintain a pretty trim body by working out and swimming on a regular basis. I have thought about taking my experience to a new level for a long time but never had the nerve or the opportunity to try. This recently changed and I wanted to tell everyone t about it because it has changed m life. This account is true and only the names have been modified.
I have been the typical story of a cross dresser since I was 6 years old. I started playing with my mother's clothes and was hooked at an early age for the feel of lingerie. I kept my secret and dressed whenever I got a chance which turned out to be very often since Mom worked nights and weekends. Around the age of 12 I found sports and less time by myself and so dressing took a back seat. At 13 I had a friend sleeping over and we started talking about sex and what it was all about. We both knew what "blowjobs" were and wondered what that would be like. At my friends urging, we agreed that he would if I would. We laid in the bottom bunk in a "69" position and pulled each others underwear down. After a few minutes of playing with each other we agreed to put them in our mouth. Since we didn't have a clue what we were doing, we sucked on them a little and then the fear of being caught took over. We went back to our respective beds and didn't mention it again. Although, I thought about it constantly for a long, long time. I had a brief period in college of dressing with a friend that I found also loved lingered. Since we lived in the dorm and again the fear of getting caught was so strong this only lasted a couple of months.
Instead of finishing college, I joined the military in my sophomore year and began my travels. During that time I got married, was discharged and moved back to my home state. My wife had gotten very involved in charity work and one of her groups ran a sort of "thrift shop". Because they were so helpful in the community folks were always donating bags of clothing items and my wife took on the chore of sorting the items in our garage. When folks start donating clothing it is absolutely amazing what they give. The bags contained lots of good useful clothing, but they also contained used under garments and some worn items that the group did not want to sell in the shop. These items were sorted out and placed in plastic bags that went out on the curb with our weekly trash cans. A couple of years ago my wife was out of town because of a family emergency and asked if I would put these bags out with our trash. Since I start work at 5:30 a.m. my wife always took care of the trash. I decided that since I would be leaving so early I would put the trash out the night before. I had taken our containers to the curb and went back into the garage to get the bags that she had sorted before she left. I had taken out three pretty good size bags and as I picked up the last bag from behind the tables and pulled up it caught the metal corner on the table and ripped out the bottom. Suddenly I was ankle high in hosiery, panties, bras, camisoles and a few girdle type items.
Every memory of my early years came rushing back to me at 100 miles an hour plus. I could not believe the instant excitement I felt at seeing these things. After trying to pick everything up I knew I was 6 years old again and I actually ran to the curb and brought the other bags back in the garage and quickly closed the door. I ripped open the bags and dumped all the contents on the floor and was instantly overwhelmed by the quantity and variety of items. Rummaging through the stack I found a pair of white bikini panties with lots of lace that looked to be about my size. Remembering how much I enjoyed them when I was young, I quickly decided to try on just that pair. Sitting on the old chair next to the table I took off my shoes and socks undid my belt and removed my pants. My own pair of underwear was being stretched to the limit by the raging hard on that I had gotten with my first sight of those bags contents. I slipped off my briefs and put my feet through the leg openings on those beautiful panties. As I stood and began to pull them up my legs, I was suddenly very weak and my vision became dizzy. I thought for an instant that I was passing out. I quickly sat back in the chair and closed my eyes while attempting to catch my breath. After I had regained my composure I stood and pulled the panties up tight against my butt. As the soft material gathered around my cock and balls, I knew that I had missed this and I had to make it part of my life again.
I spent most of that night sorting, finding items that would fit me and were in good condition. When finished, I had several pairs of panties, different styles of bras, garter belts, hosiery of different colors and styles, an open bottom girdle with garters and a beautiful "vintage" corset. Needless, to say I did not go into work the next day but spent the entire day changing outfits and modeling. Since my wife had not made the monthly trip to the store with inventory I decided to see what I could find to further my dressing. I found 4 pairs of shoes, a pair of platform sandals, two pair of shorter high heels and a pair of red "fuck me" pumps with 5 inch heels. I almost broke my legs learning to walk in them but by the time Sunday afternoon came around I was "good"! I also had a pretty good start of skirts, blouses and a particularly "sexy" dress. My wife was gone for the next 16 days and it was all I could do to make myself go to work. When I got home I changed and spent the night parading around the house and posing in every mirror that I happened to pass.
Over the next couple of years I discovered the internet and received so much valuable information and techniques. My wife was ecstatic when I volunteered to help her with her project and help sort the new donations. Needless to say, there were a lot of items that never found the trash bin or the thrift store. I learned how to do my make up after my first attempts turned out to look more like a clown. I was able to order a nice pair of attachable breast forms and perfect the fine art of becoming a woman. During this time I found a really expensive blond wig with lots of curls and my look really started coming together. Shortly after that I got really brave and reached out to a sister that I had found while surfing the net and she and I helped each other to make a few outings just to see if we could actually pass as two young women out for the day. To our surprise we were never challenged and our confidence continued to build. My friend was discovered by his wife when she came home by surprise one afternoon and found him in the bathroom doing his makeup dressed in his best lingerie and high heels. He purged his fem side and I did not hear from him. I found that I just couldn't make myself go out alone and went back to dressing at home.
This has been the case for the last few months, dressing when I could, watching some CD's that I had gotten, playing with my toy collection and always trying to take Dani to the highest level. I am not a "big" man, I guess you would have to call me medium sized. I don't have a lot of body hair and my facial features are not what you would call "Clark Gable" looking - so I've always tried to make Dani into a young woman who likes the "hot girl" look.
Recently my wife had to be out of town to help out her sister. I started to remember what happened the last time she had left me alone and how it changed my life. I had my fantasies but never the nerve to act on them. I had some things that I wanted to get done around the house and figured that this would be a good time to tear things up while she was gone, so I took a week off of work. Working a few hours a day and finding Dani the rest of the time was so great, but there was one task I had said I would finish and that was moving a light fixture in the dining room from one side of the room to the other. I needed to go to the building center for parts and had started to get out of my fancy underwear and put on some sweats. I decided that I would just throw on something over my lingered and go for it. I left on my garter belt hooked to the white thigh-highs and my bright read satin and lace thong panty. I sort of took off my make up but if you looked closely you could tell I had been wearing it. Reluctantly I removed my bra and the breast forms while I threw on a pair of jeans, a tee shirt and a pair of high top shoes.
I went to the local building center and found my way to the electrical supply department. It was around 1 o'clock in the afternoon on Wednesday and they weren't busy except for a few obvious contractors who were buying job materials. As I walked down the aisle looking for the supplies needed for my job there was a young man digging through the bins looking for something particular. He looked my way and I smiled and said a soft hi. He smiled and returned the acknowledgement. I found some things that I needed on the bottom set of bins and I bent down to pick them up. I moved further down and was trying to figure out what else I needed. Bending down again I knelt on one knee and leaned forward to look through several electrical pieces when I heard a soft voice from behind saying:
"Those are really nice red panties you're showing".
"Excuse me" I said turning in his direction.
"He raised his eyebrow and said "I really like your panties and I bet they really look nice with your white stockings"
Looking down I realized that I had forgotten to put socks on over my hosiery. I started to come up with some kind of a rebuttal, but I figured that there was not much sense in that since I had been caught with my undies showing.
Deciding to be really bold, I looked him directly in the eye, smiled and said; "How nice of you to notice."
He smiled a gorgeous smile. "So what's a pretty pair of red panties doing in the electrical aisle"?
Deciding to play the role of the helpless female I gave him and confused glance and said "I have a project at home that I'm not quite sure how to do and all of these different parts are not helping my confusion "
Moving closer he said, "Maybe I can help, I'm an electrician. What is it you're trying to do?"
I explained that I wanted to move a light fixture and I needed to buy the proper supplies.
"Have you ever done anything like that before" he asked?
Continuing to play my part I lied with a nice smile, "No, I'm not much good at using my hands for things like that."
Moving behind me he started to show me the parts that he thought I would need. As he did so his hand brushed across my ass more than once. Finding no resistance on my part he began to gently rub the curve of one cheek while pointing to the shelf.
Turning to face him, I said "that's pretty bold for someone whose name I don't even know".
I extended my hand while saying, "Hello, my name is Dani".
Removing his hand from my ass he gently took my hand in his, gave me that killer smile and said "my name in Josh, I'm very glad to meet you Dani."
I didn't know where this was going but I figured I'd better be checking this boy over. Stealing a quick look at his hand I found the gold band on his left hand. He was about 28 or 29, a little over 6 feet with a really nice athletic body. His skin was a nice brown from the outdoor work that he did and his curly light brown hair and piercing eyes made for one great looking man.
Still holding my hand in his, he said "Look, I'm between jobs today and I don't have to start the next one until tomorrow morning. Why don't you let me come take a look at your project and maybe I can help you get it done?"
Oh man, the moment of truth!!!! I had fantasized about situations like this every time I played with my special toys, but I never thought it would happen or if I would actually act on it.
Suddenly I heard myself saying, "That would be so great! Why don't you follow me to my house and you can take a look at the fixtures?" I couldn't believe that I was saying this. It was like Dani had suddenly gained a mind of her own and I was just along for the ride. Maybe it was the situation, maybe it was getting caught and him seeing my red panties or maybe all those years of imagining this meant more than I thought.
Josh bought some supplies for both his next job and mine and followed me to the parking lot. I told him," I only live a few blocks from here, why don't you just follow me?"
We pulled out of the parking lot and I kept looking in the rearview mirror and asking myself "what the hell do you think you're doing? Why don't you just speed up and lose him in the traffic? Chalk this up to a nice experience and forget it?"
I kept thinking this right up to the point I pulled in my driveway and held my breath while he pulled his truck into the driveway next to my car. He came around to my car carrying his tool belt and a small ladder and we proceeded up the walk and into the front door. He asked to see the light fixture and I took him into the dining room where he started messing with the fixture and asking me where exactly did I want it moved. He was every bit the professional. I thought maybe I had just imaged everything up to now and he was only going to move the fixture, give me a bill and leave.
Now I was really confused, what was he trying to do? I began to get upset. I kept thinking "here I've gone out on a very uncomfortable limb and he's not going to take advantage of it." Josh had set up his ladder and was standing on the 2nd step poking around in the ceiling fixture. I decided that if I was every going to go through with this that today was that day.
"Josh would you like something to drink" I asked?
"If you got a beer that would be great!" he said without looking down.
"I sure do, but I have to go to the basement for it. I'll be right back in a few minutes". I headed out to get the beers but went to the bedroom first. I removed my jeans and found my "fuck me" pumps. I attached my breast forms, did a quick make up job, put on my long blond wig and slipped into a long white silk blouse with only the bottom three buttons closed. I looked in the mirror and was quite satisfied with what I saw. I heard a drill from the dining room and figured Josh had started moving the light fixture. Suddenly I couldn't breathe and sat on the edge of the bed while I asked myself, "is this really what you want to do? What if he doesn't? Do you really want a man for Dani? I decided that, YES I did want to live out this fantasy and if Josh didn't well then it was his loss. Picking up a small bag of my special toys I went to the basement, got the beers and went back to the dining room. Josh was still on the ladder and attaching the light fixture to the new location in the ceiling.
Approaching the ladder, I asked "Everything going alright".
"Just fine" he said without looking down. "Just a minute and I'll have it all done for you."
I walked over to the ladder and hugged his right leg while running my hand up just to his crotch. I could feel his leg tremble as I continued to rub his upper thigh. "Should I hold you up there so you don't fall", I asked in my best female voice?
He looked down at me and I heard "Holy shit! Who are you?"
Letting go of his leg I said" Josh, it's me Dani".
"Damn, you surprised me. Wow, I thought you were just a dude who liked to wear women's underwear, I didn't know you are a - a -a"
"A what", I asked.
"You know someone that goes all the way trying to look like a woman."
"Yes Josh, I'm a cross dresser. Does this bother you or make you uncomfortable?"
"No, not at all. It's just that you really surprised me. I thought you were somebody else. I mean you really look great. No, damn you like absolutely beautiful. If I didn't know it I would swear you were an actual girl."
I told him how much I appreciated the complement and how glad I was that he was here. I suggested that we take our beer into the family room and get comfortable. We set on the big overstuffed love seat and sipped on our beer. I asked him what had made him approach me at the store since I had noticed he was married.
He told me he had been married for a couple of years and it seemed his wife had lost interest in him. He explained that he had a couple of near bi experiences while he was in college and he had never forgotten them. . Lately he had begun to think about them more often and that he really wanted to try. When he saw my red panties and white stocking peeking out from around my jeans he thought he might just see where it would lead. He said he was feeling pretty bold until he got into the house and didn't know what to do next or if he had mis-read me so he thought he would just fix my light and leave.
I told him how glad I was that he was here and I was happy that he shared that with me. I told him a little about how Dani came to be and that I had really been wishing for a moment like this. I offered him an out but that I'd really like for him to stay awhile.
He gave me that killer smile and I just sort of melted into the moment. I asked him if I could put in a video and proceeded to put in my most hard core shemale movie and muted the sound. I returned to the sofa, picked up my beer and offered him a toast, "to new friends and new experiences." Clinking out bottles together he smiled we took a drink. Putting my beer down on the table I reached over and lightly kissed him on the lips. Then while I planted soft kisses up and down his neck I reached for that special place between his legs. I touched him with great anticipation and shivered when I felt that growing mass under my hand. I kissed him again and this time our tongues started a slow dance of lust. His cock was getting harder and I was rubbing harder. He put his arm around me and began to rub the top of my ass cheeks which sent me into the next level of pleasure.
While we continued our kissing I unbuttoned his jeans and was able to get my hand inside. What a man - no underwear! His 7 inch cock filled my hand and it was hard, warm and just felt so damned good. I moved my hand down and felt his balls, they were big and warm - I never wanted to let go. We continued to kiss and were still rubbing when I just could not take it any more. I got up and knelt in front of him. Reaching down I untied his boots and removed them while I rubbed his feet. Then I slowly removed his socks and sucked on each of his ten toes before I pulled him to his feet and slid his jeans down and off. I had him set back on the loveseat and crawled in between those beautiful tanned legs while taking his cock in both hands and just holding it. Leaning forward I put just the head of his cock in my mouth and rubbed it all over with my tongue. I though back to that time so long ago when my childhood friend's cock was in my mouth and it didn't come close to this.
I started to move my head forward, slowly inching his cock further into my mouth until my lips had reached the base. Thank goodness for all that practice with my toys. I slowly moved upward until the head gently slipped from my lips. Looking up I was pleased to see he had his head back on the sofa, his eyes closed and a look of pure pleasure on his face. Deciding he was more that ready I ran my hands up under his t-shirt and rubbed both of his nipples while I placed the tip of his cock on my lips. Wetting my lips and easing him into my mouth I starting bobbing my head up and down. Each time taking a different amount in and out of my hot mouth. After a few minutes I could feel his leg muscles beginning to tighten, his breathing growing louder and his hands found the back of my head. I increased the speed of my bobbing until I felt the shudder start in his legs. When I knew it was close I pulled up with just the head in my mouth and felt the first spurt of cum in my mouth. After several more spurts I had a full mouth of his juices. Pulling up I looked up at him and he looked at me with pure lust in his eyes. Opening my lips just enough for him to see the contents in my mouth I swallowed his cum and immediately started to clean that beautiful cock with my mouth. After he regained his composure I got up and sat next to him on the loveseat and reached out to hold his softening cock in my hands. I was in such a state of bliss. I had just given this man my very first blowjob and I loved it. I kept telling myself, "you are now a certified cocksucker and I just kept smiling.
He smiled while looking at me and said, "That had to be the best blowjob I have ever had. How did you learn to do that"?
"I know what feels good for me and I just tried to take that up a notch or two".
Not really knowing what to do or what was going to happen next I was pleasantly surprised when he turned, took me in both of his arms and kissed me deep and long. Our tongues resumed their dance of lust while he started to explore my body with his hands. He reached down and unbuttoned the blouse and laid it back. He started to kiss my neck and rubbing my bra. He eased me back onto the sofa and started to kiss his way from my neck down to my navel while his hands rubbed their way up and down my nylon covered legs. He placed his face between my legs and started to rub his lips on the nylon covered lump between my legs. Hooking his fingers into the top of my red panties he inched them down very slowly while placing tiny wet kissed on each square inch of newly exposed skin. When my panties were down far enough he took hold of my red hot flesh and pulled it up from its tucked position between my legs. Oh baby, I couldn't believe I was that excited and hot. My whole body felt like it was on fire. He continued his tiny kisses up and down my cock while licking it like an ice cream cone.
I placed my hands on either side of his head and whispered, "You don't have to do that".
"Oh yes I do. I really want to"! At that point he placed me in his mouth and I thought I had gone to heaven.
His hands had gone under my butt and he was massaging each cheek while he ran my cock in and out of his mouth. I measure about 6 inches and he tried his best to take it all in but couldn't without gagging. I took hold of his head and guided his motions to keep him from going to deep. After a few minutes of this I guided his head to just hold my boy clit in his mouth. I got my breath back and I pulled him up to lie beside me and began to kiss his face. I didn't want to cum just quite yet. We continued to lie next to each other exploring each other with our hands and sharing kisses. Finally I made up my mind that I wanted to take this to the ultimate level and I wanted us to share each other completely...
Putting my hand on his cheek and kissing each of his eyelids, I asked in my most sincere voice, "Josh, I can't believe that just happened and I can't tell you how happy I am that it did. I have told myself for a long time that I didn't want to be with a man, but I guess I was really lying to myself. Thank you!"
Smiling he said, "I've always wondered too since I ran away from the opportunity before. I can't believe how fantastic that was, so thank you!"
Looking deep into his eyes, I made a decision. "Josh, would you make love to me? Would you make love to me like a woman? I want you to fuck my virgin ass."
He kissed me long and hard and said, "If it's what you want!"
I reached for my small bag of toys, while Josh took off his shirt and I almost lost my breath when I saw that beautiful tanned, athletic chest. I sat on the sofa and took his cock in my mouth. After a few minutes he was getting hard so I took his hand, stood up and brought him to his feet. I lay on the table in front of the sofa and motioned Josh to join me. He laid over me balancing his weight on his arms and kissed me deep and long. I had him kneel in front of the table while I took a tube of KY from the bag and put a good coat on his hard cock. I laid back and using my hand I put a large dab of KY all over the entrance to my backdoor. Finding a small butt plug in my bag I coated it up and put it inside my hole. Josh watched in amazement as I got ready for him.
Removing the plug I asked him, "Josh, will you please put your beautiful cock inside?"
Without responding, he put the tip just at the entrance. Guiding his hip I instructed him to just put the tip in and hold it there. He lightly pushed and the head found its way inside. He stopped and held himself just inside. "Can you push in just a little?" As he did the head popped inside and I thought I stop breathing. There was not much pain but there was a ton of pleasure. "A little at a time now." Josh began a slow process of pushing in just a little and staying there for a moment. Before I knew it he had put the entire length of his shaft inside and his balls were resting on my ass cheeks. I had played with some pretty good size toys over the years, but I had never felt the pleasure of a real, live cock. The feel, the heat and the movement were absolutely phenomenal. I began to cry from the pleasure that I was feeling.
"Are you okay, Josh asked?"
"I have never been better. Now would you treat me like your girl and fuck me?"
Josh answered by slowly moving his hips backward and withdrawing to just the tip. He began to move in and out increasing both his depth and his speed. I couldn't believe the feelings that running through my entire body. I couldn't believe how good it felt. I couldn't believe that I had waited this long to experience this. Josh reached down and put my legs over his shoulders and leaned forward to kiss me extremely hard. He straightened up and gave me that killer smile as he began to pump his hips very hard and very quickly. I was moaning and moving my head from side to side while he had his head back with his eyes closed. Suddenly he stiffened and pushed all the way in as he started to shoot his cum deep into my body. At that point I arched my back and shot streams into the air - without touching myself. Josh fell on top of me and we just laid there trying to catch our breath.
It took a couple of minutes but we finally got it together and moved up to the sofa. We held each other kissing and just being quiet. Josh asked me if he could take a shower before he went home and I showed him to the guest bath, got him a towel. I kissed him again and left him with the water running. I went to my room, took off my outfit and got in the shower myself. Getting out I redid my makeup, fixed my hair and put on a fresh set of panties, black thigh highs, a pair of 3 inch heels with a black mini and a white blouse. When I finally came out Josh was on the ladder finishing my fixture work. I fixed us a small lunch and watched his body as he completed the job. After we ate he gathered his tools and said he had to be getting home. I walked him to the door and he kissed me with a long, deep and passionate kiss. He asked if he could see me again and I quickly said yes and then he was gone.
I couldn't believe what had happened. I couldn't believe I had gone out that far. I couldn't believe how glad I was and I couldn't wait to see Josh again.
Josh and I have become very close friends. We have been together a few times since that day, when we find the opportunity, but it will never be as special as that first time. I do have some electrical work to be done and my wife is going to visit her sister...
If you enjoyed my first time as much as I did, let me hear from you DaniTgirl06@aol.com