tagTranssexuals & CrossdressersHot Summer Night at Jacques

Hot Summer Night at Jacques


I sat on a red leather bar stool. To the world I looked like an attractive heterosexual male, wearing thin cotton summer slacks and a black tee shirt. I have sandy brown hair with bright blue eyes. My body is slender from running and swimming. I am about 5'11" and weigh about 160lbs. On the night at Jacques, I was about 30 though I look younger. My hair is long and feathered back. My face is clean, marked by full lips and long eyelashes for which most women would die. I have been called the perfect Ken doll, and receive advances from both sexes often. I am probably too nice though. I have trouble with relationships always fearing the break up and hurting someone because I am not as attracted to them as they are to me. As an adult I avoided relationships with both sexes. I guess I was kind of a loner that everyone likes but no one really knows.

For the most part I have considered myself heterosexual, but have one reoccurring fantasy, and up until the night of this story had only experienced one bi-sexual experience. This night, in August a few years ago, I was sitting there nervously on this old red leather bar stool. I could feel the cool chrome from the stool's legs through my thin cotton slacks. What no one could see was that under my slacks I wore a pair of silky nude nylons I had purchased from a local CVS that day. Under the nylons I wore a blue pair of Victoria Secret Second Skin panties.

This night, I was intent on exploring a fantasy, a recurring fantasy that often caused me to waste hours on the computer or special nights in the bathroom, exploring feminine looks and feels.

The Bar I sat in is called Jacques and is in Boston. It is a transvestite and cross dresser hang out, and has a regular drag show. I had known about it for a long time, and even been inside once before, but never wearing panties. Being there made my stomach tighten. I felt a stir in my slacks under the nylons and shiny blue tight panties. There was something to being out wearing these things, knowing that if someone looked closely they might see a panty line, or that the panties themselves might be visibly through the light colored slacks. It was a mixture of fear and erotic energy.

I planned or told myself I was just going to find a safe place and watch what the scene was like. Walking in I looked around to see who was watching me. I had to give an ID to a bouncer and pay $5.00. Showing someone an ID made me nervous but it was just a cursory glance. The bar area was to my left, on the far side of a pool table. Inside it was dark, but you could see. The bar area seemed safe, away from the performers who would be beyond the bar in the back. It was also safe at the moment from various sexy transvestites who walked about.

I ordered a beer from a young transvestite bartender. The bartender had a false pink wig. She had a white silk blouse and wore a patent leather micro mini skirt, hot pink. She stopped when serving me and smiled. My stomach fluttered. I have always loved shinny leather and PVC. Seeing it on a young transvestite definitely stimulated me. I could see below the skirt she wore really sexy garters and silky nylons.

I sipped my beer pretending to watch the Red Sox for a time. I acted the part of a visiting business person who had stumbled in by chance. A drag show began around the other side of the bar. The bartender suggested I move in to see it. A few beers had now gone down and I became brave, for a moment. I got up and walked deeper into the space, finding a small table back by a stage. I had the table to myself.

A very convincing tall brown skinned performer came onto the stage and began singing. She was dressed in a short black mini dress which made her extremely sexy. Her dress was made of a silky material and was tight. It emphasized her extremely long legs, and enticing barely hidden crotch, because it was so short. She also wore fish net nylons and incredible fuck me boots, white patent or PVC leather. The boots came just above her knees and flared out at the top. The boots also had spiked heals. I believe she was lip singing to a Tina Turner song, What's Love Got to Do or something like that. My beer was empty in minutes, as I tried to look casual.

I remember her song ended. A cross dresser or transvestite sat next to me. I was very nervous but began a conversation. This girl was white, perhaps a bit heavy, and was dressed in a pink cotton dress with a red bow tied on her back. She had smooth legs covered in white stockings. She was not necessarily attractive to me but she was a guy dressed as a convincing girl, and therefore exotic in some way. I remained nervous in her presence and stuttered answers to her questions. She had high heals and frizzled blond hair, red lipstick and lots of eye make up. She told me I was so cute and should not be alone. I asked her what name was to try to say something. She said Holly. I struggled through some more chit chat and then she left to perform, saying she would be back to check on me.

The tall black transvestite came out of the back and soon took her place. She leaned over and put her hand on my knee. It was an electric feeling, especially knowing under my cotton slacks I wore nylons and panties. I was sure my cock was leaking a bit. We talked though I do not recall about what. I began to compliment her on her looks and how sexy she was. This girl I found incredibly sexy. I was not sure if I wanted to be with her or be like her, however. I had never been with a Tgirl before, and besides one incident at a rest stop when I first got my license, at 16, I had never been with a guy. On that occasion I had been driving home from the beach when a very feminine guy had looked at me and licked his lips. It for some reason had turned me on, and I started to look back at him. He motioned me into a rest stop and I followed. He climbed into my car and masturbated me to a quick and embarrassing orgasm. He then placed my hand on his pennies and had me stroke him. He also came quickly, as shame began to set in, in the back of my brain.

Veronica left saying she had some more songs to sing, but she always came back to check on me. She sang three more songs at intervals, during which several other girls sat and talked to me. I consumed at least 6 beers as the night wore on. As I relaxed I began to angle towards driving this sexy girl home. She was named Veronica I learned. She was a "full time girl" she said. She loved cute boys like me. After her last song she returned pushing a dark skinned Latino girl away. That caused me to blush a bit. I guess she liked me. I jumped in and asked her if I could drive her home, if she was done. She accepted, and at closing time we left Jacques together, walking towards my red Volkswagen bug, full of my "regular" self.

As we drove she put her hand on my leg and asked me what I was into. I stammered for a moment and then confessed. I said I had nylons on right that minute and a pair of panties underneath. I was incredibly attracted to transvestites but also liked to dress. She laughed loudly and said she had guessed I wanted to dress. She said the other girls would not believe her but she had guessed. She asked to see my panties and began to unhook my belt. I squirmed in my seat as I drove. She feigned shock at seeing the nylons and panties. She complimented me on my choice of panties, and began to rub me through the nylons. At the same time she admonished me to drive safely.

As we drove she talked. She told me she was into seeing boys like me shoot cum to great heights. She loved watching cum squirt from a cock she said. It was what she was into. She asked me if I shot cum like that. I admitted when dressed or wearing panties I did, which is very true.

Directing me into Cambridge down a side street we arrived at her apartment. She told me to pull over and park. She told me to tilt my wheel up and pull my pants down. She began to rub me again through my nylons, putting a hand under my ass and feeling my balls. She ran long fingers with bright red nails along the outline of my cock. The wet stain at the end of my cock grew larger in the blue silky panties.

She pulled my nylons down and rubbed me again just through the panties. The panties shown, sparkling a bit, almost a purple, the wet spot black against the material. Veronica soon pulled them down as well and with expert hands began to caress my cock. A street light allowed both of us to see my slick cock head glistening with pre-cum. While doing this she took one of her hands and ran it again under my ass. She touched my bud. The whole experience exploded into a series of bright lights as I shut my eyes. I whimpered and began to cum. My cum shot high into the air landing on the windshield, visor and roof of the car. Veronica licked her lipped and looked up at me with a huge grin.

That was incredible she said. You are so sexy I think I want you to come in. You can borrow some clothing and I will dress you. That is as long as you think you can shoot like that again. I told her I could. I asked her if she would let me touch her cock through her nylons. She was apprehensive at first, telling me she was really into watching others cum. As we exited the car however, she relented saying yes I could but only when we were inside.

We climbed to the third floor in a dimly lit but clean stair well. She opened an old wooden door with too locks. We entered. Her place had a single throw rug, leopard skin and a black leather couch. It had a compact walk in kitchen with counter to the right of the door, and a large flat screen TV on a TV cabinet to the left. A door ran into what appeared to be a bed room beyond the TV. Next to this door a small hallway ran into a bathroom lit by a night light. On the wall across from the door was a bank of windows covered by simple blinds that were shut.

No lights were on inside but street light allowed us to see. As she shut the door she turned to me. She was taller than me by three inches or so, with her heals. She pushed me up against the door and began to kiss me. I had never kissed a boy or transvestite before but found it exciting. Her tongue darted in and out of my mouth, larger than a real girl but so sexy. She allowed me to feel her ass over her the smooth tight mini dress. The dress was shinny and made of silk or a nylon with spandex. I was turned on at a new level as I stood there, but wanted so much to feel her cock. It was to be part of the fantasy or experience. Other than that one time, I had never felt a cock before and something drove me forward to that end. I ran my hand up the inside of her thigh and felt her reaction, a gasp and tension in her muscles. I felt her cock through patent leather panties. It was larger than mine, probably 7 inches. It was hard. I was so horny.

I slipped into a fantasy; I was the sex slave of an Amazon woman with a cock, my sole desire to please her. My second hand moved under the short dress and felt her ass. Her nylons were held up by garters. It was an exotic feeling to feel the smooth garters over the slick cool panties. The panties were tight. I loved it. I rubbed her for a time and then she pulled away and led me to the couch. As we walked she told me I was a good kisser. I told her I was so turned on.

She began to unbutton my pants and pulled them down. I stepped out of my pants feeling sexy in my nylons, exposed. She pulled me towards her again this time running her hands on my ass. Veronica left me standing by the couch and strutted to the bedroom without a word. I stood for a moment alone. She returned with a short skirt, it was a mini skirt, black, made of vinyl. She also held in her hand a rayon blouse, and heals.

She had me step into the skirt. I was drunk with ecstasy as she raised it up my smooth legs. She then pulled my black tee shirt over my head, tweaking my nipples as the cool air struck them. She leaned down and licked me, my nipples and chest, then stood again. She had me pull the blouse over my head without unbuttoning it, and then handed me the 3" heals, which were black with a wide base. I put them on, and was suddenly her height.

We kissed again, this time me feeling so much more girly than before. I was still drunk in a way, unable to fathom any consequences or risks; simply beyond the bounds of common sense or inhibition. I return to her cock, this time feeling confident of her permission as I bent down to inspect it. She allowed me that never moving from her position as I ran my hand over its outline in the panties. I could feel her smooth hairless legs. A faint sex smell combined with the smell of the leather. I kissed it, her cock. Veronica again tensed, I could feel it. My hands pulled her ass to me and I licked the head through the smooth leather, running my tongue along the shaft.

I hooked my thumbs above her hips on the top of the panties and pulled them down. Veronica wisely wore a gaff but the gaff had become askew due to our actions. I found a tie on her hip and pulled. The gaff came away and a beautiful brown cock sprang at me, hairless and smooth. It was cut and danced about for a second before hardening into an upright position. My hands caressed it as I stared at it for a moment. There was no second thought about what I was doing, only excitement as I leaned forward to take the tip into my mouth.

The cock was so smooth, like satin or fine valor. I was amazed. All the talk about cock sucking, I found it easy. I enjoyed it from the start, the feeling of that smooth as silk rod in my mouth, on my tongue. I played with the tip for sometime, until I felt Veronica's hands slide up my neck and softly urge me down onto the shaft. To do as she wished was my goal and I relished her guidance as she pushed me deeper, or it deeper into me. I did not gage as it slipped into the depths of my throat, instead relaxing, feeling it slip in and out. My hands explored her firm ass until I found her cherry. She bucked forward, in and out slowly, as I began to tease and tickle her bud. It was quick; she tensed and began to cum. I felt her hands leave my head, but tried to swallow at first. Then after the first shot, I pulled out and watched as she exploded onto my hair and face, huge amounts of hot cream, again and again.

All that talk of lasting for a long time in stories I find crazy. When sex is hot orgasm happens quick. I feel it start and am quickly beyond the point of being able to stop it. Veronica knew I was so close. I probably would have cum standing there had she even slightly touched me. Instead, she told me to lay on the carpet. She left me alone for a moment, removing her dress to show a slim, sculpted, and slender body. There was no body hair. She unzipped her boots and removed them, looking at me as she did it. She had breasts, small implants, covered in a sexy black patent leather bra. Veronica skin was light brown, and glistened in the street light coming through the windows. Her lips were full with sticky candy red lipstick. I looked up to see her wavy hair framing her sexy eyes.

She knelt beside me in her bra, panties, garters and nylons. She pulled my shiny tight patent leather skirt up a bit so that it bunched around my waste. This exposed my nylons and panties to her. She lowered them again, the nylons first and then the panties, down to my knees. She leaned forward and took my sticky cock in her mouth, so softly. Her lips played with my cock head, and her tongue danced around its flared glands. Meanwhile, she also began to lube my ass with cum from my hair and face, her cum. I felt her thumb on my bud, smooth and slippery. It slid into my ass, deep into my ass. I arched my back in a girly sexual pose. I imagined I looked like so many of the bikini model photos I had seen. I trembled and shook, my eyes rolling in my head. I ground down on her thumb and up into her mouth. It felt an ecstasy that I never imagined possible.

Suddenly I came. I shot spurt after spurt high into the air, as Veronica watched from cock level. Some landed on her head and some on her back. She laughed as I continued to cum, just seeping now. I felt hollow. It literally took minutes before I could speak again, minutes before I knew what I had done, or perhaps become.

I lay there and Veronica climbed onto of me. We were covered in our own cum. She rotated her hips softly mashing her hardening cock into mine. I felt so sexy, our cum mingled together, sliding together. It was so slippery and sexy. I was so happy, and stayed hard despite knowing I had to be out of sperm.

There was so much to do and try with Veronica and I knew it could not all be done in one night. I see her regularly now, like sex therapy. We stay distant in some ways, our lives progressing on each day we are apart. When we are alone together though, we are one sexual explosion after another.

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by Anonymous

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by Anonymous08/27/17


Still in Boston. Was real. Still a hard core junky of sexy cd's and crossdressing. Life goes on and you get what you can out of it. Always interested tomeet folks for fun though.

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