Transvestite

My first time with Joe _(0)

/ Categories: Gay, Hardcore, Oral Sex, Transvestite, True Story / Gay, Hardcore, Oral Sex, Transvestite, True Story / By

Hey everyone this is the same true story I wrote a few years back on a previous account (BisexualCockWhore) but in much greater detail for all you viewers 😉 If you want to read the shorter version I wrote on a previous account go to the link below: http://stories.xnxx.com/story/28858/My_first_time_with_Joe By the time I was 21, I had moved out of my old house and into a flat just outside of Birmingham City Centre, it wasn’t much but for me, it was home. A place to call my own. A place where I could cross-dress freely without fear of getting caught out with a dildo in my ass. For the first week or so I didn’t venture out much, unless I paying rent upfront or getting food and drinks from the corner shop. I would stay …

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The Maid in me

/ Categories: Anal, Bi-sexual, Cum Swallowing, Fantasy, Transgendered, Transsexual, Transvestite / Anal, Bi-sexual, Cum Swallowing, Fantasy, Transgendered, Transsexual, Transvestite / By

First let me start off about myself, I am 24 years old and I am a closet CD (Crossdresser). Womens lingere and clothing turns me on, as well as their sex appeal to men. I came home from school and decided to take a shower. I needed to make sure I was shaved and smooth for my mistress. She would be home soon, and I needed to start dinner and have it ready. As I finished my shower I made sure I was smooth for my mistress. I powdered dry and wrapped a towel around me and headed to my room. As I entered my room it was nice and warm from the space heater I had running. I slipped off my towel and slipped into my Satin white panties. My white stockings felt better …

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I Just Knew It Felt So Right

/ Categories: Anal, Blowjob, Cum Swallowing, Transvestite, True Story / Anal, Blowjob, Cum Swallowing, Transvestite, True Story / By

It was never questioned when to do it. It was never questioned why I would do it. Not to me at least. I couldn’t control it. I just knew it felt so right. From the time that I was 7 years old I knew I had an affinity for feeling like a girl. I always watched TV and would daydream about wearing dresses and makeup. By the time I put a pair of satin panties on my crotch for the first time when I was 12, I knew whatever I was doing couldn’t be so wrong if it felt this right. It felt good, I would feel my crotch zing and shiver with excitement, cool excitement as I felt the fabric shimmy up my teenage boy thighs and snugly grab and cradle my little boy …

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The First Time Part (one)

/ Categories: Fantasy, Transgendered, Transsexual, Transvestite / Fantasy, Transgendered, Transsexual, Transvestite / By

This is my first story and my true fantasy how i would like my first experience to be, so i hope you like it and try not to be too harsh with me i am a little sensitive. I hope the theme covers all without offending too many of you cute ladies and women or girls… Love you all and hope you enjoy. The First Time We Were Alone. As I lay you down and kiss you passionately until the faint moans try to escape your throat. My hands explore your body until I find your pert tiny breasts that attracted me to your slim petite frame. How your silky clothes cling to your sensual hips. My erection is trying to escape my trousers as we embrace even closer, I can feel you arousing through …

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FRANCESCA’S HUNG TRANNY

/ Categories: Bi-sexual, Blowjob, Cuckold, Cum Swallowing, Erotica, Exhibitionism, Hardcore, Masturbation, Oral Sex, Threesome, Transvestite, True Story, Voyeurism, Written by women / Bi-sexual, Blowjob, Cuckold, Cum Swallowing, Erotica, Exhibitionism, Hardcore, Masturbation, Oral Sex, Threesome, Transvestite, True Story, Voyeurism, Written by women / By

I am Francesca, my man Raoul and me have had a number of bisexual liaisons with trannies. I am finding them increasingly exciting and challenging for me, as is Raoul. I love the challenge of blowing a man’s erection and blowing a hung tranny while my man watches is very exciting for me and a bonus challenge, especially if my man masturbates while he watches. For the last week Raoul has been tempting me with images of hung trannies. They have an added dimension for me when it comes to sexual pleasure – tits and a cock, preferably both in generous measure. By the end of the week I was hanging out to experience a new tranny. One of the images Raoul showed me was a side on shot of a tranny in panty hose …

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SARAH’S BI-SEXUAL FANTASIES

/ Categories: Ass to mouth, Bi-sexual, Blowjob, Cosplay, Cuckold, Erotica, Exhibitionism, Female exhibitionist, Group Sex, Hardcore, Lesbian, Male / Females, Masturbation, Oral Sex, Threesome, Transvestite, True Story, Voyeurism, Water Sports/Pissing / Ass to mouth, Bi-sexual, Blowjob, Cosplay, Cuckold, Erotica, Exhibitionism, Female exhibitionist, Group Sex, Hardcore, Lesbian, Male / Females, Masturbation, Oral Sex, Threesome, Transvestite, True Story, Voyeurism, Water Sports/Pissing / By

I was in my mid-twenties when I watched another couple fucking for the first time. Around the same time my then current man took me to a club where we watched one man blowing another man. They were both incredibly attractive and very talented. And the man having his cock sucked had the biggest erection I had ever seen at that stage. The first time I had two men was not long after that when I met them in the bar after a business conference a long way from home. They were both five years younger than me and real studs. The first time I had two men while another woman watched was the very next day. One of the same two men wanted his partner to watch. I made a point of turning her …

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A New Waitress in Town

/ Categories: Anal, Bi-sexual, Blowjob, Cum Swallowing, Fiction, Transvestite / Anal, Bi-sexual, Blowjob, Cum Swallowing, Fiction, Transvestite / By

THE NEW WAITRESS Moving to a new community is always difficult, especially when you’re alone, with no friends or relatives to turn to. The advantage though is that you can be anyone you want. My name is Robin and I recently graduated from a Boston University, where my family has lived since coming to the US from Ireland. I was only two years old when we came here and have no recollection of Ireland at all. I was very settled in Boston, a good school, swimming competitively on the school team, an excellent job as a waiter at an upscale restaurant, girls, you name it. Things were about to change though, as I decided to do post graduate work at a specialized tech collage in Kentucky. It would be a two-year program, which would launch …

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Trans – formation

/ Categories: Fiction, Transsexual, Transvestite / Fiction, Transsexual, Transvestite / By

Summer 2026 It were an ordinary morning. Phone rang. “Hell – Oh” I says casual like . “Is that sex change clinic?” this twat asks. “No its a fucking Chinese laundry, of course it’s sex change clinic,” I says, “What do you want?” “To become a woman,” he says. “Best of luck with that, periods, hot flushes, babies,” I says, “What we offer is a basic prickoptomy, like clean sweep or a de-bollocking if you want to be an enoch, I mean Unuch.” “Oh,” he says. “We can make a cunt hole where your cock was, “ I says, “If you want but most folk what’s interested is queers what takes it up their ass anyway so it’s a bit pointless is that.” “Oh,” he says. “Look if you just want’s to perv, we can …

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The Halloween Parade Transformation

/ Categories: Anal, Blowjob, Bondage and restriction, Cum Swallowing, Dark fiction, Fiction, Oral Sex, Reluctance, Teen, Transvestite / Anal, Blowjob, Bondage and restriction, Cum Swallowing, Dark fiction, Fiction, Oral Sex, Reluctance, Teen, Transvestite / By

The Halloween Parade Transformation by rutger 5 (An original story 2011) It all started over a bet but it ended very surprisingly and totally changed my life. I was a sophomore attending NYU in the heart of New York City when this occurred. Originally I came from Ohio and now in my second year of college I had really fallen in love with NYC and the whole city lifestyle. Back home I was from a small homogenized town which while being a safe and pleasant enough place to grow up always seemed to be lacking something I felt. It wasn’t until I began college that I realized that I was made for the city. There were four of us eating in the diner that October afternoon when I unwittingly set the course that changed my …

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The Cinema_(0)

/ Categories: Anal, Bi-sexual, Consensual Sex, Cum Swallowing, Fantasy, Gay, Group Sex, Hardcore, Oral Sex, Transvestite / Anal, Bi-sexual, Consensual Sex, Cum Swallowing, Fantasy, Gay, Group Sex, Hardcore, Oral Sex, Transvestite / By

As I stood in the sun next to my car at the back of the cinema, drawing slowly on the cigarette in my sexy black pvc skirt and tight top that showed my curves I knew what awaited me inside, but I wonder if the people walking past knew what I was upto. I had spent the last two hours becoming the sexy lady they saw standing in that car park all hints as to my male self were gone, hidden, I was now a woman, and the adult cinema was I hoped full of sexy horny guys just waiting for a girl like me. As I walk slowly from the car park to the entrance, a group of 3 guys are checking me out as they walk towards me, I love the attention my …

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Growing Up Chapter 5

/ Categories: Anal, Diary, Teen, Transvestite / Anal, Diary, Teen, Transvestite / By

Chapter 5 I go back into my little world, keep my head down, graduate High School early and I’m off to college at 17. It’s a small Liberal Arts College several hours away from the home I’m dying to get out of. I just keep on with my earlier routine of getting good grades and having few friends. Who knows? Maybe I’ll just be celibate from now on. I live in a dorm and go by my real name, Kevin. My room mate studies a lot, as do I, but he goes home every weekend and I have the room to myself. My sex life consists of masturbating while thinking about the coeds and sorority girls in my classes. There are some really cute ones of course but not a whole lot of variety. They …

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Night Shift Sissy – Chapters 1-4

/ Categories: Authoritarian, Black, Blackmail, Blowjob, Cum Swallowing, Erotica, Fiction, Gay, Humiliation, Job/Place-of-work, Oral Sex, Transvestite / Authoritarian, Black, Blackmail, Blowjob, Cum Swallowing, Erotica, Fiction, Gay, Humiliation, Job/Place-of-work, Oral Sex, Transvestite / By

Night Shift Sissy Disclaimer: This is a work of fiction and fantasy. Any resemblance to real persons, places, or events are coincidental. This story is not intended to be an accurate reflection of any particular lifestyle. I could never understand why my coworkers always balked at working nights. Every shift I took, I got more done in a few hours than I ever did while trying to concentrate with the distractions of the full office going about their own business. It also allowed me to indulge the fetishes that I did my best to keep secret. I would leave the house dressed in my sluttiest outfits and make up, my cock locked up in the smallest chastity device I could find, and enjoy wandering through the twenty-story office building, the echoes of my stilettos clicking …

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TWO JOCKS FOR OUR SEXUAL PLEASURE

/ Categories: Asian, Bi-sexual, Blowjob, Boy, Consensual Sex, Diary, Erotica, Exhibitionism, Female / Girl, Group Sex, Male / Females, Male / Older Female, Male/Teen Female, Males / Females, Older Female / Males, Older Male / Female, Oral Sex, Threesome, Transvestite, Voyeurism, Written by women, Young / Asian, Bi-sexual, Blowjob, Boy, Consensual Sex, Diary, Erotica, Exhibitionism, Female / Girl, Group Sex, Male / Females, Male / Older Female, Male/Teen Female, Males / Females, Older Female / Males, Older Male / Female, Oral Sex, Threesome, Transvestite, Voyeurism, Written by women, Young / By

We also had to email some up to date pics, we sent two up to date pics, one of us front on, naked holding hands, my man flaunting a boner, me in heels, then a second pic, me with my back to the camera, flaunting my big ass. “We made a list of of some of our preferences, five in all, and they all came to fruition, two young bi men to share, two bi women a little younger than us to share and some other very exciting combinations.” My first preference with Roger’s full approval was two men for us, two jocks, early twenties, one jock for me, cunnilingus, to tongue fuck me, one jock for my man, to give him fellatio, a blow job, while we watch each other. My second preference, again …

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Suzy Unleashed Chapter 3

/ Categories: Fiction, Interracial, Slavery, Transsexual, Transvestite / Fiction, Interracial, Slavery, Transsexual, Transvestite / By

I woke up on Sunday morning to the sensation of Kathy’s fingers running up and down my panty-covered dick. When I looked at her she grinned and purred, “You have such a nice clit, Suzy! I love it!” “You do?” I asked in surprise. “Oh, yes,” she smiled. “It’s such a nice big clit! No wonder you’re always so horny!” “Big?” I gulped. “Yesterday you said it was pathetic!” “No, darling, I said my husband’s dick is pathetic and it is. Why his dick isn’t any bigger than your clit! Of course, what qualifies as a big clit would still be a tiny, ridiculous little dick. On a man, this would be laughable. On a cunt like you, it’s perfect!” I blushed as she continued to rub my erection. “Are you horny, Suzy?” she asked. …

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The Lawyer’s Package

/ Categories: Anal, BDSM, Bondage and restriction, Discipline, Fiction, Male / Females, Toys, Transvestite / Anal, BDSM, Bondage and restriction, Discipline, Fiction, Male / Females, Toys, Transvestite / By

Allow me to introduce myself and relay a most unique experience I have had in my life. My name is Elizabeth Moore but I commonly go by Liz. Having worked at a small law firm for about ten years, I have risen to the position of the Office Manager. While the position carries many significant responsibilities, there are times I regard it as nothing more than babysitter for the dozen or so lawyers, and equal number of paralegals, the numerous office assistances. The firm has four partners covering a variety of specialties with each having a stable of young attorneys that work with them. As the Office Manager, it is critical for me to get to know everyone on the staff, to insure they have everything necessary to perform their jobs and oversee the billing …

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Kalynns Ass part two_(0)

/ Categories: Transvestite, True Story / Transvestite, True Story / By

My mom had come from her trip. I helped her with her bags, she was telling me all about it, how much fun it had been. I was happy for her, I didn’t know how to tell her that Mr. Walker had taken my virgin ass. I wanted to I knew she probably wouldn’t be mad at me or Mr. Walker, but I held back. The phone rang, Mom answered it, “Hi James, we had fun as usual”. She got quite, and was just answering with “yes” and “good”. After about fifteen minutes she got off the phone and walked into the living room. Looking at she said “Kalynn is there something you want to tell me?” I was very nervous, but with Mom I could always say what was on my mind, so I …

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Summer vacation changed whole life pt1

/ Categories: Anal, Bi-sexual, Blowjob, Body modification, Cum Swallowing, Transgendered, Transsexual, Transvestite, True Story / Anal, Bi-sexual, Blowjob, Body modification, Cum Swallowing, Transgendered, Transsexual, Transvestite, True Story / By

Hi I am maxi ( before incident max ) I am going to tell you how an incident changed my whole life . My biological parents died when I was 3 years old , I have a sister she is 2 years older to me . so from then we were raised by my aunt she is not married .my sister and aunt both loved me a lot . During my childhood my aunt used dress me as a girl very often she even used take me out as girl for girls parties. even I liked being dressed as girl, but when I grew older I stopped dressing as girl . I was a straight guy and was attracted for girls and I even had few girl friends . But at times I used think …

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My Hidden Secrets

/ Categories: Anal, Asian, Ass to mouth, Blowjob, Cum Swallowing, Fiction, Hardcore, Slavery, Transsexual, Transvestite / Anal, Asian, Ass to mouth, Blowjob, Cum Swallowing, Fiction, Hardcore, Slavery, Transsexual, Transvestite / By

This is like my third story so like I have said in my last ones, it isn’t all that great. It’s been a while since I made a story, I apologize for that, been kinda busy and whatnot. This story is completely fictional. Just to let people know, I really don’t want any hate comments or anything, if you don’t like this type of story, then why read it in the first place? I do want advice on how to make it better though, the more the better, thanks =) _________________________________________________________________________________ All my life I grew up wanting to be a girl, but wanting to be a guy too, it was kinda hard for me to explain… As a kid growing up to a teenager I had a lot of sexual fantasies, about everything, I …

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The Bet_(1)

/ Categories: Blowjob, Fiction, Transvestite / Blowjob, Fiction, Transvestite / By

My friend Cristina and I were just sitting around watching porn. It’s something we do for fun now and then. Believe it or not, it has never led to anything. A scene came on where a guy was put in a wig and satin nightgown and fucked by a beautiful blond dominatrix with a strap on. We laughed at what an ugly girl he made and somehow it came up that I had a girlish look to me. She said that I would look much more like a girl in the wig and nightgown than the guy from the movie. I just smiled. Later that day out of nowhere, she told me that she’d like to test that theory. She wondered if I’d let her dress me up. Though about it for a moment and …

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Jessy

/ Categories: Coercion, Fiction, Transvestite / Coercion, Fiction, Transvestite / By

I was in my attic looking for lamp that I had stored for my sister.  It was getting hot so I decided to open a couple of dormer windows to let some air flow.  When I opened the last of the thee windows which was on the back of the house I could hear music coming from my neighbors back yard.  I knew that they had just left for a 2 week trip to Europe and only their 19 year old son, Jessy, was home so I was a bit surprised to see a sexy young lady laying on her stomach sunning by the pool in a pink thong.   I used my camera and snapped a few pics,  I zoomed in and was able to get some pretty good ones.  She raised up on …

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