Transvestite

Danny Boy, Jr – A Halloween Story

/ Categories: Bi-sexual, Erotica, Fantasy, Transsexual, Transvestite / Bi-sexual, Erotica, Fantasy, Transsexual, Transvestite / By

= = = = = = = = = = = = = = = = = = = = This story references events which occurred in a previous Halloween story of mine called “A Favor for Danny Boy.” But this story stands totally on its own. = = = = = = = = = = = = = = = = = = = = WARNING! All of my writing is intended for adults over the age of 18 ONLY. Stories may contain strong or even extreme sexual content. All people and events depicted are fictional and any resemblance to persons living or dead is purely coincidental. Actions, situations, and responses are fictional ONLY and should not be attempted in real life. All characters involved in sexual activity in this story are over …

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Kelly – Part 2

/ Categories: Anal, Fantasy, Oral Sex, Romance, Teen Male / Teen Male, Transgendered, Transvestite / Anal, Fantasy, Oral Sex, Romance, Teen Male / Teen Male, Transgendered, Transvestite / By

I was in shock. In the short span of a few minutes, my best friend Kevin had become Kelly. Kevin was a slender guy, with soft brown eyes, medium length brown hair which he swept down in typical emo/hipster fashion. Kelly was adorable. She was smoothly shaven beneath her clothes, wearing black lacy panties. She even had a semblance of curves. Beneath Kevin’s baggy clothes, hidden, was a delicious figure. Kelly stood in front of me, beaming down at me. She shifted her weight onto one of her hips, and placed her hands at her sides. “So? How do I look?” I couldn’t begin to describe. I could still see Kevin in there, but there was more. For me, there was a woman standing in front of me. She was a little boyish in figure, …

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The Nightstalker and the Sissy (or Sissy is Sodomized)

/ Categories: Anal, Ass to mouth, Dark fiction, Domination/submission, Fantasy, Reluctance, Spanking, Transvestite / Anal, Ass to mouth, Dark fiction, Domination/submission, Fantasy, Reluctance, Spanking, Transvestite / By

For what had to be the third time since I sat there my body shifted in my seat trying to remain comfortable. As I did my eyes stayed focused on your house but as of yet there were no changes. Finally what I’d been waiting for occurred as I watched the downstairs light go out and the windows turn black. The engine comes to life as I turn the ignition and switch on the headlights. It takes less than five minutes driving and I’m parked in my driveway. Checking my pockets I insure that nothing is forgotten in my zeal to begin the night’s activities. Though it is only September the night is cool as I zip my light, black jacket to my neck as rain falls lightly like heaven’s tears. With my hands jammed …

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Melanie Catches Me Wearing Her Panties

/ Categories: Blowjob, Dark fiction, Domination/submission, Female Domination, Fiction, Foot or shoe fetish, Male / Female Teens, Masturbation, Oral Sex, Teen, Transvestite, Young / Blowjob, Dark fiction, Domination/submission, Female Domination, Fiction, Foot or shoe fetish, Male / Female Teens, Masturbation, Oral Sex, Teen, Transvestite, Young / By

A complete work of fiction involving consenting adult siblings. Melanie Walks in on Me My sister, Melanie, is an 18-year old senior, and star soccer player. My name is Mike, and I am her older brother. We are just a little over a year apart. I am 6’0”, 185, dark hair, and a decent build. I played on the varsity football team in high school, and turned down an offer to play collegiately out of state, simply because I didn’t want to be 15 hours from home and have no family or friends nearby. The outcome for those types of players aren’t favorable in many instances, so I chose to play for the local community college instead. Mel is totally a fucking knockout. She is 5’7, weighs about 110 pounds, 34C tits, perfectly toned legs, …

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Biker Daddy Don – Story 1

/ Categories: Drug, Reluctance, Teen, Transvestite, True Story / Drug, Reluctance, Teen, Transvestite, True Story / By

Biker Daddy Don – Story 1 During the summer when I was a teen I had been selling magazines for extra money. I wore shiny pantyhose and either silky panties or a silky slip under my clothes everywhere I went. I was out going door to door when I came to house that had a man in his late 40’s working on a Harley in his drive way. On that day I had worn a shiny tan pair of exercise tights with some white silky panties over top of them that were a size too big. I liked the way they slid around with ease on my shiny hose covered cock. Anyway, as I approached him he stood up and wiped his hands off. I did my usual greeting and introduction to what I wanted, …

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My first cock was a crossdressers

/ Categories: Blowjob, Cum Swallowing, Oral Sex, Reluctance, Transvestite, True Story / Blowjob, Cum Swallowing, Oral Sex, Reluctance, Transvestite, True Story / By

One friday night back when I was 25 I was in the chat rooms looking for a little action. I had chat with a few ladies that got me nice and hard,but no of them lived in the same city as me and i was looking for more hands on fun. At about midnight a message popped up. “Hi I’m DeeDee whats your name?” “My name is Joe.” I respond. “Hi joe how old are you and where are you from?” She asked me. I tell her my age and where im from. She tells me where she is and its not far from my place. So i ask”How old are your and what are you looking for tonight?” Hoping to get some action. She responded with”I’m 35 m crossdresser,I’m very passable.” “I even get …

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Sam to Samantha_(1)

/ Categories: Anal, Blackmail, Fantasy, Reluctance, Transvestite, Young / Anal, Blackmail, Fantasy, Reluctance, Transvestite, Young / By

Hi my name is Jason and I’m 19 years old. I was living with my parents and looking for a job and a place of my own. I did have a job but it was just a part time job at some restaurant, just to kill some time. Anyways, one day my mum called me downstairs and said that Mrs. Fletcher from across the street was asking for me. I went downstairs and there she was waiting for me. Seeing me she said “Jason, hi, I’m going on a business trip for about two weeks and was wondering if you could look just check up on my son while I was gone.” Mrs. Fletcher was actually fairly good-looking with red hair and light blue eyes. She lived alone with her teenage son Sam. Sam was …

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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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