Crossdressers indian porn

1 year ago

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My crossdressing fantasies Free Sex Stories and Adult Erotica Stories

I had an affinity towards women’s clothes and have a lot of crossdressing fantasies. The soft silks, shimmery fabrics and bold colours – I loved them all. But I was a boy and all my friends would laugh if ever a boy wore a pink shirt. And I loved hose colours. I wanted to raid my mom’s closet, wear her dresses, put on makeup and strut like the diva that I was. But I held this in me for many years, until one night I saw my parents. They had dressed up in costumes I believe. My mom was a...

4 years ago

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Room 209 First Sex as a Crossdresser

crossdresser – trans – interracial – lgbt – first time – virgin – black cock – crossdressing – natural tits – braI've been crossdressing for much of my life, as far back as I can remember. I would even go to sleep as a k** and pray that I would wake up in a girl's body. In the last few years, now that I live by myself, I spent about $1,000 on a whole wardrobe of women's clothes for myself - bras, thongs, dresses, tops, stockings, lingerie, make-up, perfume, etc... I have also been overweight...

3 years ago

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Confession and testament of a crossdresser

Italy, september 2011. Sorry for bad english, I try to write correctly but don't know if I did. From tonight, I was a crossdresser. I'm been crossdresser from 12 to one day before my 27th birthday. Irony. I begin to have an answer to the question: "What feel girl?" Yes, a simple question. What feel girl when wear panty, tights, dress, skirt? What feel a woman in heels, purse, with her hair falling down the shoulder? What feel a teenage when begin to make up herself? When wear lipstick,...

2 years ago

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The Photographer And The Sissy

I was 2twenty-two, closeted fully and living out my sex life in fantasy and on the internet. I had discovered my love of dicks in my teens, followed a few years later by my fetish for dressing up like a girl. I have no idea why, but the sight of my own body in tights, knickers, stockings and heels made my boy pussy (dick) wetter (harder) than anything else, straight or gay.Luckily, I lived alone (in a private studio apartment, in a major city in the Netherlands), so I could basically live out...

1 year ago

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First time crossdressing with another CD

This is part one of a story, from a former user. I’d like to read the continuation, or anything else written by them. I enjoy the stories as much as the pics and videos, they all get to the right part of me. Any help would be great. First Time Crossdressing with a mate part 1 This is a work of fiction, though someday I hope to make it a reality. —– It was the height of summer, and my girlfriend was out of town for 2 weeks. I’d had a handful of experiences with guys before, but ever since I...

2 years ago

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Alexia s Tale Chapter 2 Online Exploration

Looks like it's never gonna stop," Alexia muttered, the warm vapor from the cocoa rising past her face like a discounted sauna. Her voice pitched higher, much to her liking, she continued, "twenty-four years old, with a job as a writer. Yet I'm bored."The maroon cardigan wrapped her exposed shoulders, but did little to envelop her breasts upon which she rested her hands that held the cocoa. Her legs, warmed by the stockings, lay crossed to one side, elegantly covering what the skirt wouldn't....

2 years ago

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Sharon Goes The Distance

When I woke up Saturday morning, I knew it would be a very eventful day. My wife, Donna, had been making plans for quite some time, which included me dressing up as Sharon, my female alter ego. Three years ago, I had confessed to Donna my desire to wear feminine attire from time to time and she had embraced it more than I could ever imagine. In fact, she took pictures of me all dressed up or even while she fucked me with her large strap on dildo. We posted these photos on a free, picture...

3 years ago

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Cd crossdresser sissy caught by mom and dad

Backstory - I just turned 19, in college and still live in my hometown with my parents. I've been crossdressing on and off for the last probably 10-12 years. Till I was about 15 it was just whatever my sister or mom had that I could get my hands on while they were gone. Then when I was 15, I would order some online, or sneak out and go to a store right before they'd close. I've only told two girls, one who didn't believe me and the other who was supportive but didn't really care. For the last...

3 years ago

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Nice surprise for the delivery man

I'm a crossdresser in my early 20's and still live at home unfortunately. The day started as it usually does when I'm home alone, dressing up. On this day I had gone for a pink G-string with a matching bra, my breast forms, and some tight leggings which showed off my pert bum very nicely. A black lace top and of course my light brown shoulder-length wig and my make-up. I was in a bit of a horny mood so I went for the red lipstick and lip gloss to give them a sparkle, red nail varnish with...

2 years ago

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First time crossdressing with another CD

This is part one of a story, from a former user. I'd like to read the continuation, or anything else written by them. I enjoy the stories as much as the pics and videos, they all get to the right part of me. Any help would be great.First Time Crossdressing with a mate part 1 This is a work of fiction, though someday I hope to make it a reality. ----- It was the height of summer, and my girlfriend was out of town for 2 weeks. I'd had a handful of experiences with guys before, but ever since I...

4 years ago

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Crossdressing With My Mami

Hii, mere naam ankit hai. Main mumbai ka rahnewala hoo. Yeh kahani meri or meri mami ki hai jab hum sath me crossdressing kiya karte hai. Meri mami ma naam sabita hai. Unki lambai 5ft or woh thodi moti type ki hai. Unka koi baby nhi. Lekin fashion ke mamlo me save age rahti hai. Jab mai 10std me padta tha tab meri mami or mama culcutta se mumbai aaye. Yaha aane ki unki ek hee wajah thi paisa. Mujhe pahle se hee porn video dekhna achcha lagta tha. Mujhe femdom, bdsm, bondage jaisi porn bahut...

1 year ago

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Crossdress Sex 8211 Mami Fucks Using Strapon

Hi my name is Sunil(although I call myself Sunita). I 29 and I am a beautiful crossdresser with very nice body. I own three beauty parlor in Delhi, and I am always dressed as a girl. I go out wearing woman clothing and no one can say that I am a boy. Now coming to the story, it happened 10 years ago. I was 19 then. I was bottom crossdresser then also and had sex with many top guys until then. I was fair and my body was very girly. I had a round bubbly ass although my boobs weren’t developed...

1 year ago

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A Paper to The Society of Crossdressing Hardware Engineers

SOME NOTES ON THE DESIGN OF CROSSDRESSING HARDWARE There are several difficulties to be overcome in the design of self-crossdressing hardware. This paper will enumerate them and offer suggestions to remediate the problems. 1) Determining the sex of the hardware. Actually, determining the sex of the hardware is not a formidable task. The primary problem occurs because design engineers have no discernible knowledge of sex. After all, anyone who spends their day in front of a...

3 years ago

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Crossdressed in public

hi ppl i m rohit….i m 16 yrs old and i live in delhi…i love to crossdress when i m all alone. i hv been doing this sicne i was 13 yrs old.i used to wear my mom’s clothes n gaze myself at mirror. though i was not a gay but i wanted to try gay sex once by turning to a women. it was in d month of june when my parents had to go to noida for some work and i was left all alone at home for a week. one evening i thought i should try crossdressing and go out to enjoy in public n tease some ppl.i...

2 years ago

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A Maid Story

It had been a long day and Paul was tired.   After a week of traveling and a full day of meetings, Paul was ready to unwind with his wife, Marie.   They were what many people might describe as soul-mates. They were best friends who shared their deepest, darkest secrets with one another and who regularly consulted with one another on a wide variety of topics. Their love life had suffered lately and had grown somewhat predictable but that didn’t bother Paul too much.   There was so much...

2 years ago

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Dan Becomes Dawn Chapters Three Six

Chapter Three: Coming Out! I felt much more confident, to the point of euphoria, as I drove to meet Andrew and Marie. Just having the seat belt bisect my bosom was a thrill.I found the correct address, parked in the driveway, took a deep breath, retrieved my purse and the bottle of vodka, went up the steps to the front door.Seconds after I rang the doorbell, Andrew answered. "Good evening, Dawn. You look fantastic. Please come in.""Thank you, Andrew. I am just a little nervous." I handed him...

2 years ago

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Dawn Visits Kansas Chapters Twelve Eighteen

Chapter Twelve: MondayPart 1: Morning – County Clerk’s OfficeI woke at sunrise, eased out of bed, trying to not disturb Patti, gathered clothing, and went into the bathroom. Showered and shaved, I put on panties and bra, did my makeup, put on my wig and stud earrings. I slipped on my navy floral V-neck dress and tip-toed out of the bedroom, closing the door before slipping on my black open-toe two-inch heels.I went into the kitchen and started a pot of coffee, then to the office and powered up...

3 years ago

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My Crossed Life Chapter 6 Valleys Peaks The Professor

The sexual high of Halloween weekend came crashing down three weeks later when Missy stopped by my house unexpectedly. She was in tears. I assumed the worst, thinking something had happened at school. It was far worse. Missy’s brother and I had grown apart. I was a jock by day, diva by night kind of guy. He was kind of a stoner who had abandoned our friend group. So while it wasn’t surprising he wasn’t the one delivering the news, having a tearful Missy show up at my front door was.“My family...

4 years ago

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Meeting an Asian Sissy

The first time I saw Zoey was on a hookup site.  Asian. Mid-twenties. Long black hair. Dressed in a royal blue satin corset, panties, black stockings, and high heels.  She didn't show her face or her cock. Just a sexy body in lingerie.It was just still photos on that first post.  But over the course of a year, I saw more ads posted to different sites.  Sometimes there'd be videos. In one she rode a dildo in a leather dress and stroked her cock.  She was getting bolder. She posted links to an...

2 years ago

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Attractive To A Fault

Events in our lives can often change us in ways we never expect. In my case I certainly felt different as a young boy. I possessed very real, mysterious, unexplainable, emotions that I can describe only as feminine needs, in spite of being athletic and quite normal in appearance. These internal feline longings and desires were intense and drew me to all kinds of feminine things.I knew that I loved to feel like and even look like a girl. In my youth I would secretly dress up like one though my...

2 years ago

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Frank

Frank didn’t vocalize his orgasms. So I never knew he’d cum until he stopped his motion and pulled out of me. Then I’d look over my shoulder with a smile and ask, “Did you cum?”And Frank, already backing off the bed, his big cock curving downward now, would reply, “Yeah.”Although normally quite chatty, in the immediate aftermath of sex Frank turned into a man of few words, a regular Clint Eastwood (though not nearly as tall or handsome). Without having to be asked I would back off the bed as...

1 year ago

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Experiences Of A Crossdresser

This is an introduction to my crossdressing experiences – touching upon highlights along my journey. I will write more about these, and other encounters in detail, in time. These really are all true stories, no embellishments whatsoever.I had always been fascinated with women's clothing, specifically tights (pantyhose) and anything silky and sheer, like slips and sheer blouses. I would typically be drawn to anything black, but did have a fondness for nude tights and white slips, also. I usually...

3 years ago

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Blackmailed Crossdresser part II

A few weeks after that first incident with Stefan where he had blackmailed me into having sex with him, I got a text message off him. I was a bit surprised, as we had managed to ignore each other in work. I was growing optimistic that this incident was behind me. Even though it was left me feeling violated and with lots of confused feelings about myself.I was shocked to open the message on my phone and seen two pictures of him fucking me in the hotel! I was on all fours on he bed, in bustier,...

2 years ago

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Crossdresser Turns Gay To Seduce His Tailor

Hi all! I am a family man with a loving wife, but she doesn’t know about my crossdressing. It just so happened that she had gone to her mother’s place during her pregnancy, and I got ample time for my crossdressing. I did all of my shopping on Myntra and bought myself some nice soft satin sarees, dresses, gowns, tops, high-heel shoes, a makeup kit, perfumes, and loads of bras. I was waiting for the delivery like a curious kid waits for their birthday gifts. Finally, the day arrived and the...

3 years ago

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Bisexual Crossdresser Fucked By Drunken Roommate

Hello, people. I am Sahil. I am currently living in Mumbai in a shared apartment with my roommate Raj. We both doing our engineering from different colleges in Mumbai. This story is based on my and my roommate’s real life experience. Which is how I am engaged in a sexual relationship with Raj. Let us start with the introduction. Introduction: Sahil The author of the story. I am 24 years old. Since I was at 14 I have a very strange fantasy of Crossdressing as a beautiful girl. Whenever I was...

4 years ago

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Dressing up

This is a series of stories rather than one story. It talks of my experiences as a crossdresser. My first experience as a crossdresser came as a teenager when I tried out some of the clothes belonging to a woman who was staying at our home. She was a gorgeous French woman with very pretty clothes and I did enjoy trying them on, but primarily as it got me closer to this woman who was way out of my league. When away from home the first time I bought a few clothes through a mail order catalogue -...

3 years ago

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Jessi s coming out party

Hi everyone. My name is Jessi, I'm 23 and I have been a crossdresser for over three years. Recently I decided to go full time and was going to met up with some friends to come out to them. I arranged to go hang out with them at my friend Derek's house, them thinking I was still coming as my old self. My roommate, who started my path into crossdressing (that's a whole other story), told me if I was going to come out to friends that I should do it in style. She lent me her cream colored dress...

3 years ago

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We All Have Our Stories

I want to present a few short vignettes concerning crossdressing. A most interesting and individual form of sexual gratification and fulfillment. The first story concerns a strong man, happily married and happy with the sex he is getting from his wife, but something seems missing in his life. He often walks the streets and window shops, but seems to be drawn to the windows displaying ladies' wear, from dresses, to frilly underwear, to stylish shoes. He is drawn to it all. And he forms the...

3 years ago

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A Crossdresser 8217 s Life

Hi! This is my first story on ISS so don’t be harsh on me. This isn’t a real story, but a fantasy which i am going to share with you,though the characters are real. I am a boy(21)(crossdresser) doing my engineering in Bangalore in a reputed college. I stay at one of my fathers friends house, his name is Rajesh. His first wife died due to cancer so he married again. His new wifes name is Rajni. Rajni, in her 30s, is a damn hot woman with a plus size figure. Now lets move on to story… Initially i...

4 years ago

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If the Crossdress fits

If the Crossdress fits... I didn't know what to expect when Maxine opened the door to her loft. I hadn't really thought about it, but there she was, holding it open for me. Her place looked like the hideout of a very stylish, sophisticated thief, who had just robbed a Sanrio store. That is to say all the furniture was sleek and minimalistic, classy even, but it was piled high with cute Japanese toys. A large window overlooking the arts district dominated the loft's main room. I...

2 years ago

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Danni The Crossdresser First Time Sissy

by - sissy debbie This is a true story about what happened to me after graduating high school and how I became a sissy for woman who was nearly twice as old as me. --------------------- The summer after my senior year of high school a neighbor asked me to look after her house and her cat for a week while she took a trip with some friends. Her name was Heidi and she was an attractive woman about 38 years old. She just wanted me to stop in and check on everything a few times. I...

1 year ago

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Nenu Crossdresser Nunchi Gay

Hi, na peru ajay. nenu tenth class ki vachinappatiki naku crossdressing alavatu ayyindi. enduko emo telidu, kani adavalla laga chira, jackettu vesukovatam istham. mukhamga Bra and Panty. ma inti venaka oka portion lo vunde oka ammayyi thana battalu vutiki bayata aresedi. ala aresina vatilo thana Bra lu kuda vundevi. mamuluga avi sayantram avi tisesedi. kani oko sari marichipoyo emo battalu tisedi kadu. ala tiyanappudo leka oko sari Valla bathroom lone vadilesina battallono (valla bathroom...

3 years ago

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Losing my virginity

I'm a 21 year old attractive crossdresser from Mumbai, India. I am sharing a true story of how my roommate turned into a permanent fuck buddy!I've been crossdressing for 10 yrs now and have my own collection of all kinds of stuff you can think of. I moved into the city 2 years back and rented an apartment with a guy called Vishal who I didn't know at the time. The first few days went in unpacking and setting up my room and trying to build a decent rapport with Vishal, have some drinks once a...

2 years ago

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Ray and the Halloween Party

   I have had sex with a few guys since my last story but there nothing much worth writing about so I thought I would “go retro” and tell you about a hot experience I had in my senior year of high school.    At that time I kept my crossdressing pretty much private and only a handful of people knew about my slutty side as Lisa. Even most of my best friends had no clue. (At least that’s what I thought at the time.) One of my best friends was a good looking guy named Ray. Ray lived...

1 year ago

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It s A Family Affair

It wasn't unusual to receive a phone call from Rebecca at eleven o'clock in the evening. Since her recent divorce, she often called for a chat with my wife Linda. "Hey, gorgeous!" I answered the call on the landline.Rebecca, aka Becky, aka Bex is a "special" friend.  She has known of my crossdressing for over twenty years, during which time she has been a major contributor to my wardrobe. She's an attractive brunette, has a great figure, and her shoe size is the same as mine. Only a week ago...

2 years ago

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Friday night crossdressing fun part two

Friday night crossdressing. Doing a favor for a gay neighbor gets me more exposure when a friend finds out I like crossdressing. Continued… Gail walks up to Candice, leans over and they start making out. Before I knew it everyone had a partner and they were all making out except Mark and I. As I said before, Mark and I have known eachother since grade four. I heard he made a pass to another guy once but I thought it was just a rumor. I've always liked crossdressing but didn't consider...

3 years ago

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First Time Full Dressed Up

I had always wondered what it was like to get dressed up as a woman and go outside. One day the opportunity came.  I didn’t go crazy, nothing super public, but outside nonetheless.My wife was out of town on business and there was a bag of clothes we were going to donate, and inside was a pink office-type suit: skirt, white blouse, and pink jacket.  I had bought a pair of pantyhose earlier and had access to wigs and costume jewelry. I find pantyhose very sexy and had beat off and cum in them...

1 year ago

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Crossdressing Hooker and the Creampie

I've always had a feminine body, slim but some female curves so I've been able to pull of being woman in public a few times already. I started by placing an ad in the local erotic escort guide with some of my best pictures and immediately got replies from interested men. I decided to call one of them who wanted to bring a buddy and we set a date at a local hotel for 8 pm. I wanted to look amazing for the first time so I started by shaving and making sure I had no body hair...

2 years ago

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Where Did My Damn Key Go Part 3

Four days; I've dealt with four grueling days of not being able to touch myself. Jesus, how can anyone even do this without even going insane?!Ever since I crossed paths with that dominating bimbo, my entire routine had changed. And to be honest, I was surprised at how much sex was in my life. From the moment I woke up to the second I crashed and fell asleep, my mind was very frequently in the gutter, wondering when I was going to get some ass or where can I go to beat one off real quick....

1 year ago

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Unexpected Turn of Events

I sat in my favourite bar sipping at my glass of Chardonnay; I had been coming to ‘The R Lounge’ for a couple of years. I watched the guy talking to his friends across the room. They were all dressed with a bit if style but he had caught my attention. He was wearing trousers with a casual blue and black stripped shirt. He was probably five feet nine inches tall. He had an average build; not to slim but trim enough to know that he tried to stay fit. I guessed he was around forty years old. But...

4 years ago

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Ladies Night at the Leather Bar Part 2

Now that you've met Chloe in Part One:Today I want to remind myself of how much I owe her for luring me into the circumstances wherein I met a beautiful man, a man who would change not only my life, but my basic conception of myself. I found him in the most unexpected of places. A place where Chloe brought me.SUMMER 2011. THE SAN FERNANDO VALLEY.I had just gotten home from work, put on my makeup and changed into some old, torn black fishnets and garter belt, but I couldn't decide on a top. I...

3 years ago

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576 Shadow Oak Drive Part 2

As Molly drove down the highway, I sat in the passenger seat. Although I had always had a feminine side, I was experiencing all kinds of new emotions and feelings that I hadn't felt before when dressed. I don't know exactly what brought it out. Maybe it was the love and support of Molly. Maybe it was seeing myself truly dolled-up for the first time, seeing my own cleavage, having my manhood taped and pushed back. Whatever it was, for the first time in my life I felt more girl than man. Molly...

1 year ago

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576 Shadow Oak Drive Part 1

I met Molly on a seemingly random day. How could I ever have known she would change me forever? It was late April and I was working behind the cash register of a local department store. I was eighteen, just out of high school, and didn't have any sort of plan for my future. I figured that I would take a least a year off before applying to any universities. I liked working at the department store not only because of the discounts, but because I had figured out a way to sneak some of the clothes,...

3 years ago

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The Adventures of Patty

“You're wearing my things again!” Brenda screamed when she came home early from community college and found me prancing around the house in one of her short skirts. “Take them off, you little pervert!” It wouldn't be nearly as bad if I were her little sister and trying on her clothes but I was her brother. But it wasn't as bad as it could be. I mean, if she knew what Tommy and I had been doing just two short hours ago, she'd really be pissed. Truthfully, Tommy and I had never really done...

2 years ago

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Pam s First Time

Just a few days of spring break left and I was planning on making the most of it. Well, the most for me anyway. I'm a crossdresser and I have been for a long time. All through high school I'd secretly dressed, slowly building a wardrobe of pretty panties, a few skirts and blouses, bras, my silicon boobies, and most importantly, my shoes. The most important thing I had going for me, at least from my point of view, was my stature, which was slight, no, it was petite. I have one year of college...

2 years ago

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Not Crossing The Line

When I was a kid I had a book called, ‘What Do People Do All Day?’ It made a start at teaching me about the variety of jobs that exist in the world. As an adult I feel it would be equally beneficial if there was a book as simple as that one which answered the question, ‘Why do people do the things they do?’ Part of the trouble is that I often do not even understand my own motivation, particularly for those things I feel uneasy about sharing with others. For my normal side, I married an...

2 years ago

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CD crossdresser daughter rsquo s bitch

Note : This story is completely fictional!How did I end up like this? On my hands and knees dressed in just sexy stockings and suspenders and a lacy corset, my face in slutty make up, my lips wrapped around my daughter's boyfriend's cock while my daughter herself rammed an eight inch strapon up my arse. The worst of it was, humiliated though I felt, this was really turning me on. This is the story of how I became my daughter's bitch and how I came to love it.I suppose I shouldn't have let...

2 years ago

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The Bodysuit

“The process is actually very simple Mr. Smith,” she said.“It is very much like 3D printing, just using different materials and in a printer that prints on your body. We can print anything on top of your body to make you look however you want. The technology was originally developed for use in movie special effects, but we have seen there are, well, more personal uses that some of our clients like to use the service for.”How could I pass on this I thought. The chance to have a body in effect...

4 years ago

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Tied and Taken

I had always had fun and gotten excitement from crossdressing and bondage play. After my first encounter with Chris, I was forced to accept the fact that I had desires and needs that I had suppressed for years. After having been tied up and mouth fucked by Chris, I realized that I didn't just like dressing up like a girl. I just didn't get a kick out of being tied up. I wanted to be a "damsel in distress" at the mercy of a man, to be helpless before him, to be used as a woman as he saw fit. My...

3 years ago

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Duped Into Being a Crossdressing Bull Part I

During my second year in college I was in between girlfriends and at the time I was greatly indulging in my crossdressing fantasies. I spent a lot of time in lingerie sections of stores buying bargain panties and bras since that is all that I could afford. The pickings were fairly slim for a big guy, so I developed a love of granny panties because those are so easy to find at a store like Walmart or Target. Craig's List and similar websites did not yet exist at this time (including Fet-Life)...

1 year ago

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Becoming John Collins Mistress Part Two

The next day, everyone was a bit hung over. I needed to pick up my car, which I’d left at the bar the night before. Joe said it was on his way and he’d be glad to take me. I borrowed a raincoat from John to wear over my skimpy outfit, then Joe and I headed out. Joe was making eyes at me during the drive, and I decided it would be best to come clean. “Joe, there’s something you should know about me,” I started. Joe quickly said, “Hey, baby, there’s a lot I’d like to know about you.” “Yeah,...

1 year ago

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Hitchhiking teen crossdresser

It was a 200 mile journey from the city to the outskirts of a small town by the countryside where I live, I have hitchhiked this road many a time but this day proves to be an exhilarating adventure into my first cross-dressing sexual encounter, I had my large backpack I carried with me with my belongings including in secret my lingerie, heels makeup etc. about 60 or so miles out a 4 wheel drive hauling a horse trailer pulled up alongside me, rolled down the passenger window a man who seemed to...

1 year ago

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Milwaukee Cuckold rsquo s Wife and the Crossdresser

Judy used several sites over the years to find her friends with benefits. She never tells me until afterwards what she has done. It’s rare she tells me anything in advance. One day she advised me the k**s were at my parents and she was entertaining that night and I would have to stay in the family room. My curiosity was getting the better of me.She went and took a shower and asked me to come in and shave her pussy. She had me paint her fingernails and toenails. Once she was ready she put on her...

2 years ago

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Crossdresser for mature couple

I am a bi crossdresser....love some pussy or cock. I registered on an fabswingers looking for a meeting with similar people.I was actively looking for an older couple to have some fun with. To cut a long story short, I finally got talking to a guy called Bill. He and his wife could entertain a gurl like me for a fun filled evening, if I was game. We both had a list of dos and donts for the night and we went over a few ground rules etc.I was to be their maid and waitress for the evening. They...

1 year ago

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A Crossdresser s Night in the Park

Last night I was on line in a crossdresser chat room where I was talking with Master Brian about me being a pain loving, submissive, bisexual crossdresser who was looking a master to use and abuse me. As we talked Master Brian asked me if I was dressed as a woman while I was on line with him. I told him that I was and then he asked me what I was wearing. I told him that I was all dressed up wearing a black silk mini skirtwith a black stretchy lace blouse. Master Brian then asked me what I had...

3 years ago

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First crossdressing experience 3 cocks in1 hr pa

I started with crossdressing a few month ago, first just panties or strings when i had a wank over videos and pics of other crossdresser getting taken or dominant trannies and women humping devot men.By now i wear black stockings and suspender belt, a white lace string, black shiny mini skirt, white blouse, 4" black heels and a blonde wig.I also had an extreme urge in me to feel a real cock in my arse, to satisfy these needs i began to visit adult cinemas in my area, first just with stockings...

3 years ago

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The story of how i began crossdressing Part 1 3

Entry #1:I guess i was 17 years old and broke up with my first gf back then. barely had any sex, so was horny all the time :PI decided to look online for couples and women who would be interested in camming with me, and a mistress responded to one of my advertisements on some swinger site (i cant remember why i actually registered there) She told me she’s looking for a slave to entertain “them”Thought it was a spelling mistake (since it was german its not really much of a difference)So i agreed...

2 years ago

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A Crossdresser rsquo s Life

Initially i use to wear my sisters dresses or my mothers bra,panties,saree,blouse,petticoat and see myself in a mirror and admire myself. Though i wasnt so good at makeup, i used to apply lipstick and put some jewellery items. It couldnt make me look like a girl but the feel of women’s clothes turned me on. And then i used to masturbate after my every crossdressing session, thinking about being fucked by a guy. But then as i grew up chances of being alone became less and i had to kill my desire...

1 year ago

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firsts time I m seen as cd crossdresser

From a young age I liked dressing up in womens lingerie and clothing.... as I got older I grew up over weight a little and more so the older I got..... by the time I was I was in my late teens I had nice size breasts....nice enough to fill a bra. So worked up the courage to buy some lingerie online and when I received it in the mail I was so excited. I couldn't wait to try everything on.... I had brought a white lace bra, matching panties and white suspenders and stockings.....I tried them...

2 years ago

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Teenage crossdresser

Here are the usual disclaimers this story is for adults only if you are viewing this andare not 18 years of age or older please close this page immediatly.There is no cross dressing in the story but this is how I began my transformation fromregular boy into cock suckking teenage crossdresser.We were having a really hot heat wave. i meat with my older brother (wear red shorts, and a black T-shirt) wanted me to get out of the house and off the computer so she suggested a movie. I felt wierd going...

1 year ago

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Losing my crossdressing virginity

This is the true story of my first time with a man while fully crossdressed.I answered an ad in the local paper for a guy looking to meet a crossdresser and exchanged some text messages before agreeing to meet.I took the bus to where we had arranged to meet, it was a flat in a not great area of town. Nervously I rang the buzzer and entered the block, getting the lift to the fourth floor I went to the door and rang the bell.The door was answered by a man in his early fifties of middle eastern...

1 year ago

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Two Girls Are Better Than One

My girlfriend, Sherry, had nice, big C-cup titties and a face like a young Marilyn Monroe. Needless to say, she got hit on by lots of men wherever she went. She was also a nyphomaniac who liked to be fucked ten times a day, so we had a great sex life. She found out I enjoyed wearing lingerie, so, as part of our sex play, she would dress me up in her panties and bras and stockings and put lipstick and makeup and eye shadow on me. This kept me hard for her for hours and she really enjoyed all the...

4 years ago

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crossdresser s 1st time

hi, im new to this. this happened about 3 years ago now.I had started off the night being at my ex gfs house looking at her sexy underwear thinking how it would feel etc. so, having just started a new job I felt it was time to relax a little while she was out working (from 10pm til 6am). from this simple thought I became massively aroused and started trying on her underwear, make up, and even a wig that was in the apartment. soon enough, I was looking like a slutty crossdresser.I thought enough...

2 years ago

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first time web hook up crossdressing dominatrix

crossdressing has always been my secret pleasure I even had a cache of out fits make up wigs and heels. it started when I was younger but evolved as I got older, now as I got older ive refined my skills and abilities and can pass as a girl when dressed. I had fooled around with guys before but I had never dressed for one only indulging in self pleasure with toys and my fingers. when I got off work on friday I was excited for the up coming three day weekend going home to get dressed up maybe go...

3 years ago

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The story of how i began crossdressing

This is copied from my blog http://cdcutiepie.tumblr.com, so the main updates will be therei did think it would be nice to have it up here as well though :)Entry #1:I guess i was 17 years old and broke up with my first gf back then. barely had any sex, so was horny all the time :PI decided to look online for couples and women who would be interested in camming with me, and a mistress responded to one of my advertisements on some swinger site (i cant remember why i actually registered there) She...

3 years ago

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Crossdressing Karte Hue Pakad Liya

Hello indian sex stories dot net friends , my name is preeti(fake name) age 20. Ye baat kafi purani hai lagbhag 3 saal pehle ki . Mai ek part time crossdresser tha aur mujhe meri chachi bahut pasand thi aur hain . To mai jab vo aur ya koi b ghar pe nahi hota tha to mai unke room mai jake unke innerwear pehnta tha . Aur jaise ki mujhe bondage bahut pasand hai to chachi ke kapde pehnke self bondage karta tha jab ghar pe koi ni hota tha . Isi tarah ek din ghar pe koi ni tha aur mai chachi k room...

3 years ago

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mature crossdresser 18 year old PART 1

Myself being a fulltime crossdresser and wear mini skirt and dresses all the time an high heels. A few weeks ago some new people move in across the street from me to be extact it was a woman and her 18 yr son.I talked to her few times and she was very nice and in our talks asked her if it bother her that i was a cd/tv she said nope. Well after couple weeks we became good friends and found out her son was shy and kind of a nerd. One day she came over to me and was little upset over something she...

1 year ago

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My first time with another crossdresser

In this story, I'll go in depth on how I became the "girl" that i am today. It all started when i was about 5 years old. I obviously wasnt sexualy active way back then, but thats the age i remember i fell in love with pantyhose. One night after my parents came back from a wedding, i was home with my brother and sister. They came home, changed and what not and went to bed. well my mother who changed in the bathroom left everything that she wore in there. i happened to pick up her pair of sheer...

3 years ago

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Crossdresser wanting some dick on the road

I`ve been crossdressing since I was 20 years old.One of my favorite things to do is get all dressed up in womens clothes and drive around on the open road.Several years ago I was mad at my ex wife for doing some stupid shit with our checking account and we were split up for some well needed cooling off time.The more I got to thinking about her stupidity the more I got to smoking some pot and drinking a few mixed drinks to get the crap off my mind.I got pretty stoned and decided to get dolled...

1 year ago

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Crossdressing Charlie Episode 11 Under His Thumb

CROSSDRESSING CHARLIE Episode 11 UNDER HIS THUMB Prue watched him get into the car from the top of the steps. Dave, who was still standing outside of his car, stared at Prue maliciously. She returned the gesture, glaring intently with apprehension before watching him swing into the car. Dave was quieter than usual as he settled himself at the wheel. He looked unnerved, doubtful, and even a little irritated. He turned the key in the ignition and the engine revved up like a vicious...

1 year ago

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Summer dressing

It was the mid 1980s, I was 20 years old and it was the summer holidays. For the long break from college I'd managed to find a vacation job in Kent in the south of England. It wasn't brilliant but I was going to get some experience of working with computers, and earn a bit of money to keep me going during term time. The company was based in a small town where I had found a room in a house with a fairly old-fashioned landlady. The freedom of being fairly anonymous in this new job and town was...

2 years ago

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Teenage CD Awakening Part II

I had crossed the Rubicon. I had tried on my sister's panties for the first time. Now I felt guilty. Incredibly guilty, and dirty. I went to school as normal the next day, but despite the guilt I couldn't get the amazing thrill of trying on that little pair of blue and white striped cotton panties out of my head. As 3.30pm and with it the school bell neared, the overwhelming urge to do it again overcame my guilt. I was ready and willing to try on my sister's panties once more, as soon as...

4 years ago

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The Crossdresser Body Swap Part 1

The Crossdresser Body Swap Chapter 1 Ashleigh finished polishing her toenails with a final dab of red nail paint. She rolled onto her belly whilst letting her feet dangle off the bed to dry. She noticed the time on her phone and let out a sigh of annoyance, her neighbours would be coming around for another dinner night soon. Ashleigh always thought they were a weird bunch, always practicing meditation in their garden, plus their house was littered with all this voodoo and spiritual...

2 years ago

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Put it on

I was living and working in London, my first job after college. No chance of having a place of my own with these crazy house prices and this being my first job at the age of 23, so I rented a room from a guy older than me, in his mid-30s. His name was Steve and he was a masculine type, split up from his wife but seeing a feisty Spanish woman called Manuela. There were big arguments now and again but at least the sex sounded good, if the rather loud sighs, moans, groans and shrieking I could...

3 years ago

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A Tale of Two Clitties

A Tale of Two ClittiesOne day I was checking out the bulletin board in a local adult bookstore. My eyes danced across the listings. Dungeon masters, couples looking for a third, but then I stopped, there it was, "Lonely virgin crossdresser seeks same". My heart jumped in my chest, and my cock twitched in anticipation. I tore off a tab with her number and promised my feminine side I'd call.A few days later I finally worked up the nerve to call her. I had battled all the familiar fears; would I...

3 years ago

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Webmeets Diary Ch 04

Note to the reader: In this diary I will tell the true stories of my sexual encounters that have come about thanks to the internet. Some more precise details such as names and places will be left out to protect mine and others privacy, and also because they don't matter, but otherwise I will try to be as accurate and truthful as possible.As I neared the end of my university course I had less and less time for playing around on adult personals sites, and spent most of my free time planning my...

1 year ago

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Been A Long Time

Once I got married I pretty much gave up my crossdressing lifestyle to lead a more "normal" life.You know,settle down,have a couple of kids. I was a happily married man with two kids,what could be missing? Well one day while at work,I was on the internet and stumbled onto a crossdressing website,and all kinds of memories came rushing back to me. The feeling of sexy panties,bras and hose.The feel of a hard cock pushing it's way past my lips and down my throat.The taste of a hot load of cum. As...

2 years ago

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First time with a man

I have been crossdressing since the age of 11 years old. I never really considered myself anything other than straight. Up until I turned 19. I often fantasized about other guys when I was dressed but that's as far as I took it. The year was 1984 and one day I decided to stay home from work to play. I get dressed up in a pair of purple satin string bikini panties,matching bra,black thigh highs and garter and a short silk spaghetti strap nightie,that barely covered my ass. After playing around...

3 years ago

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Crossdressing Vignettes True Story

I went through a period in the '80s and '90s when I was very much into crossdressing and being a bottom. I didn't write these events down at the time, but I wish I had. As the events come to memory, I'll write and post them. Here's one such story:In the '90s, I was married, and my wife didn't (as far as I knew, anyway) know about my bi or crossdressing interests. I loved her very much, but I had these other desires I never shared with her. I kept a small bag of lingerie, condoms, and lube...

2 years ago

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Bo s Dumb Luck Part One

The year I graduated from a school in 1987, I started working at the hospital full time.I was born in 1969, and the Woodstock gen was my parents; I grew up to excellent music, the smell of some pot and incense, and pretty loose morals. There were disciplines out there I follow. I believed in some; I do not believe in others.Dad is a mechanical engineer. Mom called him "your smart mother fucker", mom was always kissing dad; in return, dad was ever feeling her up, and they had lots of affection...

2 years ago

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Brittany s Adventures Part 1

You can say everything started at a young age when I started having this new but strange desire to look through my sister's clothes and underwear drawer. A little while after when everyone was out of the house and I made sure nobody was coming back I tried them on. It was at sixteen when I put on my first pair of panties and it changed my world forever. I still remember that magical feeling when the skirt fit me just right and curved my body into this beautiful feminine form.As a growing...

4 years ago

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Dawn And Patti Move To Denver

Part One: Preparing to MoveI returned from two weeks in Kansas with Patti. During that time, she insisted I dress as a woman. This had worked until my purse spilled and Patti’s friend Brenda Hess picked up my driver's license. Fortunately, Brenda was very accepting, even encouraging me to transition into living as a female full-time.Patti and I were introduced to swinging with Brenda and her boyfriend, Martin. The initial purpose of my trip was to appraise the property Patti’s parents had owned...

3 years ago

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Second Encounter

We have arranged our second encounter to be at a beach house in Duck, on the Outer Banks of North Carolina. You have made the arrangements and sent me the address, and I am to meet you there.I am filled with anticipation as I pack my bags. I include my makeup, wig, sexy teddy, stockings, and my latest purchase, a 38D silicone breastplate complete with realistic nipples. I also pack a one-piece bathing suit and several sundresses and sandals.I arrive at the address and am impressed by how...

3 years ago

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A First Time For Everything

Matt looked exceptionally young for his age and blessed with a complexion that meant he wasn’t all that troubled by facial hair. Spots were non-existent, always had been, even in his teens. Yet at twenty-eight years old you could never classify him as normal. His slim body, born out of long legs and a standard-sized upper torso fulfilled all his needs. He couldn’t be described as ripped at all. In fact, with the right hair, makeup and clothes he would pass as a woman.It wasn’t that he hadn’t...

1 year ago

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Son s Bikini

It was a hot day. I told my mom, “I'm going to cool off in the pool.” My sister, Jan, was already out there sunning herself.Mom eyed me over. “You know, Mark, that swimsuit of yours is getting kind of old. You should get a new one. I'll look online to see what I can find for you.”Mom and Dad divorced several years back, but the split was amicable. Jan and I stayed with our mother as Dad traveled a lot. Mom did well working as an executive in a local company. Jan and I each had jobs elsewhere. I...

2 years ago

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My Transition Chapter 4 Crossdressing I

I was a straight-acting 24-year old slim and fit man, once upon a time. Then Sally got inside my head and now, I crave cock. I have evolved from being a school-jock and a dick to being fucked by an older man, then on the weekends by a DJ. I had my ass broken in by a big black guy when the club I frequent was closed. Only for a motorbike gang to dress me as a girl and fuck me silly. At work, I dared not test the waters and dress like a woman but at night I evolved into a full-on...

3 years ago

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My Crossed Life Chapter 5 A Very Happy Halloween

The days couldn’t go by fast enough as I patiently waited for the last weekend of October. While crossdressing on Halloween seemed all too cliché, Missy and I had collaborated on quite an outfit that undoubtedly would be my most outlandish and revealing look yet. Missy and her friend Laura had decided that a trio of slutty pirates would be the perfect opportunity for Jenni to make her college campus debut. Missy said she was up for the challenge to make me undeniably passable as long as I was...

3 years ago

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Crossdresser Got Caught By The Neighbor

Hello readers, my name is Rajesh, a 24-year-old guy who likes to dress like a girl. I am in Australia now.  This story will tell you how a crossdresser got caught by a neighbor and had to do whatever the neighbor ordered. His name is Roy (name changed), he is 6’1 height with a well-built body, and he is in his late 50’s. I recently had to move to another unit as my old unit’s lease got finished. On a Friday morning, I was leaving for my office. I saw an old man (who lives in the next door unit)...

2 years ago

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My First Walk On The Wild Side

It wasn't until I was in my mid-twenties that I plucked up the courage to leave the house dressed as a young woman. Initially, it was short walks to the end of our street (a relatively quiet suburban road in a relatively quiet town). My hair was fairly long in those days, with blonde streaks through a feather-cut. I'd comb down a fringe to my brows to give me a more feminine look. Over the years, I had tinkered with make-up, and by the time I was ready for a "Walks On The Wild Side", I was...

3 years ago

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Pinked

At twenty-five, everyone Brad knew said he looked a lot younger, more like nineteen. He'd still get carded at bars which both intrigued and annoyed him. He had a good if boring office job and had his own apartment. Like most guys, he also watched a lot of porn at home and would jack off. At first, it was just the usual stuff, large breasted women sucking and fucking big stiff cocks, drinking their cum or getting facials. After a while though, he'd ventured into more what he considered bisexual...

3 years ago

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Amazing Night With A Sexy Crossdresser

Any ways, it had been awhile, and I wasn’t in any sort of relationship at the time, and the thought of being with a tranny again had started to be on my mind. Luckily, this was before Craigslist dropped its casual encounters section, so it was relatively easy to look for hook ups, and being there was a TS/Crossdresser section, I could easily contact one. I remember looking through postings, hoping to find one that was attractive enough, because as I’m sure you know, many cross dressers and...

3 years ago

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Spying on my sissy slut husband

Part oneI am married to a very sweet guy. We are both twenty-two years old and have been married for two years.  Our sex life is great; he is very horny and affectionate.  I never have to ask for sex as he is always willing and able.He is a Social worker and I am a nurse.  We met while he was in the hospital where I work.  He was working on a child abuse case.  He isn’t a hunk by any means, in fact, quite the opposite; he is very feminine.  Maybe him being this way attracted me to him as I had...

2 years ago

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Ashley s Crossdressing Adventures

It's Sunday and Mommy wants to hear what sissy things I have been up to, and don't leave anything out Sissy Ash, Don't be shy, out with it sissy, I already know you love being a complete sissy!Did you buy anything sissy? Yes Mommy, I did, I want to hear, everything you bought you little sissy, let mommy remove your bra, to access your sissy nipples,Mommy I bought 4 pairs of sheer nylon panties to add to my collection, pink, blue, white and yellow.What else sissy? I ordered 3 packages of...

2 years ago

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The Train Comes Off The Tracks Chapter 2

I arrived home after a crazy night at work. To recap; my supervisor found me wearing women’s underwear, made me eat her out, then fucked me with her nightstick. Now I am basically her bitch. What is my next step? She said I should be better prepared. How the heck could you be prepared for what happened last night? Never in a million years would I have guessed my supervisor would be pegging me with a nightstick. I had to decide how far I was willing to go with this, and figure out what I needed...

2 years ago

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First time crossdressing with a friend

My lovely new Malaysian friend emerged from the bathroom, moving shyly in the low light. He was wearing thigh-high stockings, cute little panties and a matching top that was tied at the front.My heart leaped at this gorgeous sight. He had advertised that he wanted to hook up with someone who appreciated fembois, and I was very eager to indulge his fantasies and mine!We had agreed that we were going to enjoy a girl's night together, and so he started playing some lesbian porn on his computer....

2 years ago

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The Making of Kairi Fox Part 2

For the next few days, it was safe to say my anxiety was through the roof. Every notification, email and slight noise from my laptop sent me into a frenzy of confusion and a little bit of horniness. Someone had been recording my dress-up sessions through my webcam. I had taped over it now and made sure that nothing could be seen. Everything I did online was careful, and I began using a VPN just for extra security. Sarina. Mistress, apparently. She already knew, though. Fuck.My days were wrought...

3 years ago

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Pleasing Bill A Crossdressing Story 2

“That’s what i like to hear. Now at 12AM tomorrow i want you to be at our house dressed up in the sexiest outfit that you can get your hands on. I’ll text you our address.” “I can't. My family are still at home by 12.” I pleaded. “That’s not my concern. Now this is your first task i’m telling you to do. Are you going to fail me already? Because you be here at 12 o'clock on the dot or you can forget about ever seeing me again.” Bill said annoyed. I couldn't disappoint him. I need to...