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Crossdressing

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11

Adventures in a Woman’s Body – Chapter 4: Public Humiliation

Used as a playtoy at the mall

I stepped out of the shower and began to dry myself with a towel. On this bright Monday morning, all I could think about was what happened on Friday night. After being gangbanged and cumed on thoroughly, Daddy drove me home that night. On our way there, he explained to me the situation that I am in. Daddy took out his phone and showed me pictures he had taken of me being a dirty little whore....Read On

78

My First Time in a Dress

How I Became a Crossdresser

PART-1 When I was younger I used to go and stay at my grandmas house during the summer. It was a small country town with about 15,000 people. She lived on a quiet street and there was only a couple of other kids close to my age. I used to go and hang out with one guy, Dan who was about 3 yrs older than I and his sister, Pam who was my age. Dan and I used to go mess around everyday....Read On

40

Picked up in the Toilets

How an encounter in a public toilet turns into a lot more.

Here I was just turned 16, I liked to dress in girl's clothes and was very curious about cock, no about sex. Oh, god yes! My hormones were driving me mad with the desire to not only dress up whenever I could but also to have sex. Anything I saw in newspapers or magazines about women, girls or with sexual meaning had my mind just a blur of indecent thoughts. This particular day I had...Read On

40

The Adult Theatre

A true story with the name and location changed for a good lush friend.

I got to the hotel early so that I could get myself fully prepared to meet a guy I had been chatting with via a chat room. I decided to wear my favorite pink check mini skirt with my sexiest pink undies to match. I added a white silk blouse and a white garter belt with some white stockings. I took time applying my make up, making sure I had dark sultry eyes and perfect red lips, I wanted to...Read On

38

What a Girl Wants

'Katie' finally fulfills her fantasy of having sex with a man.

"Come on, Katie. Give in to your desires. You've gone this far. You're almost there. You're so close to your goals and dreams of being treated like a lady. Accept it. Embrace it. Give in and complete your journey. Tell me what you want." Todd and I had been friends for years and even co-workers at one point in our respective careers. It had been almost ten years since I'd seen him and it...Read On

33

Wife's crossdressing fantasy Part 3

I had to find a way to repay my wife for the wonderful anniversary gift she game me.

This is a work of fiction. Any resemblance to any person, or incident is strictly coincidental. My Wife's Cross dressing Fantasy 3 Then my wife looked at me and said “Happy anniversary darling.” How did she know the effect this experience would have on me. I was changed forever. It was such a wonderful experience. She deserved that I come up with something just as exciting for her,...Read On

33

Gang banged at a private club

This is what happened when a friend took me to a private members only gay, bi, and transgender party

After yet another hot weekend at my friend Heberto’s house, I was packing up and getting ready to go home when he told me he had something “special" in mind for us next weekend. I begged him to tell me what he had in mind but he refused. So I left. My curiosity was peaked. The week dragged on thinking about all of the possibilities. The anticipation was killing me. Finally Friday...Read On

33

A Fantasy

This is something that I’ve always dreamed would happen…

I have been dressing in women’sclothes since I was little. My grandmother used to dress me up in her old dresses and pretend I was her granddaughter. As I grew older it started becoming more of a sexual fascination and turn on for me. I have been more a closet cross dresser getting clothes here and there and then dressing up and having incredible masturbation sessions looking at tranny...Read On

29

Roomate

An introduction to a new side of my roomate

Roommate It had been a hell of a year with a divorce, a new job that had me traveling more and having to move into shared housing because my ex was sucking my bank account dry. Carl, my roommate, was a decent enough guy. I found the room on dougslist.org and we seemed to be compatible. He was neat without being compulsive about it, was a working student and was not inclined to throw...Read On

23

A Nanny Femtastic - 7

A NANNY FEMTASTIC! Chapter 7 After that first dinner Bradley and Felicity retired to their bedroom. And even though they were in a separate wing of the sprawling villa I could hear them making love! I thought of what Felicity felt as a transsexual woman having had a vagina created out of what was her penis. To feel Bradley rigid penis inside her. I wondered how nice it would be to put on...Read On

16

Busted by a bud

Caught on home turf.

It's a hot summer day in 1994. Nowhere is a small, fairly poor, rural Illinois town; the kind of town where nobody locks their doors. Summer seems to be an average 19 year old. He goes to a small community college and works on the weekend's. He's kind of quiet and doesn't like to be around his parents. Both parents have jobs where they have to work the night shift. Summer's mom works for...Read On

16

Wedding Night For Ken And Barbie: Part One

Catching the garter at my cousin's wedding gets me a honeymoon fuck like the bride.

When I went to my cousin's wedding in Monterey, California stag, at the reception dinner she had me seated next to the only other male stag invitee, the photographer. He was my age and tall and we hit it off, immediately. Ken was a sports car enthusiast and he told me about the thrilling rides he took along the Pacific Coast Highway. He talked about the beautiful views at scenic lookout...Read On

58

The Perfect Choice

A girl works to turn her boyfriend into her toy

Andrew had moved in with Hannah a few short months ago and so far everything was going just the way she wanted. She was an endless tease; wearing short skirts and dresses when they were out during the day or tiny shorts and vest tops when they were at home together. She did everything she could to turn Andrew on, and it was working perfectly.She hadn't slept with him yet and the tension...Read On

32

Cindytranee meets the maintenance crew

Cindytranee gets caught crossdressing and gets fucked by three men

This is a true story that happened a few years ago when Iwas living in an apartment complex while looking for a house. I had taken a small one bedroom on the 2 nd floor. It was very nice and private and I really enjoyed being there. This was the first time in years that I had lived alone and I loved it. It gave me the freedom to enjoy my favorite thing, cross dressing and having sex with as...Read On

27

The Slut Within

This is my first story. If you like it please comment and I will write chapter two :)

I was 22 years old at the time, and I had been crossdressing for a few years. For some reason I could never control my desire to put on women's clothes and prance around my apartment looking all sexy and slutty. Normally I can never decide what specifically to wear as I like to change it up all the time, from wearing latex lingerie to sexy roleplay outfits and beyond. I am 5'9 with a...Read On

22

The Pageant

An unusual end-of-summer beauty pageant spices up a young man's relationship

I was happy to finally get a job, a decent job, at Sweeney, Burke, and Garcia, a law firm in Savannah, my hometown of about 25 years. The economy was still hurting and I was days away from making a decision to move to another city, so I was grateful for the opportunity that came my way to remain in my beloved city. I was hired as a temporary executive assistant for one of their...Read On

15

Crossroads Ch.02

A young crossdresser take things farther.

The second chapter in this crazy little tale. I really loved my little adventure out as a woman. I liked the power I had over men. I was seriously thinking that I would like to live as a woman full time. That would be quite a commitment and one that would change my life forever. As I said before I worked for a really liberal company and one day I got up some courage and went to...Read On

15

In Wonderland, Pt.1

Costume mandatory...

When I was in high school I was always very camp, which was probably why almost all of my friends were girls. This was definitely why I first ended up crossdressing. I was sixteen and round one of my 'girlfriends' house for a few drinks on Halloween before we went to a house party nearby. I never much cared for Halloween, so just came as myself. When I came in they all sighed since I wasn't in...Read On

10

Becoming LoriAnn - Part 3

LoriAnn takes another step towards becoming the slutty gurl she wants to be

I was enjoying my new found sexual freedom. My first steps were slow and easy but nothing felt more exciting than discovering the feel and taste of a new hot, hard cock. The boys at school never really bothered me about regular sex and long as they got to shoot their big hot creamy loads down my throat or all over my tits, and I was happy each time I was able to swallow one of those...Read On

10

Queen of all Hearts

College Queen finds the King!

Justin sprawled himself on the sofa, dressed in his pretty frock. He flicked through the TV channels, feeling rather content. Justin was always different, even as a child, he preferred to play with girls, with their dolls, and wanted to wear frocks and dresses. His mother encouraged his development by taking him to ballet classes, needlework, and flower arranging. Justin relished his...Read On

10

I Still Love You Tomorrow

How could she be so forgiving? I didn't understand... Caught with the evidence of my secret on my face, my body, and in my hair, I was frozen by her stare as she stood in the bedroom doorway, eyes wide as teacups. “Oh,' she said, too shocked for anything more. I had lied to her! I wouldn't have blamed her if she had left me in that instant, but she stayed. Why? How? We sat together...Read On

10

In Wonderland, Pt. 3

'Tilly' spent the night at Chris Smith's house, waking to find it impossible to avoid Leila Smith, a friend, peer and beauty queen. She was not best pleased about the situation, but helped to protect Tilly's true identity in lending out a girls uniform, one purposefully as feminine as she owned. Chris was just about to give them a lift to school... I shuffled down the stairs,...Read On

56

Do you want to wear my skirt?

Katie caught me looking at her skirt and made me wear it.

As I sat in the meeting I couldn't take my eyes off her. She was young and so cute and she was wearing a short pleated wool skirt. The skirt was a pink and light blue plaid color. She would cross her legs and pull the skirt down being sure not to show too much. When we went on a break many of us went outside. It was a nice comfortable fall day. I watched as she came out and stood by herself....Read On

36

An Uneven Romance

He picks up the girl of his dreams only to find himself being used

I couldn’t believe I’d gotten her home with me. We’d met in a bar when I was drinking with my friends, I spotted her early in the night but didn’t have the courage to talk to her. She looked perfect. She was slim, with long red hair that came down to a tight, round ass. When she turned around, I saw she had a truly beautiful face but there was a sexy, dangerous look in her eyes that scared...Read On

31

Not Your Typical Traffic Stop

Stephanie's run in with the law turns steamy and dirty.

Hi my name is Stephanie and this is a fiction based on my dirty desires. I was making a risky trip to my local adult video store dressed as Stephanie. The sun was setting and the drive was only 10 minutes, tops. I figured with low light and close proximity of my playground of debauchery, I would be safe. I admit because of nerves I had my black 'fuck me' heels hard on the gas. My heart...Read On

31

I become my wife's girlfriend. Part II.

This day at work was unusually tedious and seemed like it was never going to end. At the beginning I occasionally dropped my boss's cup and the coffee poured on floor, but luckily the cup survived. After this some guy stepped on my toe and caused me much pain, I bent to touch it and suddenly had a feeling like my butthole was cut by the string of thong. Later my boss was very angry all the day,...Read On

19

Telling Mom I'm A Crossdresser Part 8: Bus Driver's and Cops

Part 8 enjoy and please comment at the bottom ;)

My mom and I spent the next few days practicing and exercising with the stripper pole until we felt confident and extremely sexy while doing it, which I have to admit did not take long. One night I came home late from my part time job I had at a local restaurant and took the bus home. I didn't have a car because I hadn’t decided on what car I wanted to get yet and what I could afford. I...Read On

19

Christina and Cheryl

Girlfriend makes me cross dress and fulfill her fantasies.

Christina and I had been dating for nearly two years. Within six months into our relationship, I confessed that I enjoyed dressing in women's clothing. She'd been more than accepting and encouraged me to indulge in this. She'd bought me bras, made me wear panties, painted my nails, and given me make overs. Seeing how horny it would make me turned her on even more so. I knew Christina was bi...Read On

14

Explorations beyond my expectations

My introduction to pegging, cross dressing and so much more

I was nineteen at the time and Lili was my first college girlfriend. She was a virgin when we met. I had only had one intimate girlfriend before her. We loved to explore together and every weekend her roommate would leave town on Friday night and wouldn't return until Sunday evening, giving us plenty of time to explore and play. She knew I liked ass play from conversations about things...Read On

14

A Nanny Femtastic - 5

A NANNY FEMTASTIC! Chapter 5 ... I looked gorgeous now with my ample breasts and thin waist! I would really enjoy this upcoming holiday! The electrolysis treatments had continued, and I now was pretty hairless and did not need to shave or wax. I did however remove all my pubic hair and became obsessed with having a completely hairless body. This included around my scrotum...Read On