Crossdresser Caught Stories

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Orientation
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Infinite Scroll

Driving Her Home

by bored_doe on Sep 16, 2017
BDSM

Alan smiled at the perky blonde college student in the passenger seat of his sedan. "So Catelyn, have you figured out what your major is going to be yet?" "Mister Denny, are you wearing makeup?" It wasn't a question, it was a challenge. Her brown eyes watched him without flinching, waiting to see how he'd respond. The question was so unexpected, it knifed...

The Glass Door

by JackOLantern on Oct 16, 2018
Fantasy

((Author's note: I have made this story open to the public. I encourage people to post their own chapters and threads. If you are a potential writer want an idea of how the mirror works, read the first handful of chapters in my main thread to get an idea. You are under no obligation to make it function in the same way unless you want to, however. Have fun wi...

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Home in the Hills Pt. 01

by ValoryG on Dec 10, 2019
Transgender & Crossdressers

All names and characters in this story are fictional and have no connection with any actual person living or dead. ***** Jonathon Worley is in his sophomore year at Onanoma State University, majoring - at least for the time being - in art history. He's the third child in his family, and after his parents paid for the first two to go to college, there was...

Ugly Duckling to Sissy Princess

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

All names have been changed to protect the guilty. ***** Being a very short guy (5'3") with a small frame has been a major handicap in my quest for female companionship. Having a micro penis was the nail in my coffin. Throughout my youth, I was ignored or rejected by girls. I had my first girlfriend in college, Caroline Fletcher. She was smart, beautiful,...

Eric's Dreams Pt. 03

by Genevieve_Ohara on Jul 14, 2020
Transgender & Crossdressers

Eric kept thinking about his sex problem. He was a crossdresser. But most gay men didn't like that. The sex, yes, but not the crossdressing. Gay men, at least most gay men, had no interest in lipstick and lingerie, and the thrill of passing as a woman. They wanted to fuck and be fucked by men. They wanted to have their cocks sucked by men. And they wanted to...

Mistress Chantel, Tranny Dominatrix Ch. 02

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Two: A Day in the Life of Tranny Dominatrix Chantel Waking up into another morning where this transvestite dominatrix gets to dress up and enjoy her life of toying with sub men and sissies/crossdressers. Working hard to get my femme look down over the last couple of years prior to operating this Dominatrix business, I enter my very lady-like powder...

Sarah Shared the Hot Tub and Sauna

by SarahCD on Feb 26, 2019
Transgender & Crossdressers

I first published this experience a few years ago. I prefer to call them 'experiences' since the term 'story' implies fiction to me. My experiences are based upon my real life. Since I started posting my experiences my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more detail and corrected some...

Kissing Crossdressers Pt. 01

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

It started when Carla, my hot sexy wife went away on a spa break a few days with some of her girlfriends. Carla is 40 (I'm 48), has blonde hair, blue eyes, 34DD tits and a curvaceous ass. She works long hours in a busy office as a manager, I work in a local library and my job is far less stressful than hers. And her job has definitely taken its toll on our s...

My First Crossdresser

by Jay876 on Jul 31, 2019
Transgender & Crossdressers

Monday A year ago. I was sitting in my flat, as a university student just browsing the men on grindr. I was inexperienced at the time and I had only been with one man, and that was just for oral. So, I was intrigued when I saw someone on my page, just nine meters away. A crossdresser, stocky, but wearing a maid costume, with his ass bent towards the camera....

A Sissy in the 22nd Century

by JerkGently on Jul 1, 2020
Transsexual

In a future not too far flung, humanity has progressed to a stage where almost all production and provision of society’s needs is automated. With no need to work, all citizens are instead driven to find lifestyles that fulfil their own and each other’s fundamental desires. This is achieved by the medium of an overruling system of artificial intelligences and...

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