Caught Crossdressing Stories

164,111 results
Orientation
Length
Source
Infinite Scroll

A Transvestite Odyssey

by lynntg0444 on Mar 18, 2020
Transgender & Crossdressers

I like playing a girl, but it's complicated. I have always been more attracted to women than men, and had many relationships with women including two marriages. As a young man I had several sexual experiences where I played a feminine role. Wearing girly things was a real turn-on for me, and it seemed to make it less queer for us both. I would later learn th...

Stacy and Matt

by mattpantyhose on Jan 28, 2020
Fetish

Matt's bliss ended almost as soon as it had begun. The girl he had met and who not only was pretty and smart, but also enjoyed his crossdressing decided that career was her priority after merely few weeks of their relationship; the two broke up as she moved to a different distant city. Matt still had a good job, amazing boss and sympathetic co-workers, but d...

Caught en Femme

by RisqueRavisher on Sep 12, 2017
Transsexuals & Crossdressers

This is the very first story I've written and uploaded here. I'm sort of nervous because it's probably not the best. Don't forget to rate and whatnot. Give me feedback/tips on things to improve on. I'm always looking to improve. Anyway, enjoy xx ***** "I'm going to be home a little bit later, babe," my wife, Annie, called from the alcove. "I'm going out wi...

Jeff Crossdresses More & More

by TurningintoCD on Sep 12, 2017
Transsexuals & Crossdressers

My name is Jeff. I date girls every now and then but I always masturbate about dressing up as a hot chick and seducing a hunky guy. My biggest turn on is putting on women's clothes and makeup. I never really had a chance to explore it much when I was growing up. In college I had a secret stash of 1 stick of lipstick, and when I felt really dangerous, I wou...

Passion over Lust

by sarahchica96 on Sep 5, 2018
Transsexuals & Crossdressers

Introduction I' am living the dream, the dream of maintaining the balance as a regular straight guy and my bisexual crossdressing side Sarah. The 4 years of hard work at University started paying dividends, I landed a job as a legal advisor for one of the top businessmen in London Mr Hayat. My job paid well which enabled me to buy a studio apartment via a...

The Good Wife

by komrad1156 on Sep 13, 2017
Transsexuals & Crossdressers

Chapter One "Let's go! Dig deep!" Jason told himself as he passed the nine-mile point. Just one more to go—for today. Running was one of his four biggest passions in life. He also loved his job more than most people. At least he thought that was the case based on the way most people talked about "work." For Jason, work was fun. He couldn't wait to get there...

The Futa next door

by Abusedbyfuta on Jan 11, 2019
BDSM

You have lived in the same l cul de sacyour entire life. It's not a bad place to life, very much a part of suburban America. It's just not very exciting. You live in a large White House that looks the same as all the others on the street, probably a ploy by the developer to keep costs down. Every day you see the same boring neighbors, have the same boring ro...

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Sexual Scenarios

by zig322 on Dec 7, 2019
Fan Fiction

What we have here is a series of sexual scenarios from anime, cartoons, comics, tv shows, video games, movies, and even some original ideas. These scenarios will involve: spanking, ENF, forced feminization and crossdressing, foot fetish, tickling, LGBTQ, mind control, incest, any other perverted thing anyone can think of, and of course sex (consent or non-co...

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In For a Penny...

by TheHellWasIThinking on Sep 15, 2017
Fetish

To the reader: After I'd finished this story, I didn't know where to put it. It contains elements of several Lit categories, and I probably could have put it in any one of them. In the end, I decided to put it in Fetish, although it's very much a Loving Wives tale, as you'll soon see. NOTE: Every word of this is true. (Except for "Every word of this is true...

Curse of the Living Clothes

by calx86 on Jan 8, 2020
Fantasy

There are several stories out there involving living clothes but I want to leave this open to allow many collective authors to be as creative as possible. For example, you can write a story about clothes simply coming to life and stripping their wearer, leaving them nude and embarrassed or maybe the living clothes forces someone to wear them and turns them i...

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