Caught Dressed As A Girl Stories

361,457 results
Orientation
Length
Source
Infinite Scroll

Sissy's First Boyfriend

by kprice1984 on Jun 5, 2019
Transgender & Crossdressers

For those who have read my previous works Crossdresser's Unexpected First Time, thanks for your ratings! This story has a lot of true components, "based on real events", but is ultimately, fiction. ------------------------------------------------------------------------------------------ Since my first time with a man while I was dressed as a woman, about...

Gladiatress Ch. 02 Pt. 01

by nightvoice2 on Sep 25, 2017
Sci-Fi & Fantasy

Selen noticed him as soon as he entered the bar. He looked quite different from the barflies that usually frequented the place: tall and noble with expensive-looking burgundy and gold coloured robes. He was flanked by two larger men, who had the nervous energy, darting eyes and well-developed bodies of bodyguards. She was only working here until the end of...

Wanda Frat House Trophy

by Pugzilla on Oct 8, 2019
Exhibitionist & Voyeur

Raphael Duran was an unusual choice for membership in the Tau Iota Tau fraternal organization. He would be the first Hispanic member of the group ever. It was a move that wouldn't have been considered an option in the past but Duran was considered an exceptional find by the rest of the younger members of the group. In his circle of friends, he had earned t...

My First Time Is With My Teacher! Ch. 03

by football_stud on Sep 12, 2017
Erotic Couplings

None of the names are real in this story or the first one or the future ones. Thanks to Angel Love for editing assistance with this story. The next day in the morning at 6:00. "Hello?" "Hello my sexy lover." "Hi Mrs.Smith. What's up?" " MMM it is so hott to hear your voice." "Same to you and when I hear it I have a mental image of me fucking you and it...

Torontica - A Subway Friend

by Torontic on Sep 16, 2017
Romance

This isn't properly my story to tell. It was related to me a friend of mine, years after it had happened. It is his story, but I will try to do it justice in the telling. We were at a bar on College Street - one of the fashionable cookie-cutter martini lounges that have transformed Little Italy into the scenester's scene over the past decade. A few drinks h...

Dorm Floor Bitch v. 06

by GirlyCumslutBoy on Sep 16, 2017
Transsexuals & Crossdressers

It had been almost half a year since I had first dressed like a girl. I loved the feeling of the lovely lacy panties and bras on my bare, shaved skin, and the unmatched erotic feeling of wearing slutty little short miniskirts, tight t-shirts that exposed my taught tummy, and putting on whorish makeup. By now I had relished my slutty alter-ego, Michelle. But...

Orlando Trip Ch. 02

by baddad53 on Sep 17, 2017
Loving Wives

Saturday Saturday morning we woke up at the hotel in Orlando. Diane dressed in a pair of white short that just covered her ass and a button up denim shirt that she tied under her boobs. She wore her hair in a ponytail with a colorful band holding it. She was showing off her smooth, flat stomach and long, suntanned legs. She worn white sandals with bright re...

Rodney's Nude Humiliation Ch. 11

by aaronburr on Nov 7, 2017
Exhibitionist & Voyeur

Behind her cat's eyes glasses her green eyes were blazing. A note of half suppressed hysteria flavoured her voice as she issued orders. She sounded ardent, metallic, possessed. She was in fact a mad genius, driven by her own quasi-religious vision. Miss Cuff was in charge- very, very much in charge- and her project, this school production in which boys wore...

Kylie's Cups Ch. 01: First Gaze

by BuxomHarlot on Aug 31, 2017
Erotic Couplings

Based on true experiences. Names have been modified to protect privacy. ***** I had always been told I was attractive. Even though as a younger teenager, I had been slightly overweight and awkward, I had always been told I had a pretty face. At the time this story takes place, I was a college student in Boston, beginning my junior year. Through running an...

The Game

by Moxon4 on Sep 12, 2017
Loving Wives

My wife Lisa and I were sitting on the couch, talking. Nothing of any particular importance, just our usual random conversation. We were watching football, since it was Sunday, and this was our usual event for the day. We didn't have to work, and the kids were spending a week at my parents' home out of state. We were watching the Cowboys, as they are our fav...