Gay Crossdressing Stories

23,246 results
Orientation
Length
Source
Infinite Scroll

Futanari Notebook Ch. 10

by sexgundam666 on Jul 16, 2018
Sci-Fi & Fantasy

Carmen glared at her meagre pile of clothes, all crumpled and disorganised after her recent attempts at dressing herself. One shirt sported a tear along its side from when she'd tried to force it over her unfairly endowed chest, which stood out like a sore thumb on her torso. None of her bras had a hope of fitting now. She grimaced at the memory of trying to...

A School for Spanking Ch. 03

by lovethosepanties on Nov 6, 2018
BDSM

I was in my office early the following day wondering if Cecile would appear or not when at precisely 8 am there was a knock on the door. "Come in," I called out. The door opened, and Cecile came in dressed correctly in the uniform of white blouse, blue cardigan, tartan kilt and white socks. She had an air of sullen defiance on her face as she approached m...

Good Samaritan

by Ann Douglas on Oct 10, 2017
Erotic Couplings

Dalia Collins pulled her red sweater a little tighter, trying to ward off the late night chill as she walked across the parking lot to where she had parked her car. Behind her, the lights of Mickey's Place, the 24-hour Truck Stop where she worked, still shone brightly, the tables still filled with customers. It had been an extremely busy night for the 49 yea...

The Life and Tines of Slave N Ch. 02

by Discordianknot on Sep 13, 2017
BDSM

Wherein I demonstrate the importance of rigorous and intentional conditioning of a slave for complete service. As I explained in the first part of this story, I do not often rely on chastity devices these days to control N's sexual behaviors, though that wasn't always the case as I'll explain shortly. I mostly rely on the "honor system" - by which I mean an...

Shower Scenes Ch. 03

by MTL17 on Oct 15, 2018
Celebrities & Fan Fiction

Disclaimer: I do not own Pitch Perfect. I do not make any money from the writing of this story. ***** Aubrey Posen hated crying in the shower. It was so cliché. Not that it stopped her from doing it on a regular basis, it just meant that she hated it even more. And often herself. But for better or for worse this latest crying session wasn't because of some...

The Camping Trip Ch. 03

by JamesMiehoff on Oct 29, 2018
Erotic Couplings

Copyright (c) 2018 James Miehoff, All Rights Reserved. This work may not be published whether for fee or free without this copyright. ------------------ This is one of a series of stories set in what I call Universe-J. Universe-J is very much like this universe with a few exceptions. First the people tend to be a little more sexual and less hung up on...

The Implants Pt. 01

by Sissyhalo on Feb 12, 2019
Transgender & Crossdressers

It's cliche as hell but I'm a college kid and broke as fuck. So a friend passed me a chance for making some cash doing medical testing. And my first year it helped a lot. Sure there was some weirdness with some things like the fucked up deodorant that changed as the day wore on until you ended up smelling like onions or the shampoo that turned my hair gree...

Minimum Security Prison Bitch

by JonThomas_ on Dec 19, 2018
Transgender & Crossdressers

Greetings all; in my stories my characters exist in my head, but there might be real life inspirations for some of them. Who knows? As my regular readers are aware, I enjoy writing about the transgender experience from different perspectives. Here I write about a transgender woman whose experiences in prison were quite different than she expected them to...

The Game Ch. 03

by MicheleNylons on Feb 11, 2019
Transgender & Crossdressers

Chapter Three - Translucent 22 September 2007 Petra awoke mid morning; she felt a little hungover and her anus was tender. Vignettes of the previous evening played across her mind as she lay in the bed under the pink satin comforter; she had a morning hardon tenting her panties which she lazily stroked as she recalled Mick ravishing her right here in this...

Graduate Studies to Gay Pt. 02

by jamtby on Apr 9, 2019
Transgender & Crossdressers

After the night at James' apartment the previous quarter, I had tried to put all that out of my mind and concentrate on school and be normal. I did see James once on campus and he asked how I was doing. He hoped I had gotten a good grade on that paper I was writing when I met him at Jimmie's that fateful Friday night. He also said that if I wanted to earn so...