Gay Crossdresser Stories

23,018 results
Orientation
Length
Source
Infinite Scroll

Guys and Dolls

by Hiddeninplainsight on Jan 20, 2020
Transgender & Crossdressers

Note: This story is a bit of a slow burn and is longer than my earlier submissions. I hope you enjoy. Disclaimer: All of the characters depicted in this story are fictional and above the age of 18. * Pt 1. If I were a bell The heat had been stifling in the packed lecture theatre. The air conditioning had broken down in the old building again and the coll...

Hearts Academy Ch. 04

by RoseB on Mar 16, 2020
Transgender & Crossdressers

Disclaimer and Notes: Disclaimer and Notes: Hearts Academy is an dark horror/mystery story focusing on the reluctant feminization of a young artist. There are many themes such that cause it to be disturbing for those who cannot handle terror or dread well. This is a sequel to The Rose Diaries. While the characters are brand new, it does reference events an...

The Secret of the Island Pt. 01

by neoview on Sep 25, 2017
Transsexuals & Crossdressers

Hello, this is my first story I upload (not the first story I made). I am sure I didn't do a good job expressing my thoughts so please excuse me. You will notice the walls of dialogue and not so much "explaining". That's just my style but I hope to improve for the future. Anyway I expect some constructive criticism but please use simple words, I'm not stupid...

Summer in Dawson Ch. 01

by Arrowman2 on Sep 16, 2017
First Time

All characters depicted in this story are over eighteen years of age. Any resemblance to any person, living or dead, is purely coincidental. I was not happy to say the least. It was the summer before my senior year of high school, I had just turned eighteen, and how was I going to spend it? Working on my grandparent's farm in the middle of nowhere. I was...

Christian College Sex Comedy Ch. 11

by FinalStand on Sep 25, 2017
Erotic Couplings

*Anyone can be who they want to be; the challenge is being who you need to be* (Frontma delivered on several chapters this time so I can get them out to you soon. I thank her for spending all this time with me on this project) (Surprisingly there is no actual sex in this chapter, though things get close on more than one occasion) (Yes, this tale is suppos...

Tom Ch. 01

by TimT1972 on Sep 12, 2017
BDSM

Kathy was never quite sure how she came to kidnap and torture one of her own employees; it was not really her management style. She supposed she should date things from a meal she had with her old university friends Stephanie and Mel sometime in late May. After a visit to a good local restaurant they retired to Mel's house for a few glasses of white wine. Th...

Anal Sex, Ass Play, & Tossing Salad

by SusanJillParker on Sep 25, 2017
Anal

Husband introduces his wife and his sexy sister-in-law to anal sex and succeeds finally, after failing. * A sight to behold, Marcus walked in the kitchen to see his wife standing by the sink with her back to him. With the focus of his stare concentrating on the shapely roundness of her butt, his cock involuntarily pushed against his pants. So tightly firm,...

The Hunter's Trap Pt. 01

by SubsNotDubs on Feb 7, 2018
Sci-Fi & Fantasy

Author's note: Hey there! This story goes on for a while and not only teases its characters but its readers too. If you're looking for a quick read and a quick wank, I'm afraid this story might not work you. If you're looking for a nice fantasy environment, a solid exploration of the troubles of gay and kinky romance, and some good, healthy, kinky masturba...

Kinky Tales: I'm Pegged By My Wife

by silkstockingslover on Mar 27, 2019
Fetish

Summary: Note 1: This is a Halloween 2015 Contest Story. Note 2: This is one of two different versions of this story; you can read the wife's much longer version called Kinky Tales: I Pegged my Husband Note 3: This is dedicated to: The real Chris and Dani who this fantasy is written about. It is also dedicated to all married couples willing to listen...

Stay-At-Home-Fuck-Daddy

by a_bent_ampersand on Sep 12, 2017
Loving Wives

The beer bottle I'd been caught fucking burned a candle now. There in the daylight, I watched the wax cream itself over its shape. The bottle was a forty. My hands trembled as I pulled my bleached ponytail apart in front of my husband's mother's mirror. In the front room of the trailer, I could hear the sounds of a car race blare from the television's singl...