Gay Crossdresser Stories

23,018 results
Orientation
Length
Source
Infinite Scroll

Forced to Dress

by married40scouple on May 11, 2020
Transgender & Crossdressers

"Can I have two rum and cokes, please?" The sexily dressed, long-legged, thin brunette asked the bartender, speaking in a deep tone. "Lose a bet?" I asked the crossdresser who sidled up to the bar and order the drinks. "I don't want to talk about it." He replied in a husky voice. "At least you look real good." I smiled at him. "She dressed me up. I have...

Slave Tail

by Cyberweasel89 on Jul 11, 2020
Fantasy

In the kingdom of Pendragon, slavery is a burgeoning industry. Anyone can end up as one if they aren't strong or lucky enough. Slaves can be purchased, sold, and traded legally by anyone with the right business sense and magic. Slaves cannot be freed and are at the mercy of their current owner. Often kept naked to denote their sub-human status, some are cher...

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A Surprise Relationship

by canuckCD on Sep 13, 2017
Transsexuals & Crossdressers

This is a fictional story, although it is based on people I did know. "Tony" and his twin sister "Kim" are based on a set of twins I knew, who were almost identical. I did have a relationship with "Kim" for almost two years, however, the relationship with "Tony" is pure fantasy. WARNING!!! This story starts with a chapter that describes violence against one...

Epiphany At An Epiphany Party

by cd_donna on Sep 16, 2017
Transsexuals & Crossdressers

Author's note: This is an note to self I am sharing. There is no sex but lots on my own sexuality. I love adventure, but my wife only needs the traditional needs. She knows nothing about any of my sexuality adventures and would divorce me if she did find out about one of the hundreds. ** Dancing with Ladies ** I swing dance socially. I am used to going up...

Sissy Boi

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

COFFEE "Thanks for me, Raquel, I'm at the end of my tether and I don't know what to do with Dan anymore." I was meeting Raquel, one of my colleagues for coffee. She knew I was struggling with my husband, but didn't know the problem was in the bedroom. "That's alright, Jo. My pleasure." "Look what I've got to share with you is deeply embarrassing, so I beg...

My Name is Raquel Ch. 01

by Raquels_Panties on Mar 2, 2020
Transgender & Crossdressers

Chapter 1 All characters in this story, involved in sexual situations, are 18 or older and are fictional. ******** My name is Raquel and I'm a crossdresser. I didn't become Raquel until later, but this is where I came from. At this point my interests lied only in panties. I wore them as often as I could get away with, as long as I could change out of the...

Crossdressing, Piss and Sex

by Lovinhose on Apr 14, 2020
Transgender & Crossdressers

This is a work of fiction, a fantasy that I would love to come true. It also contains 'pissing' (aka 'watersports'), crossdressing, and a crossdressers sex with men, so if you are not into these subjects, this story might not be for you, you have been warned. Also, comments are welcome, but please note, I'm NOT a professional writer, if I was, I wouldn't be...

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...

Female Erotic Police Squad Pt. 03

by mattpantyhose on Sep 14, 2017
Fetish

Most of the officers of Female Erotic Police Squad enlist in the service to catch criminals. But there are also some who do it for sex. Physical love is the modern way to fight crime, but it does not necessarily mean that sex should be considered merely a tool. As long as an officer fulfilled her duties properly there was no reason for her not to take additi...

My Crossdresser Dream

by DaddyisaCD on Sep 16, 2017
Transsexuals & Crossdressers

How do I reconcile my desires? I don't know. If I did the I would have done so already would have I? Oh well, here they are. The dreams of a semi closeted cross dresser. _________________________ We will start with the easiest thing to do, yet the hardest step I have yet to take. The blow job. Taking a cock in my mouth and sucking it until it explodes. I...