Gay Crossdressing Stories

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Becoming Mindy

by mindyrose on Sep 18, 2017
Transsexuals & Crossdressers

Hi. This is my story from an unsure, shy, awkward boy that was pretty feminine to a proud, confident and comfortable transgendered girl. If you're not into reading about transgendered people and their stories, as well as their sex lives, then please move on. I know I made some foolish decisions, but I am a completely healthy person today and those decisions,...

Chrysalis of Kirsten

by KirstenEclipse on Mar 23, 2019
Transsexual

Date: March 22, 2019 Author: Kirsten Addison Subject: Chrysalis of Kirsten Chapter 1 By KirstensubTS My name is Steven aka Kirsten. This story is about how I went from a closet cross dresser to becoming a full time transsexual slave. This story is mostly true, based on my journals with dramatic license to make it more exciting and readable. Names have been c...

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A New? Weird World?

by wimil on Apr 7, 2021
Interracial

A strange family of bacteria has infected humanity during the 1850's. The bacterium(later call Femrite50) was mostly has a positive effect on humans better immunity, metabolism, and more durable so the people of the world thought as a blessing from their respective Gods that was until the kids came in the world. The bacteria amazingly ingrained itself into h...

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CD Quickie

by AtlantaCDslut on Sep 12, 2017
Transsexuals & Crossdressers

**All my stories are true** My name is Rebecca. I am 22 years old and have been cross-dressing now for about 10 yrs. At first, dressing consisted of putting on a pair of panties or just a bra. Now it consists of shopping on line for different outfits, silicone breast forms, wig, etc. When I moved down to Georgia I got a roommmate who never gave me time to...

Shattered

by kayla_femboi on Sep 16, 2017
Transsexuals & Crossdressers

The following story is mostly true. I changed the names for the sake of privacy and maybe spiced up the details a bit. A little background about me: my name is Brian, although when dressed i feminize me name to Brianna. I was a closet crossdressing sissy. I had always been effeminate growing up and a bit confused sexually. I never really dated girls. Inst...

An Evening of Crossdressing

by cockteezer on Sep 28, 2020
Transgender & Crossdressers

"I've invited my friend Denise over for dinner tonight," Mistress Sharon informed me. "We used to work together at a bridal salon many years ago." "OK, sounds good to me," I replied. "I haven't seen her in a long time. You'll really like her." Later in the day, when it came time to start the dinner preparations, I made the salad and set the table. Mistres...

Becoming My Neighbor's GF Ch. 01

by BaileyJensen on Sep 12, 2017
Transsexuals & Crossdressers

This story is focused on a guy getting swept away in the world of crossdressing, only to find his neighbor has equal interest. Pretty tame stuff, compared to everything else I write. Enjoy! ***** I had always considered myself somewhat feminine, but I never thought it would get this far. I grew up in the suburbs, and my family was always a bit out of plac...

Biker Bitch Ch. 01

by MicheleNylons on Dec 21, 2017
Transsexuals & Crossdressers

Chapter One: Cassie Cassie woke up feeling hungover, hungry, thirsty, beaten and abused. She was still chained to the billiard table in the Beasts of Burden Motorcycle Club clubhouse. She rubbed her ankle where the chain was manacled to her leg. Her nylon stocking had worn through and her skin was red and bleeding. Had it really been four days? Cassie s...

Recruiting of a Sissy Maid Ch. 01

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

[Welcome to my next story. This story has become a little different in how I planned to write it as compared to my previous stories. It has been fully written up already, as of this first uploaded chapter. Doing it this way allows me to better proof read and adjust for future chapters before uploading each. I will submit uploads on a regular basis for my rea...

Neighbor to Lover Pt. 01

by sarahchica96 on Oct 2, 2018
Transsexuals & Crossdressers

Introduction It was the summer I (Alex) and my twin sister Gina graduated from Business school, ironically Gina and I joined our family real estate business. This was a way of our parents keeping us busy and stop our procrastination about searching for jobs elsewhere. It was also the time my crossdressing persona met our neighbour Mr Parker. Backstory......