Gay Crossdresser Stories

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Sissy's Subservience to Wife Ch. 01

by JessicaSIssyGurl on Aug 1, 2018
Transsexuals & Crossdressers

Every Friday evening is my grooming ritual, shaving away every inch of body hair that has cropped up through the week, soaking myself in a bathtub to further soften my skin, red nail polish on my fingernails and toes and finally cocoa butter lathered all over before I sleep that is a thing I do every night though. But before sleeping I message my date for to...

Trixie's Adventure

by spandexman on Aug 18, 2017
Fetish

Trixie, the 19-year-old, 5'5", adorable, assistant-manager, with big baby-blue eyes, high cheekbones, a cute dimpled chin just like her gorgeous aunt, thick long curly platinum-blonde hair, and an incredible 36GG-28-33 hourglass figure that her too small red knit turtleneck sweater, skintight white riding breeches, and shiny brown riding boots hugged like a...

Mary Becomes a Whore

by Juggerhead on Jul 30, 2019
Transgender & Crossdressers

Mark was like any other ordinary 25 year old guy with a regular 9-5 job as an office executive in an finance company. He was fair, around 5 feet five inch tall and had a slender frame. Often his friends and colleagues would ridicule him for his height and thing body. He had a boring life and didn't indulge in partying or clubbing. After his divorce he went o...

Sissy Walk of Shame

by zona_loser on Mar 12, 2019
Transgender & Crossdressers

First off: This is a story about my alter ego a not so bright crossdresser who likes a bit of exposure. It also contains an element of self-bondage but not in the traditional manner. All characters are over 18 years of age and are purely a figment of my imagination. ***** I am a part time mostly closet crossdresser. I don't consider myself gay or bi and ha...

The Bargain Dress

by HeatherMaureen on Sep 25, 2017
Transsexuals & Crossdressers

I was in my late teens before I found out how submissive my dressed self was. I'd never really considered myself to be a submissive sissy crossdresser but was about to discover that I was one. I called an ad about women's dresses, heels and other things in the local bargain finder from a payphone. An older woman answered. She wasn't taken aback by my tellin...

Crossdresser Evolution Ch. 05

by pantyhigh on Aug 7, 2019
Transgender & Crossdressers

Recap - Crossdresser Evolution - Ch 01 - How I got started crossdressing I was becoming addicted to masturbating while wearing panties. Though there was still a feeling of shame surrounding it, I saw myself in these cum soaked pink panties. I could feel some sense of arousal but at the same time was ashamed that I was standing there wearing my wife's pantie...

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......

A New Me...

by teencdgirly22 on Sep 25, 2017
Transsexuals & Crossdressers

This story is completely true. I hope you enjoy it because I have been dying to write it for almost 4 years now! Hi, my name is Ashley. At the time of writing this story I am a 24 year old crossdresser living full time as a woman. It wasn't always like this however...so let me tell you about how it all began. Chapter 1: The beginning, and going out. Fla...

Amy Finally Lives Out Her Fantasies Ch. 02

by LuvAGoodPegging on Sep 11, 2017
Transsexuals & Crossdressers

(Author's Note: This is a continuation of "Amy Finally Lives Out Her Fantasies -- Shy Amy uses her strapon on Kyle". Thanx to all who provided such great feedback. Hope you like part two. Warning: this story contains male/female strapon sex, cum eating, and as the category suggests, shemale sex. If those aren't your things, you won't enjoy this story. Love t...

Mistress Chantel, Tranny Dominatrix Ch. 04

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Four: Chantel Hams it up with Kerri and Friends. Beep, beep, beep, my alarm clock goes off. Lying under my fluffy covers and on my satiny bed sheets, face mushed half buried in a pillow I awake, glance at that damn clock and see 9:00am. It's Sunday and I do not have to be up at any specific time but I do not really like sleeping in as I feel it wast...