Crossdresser First Time Stories

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Orientation
Length
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My Wife and I Became Sluts Pt. 01

by mandiejune on May 22, 2018
Transsexuals & Crossdressers

My wife Carol was away for a week due to business conference. She was blonde 25 years old 5' 5" with very sexy body and 36C breasts and very sexy bum. We had been married for 3 years and had no children. I was called Tom and 28 years old and 5' 6" and thin. I was IT systems designer and worked from home. I was also a crossdresser that my wife and Mistress al...

Sarah has Sex at a Nudist Beach

by SarahCD on Jun 4, 2019
Transgender & Crossdressers

I first published this experience a few years ago. I prefer to call them 'experiences' since the term 'story' implies fiction to me. My experiences are based upon my real life. Since I started posting my experiences, my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more detail and corrected some...

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...

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...

The Girlfriend Ch. 01

by nikkiesilk on Mar 26, 2019
Transgender & Crossdressers

"It looks like Sam has a girlfriend at last." "Huh, what?" My attention was fixed on the rugby on the TV and I really wasn't paying attention to my wife. "I said, numbnuts, that a giant sinkhole has opened up in the high street and swallowed the pub and all the customers." "Oh, OK." Rolling her eyes, she said, "What did I just say?" The game was on a kn...

A Crack in Reality

by Mr Nice Guy on Aug 20, 2018
Miscellaneous

Something is wrong. There is a crack in reality! Things are changing! Is it human made? Has it always been there? Is someone controlling it? Is there any way to stop it?!What's next? Average Office Worker Alex William Borgman, Mad Scientist Rachel Davis, College Lesbian Goth Girl Daniel, average thief Jason Willows, struggling middle class family member. M...

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Sarah Wore a Bikini to the Hot Tub

by SarahCD on Feb 11, 2019
Transgender & Crossdressers

I first published this experience a few years ago. I prefer to call them 'experiences' since the term 'story' implies fiction to me. My experiences are based upon my real life. Since I started posting my experiences my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more detail and corrected some...

Neville

by Spankedinaskirt on Jun 1, 2020
Transgender & Crossdressers

Whenever Neville completed an equality questionnaire he ticked heterosexual. That was an aspiration more than a statement of fact since he'd never had a girlfriend and no prospect of getting one. It was also not exactly true. Girls liked him as a friend, they just didn't fancy him. He was called Neville for a start, what the hell were his parents thinking....

Crossdresser Evolution Ch. 02

by pantyhigh on Apr 8, 2019
Transgender & Crossdressers

Recap - Crossdresser Evolution - Ch 01 - How I got started crossdressing I was becoming addicted to this new way of masturbating very quickly, though there was still this feeling of shame surrounding it. I made sure I deleted the browsing history and then went to the bathroom to clean up. There I saw myself in these cum soaked pink panties. I could feel som...

Gender Change: Woman for a Day

by Zekar on May 1, 2020
Transsexual

Sometimes a man wants to experience what it’s like to be a woman. In this story you will experience a makeover, go on an adventure, and at the end of the day you can go back to your old life. Maybe it’s not for you. Maybe it’s for a friend who you will take on a date. All of this is consensual and in a variety of scenarios. Starting off there are real world,...

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