Crossdressed Stories

155 results
Orientation
Length
Source
Infinite Scroll

Queen of Paradise Ch. 04

by ptpl_guy on Sep 4, 2018
Transsexuals & Crossdressers

This is a work of fiction. Names, characters, businesses, places, events, and incidents are either the products of the author's imagination or used in a fictitious manner. Any resemblance to actual persons, living or dead, or actual events is purely coincidental. ALL PERSONS DEPICTED AND/OR DESCRIBED IN THIS STORY ARE ABOVE THE AGE OF 18 EVEN IF NOT EXPLICIT...

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...

Sweet Treat

by SaucyMasquerade on Sep 14, 2017
Transsexuals & Crossdressers

I As the water streamed across the window pane, I watched Jayne pull her coat tight, dashing from the car, through the torrential rain into the house, cursing the British summer in all its soaking glory. "Steve," she called, as she hung up the coat to dry, "I've an invite here, to a fancy dress party, Helen is holding on Friday" "I'm in here," I called...

Last Minute Crossdressed Sex

by Lovinhose on Sep 14, 2017
Transsexuals & Crossdressers

I like to write and share my experiences with the world, and I prefer writing about REAL experiences, thought at some point, as in the past, when I hit a 'dry spell' and have no true story to write, I will write a piece of fantasy fiction. I am happy to say, however, that this story, while nothing special, IS TRUE, and I am happy to share it with you all. Al...

My Sexy Changes Ch. 03

by TaraJaden on Sep 16, 2017
Transsexuals & Crossdressers

I had crossdressed a few times and built a desire to do so more, and in public. As a boy growing up it was hard to find opportunities. I would dress privately and wait for the next time. My next opportunity was for Halloween. I told some friends I wanted to go as a girl, as I was surrounded by girls this went over well. I picked a black mini skirt, a one...

My Best Friends Ch. 01

by Dark_Rose90 on Sep 16, 2017
Transsexuals & Crossdressers

~The following is the true story of my awakening as a male to female transsexual which never would've been possible without all of my friends. Names and ages have been changed to protect the privacy of those friends.~ Eighteen. A tender age. I'm just a young boy finishing up my senior year in high school. My name is James, or as my friends just call me, Jim...

Life and Time of Lady Vargos Ch. 12

by rik581 on May 7, 2019
Transgender & Crossdressers

"The Way Home" Martin made his way to the study which was also where he did his daily domestic chores of over seeing the manor. Actually the decision making process had already been done it just needed his signature, but he reviewed some of the documents anyway trying to find something that would help him escape his relationship with this man. The Baron was...

My Three Mistress's

by Tiffanyuk on Sep 13, 2017
Transsexuals & Crossdressers

This is my first attempt at fiction of any kind, not just the erotic. This has been a favourite fantasy of mine for some time now, it always makes me come. I have kissed and cuddled the two women involved but that's all. Wish it could be more! I have been a cross dresser since I was about 10 years old, I started off wearing my mothers rather plain, underwea...

Boy to Bride Pt. 01 Ch. 01

by sissyscarlet on Jun 19, 2018
Transsexuals & Crossdressers

Part 1: Adam MacDonald Chapter 1: Ms. Alice the Widow Adam carefully shifted the wooden board back in to its place. If only people knew what I kept up there, Adam thought, and smirked to himself. Before he was down from the stepping stool, he looked up at the ceiling 2'x2' entry leading to the attic—an artifact left for insulation and electrical, but Adam...

Girls Club Ch. 01

by ValerieMay on Mar 7, 2018
Transsexuals & Crossdressers

I stood by the bedroom window, letting the morning sun shine bright lines across my face. I closed my eyes and inhaled deep through my nose as the hazelnut flavored steam from my coffee reminded me of when everything was so ordinary. Ken was still in the shower and I wondered how he would like seeing me in my new XL knit sweater without any pants or underwea...