Cross Dressing Stories

72,522 results
Orientation
Length
Source
Infinite Scroll

The Sewing Class

by Classygloves on Aug 18, 2017
Fetish

My wife (2nd marriage ) divorced me because she could not deal with my cross dressing. It was actually the best thing that could have ever happened to me. I proceeded to get my own apartment where I would not have to hide my wardrobe and I could come and go as I pleased. Except for going to work, I started to live dressed up as a woman almost all the time....

Magic Dress - Diana Pt. 02

by SlightlyRude on Apr 23, 2019
Transgender & Crossdressers

MEET THE GIRLS We were told to come early, and I could change into my outfit at Jason and Lucille's house. Lucille greeted us, looking very pretty and very feminine. She could easily pass. We went upstairs with our bags, and I was transformed in my favourite green dress. When we came down there were another couple of women. One had a big bust and quite cu...

First Time Cross Dressing

by fethishboy on May 1, 2003
Fetish

Lisa Smith was always a bit spoiled. She was a sexy and teasing little minx. She was 22 years old with a smoking hot body. She loved to tease and be treated like a princess. She acted all sweet and pretty but she had a wild side. She loved to control men. She loved to make her buy her stuff. She loved to cock tease. She made a lot of money on it. She loved t...

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The Switch Hitter

by Biskit on Sep 12, 2017
Transsexuals & Crossdressers

This love story could have been submitted in the Incest section but since for the most part its bisexual, transsexual and cross-dressing, I decided not to offend the incest purist and submit it here. All the characters are of course fictional. Not sure why I couldn't get one of the volunteer editors to help me, lord knows I needed one and I certainly did try...

Young Crossdress, Meets His Daddy

by Sliver02 on Sep 1, 2017
Transsexuals & Crossdressers

Well I am 28 year old male, not in best of shape. I can still run a mile in under 15 minutes, and I work 3 to 4 times a week. I try to stay in shape a little bit. Well that is enough about my physical appearance. I am also married to very beautiful wife, who I love more then the world. We have very open marriage, but there are few things she does still not k...

May Ch. 01

by Jack1107 on Oct 31, 2018
Mature

Jack was in his last term at University before his finals at the end of May. Easter had been early this year. His mum, Jean, had asked her friend May if Jack could stay with her Monday to Friday for the last term as her Town House was a two-minute walk from the University. Jack had a fifty-minute drive to it then another fifty-minute drive home in the evenin...

One Fine Day

by TomCarter on Sep 16, 2017
Transsexuals & Crossdressers

This is the story of my first date with Wendy in the summer of 1981. It is a prequel to 'Room 139', which takes place on Halloween of that year. The sex takes a back seat to the story, but hope you find something in this regardless. ************************************************** "Do you wear girl's underwear?" The question caught me off guard. Wend...

Connie at an Adult Bookstore Ch. 01

by cmorehead on Sep 13, 2017
Transsexuals & Crossdressers

Disclaimer: The following story is not intended for minors. If you are offended by sexually explicit material or it is not legal in your place of residence, please close the document now. If not, I hope you enjoy my attempt at entertaining you with stories of my adventures. * Let me start by introducing myself. My name is Connie and I am a 40-something tr...

L'histoire

by EmeliaBell on Aug 31, 2017
Fetish

I've always loved stockings. I remember when I was a little girl I found a pair of my mother's old suspenders, from when stockings were the only option, in the dressing-up box. I thought they were fascinating and wanted to try them on with some stockings, but my mother still bought my clothes and there was no way I was brave enough – or rich enough – to bu...

Fetish Club

by domme24 on Sep 12, 2017
BDSM

It had been six months since John had finally admitted to his girlfriend Rachel that he liked Femdom play. It had taken him a lot of courage, and for the first 3 and a half years of their relationship, Rachel had had no idea. After initially being hesitant, Rachel had taken to it like a duck to water getting more and more confident each time they had an oppo...