Cross Dress Stories

150,200 results
Orientation
Length
Source
Infinite Scroll

Goodbye Girl Ch. 05

by karaline on Sep 24, 2019
Erotic Couplings

The final instalment! Thank you for reading, if you've made it this far. And for the favourites and votes and *cough* comments. Thank you especially to Charles, for critiquing this chapter before I submitted it. ~ ***** "Orla!" Orla spun round. Rachel was walking awkwardly across the cobbled church yard in kitten heels, waving. It was a gloriously su...

Transforming Brent Pt. 05

by sissymissyct on Dec 2, 2019
Fetish

I awoke early, partially due to the pressure of morning wood in the chastity. Once I settled down, I showered and slipped on a robe and quietly made my way to the kitchen. I quickly familiarized myself with the layout and, finding what I needed, started cooking a nice breakfast for my mistresses and myself. Ham and cheese omelet, OJ, toast and sausage, along...

Influential Factors! Ch. 01

by gummidurango60 on Sep 12, 2017
Transsexuals & Crossdressers

Note: This is the beginning of a fictional story, the origin, in which the main character faces the love of cross-dressing or divorce. Who is she? Are there any morals? This is the origin of the base characters and will build slowly. If you're at all familiar with my stories you know that I love putting my characters through situations that either accident...

9 Stone Cum Queen Rides the Train

by 9StoneCumQueen on Sep 18, 2017
Exhibitionist & Voyeur

(This is my fourth story for Literotica) * Here I am. I'm riding the Circle Line tube train round and round. I have been round London three times already. I stay in the same seat. I drink Cherry Coke. Different men sit opposite me. Men come and go. They look up my skirt. I encourage them. I swing my legs high when I cross my legs. I am in no doubt that th...

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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Jenny's Legal Adventure Ch. 5

by Capstick on Sep 19, 2017
Loving Wives

Jenny slipped out of her still damp clothes, and held the dress up. It was a brief nurse uniform, and looked tailored to fit Meekashi. She unzipped the back, and stepped through the brief skirt, still balancing on the high heels. She had to cross her knees, and strain to force the material up over her broad hips. She could see the side seams visibly stretchi...

Black Femdom for Black Sissies

by Samuelx on Oct 15, 2017
Transsexuals & Crossdressers

"Dammit, Dalton, you're into some seriously twisted shit," Marjorie Etienne said, and the tall, curvy, dark-skinned young Haitian-Canadian woman looked at the man standing in front of her. Dalton Etienne liked to walk around the City of Ottawa, Ontario, like he owned the damn place. Six feet three inches tall, burly and chocolate-skinned, with a slick goatee...

Secrets

by Dawns on Sep 16, 2017
Transsexuals & Crossdressers

I was wearing panties that day under my black denim jeans, a habit that went back a few weeks to the Halloween party given by my sister at her home. My Brooke Shields impersonation that night, a very good one, led to jokes that I could date a guy. Cross dressing in any form is not something that I talk about. It's just something I do. It would embarrass me...

The Mistress

by Xowie on Sep 16, 2017
BDSM

It makes me laugh to think that the majority of people who see me think that I'm a librarian. I suppose that, outside of work, my dress is more than a little plain. I tend to favour knee-length skirts or trousers with sensible shirts and regular underwear. I love the fact that people who see me in the supermarket or walking along the street think that I'm a...

Halloween Cross-Dressing Bash Ch. 08

by BOSTONFICTIONWRITER on Sep 16, 2017
Transsexuals & Crossdressers

She looked down and saw that he had an erection. "All you guys are the same," she said shooting him a cold stare. "Here I am pouring out my heart to you about what my ex-husband did to me and you have an erection." "Sorry." "Do you realize how humiliated I am to find out that I blew every man in my community? Then, to find out that I blew my husband's fo...