Cross%20dressing Stories

43,513 results
Orientation
Length
Source
Infinite Scroll

Training of a Cum Slut

by niteowl2003 on Sep 12, 2017
BDSM

Part 1. Karen was blonde haired, five foot two tall and what can only be described as a BBW figure including as I found out her 44DD breasts. We actually met through the company I run filming female fantasies, and her tale there like in another story entitled The Idea chapter 3. To save you having to find this story, I will include excerpts here now. Bas...

Caroline on the Cross

by AubreyWylde on Sep 19, 2017
BDSM

Author's Note: This story is one of a series I've been working on. The premise is that there exists a private club, known as the "Villa di Dolore", dedicated to assisting its members in playing out their kinky fantasies. Each of the stories follows a member or members through a scene. A number of the stories have been posted elsewhere under my other pen name...

Halloween Cross-Dressing Bash Ch. 02

by BOSTONFICTIONWRITER on Sep 16, 2017
Transsexuals & Crossdressers

Now, having given into the urge of wearing women's clothes, safe within the acceptance that he'd surely receive at the Happy Halloween Cross-Dressing Bash, he was excited about attending and getting dressed as a woman without being made to feel foolish or being harshly judged and meanly ridiculed. He just wanted to go somewhere that he could dress as a woman...

The Change Ch. 3

by angel_reba on Sep 17, 2017
BDSM

i kneeled by the low table with my back to Him. He had brought blueberry muffins, coffee and orange juice for breakfast. i ate one of the muffins and drank three glasses of orange juice. The whole time i was eating i could feel His gaze upon my back, i could hear Him sipping on His coffee, watching me, eyeing me, and no doubt thinking about what He could fin...

Teacher's Pet

by prittyicklekitty on Sep 13, 2017
Exhibitionist & Voyeur

The view from his seat wasn't as good as he hoped for. Sitting down at the front of class was a new thing for Dave. He figured he might get a flash of stocking, or at the very least a peek at that lacy bra he had seen the outline of through her blouse as she had reached up to write at the top of the blackboard. Miss Cross was in her late 20's and small enoug...

Black Femdom for Black Gentlemen

by Samuelx on Sep 11, 2017
Transsexuals & Crossdressers

A lot of Black men in the world of BDSM fervently want to explore their submissive desires with a dominant Black woman. The problem is that a lot of dominant Black ladies in that realm only cater to the needs of submissive White dudes, and that's a damn shame. Yet those same sisters get mad when they see a brother with a White woman. Well, if Black women are...

Black Cross Dresser Chronicles

by Samuelx on Sep 16, 2017
Transsexuals & Crossdressers

What's up people? My government name is Omar Woodson but you may call Madame Orillia. The Black Canadian cross-dressing diva extraordinaire of metropolitan Toronto, Ontario. One of a few outspoken Black cross-dressers in town, and definitely one of the most wickedly fun and entertaining. Lots of Black men like to wear wigs, skirts, nylon panty hoses, bras an...

Lecturer

by oggbashan on Sep 14, 2017
Humor & Satire

Copyright Oggbashan January 2015. The author asserts the moral right to be identified as the author of this work. This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. Thank you to naokosmith for academic advice. *****************...

Abigail and Mrs. Cross Ch. 01

by cloacas on Sep 14, 2017
Erotic Couplings

It was a not unwelcome surprise to hear Abigail call my name on a Paris street. The last time had been almost eight years earlier, when she'd given my cock a last squeeze in my doorway before she drove back to her parents' house and then had returned to college. I remembered that scene well. She brushed her hair, bending slightly to the right to pull the co...

Halloween Cross-Dressing Bash Ch. 04

by BOSTONFICTIONWRITER on Sep 16, 2017
Transsexuals & Crossdressers

"If I knew you a bit better, I'd tell you the other half of the story relating to the name of the shop and what my ex-husband tricked me to do, but it's a bit risqué and I'm embarrassed that I fell for it," she said with a sexy laugh. "I'm too trusting and it's only something that I would do. I should have known better," she said hanging his dress back on th...