Caught Cross Dressing Stories

192,094 results
Orientation
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Infinite Scroll

Using Halloween to Dress as a Queen

by andtheend on Sep 19, 2017
Transsexuals & Crossdressers

A time to wear a costume, Jerry uses Halloween as his excuse to dress as a woman. Jerry loved October, his favorite month of the year, by far. The Fall was his favorite season, too. With the colorful array of leaves that crunched underfoot and the multi-colored canopy overhead, he loved the cool crisp air that made his nipples as hard as his cock. Whenever...

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...

Halloween Cross-Dressing Bash Ch. 06

by BOSTONFICTIONWRITER on Sep 14, 2017
Transsexuals & Crossdressers

Gloria left the store in the capable hands of her store manager, Sharon. After paying for his purchases, with Gloria giving Bob a very generous and unexpected 20% discount, Bob followed her car home in his pickup truck. He was just as excited to maybe have a sexual affair with her as he was with the thoughts of trying on the clothes he just bought. They sto...

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...

Anal Sex with Stranger on a Train 05

by SusanJillParker on Sep 19, 2017
Transsexuals & Crossdressers

Chapter 5 Peter finally meets Roberta again, the love of his life. In just a few minutes, Robert returned to the room dressed as Roberta. Giving him a sexy cross dressing show, by her feminine antics and charms, she obviously enjoyed being watched by Peter. With a shake of her head and with a flourish, as if releasing her sword in Zorro, the gay blade, sh...

Adventures of Alice and Alex Pt. 04

by AlexCarroll on Sep 14, 2017
Transsexuals & Crossdressers

Alex wears lingerie again, and Alice hears of his first cross-dressing experiences ... In the following days I nervously waited for Alice to mention, what had for me been a momentous occasion, and now I could not stop thinking about sex with Alice while I wore the red teddy, or perhaps the black baby-doll, and I was desperate for more. After about a week,...

Trading Spaces

by coxette on Sep 17, 2017
Celebrities & Fan Fiction

"Honey?" "Yes?" "Did you find anything you like yet?" "Yeah, I think so." Courteney emerged from the rack of clothes with two tops in hand. "I can't believe you took me out to shop. We never shop outside of magazines." "I know, but I thought it would be a nice change." David pulled out a very tacky, very bright, very David top and held it up to his wife...

My First Man

by cdloveradam on Sep 16, 2017
Transsexuals & Crossdressers

I started cross-dressing at a very young age. I believe my first time was in a pair of my moms tan pantyhose and high heels. It was a joke that my sister did on me but ever since that I kept doing it in secret. I use to wear my sisters panties, hosiery, bras, and make up. I got very good at making myself look like a woman. At 5"11 and very slim it wasn't tha...

Story of Sissy Blackmail Ch. 01

by richysissy34 on Sep 13, 2017
Transsexuals & Crossdressers

I have been debating writing this up for a while, but it truly is a really hot story, that I figured you would all enjoy... so enjoy! (And yes, the title does speak for itself; it's a true story...) ***** I began cross dressing when I was 16 years old, and I am now 21. When I was 18 I moved away to college, and began living in a dorm on campus. I chose to...

A Little Help for a Friend Pt. 02

by DrLit on Sep 15, 2017
Fetish

If you read my story, A Little Help for a Friend, you realize my wife and I used a three way to help a friend get back to having sex again after a tragedy. That friend, Julie, wanted to take us to Key West on a wild sexual adventure. All I needed to do was two expensive bikes for her; one a very expensive carbon fiber triathlon bike and the other nice road b...