Cross Dressing Stories

72,522 results
Orientation
Length
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Infinite Scroll

Hot Sex Instead of Dancing Ch. 12

by SusanJillParker on Sep 12, 2017
Transsexuals & Crossdressers

Please give me the support of your vote. * Wanting to look pretty, Walter has the uncontrollable urge to dress as a woman again. Sunday, the day of rest, Walter reflected over all that happened during the weekend. Linda had hot sex with his three friends, Jim, Henry, and Tom. Tiffany abandoned wearing her sexy nightgown to clean her kitchen in her even mo...

Freddie Becomes a Cross-Dresser Ch. 01

by BOSTONFICTIONWRITER on Sep 16, 2017
Reviews & Essays

I was determined to write a transsexual and/or cross-dressing story for Literotica's 2008 Survivor Contest. I thought that I had written a cross-dressing story when I wrote Do You Know A Cross-Dresser, Ch. 02, but that was placed in the Reviews and Essays Category. Then, I thought that I had written a transsexual story when I wrote Transsexual Sex with Vinni...

The Psychosexual Motive in Writing

by Da_Vida on Sep 16, 2017
Reviews & Essays

I have been a writer all of my life. My employment as an adult has, to a large extent, depended on my ability to get published, which I suppose makes me a professional writer. In addition to writing, I've also served as a consulting editor for a number of publications. I am no stranger to the written word. The motives for writing erotic fiction no doubt va...

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. 01

by BOSTONFICTIONWRITER on Sep 16, 2017
Transsexuals & Crossdressers

Bob went to the bathroom, locked the door, and sat on the closed toilet lid. He pulled the invitation from his wallet and unfolded it. Well worn from reading it over and again so many times, he had saved it hidden there in his wallet and in his back pocket since the beginning of September. He had received the invitation online and printed it out before delet...

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...

My Cross-Dressing Life

by roberty on Oct 10, 2017
Transsexuals & Crossdressers

The first time I learned I might be different is when a friend of mine—we were both drying off after swimming in the college pool—told me my body looked like a girl's. I'd received some looks before, but that was the first time someone came right out and told me my physique was leaning a little toward "feminine." A few weeks later, while loitering in the col...

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...