Cross%20dressing Stories

43,513 results
Orientation
Length
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Infinite Scroll

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...

Tala's First Performance

by Lisolette Gilcrest on Sep 13, 2017
Toys & Masturbation

Staring down at the ground, Tala's eyes welled up with tears, this time not out of sadness but pure horror at what she had been asked to perform. At this point she wanted desperately to please Cross and to get a reprieve for her stinging bum, but the thought of having to touch herself while sitting in front of him, as though she were on stage giving some kin...

Lost Letters to David Cross

by ella_irving on Sep 17, 2017
Celebrities & Fan Fiction

David Cross was a Jewish looking man, too Jewish if you asked some people, and was quite obviously balding. Both of these, however, were part of his charm. The final third of his charm consisted of Arrested Development's inability to afford a steady cam, or perhaps a tripod. Though, in retrospect that's more part of Arrested Development's charm, rather than...

An Artist's Lesson

by Artist101 on Sep 17, 2017
BDSM

The room was large, with a high ceiling and open beams. The man known as the Artist stood next to a large window, silhouetted against it. He was dressed simply, wearing black trousers and a black shirt. Two large theatrical spotlights were hung in the ceiling beams casting a harsh white light into the room. The double doors at the end of the room opened. Th...

Lauren Starr's Last Stand Ch. 02

by 100 Angry Bananas on Sep 2, 2017
Erotic Couplings

I. It Begins in Turtle Creek and Everything Burns Virginia twirled her grandmother's silver pendant between her slim fingers, cursing herself under her breath, wondering how she would tell Lauren about her betrayal. The pendant hung from her neck, dangling between her breasts, a gift from her dead grandmother, and Virginia had a habit of playing with it whe...

Lauren Starr's Last Stand Ch. 01

by 100 Angry Bananas on Sep 13, 2017
Erotic Couplings

I. Death Comes to Blue Oaks Cold, hard eyes, eyes the color of cooling coals, looked down the barrel and through the sight of the carefully balanced rifle. The eyes locked onto the over-alled man with sandy blonde hair and a stupid grin: Lauren Starr's target. Her heart skipped a beat, but Starr's face betrayed no emotion. As far as she was concerned, her...

Julie and the Cross

by homeboundboy on Feb 6, 2018
BDSM

In the small farming town where I grew up, the town elders took religious holidays very seriously. Each major holiday ended with a huge festival and the Spring celebration that coincided with Easter was one of the biggest of the year. It not only commemorated the holiday, which our deeply religious community celebrated with zeal, it also meant the start of t...

Cross-Dressing, Gay & Lesbian Sex 01

by SusanJillParker on Sep 13, 2017
Transsexuals & Crossdressers

There are no underage characters in this story. All characters are over the age of 18-years-old. Cross-Dressing, Gay & Lesbian Sex 1 Sometimes wishing he was born a woman, Daniel struggled with his need to cross dress. With his hands resting on her dressing table and his body leaning in for a closer and more critical look at himself in his wife's lighted,...

Cross Dressing: A Hypothesis

by Da_Vida on Sep 16, 2017
Reviews & Essays

First as a young adult and then as a psychologist, I read extensively in an attempt to find an explanation for my cross dressing behavior. Several psychological hypotheses have been proposed in the literature but I did not find any of them to be compelling. While I don't think it is an explanation for cross-dressing, one hypothesis that resonated somewhat...

Cross Dressing for Valentine's Day

by SuperHeroRalph on Sep 14, 2017
Transsexuals & Crossdressers

This is a Valentine's Day contest story. Please vote. * First time in public, Frank attends his first cross dressing Valentine's Day party. Frank was online surfing the web, when he stumbled upon a site pertinent to him. He couldn't believe what he was reading. He had no idea such a thing existed. He pushed the button on his computer to print it and to po...