Cross Dress Stories

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Freddie Becomes a Cross-Dresser Ch. 02

by BOSTONFICTIONWRITER on Sep 16, 2017
Reviews & Essays

I walked in the store and continued over to an area where there weren't too many women. Even though I wanted to cheat and buy a pair of jeans, I figured that I'd have to wear a dress to experience the real effects of cross-dressing. There, that's another insight. Cross-dressers probably, I'm thinking as I wrote my thoughts in my notebook, would rather wear d...

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...

Hot Sex Instead of Dancing Ch. 13

by SusanJillParker on Sep 12, 2017
Transsexuals & Crossdressers

Please give me the support of your vote. * Now that Linda's secret gangbang sex with his three friends is out in the open and a topic for their pillow talk discussions, Walter feels more comfortable dressing up as Wendy. With his wife gone shopping with her sister and mother and with Linda staying overnight at her sister's house, the next town over, this...

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, 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,...

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...

Hot Sex Instead of Dancing Ch. 14

by SusanJillParker on Sep 12, 2017
Transsexuals & Crossdressers

Please give me the support of your vote. * Tiffany discovers that her next door neighbor, Walter, is a cross dresser. "Walter?" Walter heard a voice that he immediately recognized. Cringing at the sound of her voice when he usually rejoiced at the sound of her voice, he was already turning a bright red in anticipation of her seeing him and him seeing her...

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...

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...

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...