Cross Dressing Stories

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Cross Dressing

by Jjdoesit1 on Sep 16, 2017
Transsexuals & Crossdressers

It all started so many years ago, in the late 70's at the tender age of 19. My older brother had married this blonde German girl. They were both 23 and she was about 5 foot 9 inches tall with a killer ass and 32 c cup breasts. I know because that's what it said on the tags in her bras. It was summer and we were all at the lake on his boat and she was weari...

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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...

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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...

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Caught Cross-Dressing!

by StephanieSeymour on Sep 13, 2017
Transsexuals & Crossdressers

I was on the bed with a vibrator jammed up my ass and my girlfriend's bra strapped to my chest when she came home early from work. She caught me scrambling for the remote to turn off the cum shot porn I had playing on the TV. "What the fuck?" she asked. "Fair question," I said. I rolled off the bed and did my best to play it off. But as my mind reached f...

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Last Time Cross Dressing

by vjak19 on Sep 16, 2017
Transsexuals & Crossdressers

After having read many submissions about one's first time I've decided to tell you about my last time dressing as a sexy woman. To get to the finale, I need to give you a little background. I am a 35 year old white male that stands 5'7" tall and weigh in at 140 pounds. I stay very fit with lots of competitive cycling, swimming and running, all sports I've...

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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...

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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,...

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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...

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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...

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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...

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