Caught Cross Dressing Stories

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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...

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...

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...

Celebrating National Nude Day Ch. 06

by BOSTONFICTIONWRITER on Sep 15, 2017
Transsexuals & Crossdressers

"Okay, who's next? Who celebrated National Nude Day with this contest in mind? Who wants to share their story with the group? Is there anyone else with a story before we close the competition and take a vote for the winner?" Everyone looked around to see who else had a story and who else had their hand raised. "Also, let's not forget the rules. You must be n...

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,...

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...

Something Had To Change

by sublocked on Sep 16, 2017
Transsexuals & Crossdressers

This was not going the way Diane had thought it would or should. Basically nothing, and yet everything, had changed in their marriage in the last six months. She watched him now, sitting on the sofa, drinking a beer, unshaven, and between picking his nose and scratching his ass, she wasn't sure what his biggest pleasure was. At least he was fit. There was...

Steve to Stephanie Ch. 01

by bad_boy_good_girl on Sep 16, 2017
Transsexuals & Crossdressers

This is my first attempt at a longer story with deeper characters and a more evolved story line. Stay tuned for the next chapter. As always comments are welcome. * Steve was mild mannered guy with a big secret. Steve was an avid cross dresser, very bi actually leaning towards being gay. Steve did not consider himself gay because he really wanted to be fem...

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...

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...