Crossdresser Caught Stories

163,967 results
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Ashley's First

by User1 on Sep 13, 2017
Erotic Couplings

She looked amazingly sweet to be doing such a nasty act at the Gold Club: tall, blond and very cool. Her name was Ashley and she had blond hair down to the small of her back and phenomenal blue eyes. I decided to blow a few hundred and take her to a private room for something more intimate than a lap dance. She was totally naked as she slid down my chest,...

April Fools Day Prank

by hannsg on Sep 17, 2017
Exhibitionist & Voyeur

Victoria was the consummate tease, she would dress provocatively but really never acknowledged any of us, no matter how hard we tried. Maybe it was because we were geeks, if we were jocks we would have had her attention. Becky, her sister was part of our group and even she didn't get any respect from Victoria. Victoria was the long blonde hair cheerleader t...

Art Class

by daphnenevada on Sep 14, 2017
Exhibitionist & Voyeur

A commissioned story for George and Veronica B, shared with permission. ~ Empty chairs circled a raised platform set upon the polished floor, on which cushions and thick blankets were arranged. The space was large, with white painted walls. Halogen lights shone down from the ceiling, illuminating the small stage and smooth concrete of the surrounding floo...

Plenty of Panties Ch. 02

by Sanzamour on Jan 30, 2018
Fetish

We were next door neighbors, Sarah and I, so after I fucked her the first time I just figured it would probably become a regular thing. I guess I just imagined she'd end up bringing over a toothbrush and spending more time at my house then she did at her own. But it had been almost a week and she hadn't even tried to contact me since then. I knew that there...

The Heart Wants

by dreadknots on Feb 26, 2019
Transgender & Crossdressers

The bus was late, again. Dan fiddled with a discarded newspaper, trying to ignore the night's cold air on his skin. It was strange to not have any company on this run. Usually, there's another guy out here, waiting for the same 119 out of town and to his sprawl of an apartment complex. But he was nowhere to be seen. Dan didn't know him, but he was kinda cute...

The Surprise

by Queen0fNights on Feb 25, 2019
BDSM

It was already getting dark as Kitten stepped off the train shivering with pleasure as the cold breeze touched her skin. It had been hot on the train, almost stifling, and at times on the journey it felt like she was burning up, the usual hunger and desire for Sir, which always grew stronger on her way to meet him, was magnified by the surprise she had plann...

Daddy

by RaggedyAnnethrax on Aug 20, 2018
Erotic Couplings

When I found out the penitentiary you're stuck in has a visitor "powwow" once a year, I was so excited. You said that you think it would be the perfect opportunity to sneak away and fuck in secret, and I quickly let you know it sounds to me like a tempting but very bad idea that could land you in a lot of trouble. We're sitting around a large bonfire for "...

Four Pieces

by Just_Words on Nov 20, 2018
Loving Wives

Marie was upstairs dressing. It was midmorning Saturday and she was headed out for her weekly shopping fun. For as long as Tom had known her, Marie had loved to shop. She didn't have to buy anything to have fun and Marie was always good with money. She just loved to shop, to try things on, and see what was new; except now Tom knew that she wasn't going shopp...

Coffee Break

by athenamystique on Sep 13, 2017
Erotic Couplings

She called him at the office. "Meet me at the coffee house in 15," she ordered sweetly, then hung up the phone. He held his phone in his hand for a moment before placing it back on his desk. It was two o'clock and his coworkers were still in their after-lunch lull. "How about some coffee on me?" He offered, precipitating his escape. Henry got on the ele...

Dear Diary: Lonely

by CaseyMcCoy on Sep 16, 2017
Toys & Masturbation

Comments and feedback are always appreciated :) I've been alone for a long while it seems. Normally, I'm ok with it...but tonight....not so much. We haven't talked in weeks and I haven't seen him in months. I'm trying to move on, but I'd kill to have him here tonight. I've been staring at the ceiling, tracing patterns on my stomach. I feel like I don't r...