Caught Cross Dressing Stories

192,094 results
Orientation
Length
Source
Infinite Scroll

Within Amie Ch. 05

by Jayleen88 on Sep 14, 2017
NonHuman

*** Hi!!! This is the FIFTH installment of WITHIN AMIE I'm a part time English speaker so naturally, there would be grammar mistakes and confusing sentences here and there LOL so I'm sorry for that. With love, Jayleen *** Darkness overwhelmed me as my arms and legs flailed uselessly in mid air. A sudden gush of cold wind blew me and thump! I could feel...

The Song Called Pleasure

by ErosInDisguise on Nov 27, 2018
Erotic Couplings

Lex's beach house was huge. The sprawling two storeyed structure spread over a sizeable piece of land on the Dumas beach. One had to drive a few miles off the coastal highway through a dense cover of palm trees and sandy road to reach it. The entrance had a spacious parking lot with a water fountain in its midst. The entrance was actually the rear of the h...

Cougar 47

by Stripemoff on Dec 10, 2017
Mature

He's looking at me; the boy is staring at ME, as I sit on the edge of the bed and slowly and seductively put on my black stockings. And that heady realisation is making me purr with delight; a young boy admiring the long shapely legs of this older woman. I must give him a sexy show, one that he will remember. I can just make him out in the dark hallway as...

Ouija

by luvpsy on Sep 25, 2017
Erotic Horror

Note: This is a ghost and horror story. If you're here looking for a sexual turn on, maybe you should choose a different story to read. If you like ghost and horror stories then I hope you'll enjoy this one. * Curious, I watched as Glenda rummaged through her wardrobe and withdrew the box. It looked like a game, one of those played on a board. "We need to...

One Two Buckle My Shoe

by severinrossetti on Sep 13, 2017
BDSM

….one two buckle my shoe…. Having spent so much of the day crouching low, or on his knees even, forcing fat feet into shoes which women would insist on having a size too small, Steve felt like some kind of Prince Charming, but with only ugly sisters to attend to. His back ached through having to bend over these vain obese women, his legs were stiff, his fin...

Chronicles of Being a House Slave Day 04

by sexualdesires69 on May 11, 2020
BDSM

Holly's first day at work as a voluntary sex slave had been far from uneventful. It was barely past lunchtime, and she already had been forced to masturbate several times, suck her boss's dick, had her pussy licked, and had multiple orgasms denied. As she finishes cleaning herself up in the shower, she can't help but wonder what other tortures await her. Ear...

Playfully His Ch. 01

by playmiss on Jun 16, 2020
BDSM

Chapter 01: To Have Resolve Note: The events in this series are based on real experiences, which have been somewhat condensed and altered to allow for presentation as a story. * My landlord, Ron, is replacing the sink in my bathroom, and so, as nature calls, he has me use the bathroom downstairs in his apartment. But I am not content to just use the bath...

Cul-De-Sac: A Story in Around Ch. 02

by ZotDragon on Sep 16, 2017
Novels and Novellas

True to her word, the beautiful Yvoine was at Travis's house in thirty minutes. He had given Sara strict instructions that she could not talk to Yvoine, at least not tonight, and she was not to interfere or interrupt the session. In preparation to Yvoine's arrival, he had insisted that they both dress, not in casual clothes, but clothing that denoted authori...

Who's the Lucky Boy?

by Egmont0409 on Sep 12, 2017
Erotic Couplings

Findlay (Finn) Regan arrived at Logan International in high spirits, having consumed five whiskies during the flight from Gatwick, England, and having patted the pretty Irish cabin attendant called Maeve on the butt to earn a huge smile and she made no attempt to move off quickly. The cheeky-faced Finn was not long out of prison, jailed for 28-days for rid...

ExBoyfriend

by Justinu247 on Jan 16, 2019
BDSM

*This story is based off the events mentioned and not mentioned in the song EX-Boyfriend, by Lil Dicky. It will be told from each characters point of view. Enjoy * EX-Boyfriend "How in the hell did I get here?" Cris thought to himself, as he was blindfolded and strapped to the Saint Andrew's Cross. I knew I shouldn't have invited Katie and her boyfriend o...