Crossdresser Caught Stories

163,967 results
Orientation
Length
Source
Infinite Scroll

My Wife, My Tormentor

by Sissyjackie2008 on Sep 16, 2017
Transsexuals & Crossdressers

I am excited by the . One of the most humiliating experiences I sufferer was caused by my first wife. I had been a crossdresser since I was little. Actually my mother started me when she dressed me as a girl for Halloween. When at 7 I started to protest, She said she had no daughter and once a year I could let her have fun. I could never refuse her so I re...

Jessica Ch. 01

by jac0879 on Mar 18, 2020
Transgender & Crossdressers

It was a familiar ritual by now. I plugged the drain of the tub and turned on the faucet to draw a hot bath. It was really a pain keeping my body hair tamed, it grew in dark and quickly but I was determined. As the water ascended in the basin, I stripped my clothes, stood in front of the sink and grabbed a razor. I quickly dispensed of every last trace of st...

Randy's Grand Reveal

by dkbeasley on May 7, 2019
Transgender & Crossdressers

I've known Randy since high school. We rode the same bus, lived less than a mile apart, were assigned to the same study halls and shared the same lunch period. This is not to say we were 'buds' back in the day but we were in shared company hundreds upon hundreds of times over a span of four years so we knew each other for sure. What I didn't know, had no clu...

Cheating

by twizted77 on Dec 26, 2018
Cheating Spouses

You never thought it would happen, but here you are after years of marriage, waiting quietly at a dark table in the corner of a hotel bar to meet someone you'd connected with online. Someone who, if things went well, you would be having sex with later tonight. You take a shot of tequila and breath deeply. It burns, but you barely feel it. You are a mixture o...

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I Adore Crossdressers

by Ab9095 on Nov 26, 2018
Transgender & Crossdressers

I adore crossdressers. Adore!! Pretty little pantied asses up in the air. Shaved dicks and balls hanging down. Pretty little assholes. Fuck Yeah!!! I love seeing their hard dicks flopping when they are riding a cock. Fucking A, when they are hot they are HOT!!! They don't have to be perfect any more than any woman does. They are ALL good. But I do love it...

Becoming A Crossdresser

by AsianCD1990 on Sep 13, 2017
Transsexuals & Crossdressers

First shot at writing, the following events of this series are a mix of true events and fantasy. Up to you to figure out what is what. I will see what the feedback is like to see when the next chapter will be posted after making the required adjustments. At 23 years of age, I find myself in a position that I never thought I would be in. Living life as a...

Glory Hole

by GateKeeper_A on Jun 11, 2014
Group Sex

Last month, you had discovered that your local adult novelty store had a glory hole. Since that day, that glory hole has been all you can think about. Every time you close your eyes, you picture a cock sliding through a hole towards you. Every time you masturbate, your mind is filled with fantasies of strange men's cocks. You shudder with a mixture of trepid...

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Finally a Princess Pt. 01

by fireandlace0533 on Sep 14, 2020
Transgender & Crossdressers

The first part, of what will be a multi part story, of a crossdresser who loves Disney getting to step out of the closet. I like to develop the characters so if you are hoping to get straight the sex you will likely be disappointed. Finally a Princess (Part 1) You could feel the excitement on the bus as it traveled along the highway. The video showed a bun...

Sarah Meets a Naughty Sex Buddy

by SarahCD on Nov 27, 2018
Transgender & Crossdressers

I first published this story a few years ago. Since then my writing skills have improved a little. While I cannot change what actually happened to me, I have added some more detail and corrected some mistakes. *** I was feeling really horny and wanted some naughty girly playtime. I posted a listing on Craig's List for a "cum buddy". I explained that I am...

Our Conquerors, Our Concubines

by Shendude on Dec 20, 2010
Science Fiction

Millenia ago, an alien race created the Ghirabo, telepathic shapeshifters intended to serve as sexual playthings, able to read their owners' minds and assume a form and personality that will fulfill their owners' desires. But the Ghirabo's Creators were wiped out, leaving them to fend for themselves. In time, the Ghirabo have become a powerful race, creating...

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