Crossdresser Caught Stories

163,967 results
Orientation
Length
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Infinite Scroll

Miracle Cure

by sharkinlace on Sep 12, 2017
Transsexuals & Crossdressers

I always had trouble with girls. Growing up I was a little bit introverted, which made socializing with people I didn't know a bit of a chore. But I never knew how to act around girls especially. Even when I was able to find the courage to talk to them, most of the time they just wanted to be friends. And the few times I actually went out on dates ended eith...

Secret Journey Ch. 02

by DrGonzo124 on Feb 11, 2019
Transgender & Crossdressers

AN: with profound thanks to Personal Deviant. 8 9 8 Suki dreamed of another time and place. A place filled with warriors drinking... feasting...fucking. Another body? His, yet not his own, to judge by the nipple clamps pinching him with a painfully arousing agony and the odd sensation along the length of his erect shaft that had to be a lattice of pie...

Gender Change: Magic Closet

by Zekar on Jan 26, 2017
Fantasy

There is magic in the world. Narnia was just the tip of the iceberg when it comes to the magic that a wardrobe or closet can do. You find yourself directly in the crosshairs of such a magical encounter. Whether malicious or benevolent, that is up to you... This is merely the introduction to a much more interesting tale. (Dear reader, if you like this story a...

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Sarah was Caught in the Hot Tub

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

I was in our complex hot tub last night. I like to go there late in the evening when it's quiet and families have left. I am a cross-dresser and I love to take the opportunity to wear girls' panties whenever I can. I find it exciting, even if no one is there to see me. Today I wore a girl's yellow string bikini bottom. I could have claimed that it was just r...

A special Christmas

by Chuveiro on Dec 17, 2018
Fetish

It was already December and I was home alone. Mommy had gone shopping all things she would use on Chiristmas dinner, which would be at our house. I went to my room and got my clothes and toys. I was a sissy, but nobody in my family knew that. The only person who lived with me was mom but she was so old she couldn't notice anything. I dressed up and started t...

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An influential Dare

by femboyslut122 on Apr 20, 2015
Fetish

As a college student most of Kyle's time was spent in class or doing work for class. He knew that others found a better balance, or lack thereof, between class work and a social life. Because of this Kyle always looked forward to the last Saturday of each month. He and his friends would get together once a month to catch up and dick around while playing tabl...

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Girlfriend's Suprise ...

by Shelly7 on Feb 6, 2020
Transsexual

My name is Johnny and I am a lonely 18 year old geeky kid, I never had a girlfriend and was always feeling left out, I had a few geeky friends, all of who was also just like me. I have a confession though ... I have always been attracted to penis's, I never liked boys or men per say, just to their parts. There had been many times when my best friend Cho and...

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the corporation

by davidigor on Oct 21, 2014
Transsexual

you arrive to the building, you've been requested to come here to sign a contract for working here the call didn't give you too much information and you can't remember having asked for a job here... but you need the money so you decided to come here the building is a big one in an important neighbourhood... but strangely, the door is in a small alley in a si...

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Sarah has Sex at a Nudist Beach

by SarahCD on Jun 4, 2019
Transgender & Crossdressers

I first published this experience a few years ago. I prefer to call them 'experiences' since the term 'story' implies fiction to me. My experiences are based upon my real life. Since I started posting my experiences, 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...

From a Husband to a Dutiful Sissy Ch. 02

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Two: My reveal, a true reveal for the sissy in me. I reach to the bottom of the stairs and at the front doorway entrance, Helen and Jenny are standing and looking at me in my black maids dress, white tights, black velvet 5 inch spike heel pumps, wig and makeup. The look on their faces seeing me dressed as such is priceless. This is the first time He...