Caught Crossdressing Stories

164,111 results
Orientation
Length
Source
Infinite Scroll

Caught in the Toilet

by Dennis_St_John on Sep 14, 2017
Transsexuals & Crossdressers

Kneeling on the floor beside the toilet, dressed in lingerie and wearing pink lipstick waiting for the door to open, my mind kept going around in circles to what led me here, wondering if I could have done anything different to prevent it. I remembered sitting on the toilet earlier today looking at my bright pink nylon and white lace panties, resisting the...

A Humiliated Tomboy

by humiliationstation on Feb 19, 2020
Exhibitionist & Voyeur

Alex sat on her bed, playing video games. She was a cute high school senior in a baggy hoodie and basketball shorts, her orange hair cropped at her shoulders. She was sucking at her braces in concentration when she was interrupted by a knock on her bedroom door.What's next? Claire, her bully Her best friends Nate and Jane What's next? Claire, her bully H...

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Bethany's Secret Ch. 3

by Wannabe Chick on Sep 25, 2017
Transsexuals & Crossdressers

-6- February 16th was my birthday and I was eagerly awaiting spending the day (and night) with my girlfriend, Bethany. I had met Bethany six months earlier, when she was just a new student in my high school. I had fallen in love with her at first sight and becoming her boyfriend became my top priority. Not long after, Bethany and I were a couple. We had a g...

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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Anime ENT

by akikuka on May 16, 2019
Exhibitionist & Voyeur

They always confused people around them of their true genders as their appearance and figure contrast their true physical self regardless of their claim. It doesn't help that most of them wear female clothing to further add our confusion(and our sexuality). They are called Traps, or Tomgirls if you will. Having the beauty that brings girls to shame, these tr...

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How Gerry Caught Me Crossdressing!

by CarrieQ on Sep 16, 2017
Transsexuals & Crossdressers

When we're young, we can be extremely naïve! This applies to almost everyone, and it's my only excuse as to how Gerry caught me crossdressing so easily. I had paid for a room in the hostel where he worked as a caretaker, and expected privacy. It simply never occurred to me that he, or anyone else for that matter, would feel at liberty to intrude upon me on t...

Sarah was Trained to be a Girl

by SarahCD on Dec 18, 2018
Transgender & Crossdressers

I love to search on-line for sites related to crossdressing, that's how I found Literotica. I've also found sites for 'Men in Panties', videos of crossdressing, girls clothes for men, etc. One time, I was really lucky, I found a site offering a weekend of 'girly training'. We would be taught how to walk, sit and act like a girl. We would be dressed the whole...

The Slut Couple

by kin1041 on Sep 30, 2019
Swinging

The Slut Couple is inspired by the cover art (made by Chromosomefarm from Hentai Foundry). The idea of a slut couple was interesting and I liked the idea of couples getting into sexy situations but coming out of it still together if not a little twisted at the end. Something like borderline netorare and such. So before we begin; who's the couple?What's next?...

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Life and Time of Lady Vargos Ch. 18

by rik581 on May 21, 2019
Transgender & Crossdressers

Chapter 18 "Changes upon Changes" Martin rolled over on his side hugging his pillow trying desperately to fall asleep. Though the curlers that Leanne had tightly wound in his hair for the night were very uncomfortable and trying to position his head to sleep in them was exhausting, it was the events of the day weighed heavily on his mind and kept him awake...

Soft Sissification

by Lying_Smitten on Feb 21, 2019
Fetish

Welcome to the softest sissy story around, but first you need to choose your character. Would you like to play as the Sissy themself, Mike, soon to be known as Mia, a 5'8 man with dark brown skin and black hair, with equally dark brown eyes, and a slightly soft build? Or would you like to play as the Sissy's sweetheart, Kate? A woman of the height of 5'6, wi...

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