Caught Crossdressing Stories

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What Craigslist Got Me!

by SissySlutPrincess on Oct 13, 2017
Transsexuals & Crossdressers

I had been crossdressing and playing by myself for years. A simple fun way to pleasure myself and satisfy my love for all things girly. I just needed more being from a small Ohio town made it tough to actually find someone to share this leisure with. Everyone knew everyone so no one wanted to get caught, but me! I decided to check out Craigslist. I posted a...

Kasey's Legs Ch. 02

by KaseyLegs on Sep 19, 2017
Transsexuals & Crossdressers

My girlfriend Darcy and I were having breakfast and talking about my first experience going down on a man. I had been dressed up in my sexiest girl clothes with my makeup and hair giving me an almost passable look. Darcy had brought me out to a club that hosted a "drag night" and I had been a hit. I kept explaining to men I was straight and I crossdressed f...

Fetishville (Adding Encouraged)

by VioletWinters on Sep 26, 2017
Fetish

Welcome to Fetishville! I am Violet, the mayor here. I know you're eager to start so let's get to it. To begin with your adventure, press the "Start Game" button on the right and find your fetish. It is pretty straight forward. If your fetish involves dominating, select [Dominant]. If it involves being dominated or being submissive, select [Submiss...

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A Crack in Reality

by Mr Nice Guy on Aug 20, 2018
Miscellaneous

Something is wrong. There is a crack in reality! Things are changing! Is it human made? Has it always been there? Is someone controlling it? Is there any way to stop it?!What's next? Average Office Worker Alex William Borgman, Mad Scientist Rachel Davis, College Lesbian Goth Girl Daniel, average thief Jason Willows, struggling middle class family member. M...

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A Day at the Beach

by Danielle987 on Sep 16, 2017
Transsexuals & Crossdressers

Bit of background to understand the context. I am Danielle, I am 18, very petite 5" 8 65kg and have long blonde hair. I have been a crossdresser since I was 12. Australia, it was the middle of summer as I was driving to my friend Kate's house. We had planned to go to the beach as I became more brave in my crossdressing adventures. Kate was the same age as...

Story Tags

by Literotica on Sep 18, 2017
How To

You've written your story, edited it within an inch of its life, and are all ready to show it to the world. You open a submission page and – what's this? Story Tags? What the bleep is a Story Tag? The larger any archive grows, the more important organization becomes. Separating stories into our current categories helps connect readers with stories they'll e...

In from the Rain Pt. 02

by dreadknots on May 21, 2018
Transsexuals & Crossdressers

Well shucks! I got some positive feedback from the first entry, and a couple people were even nice enough to comment asking for another one! Let it be said that I'm not above placating the masses. By which I mean cute crossdressing smut. A little bit shorter than the first one, but I don't really have to introduce the characters too much this time. Don't wor...

Internship

by nimt on Jul 12, 2018
Transsexual

An internship was compulsory as you approach the final year of your high school. The school believes in providing students with the opportunity to gain valuable practical experience by learning from the industry of tomorrow directly. You went for several interviews and only successful candidates get notified. In the events that the none of the companies pick...

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Second life of Emily

by Alexia Wright on Jun 3, 2015
Fetish

I have always wanted to get fucked by another man. Being 5'6" and weighing little over 60 kilos, my effeminite and near hairless body bore no signs of an able bodied alpha male, so i decided to explore my inner girl since my mother and sister are the only people i live with. It started with simple things, like my sister's school clothes, then her under...

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Dutiful Assistant

by Jagvillhem on Sep 28, 2019
Transsexual

((There might be some changes throughout the chapters. This is because I am finding out the way I like to write. I'm learning different styles and quirks. Because of this, chapters might differ in style from time to time. This is definitely a trail and error kind of thing, chapters might have changed once you re-read them, this is because I might have gone b...

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