Crossdresser Caught Stories Stories

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Literotica Monthly Awards 2020: February

by Literotica on Jul 14, 2020
Erotic Couplings

Manu and I would like to thank all the authors who submitted during the month, and all the other months for that matter! We've tallied the reader's votes, and are happy to announce the winners of February's Reader's Choice Awards. First Place ($150 Cash Prize Winner):The Beast by Averagejoe1992Second Place ($100 Cash Prize Winner):Watershed by onehitwandaT...

Crossdresser Evolution Ch. 02

by pantyhigh on Apr 8, 2019
Transgender & Crossdressers

Recap - Crossdresser Evolution - Ch 01 - How I got started crossdressing I was becoming addicted to this new way of masturbating very quickly, though there was still this feeling of shame surrounding it. I made sure I deleted the browsing history and then went to the bathroom to clean up. There I saw myself in these cum soaked pink panties. I could feel som...

Cabin in the Woods

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

Finally, I get to give you another TRUE story after a WAY too long 'dry spell'. This story is completely true (and may be a little boring maybe...would love any feedback). Only the names have been changed to blah blah blah... Anyone who is familiar with my writings knows my stories are true and not made up unless I openly state at the beginning that it's a...

Best Camping Trip Ever Ch. 04

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

*This is a work of fiction. Most of my stories are true, but I do have unrealized fantasies...that I'll try to make reality...hope you enjoy!* *Note-this is part four of my story entitled 'Best camping trip ever for CD'...if you haven't read the first three parts, or at least part two and three, you won't understand what's going on at first. I don't like to...

My Name is Raquel Ch. 01

by Raquels_Panties on Mar 2, 2020
Transgender & Crossdressers

Chapter 1 All characters in this story, involved in sexual situations, are 18 or older and are fictional. ******** My name is Raquel and I'm a crossdresser. I didn't become Raquel until later, but this is where I came from. At this point my interests lied only in panties. I wore them as often as I could get away with, as long as I could change out of the...

Tales From the Netherworlds

by JackOLantern on Jul 20, 2018
Fan Fiction

The Netherworlds. There are a countless number of them in the universe, all with their own societies and customs. Why, nearly anything you could think of could be represented in the form of one of these demonic worlds. A world that has been converted into a gigantic spa resort run by slimes that poison their customers instead of detoxifying them? Why not? A...

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Mia More

by seams_straight2me on Sep 16, 2017
Transsexuals & Crossdressers

It was 5 days after my very close encounter with Mia. I was still on very high spirit after meeting her, and fucking her. I could think of nothing else. We kept in touch via text messages and phone calls. She was "on location" for some photo shoot. One less about fashion and more about horny transsexuals having very sexy fun. She sent me a few pictures of...

My First Crossdresser Pt. 01

by Princess_Rebecca1991 on Nov 26, 2017
Transsexuals & Crossdressers

Tempting, isn't it? Being in a room or just being aware of there are drawers filled with lovely, feminine underwear. The kind of feminine garments you have dreamed of wearing for sometime, your fantasy you've longed to make a reality. How could a pair be noticed missing? There are so many and they wouldn't suspect you, not the straight going masculine male t...

Sarah Had to Give a Blowjob

by SarahCD on Dec 18, 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 details and corrected some grammatical mistakes. ---------------------------- After collage, my girlfriend's best friend, Alison, and I found ourselves working in the same city and...

Last Minute Crossdressed Sex

by Lovinhose on Sep 14, 2017
Transsexuals & Crossdressers

I like to write and share my experiences with the world, and I prefer writing about REAL experiences, thought at some point, as in the past, when I hit a 'dry spell' and have no true story to write, I will write a piece of fantasy fiction. I am happy to say, however, that this story, while nothing special, IS TRUE, and I am happy to share it with you all. Al...