Crossdresser Caught Stories

163,967 results
Orientation
Length
Source
Infinite Scroll

Recruiting of a Sissy Maid Ch. 01

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

[Welcome to my next story. This story has become a little different in how I planned to write it as compared to my previous stories. It has been fully written up already, as of this first uploaded chapter. Doing it this way allows me to better proof read and adjust for future chapters before uploading each. I will submit uploads on a regular basis for my rea...

A Surprise Relationship

by canuckCD on Sep 13, 2017
Transsexuals & Crossdressers

This is a fictional story, although it is based on people I did know. "Tony" and his twin sister "Kim" are based on a set of twins I knew, who were almost identical. I did have a relationship with "Kim" for almost two years, however, the relationship with "Tony" is pure fantasy. WARNING!!! This story starts with a chapter that describes violence against one...

The Agreement Ch. 02

by komrad1156 on Sep 18, 2017
Transsexuals & Crossdressers

Neither Sarah nor I spoke of "The Agreement" the next day. However, the following evening Sarah poured us both a glass of red wine and after a few sips said, "So.... Are we going to discuss this anytime soon?" I could tell by the playful enthusiasm in her voice she was definitely interested in talking and quite possibly following through. "Sure," I said in...

Sissy Walk of Shame

by zona_loser on Mar 12, 2019
Transgender & Crossdressers

First off: This is a story about my alter ego a not so bright crossdresser who likes a bit of exposure. It also contains an element of self-bondage but not in the traditional manner. All characters are over 18 years of age and are purely a figment of my imagination. ***** I am a part time mostly closet crossdresser. I don't consider myself gay or bi and ha...

The Ride of a Lifetime

by CuriousJ95 on Nov 6, 2018
Transgender & Crossdressers

Hi everyone, this is my first attempt at writing. I hope you enjoy and I can't wait to get some feedback from everyone. Please be honest in what you think...I can take it. This is a true fantasy of mine. *** I'm a curious man that is married to a wonderful woman but as time has passed our sex life has diminished quite a bit. We still occasionally enjoy...

My Name is Raquel Ch. 08

by Raquels_Panties on Mar 18, 2020
Transgender & Crossdressers

My name is Raquel and I'm a crossdresser. It was the weekend and Allison, my wife, had plans to sleep in. That meant she would be in bed until noon. Being a morning gal, I arose at my normal 6:00 am. I awoke in an aroused state, as usual. It didn't help matters that my manclitty was encased in a pair of nylon pastel green Warner Lace-top High-cut briefs and...

Maid to Order Ch. 02

by MicheleNylons on Oct 13, 2020
Transgender & Crossdressers

Mick had been shit unlucky. He had driven over sixty miles on the day she bought all of his girly accoutrements. He had even stayed overnight, confident that she wouldn't run into anyone that he knew while he was shopping. But, as has been said, he was shit unlucky. Of all the people in the world who happened to be in the same city, shopping in the same sho...

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...

CD Gets Fucked while House-Sitting

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

This is a true story that happened recently. I also recently submitted a four-part, runaway-imagination complete fiction story, hope you enjoyed. For anyone not familiar with me or my stories, here's a brief background. I'm middle age, white, a little overweight (hidden well with the right garments), and a married bisexual crossdresser who LOVES getting scr...

Neville

by Spankedinaskirt on Jun 1, 2020
Transgender & Crossdressers

Whenever Neville completed an equality questionnaire he ticked heterosexual. That was an aspiration more than a statement of fact since he'd never had a girlfriend and no prospect of getting one. It was also not exactly true. Girls liked him as a friend, they just didn't fancy him. He was called Neville for a start, what the hell were his parents thinking....