Caught Cross Dressing Stories

192,094 results
Orientation
Length
Source
Infinite Scroll

Kayla Caught Me Ch. 01

by lulu_dools on May 1, 2018
Transsexuals & Crossdressers

Hello there. Let me tell you what happens when you get caught... You see I am a cross dresser when I get time and have lots and lots of clothes and lingerie to play with. I keep all my female stuff in the computer room where no one ever gets to go. I am 40 years old with long curly brown hair and brown eyes. I weigh about 80kgs and am 5ft 8inches tall. I l...

Fair Is Fair Ch. 02

by bgdddy_2000 on Sep 18, 2017
Fetish

This is a product of my brain, and nothing else. There is cross dressing, bisexual contact, anal, bondage, swapping and probably some other fetishes in there. If this bothers you, why would you keep reading? ======================== Spanking and bondage came next as a direct consequence of that first night with Sue and John. Nicole and I had been having h...

Something in the Water Ch. 03

by sublocked on Sep 19, 2017
Transsexuals & Crossdressers

Something was irritating me. My feet felt odd, like they were jammed inside too-small shoes, and I couldn't spread my legs out to stretch. I awoke with a start as I realized my panties were acting like a hobble, pulled down as they were, just above my knees. As I rolled over to adjust things, my shoulders felt the bra and I moaned with the sheer ecstasy of i...

Caught by Neighbour

by Borderlands on Sep 13, 2017
Transsexuals & Crossdressers

- 1 - It was a beautiful warm day, and I had it to myself. My wife Sam was interstate on business for the week, and not due back for another five days. For me that meant housework to be done, but plenty of time to enjoy my own space, and entertain one particular hobby. I smiled to myself, and not for the first time, I stopped in front of a mirror and pulled...

MaidSally Episode 02

by cd2the9s on Sep 16, 2017
Transsexuals & Crossdressers

As I explained in my first episode, I am a kept Cross dressing Maid-servant for my Master who I also refer to Mr. G. (or G). My Master provides for me and makes my life comfortable. For this, I provide him with a willing and compliant servant. Master keeps me quite busy with daily chores and things and he uses me as he wishes. Sometimes he lets others use me...

Sarah was Caught Peeping

by SarahCD on Jan 14, 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 details and corrected some...

Made to Obey Ch. 02

by madetoobey on Jun 18, 2019
Transgender & Crossdressers

Reprise: I had been watching shemale porn when alone in my Sister-in-law's house. Tempted into wearing some of her underwear whilst masturbating, my wife (Ruth), sister-in-law (Esther) and their mother (Donna) came home much earlier than expected and caught me in the act. * I scampered up the stairs, still dressed in the suspender-belt, stockings and panti...

A Cross Dressers First Time

by webbyhose on Sep 13, 2017
Transsexuals & Crossdressers

I was in my mid 40's and divorced and living a great life. I ran my own successful from home and lived in a large house in it's own grounds at least 5 miles from my nearest neighbour. Whilst I was single I had an active sex life having been lucky enough to know 3 ladies who were unattached and had no need for a long term relationships but were happy to meet...

Dream Prom Date

by Zelonkarac on Sep 26, 2017
Science Fiction

It is that time of year again, Prom season. But this year is different, this is the Senior prom that will change everything. Sadly the only thing missing for someone is the actual prom date. Who is the protagonist or victim? (Dear reader, as you read this story please remember that if you like any of the chapters that you read please take a second to click &...

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High Heels and Stockings Tryout Ch. 02

by neon_noodle on Sep 11, 2017
Transsexuals & Crossdressers

Chapter 2: Bi-sexual Sluts in Stilettos Author's Note: Thanks to all who read and enjoyed my first story. I hope you like this one too, and get so excited by it you have to jerk off and blow a big, wet load. Enjoy! * After my first semen-splattering cross-dressing experience, I was hooked on dressing up like a slut, and masturbating in stockings and high...