Crossdresser Caught Stories

163,967 results
Orientation
Length
Source
Infinite Scroll

A Great Day Off Work

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

Days off are great. Any day off is a great day. You can catch up on things, relax, take care of business, chill out, and just have a good time. Days off also open the door to many opportunities and possibilities. This day would prove to be a very good day. My wife was working this day, and I had taken the day of from work, just because. I stayed home and d...

My Name is Raquel Ch. 03

by Raquels_Panties on Mar 2, 2020
Transgender & Crossdressers

My name is Raquel and I'm a crossdresser. I started out as a thirty-something guy with a fetish for masturbating with and in panties. I was caught and eventually transformed into a girl, Raquel, by my 18-year old stepdaughter, Jessica. Jessica unlocked my inner desires and expanded my horizons. I was now into fully dressing in all varieties of lingerie. And...

Crossdressing, Piss and Sex

by Lovinhose on Apr 14, 2020
Transgender & Crossdressers

This is a work of fiction, a fantasy that I would love to come true. It also contains 'pissing' (aka 'watersports'), crossdressing, and a crossdressers sex with men, so if you are not into these subjects, this story might not be for you, you have been warned. Also, comments are welcome, but please note, I'm NOT a professional writer, if I was, I wouldn't be...

Sissy in The Hart of the Valley

by EvelynT on Sep 16, 2017
Transsexuals & Crossdressers

The story so far; having completed the first date with Harold Plumrose and with over a month until the scheduled second date Sissy Betty Blane spends time at a t-girl club with Cindy. ***** When I got home from the Hollywood Hills I barely had the strength to remove my makeup. I was so exhausted I just wanted to flop on the bed and pass out, but I persever...

Thief Fantasy

by sissyboy26 on Apr 15, 2020
Transgender & Crossdressers

I'm a closet crossdresser. I like to go to thief stores and try on skirts, dresses, shorts and cute tops. I have a recurring fantasy about being caught trying on clothes by a man. In my fantasy, I imagine going into my favorite store. I started looking at all of the women's clothes. From a distance a man catches me looking around. For awhile, he just stays...

From a Husband to a Dutiful Sissy Ch. 08

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Readers, I so hope you are enjoying my story here. It sort of allows me to live vicariously through my words as Chantel. This story has been outlined to allow me to write it in an encompassing and linear way. I try not to wing it but to paint a story that is life-like without being boring, well at least I hope it's not. I hope my characters are believable an...

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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From Dom To Sub

by ScarlettCD on Sep 14, 2017
Transsexuals & Crossdressers

Twenty minutes to go. A few days ago I had posted an ad online looking for someone to come to my place so that I could, to quote my ad, "get treated like a tranny slut by a true Dom of a man." I kept the ad low-key and photo-less to ensure none of my colleagues from work saw it of course, but more importantly, I was a Domme in my own spare time and did not w...

The Devil You Know Ch. 01

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

Brian Davies sat on the hard toilet seat in a cubicle of the men's room on the twelfth floor of the building housing the large publishing company he worked for; he was reading the Daily Mail and trying to kill the last half hour before quitting time. As a middle-management employee he didn't really work mandated hours; he was expected to work whatever hours...

We Meet At Last

by funferet on Sep 16, 2017
Transsexuals & Crossdressers

I had been waiting for some time to meet a cross dresser I had encounters on the net. Our frequent chats online invariably ended with us being unable to co-ordinate our free time and ended in frustration at our failure to meet and satisfy our cravings. Eventually a time and date were set and I spent the intervening time in eager anticipation of our meeting....