Crossdresser Caught Stories Stories

187,637 results
Orientation
Length
Source
Infinite Scroll

Dreams

by DrLuverotica on Sep 25, 2017
Transsexuals & Crossdressers

"Hey! Hey! Wake up, wake up!" "What? Jo, what is it? What's going on?" "I think you should be telling me that!" "I don't understand." I was slowly coming round now, But I was still mystified as to why my wife had woken me at 2 a.m on a Saturday morning. "Erm your cock is as hard as nails and you were waving your ass in the air," Jo said, starting to laug...

Mistress Kira's Delights of a Crossdresser

by MistressKira on Feb 13, 2018
Transsexuals & Crossdressers

Intro Steven moaned again as he shifted forwards to steady himself on his hands and knees. Sweat stuck strands of his dark almost jet black hair to his face. His startling green eyes where closed in pleasure. Behind him Kira thrust into him. Her double d cup breasts pressed against his back each time she thrust the 8 inch strap on into his puckered openin...

From a Husband to a Dutiful Sissy Ch. 07

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Seven will also advance the time of my story here a bit. To move my story along into a lifestyle changing story I will have this chapter set seven months after Phil was outed as crossdressing sissy named Chantel. Over the last seven months, life for Chantel has become entrenched as a sissy maid and slut. The sex video productions put up online have...

Sarah Visited an Adult Book Store

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

Since I've been reading the stories here, I've learnt a new acronym, ABS, Adult Book Store. Reading these stories has made me very curious to experience a glory hole myself. At a gay beach I had sucked off a complete stranger but an ABS sounded even more fun. I picked out the sleaziest, run down store I could find around here. I've bought books there befor...

Rest Stop Romance Ch. 01: Pilot

by Dark_Rose90 on Sep 15, 2017
Transsexuals & Crossdressers

~The following is entirely fictional and just a fantasy of mine. Any likeness to actual persons or events is unintentional and coincidental. Also, this is just a Pilot. If the story gets enough positive feedback, I'll continue it on a regular basis.~ My name is Rosalie or just Rose for short. At least it is when I'm dressed up like a 20 year old college gi...

My Journey to Heaven

by Corina84 on Sep 14, 2017
Transsexuals & Crossdressers

How did I end up here? I couldn't believe what just happened! I was in a daze from what I just did. I was neither sickened or disgusted by it, I was just surprised that I had come so far. Here I was, on my knees with cum drizzling down my face. Something that I have fantasized about for years, but was never able to gather enough bravery to step out and try...

Being a T-Girl Pt. 01

by johntamilandrea on Sep 13, 2017
Transsexuals & Crossdressers

PREFACE: Hi! My name is Andrea. I am a male to female crossdresser. I am very old to literotica but I am new to writing stories. This is my first one. This is a fictional fantasy story. This is a long story for easy reading I have divided it into different parts. IF YOU DON'T LIKE TRANSFORMATION STORIES OR YOU ARE NOT 18 YEARS OLD DON'T READ THIS...! ALL TH...

Sex Ed

by britneyfan on Sep 13, 2017
Transsexuals & Crossdressers

My husband and I had quite an open marriage. We were both fairly sexually adventurous and this was reflected in how we both considered it to be ok for us to be going out and sleeping around provided we were completely honest about it and came home and told the other one all about it. In fact, after a while, we found that this recounting of our bedroom exploi...

Michele Nylons' True Stories Ch. 03

by MicheleNylons on Jul 14, 2020
Transgender & Crossdressers

This is a continuation of my True Stories series, where I tell my readers about my real life adventures. In the next two instalments I will tell you about some of my encounters that were not particularly satisfactory. As most closet Transvestites will know, there are a lot of losers out there and some of them can even be a little scary. * Story One - The R...

Sarah Meets a Friend

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

I posted a listing on Craig's List for a "cum buddy". I explained that I am a crossdresser and that I wanted to find a regular sex buddy. No commitment, just sex. I love to get on my knees to give a blow job. I had several replies. One was local and sounded promising. I don't rush into meeting with a total stranger. First I always exchange a few emails and m...