Cross Dressing Stories

72,522 results
Orientation
Length
Source
Infinite Scroll

Planting Trees

by KaseyKlein on Sep 16, 2017
Transsexuals & Crossdressers

Author's introduction. I've not published to Literotia.com for long, with just two stories up. I'm pleased with the views, the hits my work gets. I'd like to see more comments. I've received some nice letters. I've been writing in open forums for about a decade, so I'm used to ignorant comments, somehow the reader mistaking my characters for me. I write s...

Out of the Frying Pan...

by sin2win500 on Sep 16, 2017
Transsexuals & Crossdressers

Its hard for me to describe how it first happened. Sure it would be easy to say that it was a midlife crisis... if I weren't 36. The truth of it all is, I just wanted it. I didn't "have it all" but I did have a pretty damn good life. I'm married, well might be was married soon, with a job as a retail coordinator for one of the nation's most affordable, yet t...

And When I Return Ch. 01

by sublocked on Sep 25, 2017
Transsexuals & Crossdressers

The first of many chapters to come. This may not appeal to many, but I hope that those that like it, like it a lot. Smiles to all those cross dressers, fetishists, and sissies out there. * Jason had been dreaming of this for years, planning it for months, and as he lay in bed, sleepless beside his wife Jenna, he had some last minute pangs of guilt. The tw...

Something in the Water Ch. 02

by sublocked on Sep 19, 2017
Transsexuals & Crossdressers

I couldn't help it; no-one had ever accepted my cross dressing before in my life (not that I had attempted this before with anyone, as I had always been too embarrassed), and I found myself my own worst enemy. I felt ridiculous, not at all the way I had imagined it. The arousal that I had felt only moments before became burdened with the equivalent of anvil...

Trading Spaces

by coxette on Sep 17, 2017
Celebrities & Fan Fiction

"Honey?" "Yes?" "Did you find anything you like yet?" "Yeah, I think so." Courteney emerged from the rack of clothes with two tops in hand. "I can't believe you took me out to shop. We never shop outside of magazines." "I know, but I thought it would be a nice change." David pulled out a very tacky, very bright, very David top and held it up to his wife...

Frustration Pt. 05

by kalkstein1970 on Sep 19, 2017
BDSM

I woke up slumped on the floor, naked, my cock flaccid, the memory of that incredible orgasm still fresh in my mind. You were still there, lounging on a comfortable chair, legs crossed, one stiletto heel dangling, watching me with a mix of amusement and affection. "Good morning, sleeping beauty," you said. I shook my head to clear it, and stood up slowly....

Crossdresser Evolution Ch. 07

by pantyhigh on Dec 9, 2019
Transgender & Crossdressers

Recap - Crossdresser Evolution - Ch 01 - 06 I become addicted to masturbating while wearing panties. There was this part of me that was telling me that I CAN'T like this but there was another part that was saying that I DO like it. I learn about feminized men and I also learn about them sucking cocks and I taste my cum for the first time. I buy my first b...

Sarah Visits a Dominatrix

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

I had read a story about a dominatrix, her dungeon and the naughty things that happened there. I finally plucked up the courage to try out a real one. I went on-line and found a dungeon that looked very promising. The web-site advertised a list of services that they offered. Their services included bondage, spanking, submission, domination, water sports etc....

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...

Blackmailed into Submission Ch. 03

by tzleaze123 on Mar 26, 2019
Transgender & Crossdressers

After last night I am sore as hell. I hope that Mistress Brenda doesn't have some more crazy things planned for me tonight. I don't think I can possibly handle another fucking like last night. Maybe the date that I brought home with me last night will keep her mind off of me for a while. Well my little slut, you do know that's your name right? It doesn't ma...