Cross Dressing Stories

72,522 results
Orientation
Length
Source
Infinite Scroll

The New Teacher in Town Ch. 01

by lankancd on Sep 14, 2017
Transsexuals & Crossdressers

This is my first ever story submission so it's bound to have a lot of mistakes. But I welcome constructive criticism. I've been reading literotica for nearly 10 years now and I thought of giving life to my fantasies by making them stories here so that other like minded readers can hopefully read and indulge in them with me. This is a fantasy I've had for qu...

Magic Dress - Angela Pt. 02

by SlightlyRude on Feb 11, 2019
Transgender & Crossdressers

I had discovered that I liked dressing up as a woman in my time away from work. I wasn't gay and I didn't get excited by women's clothes, I just liked dressing up as a woman. Pretty clothes, not like my business suits. My dear wife Iris saw how relaxed it made me, so supported me. And in fact she decided to make me better at it. "The aim is to pass as a wom...

A Natural Sissy Ch. 05

by harv069 on Sep 15, 2017
Transsexuals & Crossdressers

Author's note: This is a story about a woman turning a man into a compliant, sissified plaything. If that idea doesn't appeal to you, don't read the story. If you like the idea, read on, and don't forget to vote and leave a comment. More will be added if comments from readers justify it. Ch. 05 Stacy's Interlude "Hi, guys. I'm Stacy, and I guess you know...

Sissy Finds a Friend

by Quietoldie on Apr 10, 2019
Transgender & Crossdressers

Andrew likes to wear women's clothes in the privacy of his home. He finds he's more comfortable dressed as a woman, and wearing frilly clothes makes his cock stiffen up nicely. He's been married to Wendy for ten years now. She discovered his fetish by accident six months ago and has come to accept his need to cross dress. When she returned home early one da...

Hot Encounters

by biggshow13 on Sep 16, 2017
Transsexuals & Crossdressers

I joined one of those swinger sites, just out of curiosity. I learned three things right off the bat. The first thing I learned is that there is a lot more men than women on those things. The second, most of the women are so swamped with responses, that they almost never respond back unless you can really catch their eye. The final thing I learned is, most o...

Hot Sex Instead of Dancing Ch. 15

by SusanJillParker on Sep 12, 2017
Interracial Love

Please give me the support of your vote. * With both sharing the same sexual fantasy, Tiffany wants to have sex with a cross dressing man dressed as a woman and Walter wants to have sex with a woman while dressed as Wendy. Give her sex? He couldn't believe what he was hearing coming out of Tiffany's mouth. As if she was his puppet and he was her marionett...

Fun With Friends Ch. 04

by HighHeeledHoney on Sep 14, 2017
Transsexuals & Crossdressers

After being used by Becca and Greg, Davina experiences a new type of pleasure. I hope you are enjoyings my experiences and fantasies.... Big thanks again to kjplotts for the help with presenting my story. As I stepped into the shower the warm water hit my body and felt great. I relaxed my ass and let Greg's cum stream down my leg. I could not believe t...

A cross dressing get together

by MrSwift on Feb 10, 2020
Transgender & Crossdressers

Just a couple of points to start with. I called it a get together because the alternatives didn't seem right. A cross dressing orgy seemed fun but too excessive. A cross dressing party was also wrong, carrying for me a sense of enforced gaiety and fun, which again was inappropriate. I settled for a get together. That would allow people to behave as they wa...

My Favorite Glove Saleslady

by Classygloves on Sep 16, 2017
Fetish

Ever since my mother bought me my very own pair of black ladies' kid gloves after she had caught me wearing her kid gloves to pleasure myself with, I have developed a very strong affection for the ladies who work at the "Ladies Glove Counters" in the better department stores. Now I know that I am dating myself, but I go back to a time when every woman had sc...

My New Look

by saracas on May 27, 2018
Transsexual

I was always a skinny slender young boy but I always liked the look of other skinny young slender boys, so I actually loved the way my body looked, so skinny and with the sexy look of a female, I would fuck my own butt with my fingers or my mothers dildos that I found in her "special drawer" ... As I became 18 I started dressing in my sisters panti...

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