Gay Crossdresser Stories

23,018 results
Orientation
Length
Source
Infinite Scroll

In For a Penny...

by TheHellWasIThinking on Sep 15, 2017
Fetish

To the reader: After I'd finished this story, I didn't know where to put it. It contains elements of several Lit categories, and I probably could have put it in any one of them. In the end, I decided to put it in Fetish, although it's very much a Loving Wives tale, as you'll soon see. NOTE: Every word of this is true. (Except for "Every word of this is true...

It All Started... Ch. 01

by trixie38cd on Sep 18, 2017
Transsexuals & Crossdressers

It all started when my sister in-law, Kim, came over after work one day to tell me my wife was just called out of town for her job. I had planned on her being gone, anyway, and so I'd left work early to get my other wardrobe out of the attic, thinking I'd have the place to myself for a few days. I just happened to be wearing a pointy cup black 36D bra, bla...

My First Crossdresser Pt. 01

by Princess_Rebecca1991 on Nov 26, 2017
Transsexuals & Crossdressers

Tempting, isn't it? Being in a room or just being aware of there are drawers filled with lovely, feminine underwear. The kind of feminine garments you have dreamed of wearing for sometime, your fantasy you've longed to make a reality. How could a pair be noticed missing? There are so many and they wouldn't suspect you, not the straight going masculine male t...

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...

From a Husband to a Dutiful Sissy Ch. 02

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Two: My reveal, a true reveal for the sissy in me. I reach to the bottom of the stairs and at the front doorway entrance, Helen and Jenny are standing and looking at me in my black maids dress, white tights, black velvet 5 inch spike heel pumps, wig and makeup. The look on their faces seeing me dressed as such is priceless. This is the first time He...

Life and Time of Lady Vargos Ch. 07

by rik581 on Mar 26, 2019
Transgender & Crossdressers

"The New Bitch of Vargos Manor" Written by: Rikki Lady Vargos begins to exert his new found powers as Lady of the House. He is able to channel many of his frustrations and anger through being tough and almost insulting to those try to accept him as the Baron's wife. As a result, word spreads and Martin is slowly becoming the Bitch of Vargos Manner. "Thank...

Your inner femboy

by SkirtSkirt on Feb 10, 2021
Transsexual

The first thing you have to ask yourself is, who are you Are you an ignorant boy about to be turned into a little cum slut?But then who was there to show you who you really are?Or did you do it to yourself? Or are you already a cum dumpster about to reveal themselves? Or maybe you want to be a slutty crossdresser that's secret gets exposed,one throat fuck at...

Open in Reader

Eric's Dreams Pt. 04

by Genevieve_Ohara on Sep 16, 2017
Transsexuals & Crossdressers

In the months following the Halloween party, Eric got a tremendous twitch in his dick and his ass simultaneously, whenever he thought about the gang bang. He never imagined such intense sexual pleasure could exist. That night, Genevieve had experienced multiple anal orgasms, as man after man rode her hard, and shot hot cum deep into her ass. And the waves of...

Bra Zen

by ValoryG on Jul 10, 2019
Transgender & Crossdressers

Millions of women are familiar with the Bobby Braxton brand of bras (BBBB), one of the brands under the corporate ownership of Simone International. Where Simone's bras from all its lines cover the spectrum from teen training bras to 48DD harnesses, the Bobby Braxton line, Simone's most expensive, specializes in sexy, fancy, often elaborate brassieres rang...

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...