Transvestite Stories

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Orientation
Length
Source
Infinite Scroll

The Flaming Girls Ch. 01

by MicheleNylons on Mar 2, 2020
Transgender & Crossdressers

Chapter One - Better off Dead Charlie Ringwald put a Consulate menthol cigarette between her lipsticked lips and lit up, drawing the smoke deep into her lungs. The smoke gave a false illusion of warmth on the bitter foggy night. She put her cigarettes back into the cheap handbag hanging from her shoulder by the thin vinyl strap and wrapped her arms around h...

Miss Guided Pt. 02

by MissMarianne on Mar 26, 2019
Transgender & Crossdressers

I arrived at Dr. Bill's office and he greeted me and we sat chit-chatting together for about ten minutes. Then, Charles and Emily arrived. Dr. Bill addressed us all. "I have read Dr. Price's diagnosis and report and I concur with her findings and recommendations. It's probably best that Dr. Price tell us about them herself. Dr. Em began saying, "Well, f...

Teach Me Trans-Mistress Ch. 02

by JoannePare on Sep 12, 2017
BDSM

Chapter 2 I Prepare All week long I thought about Ryan and what a thrill it would be to dominate and transform him into my maid, I had to control myself and not masturbate as I wanted to be full for him. On the Wednesday evening I took out all my domination instruments and the female clothing I had aside for my slave. Carefully I inspected everything and m...

Maid of Honour

by TVJoanna on Sep 16, 2017
Transsexuals & Crossdressers

As a transvestite, it had always been my dream to be a bridesmaid. My elder sister had known about my love of feminine things since we were tiny; indeed it could have been her love of dressing me up as a girl when we were children that influenced me in the direction of transvestism. So you can imagine how delighted I was when she told me that she was getting...

An Interlude, Bailey on the Prowl

by Sissy_Chantel on Nov 26, 2017
Transsexuals & Crossdressers

A little quickie story published between my continuing chapters of Recruiting a Sissy Maid... I hope you all enjoy it and find it, well hot... Characters in it will be new. All names and persons here are fictitious and any resemblance to real persons is coincidence. **************** As I sit here at my bedroom's makeup table, freshly showered, shaved, swee...

Desiree and Big John

by desireethtttv on Sep 12, 2017
Transsexuals & Crossdressers

It had been only a week since I'd introduced "Desiree, the Hot to Trot Transvestite" to my girlfriend Suzie, leaving me not a bit surprised that she chose not to spend the very next weekend at my place. While she hadn't freaked out, she was concerned I was gay since I was so convincing but I assured her I was not. I planned on revealing the truth I'd been wi...

Hostess with the Mostest Ch. 10

by MicheleNylons on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Ten -- The Hostess With The Mostest "I don't care if there's a fucking flying saucer from Mars down there; I just want some sleep," Candi replied and Millie giggled as the Skyliner made its approach into Changi airport, Singapore. The flight deck crew and the first class hostesses were rushed through customs and immigration and bussed away to a fiv...

Stockings & Stalkings Pt. 01

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Giselle applied the clear topcoat to her ruby-red lipstick; she pursed her lips as she looked at her reflection in the mirror. "There; finally finished," she smiled to herself. It had taken Giselle nearly one hour to transform from 'Gary', her male alter-ego, into Giselle, the hot transvestite staring back at her from the mirror. She smiled to herself as s...

A Midnight Swim

by desireethtttv on Sep 16, 2017
Transsexuals & Crossdressers

Relaxing by the apartment's pool one Sunday, I relived the previous evenings midnight swim in nothing more than my long baby blue Eva Picone silk gown. The water had felt so good flowing between the silk and my nude body and the walk back to the apartment even better as I had a raging hard on from the clinging sensation of the silk over my drenched body. I...

The Cause

by desireethtttv on Sep 16, 2017
Transsexuals & Crossdressers

Often I've wondered why the only thought to stir my sissy cock, some 40 years into life, is the vision of a hard, throbbing, blue veined cock arched just before my eager lips. Was it the spiked heels I pranced around the house in younger years or perhaps the love for the pale yellow slip I stole from my sister and wore secretly under my jeans and shirt while...