Transvestite Stories

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The Transvestite Stalker

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

The man sat at a corner table in the coffee shop surreptitiously eyeing off the woman sitting on a stool at bar. She was dressed in a navy blue suit; her jacket was open, revealing well-formed breasts swelling her white satin blouse, which opened to the second button so that a hint of lace bra was displayed. Her legs were crossed and her skirt had ridden up...

Sweet Transvestite

by al_Ussa on Sep 16, 2017
Transsexuals & Crossdressers

"I still can't believe you talked me into this," Rob said as he tried to slip the black fishnet stockings over his freshly shaved legs. "I know," his girlfriend called out from the fitting room behind him, "But it was such short notice. And besides, you were the only other guy I could think of who could pull off Dr. Frank N. Furter." "Yeah," he said, "But...

A Transvestite Love

by Martins on Sep 16, 2017
Transsexuals & Crossdressers

"Are you sure you want to go inside?" Heather asked. "Of course. I mean, we've come so far, haven't we?" I said. "But you know what I am." Her eyes seemed sad – her tone emotionless. Just moments earlier we were having dinner and those eyes were bright and the conversation cheerful. It was like we were in another world, but now reality was sinking in. "Lo...

The Transvestite Divorce Transcript

by desireethtttv on Aug 1, 2018
Transsexuals & Crossdressers

We begin with the plaintiff, the woman of the marriage of 33 years, from hereto within known as Mrs. S. Verses the transvestite husband we shall call Desiree. Mrs. S Attorney (referred in future testimony as AFM: Please state your reason for the divorce proceedings, if you please Mrs. S. Mrs. S: I wish to divorce my gay transvestite husband due to the lack...

Halloween Transvestite Stripper

by kristycross on Dec 2, 2019
Transgender & Crossdressers

It was Halloween Night 2018 and of course Kristy was going out to party! A local LGBT Club was having its party and I had the hottest outfit to wear dressed as a Stripper! From the Red Basque, Thong, Garter and Hose to the Black lace-up over the knee Boots and Sheer white Mini-skirt, I was looking as Hot as I felt! The 30 minute drive was un-eventful and t...

A Transvestite Odyssey

by lynntg0444 on Mar 18, 2020
Transgender & Crossdressers

I like playing a girl, but it's complicated. I have always been more attracted to women than men, and had many relationships with women including two marriages. As a young man I had several sexual experiences where I played a feminine role. Wearing girly things was a real turn-on for me, and it seemed to make it less queer for us both. I would later learn th...

The Virgin Tranny & the Bride Ch. 08

by yano on Sep 25, 2017
Transsexuals & Crossdressers

My transvestite friend Roberta writes to tell me that recent surrender of her boy pussy to her Master was, sadly, not for love but as a means of gaining embarrassing video footage to use as sexual blackmail. Master John is now teasing Roberta and she is about to embark on a new career as a call girl and prostitute. She writes: With the lining removed and m...

The Virgin Tranny & the Bride Ch. 03

by yano on Sep 25, 2017
Transsexuals & Crossdressers

My transvestite friend Roberta continues her true tale of transformation and dominance from her bisexual neighbours' as she becomes a form of sex slave both in the privacy of their home and also on the streets. Initially attracted to Margaret and her sexy underwear Roberts' secret was discovered by sex starved Margaret. She dressed in her bridal gown for hi...

Grab Bag Transvestite Story

by MicheleNylons on Sep 16, 2017
Transsexuals & Crossdressers

I am a part time transvestite, who, if I do say so myself, looks quite attractive when dressed as a woman. It has taken me years to become adept at makeup and being capable of selecting sexy clothing that is in my size and that suits me. I have also had a number of lovely encounters with other TVs and male admirers. You can read my True Stories on this site....

The Private Transvestite Detective

by MicheleNylons on Sep 16, 2017
Transsexuals & Crossdressers

The Private Transvestite Detective (Or The Undercover Dick) With apologies to the writers of the various movies from which I borrowed some inspiration (and a few good lines). Chapter One It was late Friday afternoon and I sat behind my desk smoking a cigarette, leaning back in my chair with my high-heels resting on yesterday's newspaper. I contemplated m...