Shemale Escort Stories

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Infinite Scroll

T's First Escort

by HORNYWRITERTS on Sep 26, 2017
Transsexuals & Crossdressers

I'd been waiting for about twenty minutes before the doorbell rang. Earlier that evening I decided I would finally take the plunge. I went online to Craigslist and, under the Casual Encounters Section, I found the list for Men Seeking Transsexuals and another list for Transsexuals Seeking Men. Of course, pretty much all of the ads were for escorts. A few ye...

Mad Dog - No More Heroes Ch. 06

by crimepunk on Jun 15, 2020
Novels and Novellas

6 - The Brigadier: London's commercial property market adheres to a simple rule: what goes round comes round. The market follows a simple, cyclical pattern. First there's a boom, during which companies expand and there's an increased demand for office space. Property companies buy older properties cheap to re-purpose which, inevitably, drives up prices. T...

Bar Hopping

by JJ122964 on Sep 13, 2017
Transsexuals & Crossdressers

Hello readers: I am trying something new. I hope you like it. Please comment or send feedback. ************ I was getting ready to go out for the evening with a few friends, we had planned on drinking and forgetting the day's cares away. I was dressed in jeans and good t-shirt with tennis shoes. I haven't had a good fuck in a while and I had mentioned this...

Not What He Expected

by toriroxyah on Dec 3, 2018
Transgender & Crossdressers

Luke lived in the big city of Toronto and was beginning to get a reputation in the area of being a bit of a womanizer. He would regularly pick up women at bars, fuck them and then never talk to them again. Luke was a good looking fit guy with short blond hair and a large muscular body. Luke also had a reputation of teasing, bullying and humiliating many of t...

Modelling

by HeatherMaureen on Oct 15, 2017
Transsexuals & Crossdressers

Barely legal age I entered the adult store, The clerk checking my ID leered at me, asking if I wanted to buy tokens to go into the peeps at the back. Too nervous to say yes I blushed, pocketed my ID and walked over to the magazine rack. I sidled along the magazine section slowly zeroing in on the CD/ TV/SHEMALE ones hoping no one was watching me. I glanced...

Skype Disaster Pt. 05: A Surprise Meet

by GeorgiaD on Sep 16, 2017
Transsexuals & Crossdressers

Before I continue, can I suggest that if you don't like a story you simply move on to another rather than leave stupid, pointless anonymous comments? I'm not a published author or an experienced one, but all my stories contain elements of truth which is what prompts me to write about them. To the rest of my readers I hope you enjoy my stories because I certa...

A Tranny Whores Tale: Bambi Banga

by KinkStevens on Sep 16, 2017
Transsexuals & Crossdressers

Unlike my other stories, this is not a true story all by itself, but it is a combination of true events put into one tale. Please comment. Kink ***** I sat at work struggling to keep my raging hard on at bay. I woke up horned up enough to fuck a whole in a sponge. My balls ached. I was beaming with animalistic lust. I stumbled through the work day in a se...

Pam's Shemale Experience Ch. 10

by majicman21 on Dec 2, 2019
Transgender & Crossdressers

Pam woke up, and as she remembered what day it was, a smile crept across her lips. Earlier in the week, her owner had decreed that she would not fuck Pam until Wednesday. That had been Sunday night, and now, with Monday and Tuesday past, today would be the first time in a long time she would feel that magnificent cock opening her up. It's been too long.....

Pam's Shemale Experience Ch. 08

by majicman21 on Mar 11, 2019
Transgender & Crossdressers

Content warning: one scene with a golden shower... Pam woke with a start. It took her a few seconds to hear her alarm ringing. Next to her, Tanya was still asleep, and further down on the bed, Alex was as well, her head resting on Tanya's thigh. Pam reached over to the bedside table and quickly turned off the alarm. Neither of the other women stirred....

Pam's Shemale Experience Ch. 11

by majicman21 on Jun 1, 2020
Transgender & Crossdressers

Content warning: one scene with a golden shower. "Ah, what a way to start the day," Tanya sighed, letting her cock slip from Alex's pussy. The shemale had just filled it with a load of cum, dribbles of that gift already leaking out. Pam smiled from next to them, at the possessive yet affectionate way Tanya slapped her cock onto one of Alex's thighs and...