Shemale Stories

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Orientation
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Infinite Scroll

The House of Lesslie Ch. 02

by gothicboibitch on Sep 19, 2017
Fetish

I. I woke up. Even after having taken over the House of Lesslie weeks ago, each morning was still the same, and came with the same feeling of disorientation, in need of a few moments to adjust to the realities around me, as new as they were. The bedroom around me was still darkened by heavy, burgundy curtains that allowed only a sliver of the early morni...

Pirate on the High Seas

by spitzharder on Sep 26, 2017
Transsexuals & Crossdressers

The westerly winds had been blowing steadily for the last three days as the old barque stood out to round the headland, the casual eye would not notice her stained sails were in fact quite new and only the briefest glimpse of copper showed that she had been careened recently. Salt stained timbers gave the ship a tired and dilapidated air, though the crew jum...

The Wonderful Adventures of Miss K Ch. 2

by BrettLynn on Sep 13, 2017
Transsexuals & Crossdressers

Welcome to the next installment of my wonderful adventures. I hope you enjoy reading this one as much as I enjoy writing it. I reserve all non- electronic and commercial rights to this work. If it is illegal in your jurisdiction to read this work, please do not read this story. * * * * * Miss K brushed a strain of hair out of her face as she backed her SUV...

The Office Receptionist

by cowboy109 on Sep 12, 2017
Erotic Couplings

I’m the first to admit that I don’t have much luck with the ladies. They keep their distance and turn serious around me. I guess I lack that physical hotness or pompous confidence. My job has a lot of serious and uncool people who never ventured to the gym or read a GQ article about men shaving their legs. There are also very few women. The once that are the...

A New Life

by JKBigDaddy on Sep 13, 2017
Transsexuals & Crossdressers

Bennie, age 21, lived on his own for the first time in his life. It was his first night in his new apartment. He had lived with his parents, Joanna and Chris Smart until just today. This was the start of a new life in many ways for him. Bennie, or Ben as most people called him, worked as a telecommunications tech for a local phone service. It was his first...

A Strange Romance

by toniukcd on Sep 16, 2017
Transsexuals & Crossdressers

Although I was over qualified after I graduated and accepted a one as an Internet operations officer for one of the high street retailers. I was offered better jobs but I took the one with the retailers because it paid reasonably well and more importantly meant that I would have to relocate down to the East Midlands. Ever since my parents decided when I was...

Jess

by DaniW on Jun 11, 2019
Transgender & Crossdressers

I first met JD in the 6th grade at Westminster Middle school. We had several classes together and after being paired up repeatedly for science projects and other activities, we became good friends. Our days at school often extended to doing stuff together after school and on the weekends and eventually even the occasional vacation together. JD and I became i...

Wife's Friend with Benefits Ch. 04

by DarkBreezly on Apr 9, 2019
Loving Wives

Authors Note 1: I apologize for leaving this series for so long. A few of you have poked me over the months, so here it is finally. I have been working on a more visual/illustrated story line and that takes a great deal more time and effort to develop, so I wanted to get back to more story based lit. Please let me know in comment or message if you would like...

Afro Stress Relief Ch. 09

by llts1970 on Feb 3, 2020
Transgender & Crossdressers

After a hectic and traumatic weekend, it was Monday again, I was still in a state of shock after what had happened. I spent most of the day at my desk doing very little, and wondering if any of the loading bay crew had seen the photos of me kissing Drake's ass, but I thought they wouldn't recognize me, as I was fully made-up as a sissy in the picture, but I...

Wannabe Cuckold Gets Found Out

by tombrennen on Jan 20, 2020
Fetish

A little about myself before I start the story. A trim 35 year old man that would probably be diagnosed as a sex and porn addict. As long as I can remember, I've been extremely sexual. Starring at cleavage and tight pants, led to porn mags and the occasional video, led to the internet. Once the internet exploded, so did my sexual fantasies. Shemale porn, and...