Shemale Fucks Boy Stories

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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...

Sex therapist

by qaz on Sep 1, 2016
Miscellaneous

Who do we follow?What's next? A boy A girl What's next? A boy A girl...

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Dick World

by darkness_drearing on Dec 25, 2019
Bisexual

For contributors As was stated at the top: while there were will be two general threads to go off of (for a guy and girl), feel free to create your own characters or scenarios. The only shared premise among them needs to be that they find themselves, however you decide that happens, in this universe and, as The Eagles would say, "You can check out any t...

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Shemale Fun

by orangemaestro on Sep 26, 2017
Transsexual

You are a good-looking man in your mid-twenties. You are 5'10, 170 lbs., and in good shape, with some muscle definition. You have always considered yourself a man's man, but lately you have developed a curiosity about women with...something more. When you fantasize, you sometimes find yourself imagining a cock between the girl's legs. Pretty soon, that's the...

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Shemale Tales: The Christmas Party

by silkstockingslover on Sep 2, 2017
Illustrated

Summary: Young woman discovers the perfect man... a woman with a dick. Note 1: This is a Christmas 2016 Contest Story so please vote. Note 2: Thanks to TexBeethoven, Robert, Dave, and Wayne for editing. Shemale Tales: The Christmas Party I'd been working at the firm for only a couple of weeks and originally wasn't planning on attending the staff Christ...

Sex Toys and Websites

by Equinella on Sep 14, 2017
Fetish

I didn't tell my girlfriend that I was moving out; just packed my stuff and disappeared while she was at work. There was no need to say anything. After weeks of sleeping on the couch she wasn't going to miss me. My new apartment was furnished so the move mostly involved traipsing boxes up the stairs and finding the right shelf, cupboard or drawer for their...

Alpha Gamma's Secret Ch. 2

by Wannabe Chick on Sep 11, 2017
Transsexuals & Crossdressers

-4- Molly awoke to the annoying sound of her alarm beeping. Groggily, she reached over to her night table and turned it off. It was 7:00 AM, way too early for a 19-year-old college girl to be awake, in her opinion. As she stirred, her girlfriend wiggled up against her, eager for body heat. Molly smiled and looked over at Gina – her girlfriend, lesbian lover...

Making More Dreams Come True

by Writer345 on Apr 4, 2018
Transsexuals & Crossdressers

Just a couple of points, this story is written in British-English so the spelling and grammar may well differ from that of the particular dialect in which you were educated. It is also FICTION: anonymous please take note! The events depicted in this story take place in the months following the end of Making Dreams Come True and so may possibly make more se...

SheMale Sirens Ch. 04

by WhiskeyIsGood on Sep 25, 2017
Transsexuals & Crossdressers

I never thought I would wind up in what many would have thought was just some fantasy world. I would have considered myself one of those people who thought it was just someone's fantasy. I happened to stumble upon Anthemusa by total accident, which I would later learn was really how the majority of the men on the Island came across it. I had been heading t...

Introducing Virginia Holton

by JonathanStone on Sep 16, 2017
Transsexuals & Crossdressers

A warm spring south Florida sun poured through the darkened windows of Marla Holton's corner office, brightening the firm surface of the sky blue carpet and even revealing "fribbles," her description of the tiny bits of whatever that a good vacuuming by the cleaning crew would clear away tonight. Marla Holton had a PowerPoint slide presentation that she need...