Shemale Fuck Guys Stories

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Mommy's Slave

by Futafan567 on Dec 7, 2019
Transsexual

You are Jim. You are 18 years old and live in an average sized home with your mother Jennifer (Jen for short). Being homeschooled for most of your life, you never went outside very often. In fact your only “friends” are the two girls Amy and Mary who live across the street. You are really only friends with them because they live so close but you were never t...

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Hot Massage

by william125 on Sep 26, 2017
Transsexual

It's been a busy day at the spa. You decided to stay on working at the spa in your university town over the summer break rather than move back in with your parents. The spa offered an excellent training program for new starters and you found you were a natural. You quickly went from collecting used towels to massaging regular clients. As you wash the oil fro...

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Romina Ch. 01

by Lubba on Sep 13, 2017
Transsexuals & Crossdressers

I was round at some male friends flat having a few beers after a night out. When none of us got lucky on a night out it became the norm for us to watch one of the many porn videos they had collected over the years. One of the guys had returned recently from Amsterdam and bought a few budget films which had trailers at the beginning of some fetish films. We...

Blossoming Shemale Ch. 02

by TheTitLover on Sep 25, 2017
Transsexuals & Crossdressers

This is inspired by:http://www.literotica.com/s/reluctant-shemale tawnysuede's Reluctant Shemale if you enjoyed it, I hope you'll enjoy this series. * * * My name was James. It was, before everything that happened, anyway. I'd come from pretty good stock, as the snooty, upper class would likely say. I guess I still did, although it would take a DNA test to...

Trip to London Pt. 02

by plez2tease on Sep 17, 2017
Loving Wives

I wake up early Tuesday morning and feel a little excited. Today is the day my husband and his friend have been planning for over a month to make happen. The only part I know about the plan is that I am supposed to dress in what my husband has provided me for the day and that a car would be here at the hotel around 11am to take me to some place. I was told t...

Tits Have Benefits Ch. 10

by hottchic on Sep 18, 2017
Transsexuals & Crossdressers

Did Andrea die in a hate crime, killed by 2 Rapists? If Andrea did die how can she write the story? The answers to these questions and more will now be revealed..... "Unexplained events in our lives have led many of us to the conclusion that there are some events which clearly fall into the realm of what might be called paranormal or supernatural. Many...

The Deviants' Room

by sissyrikki17 on Oct 14, 2017
Transsexuals & Crossdressers

Upstate New York, 2007 - Day 1 They all kept talking—bitching—about "sloppy seconds" but if you're drunk enough, and these guys were drunk most all the time, you don't really care about dipping your wick into a hole filled to overflowing with other guys' junk. You just stick it in, numbly hump for a few minutes, then make your own delirious contribution to...

Shortening His Sentence Ch. 02

by SugarandSalt on Sep 11, 2017
Transsexuals & Crossdressers

I knew when writing the first chapter that I'd get around to writing a follow-up chapter. This one definitely requires another installment sometime as well. I mentioned at the start of the last chapter that there wouldn't be tons of sex from the get-go, the same can't be said for this chapter. ;) * Foster's tongue lapped at Miss Julia's cock head. It'd bee...

Create a Shemale

by wsauthor on Sep 29, 2018
Science Fiction

*Author’s note: This story is Public, if you have an idea, start writing!* Robots, science and chemistry have all advanced further than the public is aware of. Due to patents and trade secrets, nobody knew it was even possible to create a sex bot. They can have gravity defying shapes and sizes. They can even alter their owner with chemical cocktails. Cockbot...

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A Shemale Vacation Ch. 02

by britneyfan on Sep 12, 2017
Transsexuals & Crossdressers

We sat there staring despondently at the ground. We had searched through all our bags and pockets and had nothing like the money we needed to pay for the hot sex sessions we had each enjoyed with the hot, hung Dutch whore. The guy, the pimp, who had previously been all smiles and friendly encouragement, very quickly changed in demeanour when he discovered we...