Shemale Fucks Guy 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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A Son's Virginity: A Christmas Tale

by silkstockingslover on Dec 11, 2018
Illustrated

Summary: A mom gives her son the best Christmas present ever. Note 1: This is a 2018 Holiday Season Contest story so please vote. Note 2: Thanks to Tex Beethoven, Wayne and Robert for editing this story. 2018 had been a tough year for our family. First, a small fire in our house led to our losing almost all our family photos, among other less significa...

Brazilian Shemale

by Thorsten007 on Dec 30, 2017
Transsexual

Rules: Needs to be a brazilian shemale with big tits, a fat cock and a nice round bubble butt! Feel free to continue and create new storylines.What's next? James Kingston Pablo What's next? James Kingston Pablo...

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The Neighbour Who Had It All

by TheTitLover on Sep 25, 2017
Transsexuals & Crossdressers

Not my usual fare, if I have enough stories to be considered usual. Shemale, transsexual, chick with a dick, whatever you want to call it, it's here, so fair warning. I'd also consider it a bit of a romance story, though not a straightforward one. There's also some master/slave, not very much, it's more a hint of where their relationship will probably go i...

Blossoming Shemale Ch. 03

by TheTitLover on Sep 25, 2017
Transsexuals & Crossdressers

This is inspired by tawnysuede's Reluctant Shemale: http://www.literotica.com/s/reluctant-shemale If you enjoyed it, I hope you'll enjoy this series. A note on political correctness: I have come to learn just a tiny bit about the transgender community, and by that I mean that I've learned that words such as shemale, transsexual and dickgirl are offensive...

Kinky Bride Confessions Ch. 11

by yano on Sep 16, 2017
Interracial Love

So my girlfriend Emma had just been married in her first porno wedding for the Kinky Brides Group and now ends her story with a shocking honeymoon. "Returning to the altar we found the bed covered in a white satin sheet and climbed on to it. We were to begin in the traditional position, my legs wide apart as I watched Jay straddle me and then point ten inc...

Heather in Leather

by Inktligent on Sep 14, 2017
Fetish

Dan walked into his video rental store and headed to the back section. As he moved past the curtain, he saw a good looking woman was also looking for some porn. It wasn't very often that he saw females in here, and he felt slightly uncomfortable. Starting on the opposite end of the XXX video shelves, Dan sifted through the hundreds of titles. He looked for...

Shrunken at home with Futanari Sisters

by starwarsalpha1 on Jan 22, 2021
Transsexual

With the blessing of Mr.z I am transferring his story "Shrunken at home with Shemale Sisters" to this site. First thing you may have noticed is I changed the name slightly. I just like Futanari better than Shemale personally. If you know the original then you know the ages where lower then what this site allows, so I've gone to the liberty of uppin...

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Shemale im Urlaub

by HansmAyer on Jul 28, 2019
Transsexual

Als Hans sich entscheidet alleine in den den Urlaub zufahren, fällt seine Wahl auf Amsterdam. Er hat sich im voraus erkundigt und sich besonders über das Nachtleben und den Rotlichtbezirk informiert. Hans hat schon länger Fantasien mit Transen und ist gespannt was der Urlaub mit sich bringt. In Amsterdam angekommen verbringt er den Tag als klassischer Touris...

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Birth of a New Sissy Ch. 01

by AltErik on Sep 18, 2017
Transsexuals & Crossdressers

Usual disclaimers, though if you are already browsing stories on this site, you must have an idea what you're getting into by now. ;-) This story contains male to male sex, Crossdressing and Dominant/Submissive themes, so if this is a problem . . . wave off! This story is fictional story based on a fantasy of mine. While it is fiction, I did use myself an...