Shemale Fuck Guy Stories

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Infinite Scroll

Pam's Shemale Experience Ch. 05

by majicman21 on Sep 12, 2017
Transsexuals & Crossdressers

"Take it, slut, right down your throat!" "That's right, take it, fuck yes, choke on it!" "Fuck yes, babe, that feels so fucking good!" Pam swooned, kneeling subserviently as her temporary owner took her pleasure. "Fuck, Pam, your throat feels so good!" The lustful shemale was as usual in total control. One hand had a fistful of Pam's hair, while the oth...

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...

My Speciality

by jazz4bj on May 11, 2020
Exhibitionist & Voyeur

I turned 19 and was pretty sure I was hot enough as a female to get hired by the porn industry and continue working till I am considered a milf. Why specifically? I would love to suck the biggest dicks and swallow the entire thick cum loads. My favorite thing in the world and here is how it went.. Pretty, teen sexy and a nice tanned and toned body with perk...

The Sexiest Shemales Ch. 01

by cleanly_shaven on Sep 13, 2017
Transsexuals & Crossdressers

When I wake up in the morning, I wake up next to the sexiest shemale in the world...right after me, of course. I woke up this morning next to Holly, my beautiful shemale girlfriend. She was still sleeping in our big bed. The sun was shining in on our bed with our white sheets and white comforter. She was naked of course, except for a bright pink g-string....

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...

Life for Futa

by GCStarnen on Jul 22, 2018
Fetish

Disclaimer: This story is the story "Living in a Futanari society"/Shemale Worldo but kind of reborn, somethings in the story have been edited here and there and some characters names and traits they have might also change from the original. (Such as the mothers name being changed). Also this story is hugely inspired by Futanari World/Shemale World...

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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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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...

Small Cock Frustration Pt. 03

by jamtby on Oct 8, 2019
Transgender & Crossdressers

Standing admiring my new look and getting to feel more comfortable with myself, the door to the garage opened. Carla called out, "Honey, I am home. Where are you?" Grabbing a towel, I wrapped it around my waist. "I'm in the master bedroom ready to take a shower." Carla entered the room and gave me a peck on the cheek. "How have you been this weekend?" she...