Dominant Shemale Fucks Guy Stories

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Infinite Scroll

A Shemale Shock: A MILF Falls

by silkstockingslover on Sep 25, 2017
Illustrated

Summary: Mom catches her daughter with a teenage shemale and.... Note 1: This is a Nude Day 2017 Contest Story so please vote. Note 2: Thanks to Tex Beethoven, Robert, and David for editing this story. I was having a bad day. I'd spilt coffee on myself on the drive to work. I'd gotten a rip in my nylons. And I'd forgotten my notes for tonight's intervi...

My Transformation into a Shemale Ch. 02

by jamtby on May 29, 2018
Transsexuals & Crossdressers

"We have a party tomorrow night and you are the guest of honor. My friends and guests will find you to be very attractive. You will need to make a few changes but I am the one driving them. Kyle will be my assistant and your trainer. "First, what do you know about shemale?" That question stopped me. I muttered nothing as I started to move my hands to cover...

The Devil's Harem Outfit

by Miles63 on Sep 18, 2017
Transsexuals & Crossdressers

Author's Note: Hey guys, when I was finishing my last story I found a file with this story half finished and I thought, what the hell lets finish it. Now this is a very very dark story with strong erotic horror themes that some may not find pleasing. There is some strong incest thrown in too. If you are not into that this may not be the story for you. Other...

A Girl with Something Extra

by TonyXxx on Jul 30, 2019
Transgender & Crossdressers

I found her online. She was exactly what I was in the mood for. A girl with something extra. After trading pics, a little email flirting, she invited me over. I tucked my hardon back in my pants and drove over, just hoping she was as hot as her photos. Yet when she opened her door, she looked even better... A beautiful woman with a great figure, a pretty...

HypnoSissy: Educated to be Pegged

by silkstockingslover on Aug 13, 2019
Fetish

Summary: Cock sucker's training is advanced to hypno videos on anal sex. WARNING PLEASE READ: -This is a hypnosis story with potentially influential subliminal messages within it. -The story also contains hypnosis video scenes. -So if you begin behaving differently after reading this story and all your friends start pointing fingers, don't come crying to...

Pam's Shemale Experience Ch. 07

by majicman21 on Aug 20, 2018
Transsexuals & Crossdressers

Author's Note: While this is quite obviously a continuation of Pam's Shemale Experience, it also follows 'Pam's Gangbang Experience' from the Group Sex category, 'Pam's Lesbian Experience' from the Lesbian Sex category, and 'Pam's Threesome Experience' from the Loving Wives category. Reading those three stories might not be necessary to enjoy this one, but i...

Fuck a shemale

by joachim on Dec 14, 2005
Fetish

Congratulations! You've been selected by AR Industries to take part in their AR Sex Suite Programs. Based on the responses you gave on our survey, we've determined that you have an interest in screwing chicks with dicks. Before we begin, we'll just need to figure out what exactly you're looking for: your partner's race, breast size, penis size, and outfit th...

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Ex-Cellmate Looks Him Up

by SugarandSalt on Sep 11, 2017
Transsexuals & Crossdressers

Everything was going to be perfect. Nathan hummed an upbeat tune to himself as he set the table. His girlfriend would arrive for their dinner in any time now. Nathan checked the food simmering on the stove for the second time in as many minutes. He heard a knock at the door. "Be there in a minute," Nathan called out from the kitchen. He quickly ran a comb...

Hell of a ride

by Nqjim on Jul 18, 2018
Transsexual

(Would you like a German translation? I can make one as German. ) Hello. This story started as roleplay between me and a very sweet and sexy Girl from Kent. (If you read this. I hope it goes on for a very long time. Every word from you is pure sexy gold). I will write this story out of our two perspectives. so you can play the "innocent" Hitch-hiki...

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Shemale Devil in Disguise Pt. 03

by Chomedey on Mar 2, 2020
Transgender & Crossdressers

This story is the continuation of Shemale devil in disguise, part 02 Mid-July 2018: About two months have passed since I went back to my parents for work and almost a month since me and Joel decided to do some investigation about Rebecca. Okay, I'll admit, we didn't find too much. We both added her on Facebook but she never accepted the friend request. We d...