Shemale Fucking Guy Stories

242,521 results
Orientation
Length
Source
Infinite Scroll

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...

Sissy/Cock Sucker Dictionary

by silkstockingslover on Jun 12, 2019
Reviews & Essays

Summary: A list of terms to aid in understanding the activities and nature of sissies and cock suckers. Note 1: The author's source material isn't Webster's Dictionary or anything similar, but is drawn from many years of interest in matters sexual and countless conversations, both spoken and online, with other perverts. Note 2: Thanks to Tex Beethoven and...

Shemale Utopia

by Lewd_Ruby on Jun 15, 2016
Transsexual

*De-De-De-De-Deep* *De-De-De-De-Deep* *Click* I gently pressed the large red button atop my alarm clock to stop the annoying racket of those high pitched beeps. Sitting up I began to take a look around at my surroundings, Beige wallpaper spread across the walls, the odd video game poster stuck on lazily with some blu-tack. Letting out a small sigh I swung my...

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Craving Shemale Cock Ch. 01

by jeritza on Oct 22, 2019
Transgender & Crossdressers

I stood nervously on the dark cobblestone alley street, in front of the unmarked door, running through the possibilities in my head, speaking under my breath. I was thinking of all the events that led me to this moment - the perverted path I had gone down. This is it. This is finally happening. No turning back now. Dear god, no turning back now. *** I was...

Poke-Futa

by Sex-Shooter on Dec 6, 2020
Fan Fiction

A light came upon a mysterious figure, feminine with a bulge between the legs, and the figure waved. Then she spoke cheerfully: Hello there, [Redacted]! My name is Professor [Redacted] and welcome to the [Redacted] region! Before we start, let me tell you about the world. Our world is filled with Pokemon, special creatures that resemble us in terms of body s...

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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...

Erin and the Shemale

by kimberlykitten on Sep 25, 2017
Transsexuals & Crossdressers

Erin was up bright and early on Friday, getting a good hour jog into her schedule. She didn't have to be in class until two hours from now. As she was jogging, earlier male joggers had passed her by with their eyes directly on her bouncing melons. Even wearing two sports bras and two regular bras weren't enough to hold Erin's gargantuan jugs down. Erin did...

Por que

by Ssrd33 on Apr 22, 2019
Transsexual

We're all super, for some reason my mouth felt tired and had a taste, my ass hurt, the other night we were having a great time on a record. It's the only thing I remembered from the other night. Suddenly the teacher said that a new student was going to enter. We were excited by a new student, fresh meat. The teacher said that his name was Melany, for some re...

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Pegged for Love

by silkstockingslover on Jan 31, 2018
Fetish

Summary: Straight guy is pegged by the girl of his dreams. This is a 2018 Valentine's Day story so please vote. Thanks to Tex Beethoven, thor_ph, Robert, and Wayne for editing. Pegged for Love It is probably the truest saying in the world: you can't just be friends with a girl of the opposite sex. I mean it may be possible when you're an adult or marri...

Mistress M Pt. 03

by humblersub on Mar 2, 2020
BDSM

He was once again in her bed between her legs. He had lost track of her orgasms at about twelve. She was way past that now. He had also lost track of time. He never tired of making her cum. And she never tired of him being between her legs. She had given him increasing license to do what he wanted with his tongue and fingers when he was between her legs. He...