Shemale Fuck Male Stories

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The White Slave

by mspbottom4black on Oct 6, 2020
Interracial Love

Editor's Note: this submission contains raceplay and femdom content. * Not long ago it was a straight and stuffy white male. it was arrogant and self-satisfied with its white male social and economic leverage and advantages. In the rat-race of white society it suppressed its submissive white side. But from time to time it would slip into daydreams of hav...

Trip Of A Lifetime Or Was It?

by submarie on Sep 17, 2017
Loving Wives

They had been together 5 years, most of them happy. Maria was a tall woman, 5'10 without shoes. Brunette hair to her shoulders, dark brown eyes and slim figure. She was rapidly approaching her 35th Birthday, with a failed marriage behind her; she had recently started seeing a man she worked with. Her partner, Glenn who was 45, had also been married and had l...

The Spider's Brothel

by Miles63 on Sep 13, 2017
Erotic Horror

Author's Note: Well, a chapter of a story I have been working on has been deleted as my external hard drive is bust! So I finished this story for the Halloween contest, a late late entry but enjoy. This has since been re-edited on 10/25/2013 as I feel the bad grammar mistakes have effected the rating of this story which is unfortunate as I'm very proud of t...

Abducted... by Aliens

by silent_one__ on Sep 19, 2017
Sci-Fi & Fantasy

Disclaimer: This story contains sexual content between a male and futanari, shemale, etc. Any names referenced in its writing that bear resemblance to actual people is purely coincidental. All characters referenced are 18 years old (or older). Thank You and Enjoy. ***** Abducted ... by Aliens Prologue: Unknown to the people of Earth, alien spaceships ha...

She-Male Chronicles Ch. 2

by Anal Slave on Sep 12, 2017
Loving Wives

Shemale Chronicles Pt. 2 Well here I am again bent over the edge of the bed while my wife fucks me with her strap-on dildo. I am grinding my ass down hard on her big toy and she is fucking me with force. My cock is limp and is swinging around like a big clit but I enjoy getting ass fucked and my wife loves to fuck me with her strap-on sometimes she will s...

Reason? Nah.

by curdles on Nov 8, 2020
Bisexual

"Oh, fuck!" she gasped as soon as my cock had slid out of her throat. She had held it there for almost a full minute, massaging my balls with her tongue all the while. We hadn't seen each other for almost a week, so our appetites rivaled those of Erysichthon of Thessaly. "I'm almost there," I said, stroking my shaft. "Open up,"...

Anal Fuck Toys

by RedragonLite on Jul 12, 2020
Fetish

Join the CHYOA Fan Server and discuss this story and many more with the community: https://discord.gg/DQn3bVH If you want to support me and my work, please check out my Patreon: https://www.patreon.com/redragonlite This is the first and last chapter out of context. Here the premise will be explained, and all characters you may choose from are listed, each...

Shemale Sisters Ch. 01: Creating a Slut

by hfernandez1983 on Sep 13, 2017
Illustrated

*-*-* *-*-* So, I have been away for a while. Things have been really busy lately, but now I finally have some time to start some writing again. I have tried my hand at writing a straight story on forced sex, a couple of lesbian stories and a couple of transsexual stories. I find that I get quite a few hits on the transsexual stories and that I don't ge...

Shemale Stories: A MILF Fucked

by silkstockingslover on Sep 25, 2017
Illustrated

Summary: Lonely MILF walks in on teen girl masturbating and.... Note 1: Thanks to Hernandez for doing the photos for this story as well as the plot bunny that led to the final story. Note 2: This is a 2017 April Fool's Day Contest story so please vote. Note 3: Thanks Tex Beethoven, Robert, goamz, With my daughter Simone away at band camp as a counsello...

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...