Shemale Island Stories

19,185 results
Orientation
Length
Source
Infinite Scroll

Shipwrecked Pt. 03

by JJ122964 on Sep 13, 2017
Transsexuals & Crossdressers

I am Sorry, but I have to break up the forum portion of this story. Otherwise it would be too long. I hope you like the series and please comment. Thanks J. ********** The tasting house. I woke up to the feeling my ass being penetrated by something. I was still on the X and being cleaned again. I saw that my loincloth was on the table and the ooze was on...

Hentai Heaven

by hornyboi666 on Sep 28, 2020
Fantasy

=============================================================================== Important notes: 1- It seems that I am not a good writer. as of now, I wrote 17 chapters about (John - North Korean 21 yrs old boy). I made an effort to make it a story with a sex scene in each chapter and build up a story. If you are in rush or not sure if you will like it or no...

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SheMale Sirens Ch. 03

by WhiskeyIsGood on Sep 25, 2017
Transsexuals & Crossdressers

Chapters 1 and 2 seem to have done great, so here is number 3. This will probably be the last one. In the future though, I plan on doing a longer series based off of this, but it will focus on one main character and him adjusting to life in Anthemusa. I don't intend to start that right away, as I have a few other ideas in mind before the end of the year, but...

Letters from a Stalker

by Cinner on Sep 19, 2017
Transsexuals & Crossdressers

"How long have you been receiving these letters?" Det. Anton Judge asked the distraught woman seated in the visitor chair in his office. "About three months," she replied, clenching her fist and raising it to her mouth. "At first I thought that it was a sick joke from one of my idiot friends to celebrate Halloween, but after the second one I began to have m...

Pam's Shemale Experience Ch. 10

by majicman21 on Dec 2, 2019
Transgender & Crossdressers

Pam woke up, and as she remembered what day it was, a smile crept across her lips. Earlier in the week, her owner had decreed that she would not fuck Pam until Wednesday. That had been Sunday night, and now, with Monday and Tuesday past, today would be the first time in a long time she would feel that magnificent cock opening her up. It's been too long.....

Pam's Shemale Experience Ch. 08

by majicman21 on Mar 11, 2019
Transgender & Crossdressers

Content warning: one scene with a golden shower... Pam woke with a start. It took her a few seconds to hear her alarm ringing. Next to her, Tanya was still asleep, and further down on the bed, Alex was as well, her head resting on Tanya's thigh. Pam reached over to the bedside table and quickly turned off the alarm. Neither of the other women stirred....

The Secret of the Island Pt. 04

by neoview on Oct 30, 2018
Sci-Fi & Fantasy

You thought the story had died but it was just my lazy ass refusing to continue. Also I was busy with my girlfriend so I couldn't really focus. Yes, I have a girlfriend now. Well "she" prefers to be called a girl even if she isn't. Without her I would finish this story much faster, but... she gave me some interesting ideas which were too good to ignore. ***...

Pam's Shemale Experience Ch. 11

by majicman21 on Jun 1, 2020
Transgender & Crossdressers

Content warning: one scene with a golden shower. "Ah, what a way to start the day," Tanya sighed, letting her cock slip from Alex's pussy. The shemale had just filled it with a load of cum, dribbles of that gift already leaking out. Pam smiled from next to them, at the possessive yet affectionate way Tanya slapped her cock onto one of Alex's thighs 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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The Gym Ch. 4

by Kip Carson on Sep 14, 2017
Group Sex

John arrived at Kate's house at 6:50 pm. She answered the door in a very tight fitting short dress. "Damn, you look good" John told her. "Sorry I'm so early, but I was so excited about tonight" he added. "That's fine, I'm always ready early" she said. "And you look pretty damn good, too" she added. She eyed him up and down. He was wearing black dockers, a ni...