Shemale Top Stories

702 results
Orientation
Length
Category
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Infinite Scroll

Shemale Adventure Ch. 1

by girlboybootsie on Aug 18, 2017
Fetish

You: early 20's, tall boyish good looks with a lean and muscular body. Dressed in tight leather pants, from behind your tight buns are revealed by the shiny black leather, as are your cock and balls from the front. You are wearing black leather boots and a denim shirt that refuses to hide your strong broad shoulders. Me: early 30's, tall, blue eyed, consid...

A Shemale Christmas Carol

by ThomX on Sep 16, 2017
Fetish

I got a job working as a mall Santa at the local mall during the Christmas shopping season one year. It had been a real shitty year for me. My wife of almost twenty years left me for a younger man, I lost my other job due to layoffs and, on top of all that, my doctor diagnosed me with high blood pressure (gee, I wonder why?). So believe me when I say the las...

Shemale Surprise.

by ceb35 on Sep 16, 2017
Sci-Fi & Fantasy

As a single woman I do spend quite a bit of time enjoying porn flicks on my Kindle Fire. But I never imagined that anything I watched would ever happen to me. But it did! My girlfriends and I often go out to one of several bars nearby my home. We go as a group just to hand out and talk and occasionally meet new people. Some are nice and some are just compan...

Shemale Trouble

by Braids on Mar 11, 2007
Fetish

You were at a bar when it happened. You were just having a drink when a hot girl started hitting on you. You had nothing else better to do and you didn’t want to pass up an easy lay so you offered to take her back to your place for a little fun. She agreed without a question, but as you were walking out of the bar, you felt something hit the back of your hea...

Shemale city

by Ben18927e on Jun 17, 2020
Miscellaneous

I wake up to the sound of my alarm on blaring on my phone. After a couple of failed attempts to ignore it i finally get up and switch it off. Now that the alarm is no longer on, i slowly drag myself out of bed and start to get ready for the day. On the way downstairs i grab a towel, heading towards the bathroom. The water quickly comes on and i start to wash...

Shemale Midgets of AHhhhsss

on Apr 22, 2025

Your name is Johnny and you are an 18 year old nerd who experiments with powerful energy Technology , it’s a wonder you haven’t killed yourself yet with all the experiments that’s blown up on you so far. You were trying to teleport by using the greatest minds equation's since Einstein, but then tweaking them in your own way …. Trying and trying to even accid...

Tentacle

by Shemale_Lover69 on Apr 29, 2025

Before we begin, here's a little background info: You come from a distant planet, searching for live victims to lay your eggs in. On your planet, there are only males, so in order to reproduce you need to lay eggs in humanoids. You appear in the shape of a man, which is a trait your race has so you don't stand out on humanoid worlds. Unlike most humanoids, y...

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...

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...