Shemale Pee Stories

702 results
Orientation
Length
Category
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Infinite Scroll

In Service to my Mistress Ch. 01

by Aprils_slave_marie on Sep 25, 2017
BDSM

This is an absolutely true story taken from my life's journey as a Transsexual slave woman. I've lived full time for over twenty years now. -------------------------------------- As I write this my Mistress is in the bedroom with one of her many Black Bulls. Her screams of lust and orgasm reverberating through the house as he grunts and thrusts himself int...

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...

Ugly Shemale adoption

by reachNWA on Apr 22, 2025

A couple houses down from them lived Neddie, an ugly, fat, looking as midget shemale with an ugly face and terrible personality. She was humiliated because of her disgusting behavior and appearance. She'd been caught peeping and stealing underwear many times. She often got her ass kicked by women who caught her. She was a horny bastard, Neddie knew every sex...

How I Met My Shemale Pt. 04

by Eroticalover1968 on Sep 25, 2017
Group Sex

Ever hear of the expression, 'Led around by the balls'? Well, it brings back visions of an epic fuck up. Whose fault? It hardly matters. Joyce peeled around the corner, cast a delirious water-eyed glance at me. She drove over a curb—our suitcases jostled around like they were fucking. "What the hell just happened? How does Cheryl have a cock? She put it in...

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...

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 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...

Sister's Shemale Friend

by silkstockingslover on Sep 12, 2018
Illustrated

Sister's Shemale Friend Summary: Family seduced and dominated by an irresistible shemale. Note 1: This is a Summer 2018 Contest Story so please vote. Note 2: Thanks to DarkBreezly for creating the pictures in this story. Note 3: Thanks to Tex Beethoven, Robert and Wayne for editing this story. I came home from work a couple hours early, as our manager...

Becoming a Shemale's slave

by toriroxyah on Nov 6, 2018
Fetish

Scott was 6'2", 195 lbs, 30 year old business man who works for a large consulting firm. Scott was out of town on business and was staying at a high end hotel for a few days. It was his first night arriving at the hotel and he decided to stop off at the hotel bar for a drink after the long flight. It was about 3 pm when he paid the bill after three beers a...

"A Shemale Submission": A Lust Story

by silkstockingslover on Dec 23, 2019
Illustrated

"A Shemale Submission": A Lust Story Summary: Author Jasmine falls for a hot new teacher with a big cock. Note: Thanks to hfernandez1983 for the many pictures used in this story. He spent weeks getting these perfect for the many different scenes I requested. If you like the pictures in this story, please feel free to read the multi-chaptered series Cheerle...