Mistress Shemale Stories

27,874 results
Orientation
Length
Source
Infinite Scroll

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...

Making Francesca Ch. 03

by Spango on Sep 12, 2017
Transsexuals & Crossdressers

As Frank lay there on the thin mattress, listening to Justin climb the stairs, he thought about all that had happened and what he feared was still to come. The dull ache in his ass told him that Mistress Celia was definitely not someone to trifle with. He also thought about the reaction his penis had shown to the various activities he had endured since arriv...

Making Francesca Ch. 07

by Spango on Sep 16, 2017
Transsexuals & Crossdressers

After the glorious sex with Mistress Celia, Frank spent the rest of that day doing housework with Justin. His mind was all awhirl. To all outside appearances, Mistress Celia seemed to be the beautiful woman he had lusted after when she was a waitress at his favorite bar, but now he knew that underneath her clothes she hid a wonderful piece of man-meat. His n...

My Stepmother's Surprise

by sissybr on Sep 12, 2017
Transsexuals & Crossdressers

This is my first story, so I would appreciate some tips and comments. Please enjoy ^^ * My name is Robert, I'm 18, skinny and not too tall. I've never had much luck with girls, in fact I never dated one and I used to spent my days playing games on my computer and watching porn. Shemale porn. Dominant shemales fucking men. I wish i could be one of those men...

Mistress Jasmine Made Me a Slave

by Gretatv on Sep 18, 2017
Transsexuals & Crossdressers

Since long I haven't written a story so maybe I am a little rusty but I hope you enjoy it anyway. There are some autobiographic parts in it but most is fantasy, which part is real and which is fantasy I leave to you. Like any other author I do love comments too, whether they are good or bad. So please leave some words of praise or critics. Those critics whic...

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...

Mia, Shemale Slave Ch. 01

by spitzharder on Sep 13, 2017
Transsexuals & Crossdressers

It was all due to a gorgeous oriental Shemale dancer, Solange, I'd seen earlier in the evening that I, a 23 year man, was standing in an alley in the rain naked except for black hold up stockings and black lace panties. My cock peeped over the top of the panties, glistening with the rain falling upon it. My thoughts drifted back to the erotic dance Solange...

Luke and Lelia Ch. 04

by Rob Conner on Sep 17, 2017
Loving Wives

Authors note: For a full description of the characters described read "The Peachtree Training Center" written by my alter ego Robyn Conners. It gives all the details and backgrounds. It's posted at other sites. The time frame for this story is three years after the original stories. It was less than a 30-minute drive to the Peachtree Estate. It sat about a...

Making Francesca Ch. 02

by Spango on Sep 12, 2017
Transsexuals & Crossdressers

While slowly beginning to come to, Frank heard low voices somewhere off in the distance, but was unable to make out what was being said. As the grogginess began to wear off, a flood of memories came rushing into his mind; getting drunk at the bar and being caught wearing panties, being Tazed on his front porch, waking up chained to a wall in an S&M dungeon w...