Femdom Therapist Fucks Sissy Shemale Stories

35,139 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

One of the Girls

by Erotictales4u on Sep 26, 2017
Transsexuals & Crossdressers

All characters in this story are over 21 years old. This is a fictional fantasy that contains elements of both femdom and the transsexual/cross-dressers niche. This is my first attempt at a story so go easy. ***** I couldn't believe my situation. I had signed up for porn, but I had not signed up for this. I was standing naked in the dressing room and the c...

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...

My Wife, My Tormentor

by Sissyjackie2008 on Sep 16, 2017
Transsexuals & Crossdressers

I am excited by the . One of the most humiliating experiences I sufferer was caused by my first wife. I had been a crossdresser since I was little. Actually my mother started me when she dressed me as a girl for Halloween. When at 7 I started to protest, She said she had no daughter and once a year I could let her have fun. I could never refuse her so I re...

Sissy/Cock Sucker Dictionary

by silkstockingslover on Jun 12, 2019
Reviews & Essays

Summary: A list of terms to aid in understanding the activities and nature of sissies and cock suckers. Note 1: The author's source material isn't Webster's Dictionary or anything similar, but is drawn from many years of interest in matters sexual and countless conversations, both spoken and online, with other perverts. Note 2: Thanks to Tex Beethoven and...

Twenty-One More Questions

by silkstockingslover on Jan 1, 2019
Reviews & Essays

Summary: Jasmine responds to the most frequent questions asked by readers. Thanks to: Tex Beethoven, Wayne, and Robert for editing this essay. This isn't really a sequel, although it's a second part, as it addresses questions I didn't answer in 2017's Twenty Questions. 21 More Questions After 2017's 20 Questions, I received many more questions. I have n...

Secret Makes Him a Cuckold Bitch

by Subkoksukr4u on Jul 29, 2019
Fetish

Getting caught doing something kinky or sexual for some people is a turn on, for others it's humiliating. There's lots of different variations. Like when you get caught doing something with another person or get caught doing something by yourself. Anyway way you slice it, getting caught can be embarrassing to some degree. This story is about someone finding...

Mommy's Slave

by Futafan567 on Dec 7, 2019
Transsexual

You are Jim. You are 18 years old and live in an average sized home with your mother Jennifer (Jen for short). Being homeschooled for most of your life, you never went outside very often. In fact your only “friends” are the two girls Amy and Mary who live across the street. You are really only friends with them because they live so close but you were never t...

Open in Reader

One of the Girls Pt. 02

by Erotictales4u on Sep 26, 2017
Transsexuals & Crossdressers

All characters in this story are over 21 years old. This is a fictional fantasy that contains elements of both femdom, maledom and transsexual/cross-dressers niche, it is focused on humiliation. This is the second chapter of One of the Girls. Sorry for the long delay. ***** The studio lights blinded and disorientated me for a few minutes as Lana led me by...

Leap of Life

by Iamherslut on Apr 22, 2025

**_(AUTHOR'S NOTE: This is my first story. I'm writing it as a form of exercise , so I apologize in advance for the amateur style. Please, if you like, or don't like, anything, leave me a comment. I will try to change things, but cannot promise. I'd love to hear what you all think.)- - - - - - _** Richard was balls deep in the bimbo's pussy. They were on a c...

Open in Reader

The Society Ch. 03

by Barno on Sep 13, 2017
Transsexuals & Crossdressers

Heidi's erect penis was sliding in and out more easily now. When she first mounted me being gentle wasn't her first priority. It was my first match and I had almost beaten her according to the wrestling judge. In fact many in the crowd of 60 or so spectators had disagreed and showed it by booing the decision, it had been that close a contest. This didn't sit...