Sissy Squats Name Stories

165,583 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Sammi Starts Camming

by Sissy_Sammi_ on Dec 3, 2017
Transsexuals & Crossdressers

Sam had always been rather small and feminine. As a guy puberty seemed to have missed him which left him in the rather uncomfortable position of being very girly. He was only about 5'8" with a womanly rounded face, smaller waist, and slightly larger hips. He had brunette hair, which for a guy was on the longer end. His lightly tanned white skin pieced with...

Always Read Before You Sign Ch. 02

by Reaver90 on Apr 6, 2020
Transgender & Crossdressers

Sam stood outside Miss Turner's front door. The weekend was hell was for him. He couldn't sleep, he had to sit down on the toilet and pee like a girl and more importantly, he couldn't jack off. The young man feared what the beautiful woman but deadly woman had in store for him. He took a heavy breath and knocked on the door. He waited for a few seconds as t...

Sissy boy shock

on Apr 29, 2025

Story about sissy crossdressing and other good stuff. Milo was a small guy he stood 5foot 7 inches tall, he was always bullied for his feminine physique growing up. No matter what excerise he tried weight lifting, martial arts or sport he failed to gain any muscle mass. Except in one place he always had a perfectly shaped ass. He never did squats or even leg...

Open in Reader

Sammi Gets Adventurous

by Sissy_Sammi_ on Dec 3, 2017
Transsexuals & Crossdressers

Sammi has been doing cam shows and posting photos online for a few months now. She's gotten into a steady rhythm with it, and loving every second of it. She has never felt so alive as when she's fully dressed up and putting on a show for some perverts online. And the money that she brings in from her shows certainly doesn't hurt either. Over the time she's...

Special Times

by devoutmalesub on Sep 13, 2017
BDSM

Thankfully it was summer again. I have the summers off and my wife a very flexible schedule. She brings home a good portion of the dough. But, like I said, I'm glad it's summer. Now we can spend some time together. Because during the rest of the year I have many papers to grade and classes to plan. Now it is summer and when my wife is not here I clean for...

Re-tooled

by Sissyhalo on Mar 13, 2018
Transsexuals & Crossdressers

Re-tool your life. Re-tool yourself. Sick of not getting what you should? Sick to fucking hell of all these assholes getting with hot people they really don't deserve? Sick to hell of Liberals and Feminists making impossible to jump through hoops so that only the privileged people get to be happy? Sick of being a goddamned incel? Look we all know that...

A Week End with Mistress Pt. 02

by gasissynora on Oct 30, 2018
Transgender & Crossdressers

Dear readers this is my first story and I hope you enjoy it. Your comments and suggests will be most helpful. I am planning on continuing the story if the feedback is positive. This story is based in part on facts and part on fiction. I will leave it to the reader to decide which is which. ***** I arrive at Mistress Nikki''s a couple of minutes before 2:0...

Sissy Sauna

by Queen_Diana on Nov 16, 2020
Transsexual

Tommy fidgets a bit as he passes through the automated doors and into the air conditioned gym. People mill about, ranging from those who have clearly been in the gym for months on end, and those that have clearly just started. Tommy was in the middle. Anxiety and fear well up inside of him for a split second, his field of vision narrowing down into a thin fi...

Open in Reader

Sissy, Hypnotized

by Slipperylock on Apr 8, 2019
Transgender & Crossdressers

It had taken six months to get to this point. As I stepped out of the bathroom, I caught sight of myself in the full-length mirror, and shivered. I was shaved below the eyebrows, hairless and smooth, except for a cute landing strip above my locked chastity cage. Other than the cage, I looked like a thoroughly average 21 year old boy, my small and skinny fram...

End Scene

by felicia_rene on Sep 28, 2020
Transgender & Crossdressers

This is fiction so literary license allows for the omission of condoms, but our reality doesn't. Enjoy Description: When a rich wife discovers that her husband married her for her money and to add insult he turned out to be gay. ROLL CAMERA My rich wife had me over a barrel after finding out about my affair with my handsome boy toy assistant. She took a...