Sissy Gym Stories

34,000 results
Orientation
Length
Source
Infinite Scroll

A Sissy is Born Ch. 02

by 0ra11yfix8ed on Sep 13, 2017
Transsexuals & Crossdressers

Authors Note: This is, after all, Chapter Two. Reading the first chapter might enhance your enjoyment of this offering. As is often the case when I try to write a story the characters seem to move in a direction entirely different from my original outline. I hope you like where they want to go! * You turned and started back to your car so abruptly that I...

Sexual Sixpack

by SciGuy on Sep 16, 2017
Transsexuals & Crossdressers

The average person, applying contemporary community standards, would find that this work, taken as a whole, appeals to prurient interest only, and is utterly without redeeming social value. And that's what makes it fun. ***** 1.Realization So. Last night you got gang banged. Damn! It was your choice, no one slipped you any drugs, you weren't drunk. Well,...

Haven the Sissy Slut Ch. 01

by CSK on Sep 11, 2017
Transsexuals & Crossdressers

He was sitting on his couch, naked, remote in his hand watching the pre-game show for the 12:15 start time for the football game. It was the first of three blocks of games for the day. I was on my knees in front of him, dressed like a slutty maid or something with white thigh highs that were topped with little white bows, an extremely short black, frilly ski...

Quarantine Slave Ch. 01

by grizzley123 on Jun 9, 2020
Fetish

I was lonely. Only 4 days into the quarantine I was assigned to after testing positive for COVID-19. I was barely ill, but I didn't want to infect the world, and the world certainly didn't want me to share. I was supposed to stay out of the world and already I was going nuts. I was also horny as all hell. And then I got a text. Need Anything? I didn't kn...

Brick

by coldsteel on Sep 12, 2017
Erotic Couplings

Tuesday morning, Operating Room 9. The red-grey tumor stubbornly clung to the sides of the pelvis. For three hours, the two surgeons worked to coax it out. "I've got the view," said Brick. "Two Kelly clamps, scissors and a stick-tie." The instruments danced in her fingers. In seconds, the tumor was out and Brick was throwing one-handed knots deep inside...

The Whore Wife, Sissy CD Husband

by MILF4black on Jul 27, 2020
Transgender & Crossdressers

This story is completely fictional. All characters in the story are over eighteen. Prologue: The Whore wife, Sissy CD Husband "That's it, you little sissy whore, suck that cock." Jennifer told her husband as his head bobbed up and down on the strap on dildo Jennifer was wearing. Her husband, Patrick, lifted his head and the seven inch fake penis slid out...

You're Like a Little Boy at Times Ch. 03

by Myneed on Aug 30, 2017
Fetish

This is a slight twisted femdom love story that will make most sense if the chapters are read in order. The characters don't seem to want to engage in safe sex, but in the real world we should. Enjoy. All characters are over 18. ***** My heart ached for Mel. It had been another long week another long week of edging and chastity at Mel's instruction. Th...

The Awakening of a Sissy Pt. 07

by sissyjolie4u on Mar 9, 2020
Transgender & Crossdressers

I was a giddy as a school girl knowing that I would be sleeping with Tim, Curiosity was building inside me. I was going to sleep with a man for the very first time. What was the special surprise that Tim had planned for me. All night long, as we watched sissy porn, Mistress kept harassing my pussy with various levels of my trainer. I was happily enjoying us...

The Virus Lock Down

by puzziboi on Apr 14, 2020
Transgender & Crossdressers

"Okay, Lionel, have your bags packed on Saturday morning," the younger brother reminded his sibling. "I will, Blaine! What time will you be here? I'll be there around ten in the morning." "Do you want me and Freeland to ride together or do one of us need to ride with you?" "You tell me what you want. Just think about it and let me know." "Okay. And you h...

Mrs C

by pantywriter on Sep 11, 2017
Mature

This is a lengthy story covering many different subjects. Be warned that some fetish concepts are explored. ***** When Mr. Caruso next door unexpectedly passed away, I attended the funeral along with my parents. I think that the entire neighborhood turned out. The Carusos were popular, friendly people and his sudden passing shook everyone. It happened in...