Sissy Gym Stories

34,000 results
Orientation
Length
Source
Infinite Scroll

A Tale of Two Sissies Ch. 01

by SatinSlip on Mar 26, 2019
Transgender & Crossdressers

Author's Note- this story is a work of fiction. All the characters are eighteen or older unless noted otherwise. This story contains scenes of non-consensual sex, incest, interracial sex, gay sex, forced feminization, abuse, and rough sex. I hope you enjoy reading it as much as I enjoyed writing it. - ***** SMACK! My cheek stings from the big black te...

Sissy College Ch. 02

by MasterJW on Sep 11, 2017
Transsexuals & Crossdressers

All Characters 18+. Sorry for the delay. Life gets in the way sometimes. This is a sissy/interracial themed story - if these themes offend you, or you are unable to separate fantasy from reality, please read no further. Special thanks to Puzziboi for all her input. I love hearing about the mess you make in your panties, so please do leave feedback. ~~~~~ L...

Feminizing First Step Ch. 05

by antares34 on Mar 30, 2020
Transgender & Crossdressers

This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. All characters are age 19+. Chapter 5 Today began like any other. I awoke in my bed with my wireless earbuds still in my ears. The sissy hypnosis audio track was gently playing...

Submitting to Dominance Ch. 01

by _pdy_ on Sep 28, 2020
Transgender & Crossdressers

Warning: this chapter does not include explicit sex. That will come in later chapters. Instead this first chapter is meant to chronicle the beginning of Perry's descent to submission. It's meant as a setup chapter and will lay the ground work for what is to be a story of how she is taken from unsuspecting young man to insatiable crossdressing, sissy slut. Ho...

The Cuckold's Babysitter

by yumacd on Sep 26, 2017
Loving Wives

Hi, I haven't written in a while. The set-up for the sex is probably too long. I'm thinking of continuing the story. Hope you enjoy it. YumaCD === My wife, Tami, has been cucking me for a couple of years now. Most of you Literotica readers have heard the story before... - It started when I revealed my fantasy of watching her with another man one night...

Another Tasty Creampie

by Skymaker on Sep 13, 2017
Transsexuals & Crossdressers

It was 7:30 in the morning as I stepped off the treadmill. A light sweat shimmered on my fair, smooth skin. I walked into the middle of our gym room and started doing my post-workout stretches. My body ached a bit after my morning run, but it was a good feeling. Every curve felt warm, glowing, supple and sexy. I bent over at the waist to touch my toes. My b...

Set Up Ch. 01

by Sissy_Ashlee on Sep 15, 2017
Transsexuals & Crossdressers

This is my first attempt into writing an erotica story. This tale will contain themes of female domination, crossdressing, and eventually MM sex. If any of this is not you thing, please scroll on. Otherwise, please let me know how I did. ***** Since I was a teenager, I had been bicurious. Not really interested in men, but what is between their legs. My obs...

Miss Guided Pt. 03

by MissMarianne on Apr 9, 2019
Transgender & Crossdressers

That evening I went to dinner at Donna's house. Donna opened the door and was beautiful in her little black dress. She wore impeccable makeup, stiletto heels, black nylons. I felt like a frump in my plain outfit. She explained that her husband Mary Lou just got home from work and was upstairs changing. We talked and drank daiquiris for about a half hour...

Teased, Denied and Sissified Ch. 02

by subbieman on Sep 12, 2017
BDSM

I woke the next morning to a kiss on the cheek, "Hey sweetie, I'm heading into work early. I left a little note for you on your dresser. See you tonight at the mall." Opening my eyes I watched Ashley walk out of the bedroom and leave for work. I wiped the sleep out of my eyes and realized I was still wearing her panties. Did last night really happen? I rol...

A Sissy Saga Ch. 08

by Snurge on Sep 15, 2017
Novels and Novellas

In the gymnasium a practise was in progress. "One, and two, and three and four," Hardwick's voice brayed above the tinny jink, jink, jink of an elderly piano. Ten students arranged in a double row of five were dancing to the beat as he called it. It was part of Hardwick's routine. Groups of them came to him daily, either for dance, deportment or gymnastics...