Sissy Gym Stories

34,000 results
Orientation
Length
Source
Infinite Scroll

How Nathan became Natalie Ch. 02

by saintlycd on Nov 26, 2017
Transsexuals & Crossdressers

"Studying hard, sexy." Kevin's deep voice said as he entered our dorm room. I was lying on my bed on my stomach with an open notebook and chemistry text book in front of me. I was wearing what was my now typical "hanging around the dorm room" outfit was; tight short girl's athletic shorts, and a cropped girls tee shirt with our colleges logo and mascot on i...

Throne of Panties Ch. 02

by scur on Sep 16, 2017
Fetish

This story continues where "Throne of Panties" left off. A man made the mistake of allowing a stewardess to see him in panties and stockings and instead of getting a blowjob he was pushed to the ground and now another passenger becomes involved. I think both stories would benefit from being read in order. ***** "Oh really." the other passenger said. "Does...

Making Holly

by Sissyhalo on Sep 19, 2017
Transsexuals & Crossdressers

My name's Jamie and I moved back to my hometown. I had a lot of bad memories here and most of them stemmed from being bullied in high school and a lot of that came from Holt Thompson. A loud mouthed jock in school he was the center of the basketball team and really, really arrogant. I was a geek, a comic kid and dungeons and dragons kid and all that stuf...

Dreams

by DrLuverotica on Sep 25, 2017
Transsexuals & Crossdressers

"Hey! Hey! Wake up, wake up!" "What? Jo, what is it? What's going on?" "I think you should be telling me that!" "I don't understand." I was slowly coming round now, But I was still mystified as to why my wife had woken me at 2 a.m on a Saturday morning. "Erm your cock is as hard as nails and you were waving your ass in the air," Jo said, starting to laug...

The Awakening of a Sissy Pt. 05

by sissyjolie4u on Feb 3, 2020
Transgender & Crossdressers

There I was, on my knees, in very skimpy feminine undergarments, locked in a room in the back of an ABS, with 6 men and my Mistress. This was the start of what was to be the other portion of my punishment. Mistress walked toward me with that evil grin of hers. As she was approaching me, she said, "Jolie, these men are here to assist me with your punishment...

Marcia Goes Back to School

by Belongs2Beth on Sep 12, 2017
Transsexuals & Crossdressers

Authors Note: This story continues the adventures of eighteen year old Marcia (nee Marcus) Cicero. The tale opens a week after the events related in "Carol's Gifts". Marcia has shown visible signs of blossoming in the wake of Mistress Carol's injection of powerful hormones and is anticipating returning to her school for the first time as a girl. To answer an...

Close Shave

by Tomsparty on Sep 13, 2017
Transsexuals & Crossdressers

My sister, Sharon caught me naked, shaving my legs in the family bathroom. 'I thought you where in Court all afternoon.' I cried dropping the razor in surprise. My sister dressed in her smart black skirt, white blouse and black fitted jacket raised an arched eyebrow patronisingly. 'Obviously so, brother dear but my case finished early. I wasn't required f...

A Day at the Fetish Flea

by Tinababy on Jun 11, 2019
Transgender & Crossdressers

I first met Jack at the bar. It was a little uncomfortable for me talking to people there, because not only was it was a drag bar, I was drinking alone and I dreading that I might run into someone who might recognize me. I had been to the Fetish Flea that afternoon, gawking at the outlandish gear. Many booths lined the hall, and hundreds of freaky people st...

Euphoria Resort

by sissyashley4bbc on May 4, 2020
Transgender & Crossdressers

"Welcome to Euphoria!" a good looking black man said as he greeted my wife, Jess, and I. I couldn't help but notice two scantily clad maids getting our bags for us. "Come right thus way to check-in with your specialist," he directed us. We clutched each others hands and hurried in, we were giddy to get started. Euphoria was no ordinary resort, it was cou...

Stroke Slut: Goddess' Cuckold

by StrokeSlut on Oct 19, 2020
BDSM

"Well don't just stand there drooling on the doormat, come on in." The black hood had come off Stroke-Slut's head, the sudden burst of sunlight that hit his eyes was nothing compared to the radiant beauty that stood before him. Despite hours of jacking off to her on the internet, not the mention their previous sessions, he never seized to be amazed at the si...