Sissy Gym Stories

34,000 results
Orientation
Length
Source
Infinite Scroll

Discovering Amber Ch. 09

by Ms_Allison on May 6, 2019
Transgender & Crossdressers

Mistress Notes: My intentions with amber were simple at first, but became more complex over time. Our roles seemed to continuously evolve with her becoming more and more submissive and femme and my becoming more Dominant. After a year I really couldn't see her as anything but amber, even when we went to her company's holiday party (which she wore a suit and...

The New Swim Team Pt. 06-07

by Doubleganger on Sep 19, 2017
Exhibitionist & Voyeur

Disclaimer: I began writing this seven part saga in late 2015. As the old saying goes; all good things come to an end. Here are parts 6 and 7. I hope you enjoy reading them, as I did writing this chronicle. All are over 18 years of age. This story is completely fictional. None of the characters portrayed are real, also none of these sexual encounters ever...

Trixie's Chastity 01

by trixie47cd on Sep 19, 2017
Transsexuals & Crossdressers

Part 2: Trixie learns his new role. Since my wife came home early and caught me masturbating in women's frilly lace 2 month ago, so much has changed. She has taken control of my life since I begged her not to spread the story and pictures of my humiliation around town. After I made the choice of submitting to her feminization training, there really was no...

Steve's Maid

by Mixedwritings1993 on Sep 13, 2017
Fetish

Steve always had a thing for maids. He doesn't know what actually turns him on, their uniform or really the person inside the dress, but when there is a maid around; Steve can never keep his eyes away from her. Back at states when he was with his parents, he had an older lady as their house maid around her late thirties. Steve can't even count the number of...

Sissy's First Gangbang

by TaykenByDaddy on Sep 12, 2017
Transsexuals & Crossdressers

I had been seeing Daddy Larry for over a year at this point. He was the third cock I ever sucked and the one to claim my sissy virginity by being the first to fuck my ass. He was exactly my type; early 50s, stocky hairy build with a small gut and over seven thick inches of manmeat that wanted nothing more than a younger guy to drain his load. The more femini...

Little Larry Ch. 01

by pantywriter on Sep 14, 2017
Transsexuals & Crossdressers

Larry walked tiredly through the gym, his bag slung over his shoulder. He didn't really study the members as he passed. Everyone there had their own reasons for being there. And because it was a high-profile corporate gym, the disparity of people there always intrigued him. There were elderly men and women still holding onto the last vestiges of physical h...

The Clothes Shop... Pt. 01

by Manndee on Apr 10, 2018
Transsexuals & Crossdressers

I looked at my watch, "Fuck it...nearly six, ...I bet they will be closed!" I parked the car and walked towards the shop. It was raining, it was cold, a typical January Saturday. "Bradley will fucking kill me if I forget my suit!" I smiled to myself. "The man's a dick for getting married anyway!" I walked towards the door, 'Fuck, is it open?' The lights we...

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...

Cheap Sissy Whore To Call Girl

by HardSoft on Sep 15, 2017
Transsexuals & Crossdressers

I looked at the throbbing red cock within inches of my face, split seconds before I was to be showered with thick musty spunk on the back alley streets while I thought back to what had happened 24 hours ago when I was a normal 22 year old male living a normal heterosexual life. It all started when my girl friend of the time, Doreen, had filmed us having sex...

Man Disciplines Sissy Ch. 03

by LanaBehave on Aug 20, 2018
Transsexuals & Crossdressers

I watched Daddy walk to the door of the hotel suite, and I watched him open the door, and then I watched him step into the hallway. He was gone. The door closed behind him. I stood there, in my dress. In my heels and wig. I felt a shiver run through me, and I thought about Daddy, and what had just happened. I went to long mirror on the bedroom door, and I...