Sissy Gym Stories

34,000 results
Orientation
Length
Source
Infinite Scroll

The Making of Davina Ch. 01

by Timewarp10 on Oct 31, 2018
Transgender & Crossdressers

It was 1966, England had won the World Cup! The swinging sixties were in full swing. David had started working in the sale's office of Telford Safety Engineering Ltd. He held the grand title of Assistant to the Sales Manager, which meant in reality he was the office boy; he ran errands and made the tea. At eighteen, it wasn't his first job. Since leaving sch...

Sarah Worked at a Football Party

by SarahCD on Jan 7, 2019
Transgender & Crossdressers

I first published this experience a few years ago. I prefer to call them 'experiences' since the term 'story' implies fiction to me. My experiences are based upon my real life. Since I started posting my experiences, my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more details and corrected som...

Girlyboy

by Dennis_St_John on Sep 19, 2017
Transsexuals & Crossdressers

Sitting there looking at myself in the mirror while I touched up my makeup, I wondered what I'd become. The reflection gazing back at me with emerald green eyes was that of fresh faced young woman, 22 years old, dark blond, wavy shoulder length hair, a wide mouth with full pouty red lips, a strong chin and high forehead. A very good-looking young female, som...

Caught in a New Life Pt. 01

by Fibaro on Apr 20, 2020
Transgender & Crossdressers

(Hello everyone, this is a story that has been written for a very special reader of mine.) Intro Monroe Smith had everything pretty well figured out for himself. He was 43, his hair was brown and slightly greying, but his hairline hadn't really receded thanks to the hair implants he had done about a year back. He had never been a big guy when it came to mu...

Happy Marriage

by yesplease8 on Sep 25, 2017
Group Sex

Over the years of our marriage, my wife and I have been very open sexually with each other. After 15 years of wedded bliss, my sexy wife and I have come to a mutually satisfying understanding. I am sexually submissive and bi-curious, while my wife is sexually dominant and loves to humiliate me like I so desire. In the last few years, we've really enjoyed mo...

A Weekend Visit to the Office

by Marty Fisher on Jun 4, 2019
Transgender & Crossdressers

I usually work from home as I have a very private place with a wonderful view and Lord knows I've put in more than my fair share of office hours over the years. But I do occasionally elect to make visits to the office both during normal office hours and off-hours to make copies, restock my home supplies and have a cup of coffee with a long-term friend or two...

How Nathan became Natalie Ch. 03

by saintlycd on Dec 31, 2017
Transsexuals & Crossdressers

Friday came and after classes and eating a light meal it was a little after five in the evening when I paid for and checked in the room where I was going to meet Kevin. I gave myself plenty of time to get ready for him. I had decided besides wearing Jennifer's dress I would go even further and try my hand at completely dressing as a girl. I purchased some...

Hour

by DifferentBreed on Mar 18, 2020
Fetish

"I'll be back to pick you up in an hour... have fun!" Charlotte's voice trailed off as her car sped away, leaving Patrick trembling in underground parking garage, the brightly lit entrance to the mall beckoning. He turned slowly, a breeze slipping across his naked thighs. He stepped forward, his sheer pink thigh highs whispering against each other as the wi...

Sissy and Missy

by ChristopherDB on Feb 12, 2019
BDSM

Copyright 2019 Christopher D.B. * The central vacuum system made barely a sound as I made my way through the apartment. It was spacious and occupied the entire third floor. Although fully furnished and containing some of Countess Tori's personal items, she only stayed here a few nights a week. My feet were hurting, as the toe box on my pumps fit a little...

Feminized by My Girlfriend

by Trinni69 on Sep 25, 2017
Transsexuals & Crossdressers

About 6 months ago I joined a gym because I have never had a very masculine body and now that I just turned 21 it was time to finally get off my butt and try to build some muscle. That is where I met my girl friend Brook who stands 5' 9", has a fantastic body and a gorgeous face. She looks like Tia Carrere who was in Wayne's World and True Lies but in my opi...