Sissy Gym Stories

34,000 results
Orientation
Length
Source
Infinite Scroll

Eating Cum for Her

by DarlenesToy on Sep 17, 2018
Loving Wives

My wife/Mistress directs me to write these stories for her and then we do them in reality. She always takes parts of my story but changes the reality to suit her needs. This was a story about eating another man's cum. It started innocently enough. You were allowing me to jerk off and lick my precum off your nipples like normal. Then you began whispering as...

OMG My Daddy’s a Sissy (Prequel)

by fittexanman on Aug 22, 2018
Fetish

All characters are purely fictional and of legal age (over 18). * I met Deidre during my first year in college. We were neighbors on the 1st floor of Elliot Dorm. She was an art student, and I was a business major. It didn't take us long to realize that we weren't like the others at this school. As it was located in the Southern part of the country, our co...

Creating Ginger Ch. 04

by Ms_Allison on Jun 8, 2020
Transgender & Crossdressers

Author's note: This is a story of a loving, married couple who wanted to expand their boundaries. It involves crossdressing, gender play and their foray into, cuckoldry, dominance and submission. If these are not topics you are interested in, then please move along. In the below story I refer to the male character several ways but try to maintain a consiste...

Sissy Meets Daddy

by lapitup_ on Jul 2, 2018
Transsexuals & Crossdressers

I never noticed in the moment, but I had been a sissy my whole life. Growing up I was always the shortest boy, always the weakest, I never had a girlfriend, and I wasn't good at any sports. My mom always told me I would grow into a man eventually, but that never happened, even during puberty my growth was minimal. By the time I finished high school I was a...

Sissy Meets Master's Male Fiend

by sissysubTiffany on Apr 23, 2019
Transgender & Crossdressers

This is part 5 of my Master turning me into a sissy and his woman. *** Master Gene has now taught me that when I around him or his friends I will dress and act like a sissy girl thinking of being one for real. He now expects me to arrive at his house as Tiffany. No longer treated like a man I will only go by Tiffany and be his girl. I now spend every weeke...

The Hardest Kind To Be Ch. 01

by Joe Wordsworth on Sep 16, 2017
First Time

In the offhand chance that you don't find the setting clear on the issue, all characters are eighteen and legal. This is also a madly different story genre than I'm used to writing, so be kind. . . .. ... ..... She hated her. Hated... though strong and dramatic, it was the only word that summed up their relationship. Nobody would have guessed it, but i...

Sabbatical or Continuous Gang Bang?

by TonyaTV69 on Sep 12, 2017
Transsexuals & Crossdressers

My twin sister Laura had already left to go back to college this fall season, but I had decided to take off a semester as I was totally burnt out on school and needed a break. We were twins but not identical though we did look a lot alike and roughly the same size me being a few inches taller. My parents were fine with fine me taking a short break but adam...

The Descent

by pantywriter on Sep 28, 2020
Transgender & Crossdressers

It had to be too good to be true, I thought. No woman had ever come on to me like that before. She was pushy and for all intents and purposes, demanded that I escort her to this dinner date in the city. Sure, it was Valentine's Day, and she did admit earlier in the night that being mid-50s and single on this day agitated her; hence, she demanded my presence....

A Wife A Little To Understanding

by felicia_rene on Oct 12, 2020
Transgender & Crossdressers

Present day: We arrived at the 'Sissy Salon' which was a covert sex club for downlow gay wealthy men and lesbians. As his agent and pimp I collected all his performance fees. I walked into the 'Sissy Salon' to make sure that everything was in place so my sissy husband could perform. Then I went to his dressing room to make sure everything I requested for me...

Welcome Home, Ma'am

by Miss_Ds_slave on Sep 12, 2017
BDSM

He had been waiting his whole life to find someone like her. He had almost given up any hope that there was someone out there who could give him what he so needed. He had met a few women over the years that had been willing to try and give him what he desired, but it was usually just something they did for him, not something they enjoyed for their own pleasu...