Sissy Gym Stories

34,000 results
Orientation
Length
Source
Infinite Scroll

Becoming a Sissy Cuckold Ch. 01

by Pantieslave on Mar 27, 2019
Fetish

Beth and Dan were married very young, just 20 years old each. As such both were virgins when they married. Beth wasn't an outstanding beauty but very attractive with a nice body and very nice breasts, 36D. Dan, on the other hand, was rather feminine looking and wore his hair long, in a ponytail. Being slightly built, on more than one occasion he was mistaken...

My Bestfriend's Girlfriend

by Shauna_Wood on Jul 9, 2019
Transgender & Crossdressers

When I was in my early 20's I used to play a lot of online video games. First person shooters, mostly. The Battlefield series, especially. I had started playing games online with a guy named Chris who had gone to high school with my ex-fiancé. He and I had met through her and had really hit it off. We had remained close even after she and I split. He lived u...

Handyman Pt. 04

by lovedart54321 on Sep 28, 2020
Transgender & Crossdressers

I started my new job and was forced to focus my attention on learning a new field, with a strong understanding of chemicals, working around food, thorough site inspections, paperwork, etc. As much as I wanted to focus on Tony, Gina, our home, and the new living arrangements, I also didn't want to mess this up. I knew Tony had put a good word in for me, and I...

Transforming Brent Pt. 04

by sissymissyct on Dec 2, 2019
Fetish

In the morning I showered and dressed casually as directed by Mistress Wendy. My new black skinny jeans and a plain blouse with light day make up and my cork wedges. Some jewelry and my handbag and I was ready. Mistress wore leggings and a tunic top with her long hair tied up in a bun. Wearing flats, she was still much taller than me. We had a light breakfa...

Introspection Ch. 02

by edibles123 on Sep 16, 2017
Fetish

Chapter 02: The Party We dock at the chalet and Maddy informs me a couple of her friends have already arrived. She attaches a lease to my collar and sternly looks on my eyes. "For the next three days, you are my slave, Jackie, and you will follow my instructions to the letter. I will absolutely not stand for disobedience or poor behavior." I was truly sc...

Young Sissy Ch. 03

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

"Pleez...por favor...pretty pleez...fuck me..." I looked up at her with tears in my eyes, pleading to be penetrated. I didn't have to beg...nothing in the world would have stopped Lola from spraying her seed deep inside my ass...but I know it's what they wanted to hear. I regretted it immediately...well almost immediately...nothing can take away from the pur...

The Birthday Party

by today_i_am26 on Jul 27, 2020
BDSM

Chapter 1 - The Negotiation We sat, the four of us, in a coffee shop on the high street. To the causal onlooker, we probably looked like university students meeting their parents for a catch up. The reality was something quite different. My Wife, Goddess, Dominant, Keyholder, had answered an online advert on my behalf; a couple looking for a Sissy to att...

A Sissy Surprise

by nancyallen on Sep 16, 2017
Transsexuals & Crossdressers

I got home early from my night out with the girls. Jeff wasn't in the living room watching tv so I figured he was in the bedroom jerking off so he wouldn't have to bother me with a request for sex when I was toasted. I decided to surprise him and slowly made my way up the stairs. I walked into the bedroom and stopped dead in my tracks. My boyfriend was on...

Life With Miss Ida Ch. 02

by Sheermistress on Sep 12, 2017
Transsexuals & Crossdressers

When I woke the next day, Saturday – late as it was due to the long evening earlier – I started playing everything over in my mind again and kept coming up with the same result – there was nothing that suggested to me that Ida would not welcome Georgia into this relationship – she never once turned me off, nor seemed turned off by how I was dressed. She didn...

A Sissy Saga Ch. 05

by Snurge on Sep 15, 2017
Novels and Novellas

Miriam opened the door and poked her head through the gap into her daughters bedroom. "Sorry to call on you at such short notice darling, but the water boiler's buggered and I have no other choice but to ask Hardwick to go and have a look at it. I've no idea how long he's going to be, so could you take his first session?" Jennifer roused herself from the bo...