Sissy Gym Stories

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Gym Submission Ch. 04

by AltErik on Sep 16, 2017
Transsexuals & Crossdressers

************ Usual disclaimers, though if you are already browsing stories on this site, you must have an idea what you're getting into by now. ;-) This story contains Male/Male sex, Male/Female sex and Dominant/Submissive themes, so if this is a problem . . . wave off! This story is fictional story based on a fantasy of mine. I hope you enjoy it and fee...

The Awakening of a Sissy Pt. 03

by sissyjolie4u on Jan 20, 2020
Transgender & Crossdressers

As i was watching the video of Mistress and I for the 3rd or 4th time, my phone rang. "Hello my sweet Joey, how are you doing? I so enjoyed spending our time together, I'm so proud of you and the progress you are making. Are you still in your pink bra and pantie? That is such a sexy look for you, it makes you look so soft and feminine. Tomorrow we will build...

A Spring Cleaning Ch. 03

by 2decadeslocked on Jun 5, 2018
BDSM

Chapter 3 -- The Workout He didn't mind getting up at 4:30. He was up at 4:30 am every day but Sunday when he was allowed to sleep in until 6:00. Throughout the week, he was up to get to the gym, finish his workout and get back in time to be sure he had her coffee and breakfast ready by 7:00 am. His business allowed to him to do much of his work from home,...

Bike Shed Rendezvous

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

You're hopelessly under her spell, captivated by her beauty, your little cocks been taken over. With no mind of your own you long to be put in her knickers and be her girl. Beg dog beg! She's got you by a psychological lead attached to your balls and is leading you to whatever and wherever she desires. 'Please, please!' you plead. 'Emasculate me.' Sound fa...

Karate Girls Ch. 2

by jabberwok on Sep 17, 2017
BDSM

My life in school after that was much different. I was shunned by everyone. No one would eat lunch with me. Word had gotten out obviously to the whole school. My day was filled with howling laughter at every turn, and snickering behind my back. Even the chess club dropped me for fear of something happening to them. I was on my own. I would go home and disro...

Making a Sissy Jock Pt. 01

by Sissyhalo1 on Jun 1, 2020
Transgender & Crossdressers

My life changed about a year after I was done college. I'm Mason, or I was and I used to be a football jock all through high school and played all through college and after all that I kind of just never got picked up. So...what do you do with a physical education degree? Most guys taught gym or coached some places. Me? I got a massage job at a spa. There...

28 Days

by tinywhiteboi on Dec 2, 2019
Interracial Love

28 days. That's 4 weeks since my last orgasm. And I was so horny, to the point of constant distraction. It was all I could think about. My locked little penis was dripping into my panties, and my little balls were swollen. Six weeks ago my wife, Angie, caught me jerking off to interracial cuckold porn, a video with the cuck locked in chastity. She'd come ho...

Fantasy to Reality

by CuckoldDesires on Sep 15, 2017
Transsexuals & Crossdressers

I faded in and out of consciousness. My body was numb and I waded through a sea of words and images that filled my mind, struggling to focus on anything specific. Slowly I began to wake but my eyes did not open and my body remained numb. I searched for my memory, I knew it was there but I couldn't reach it, I was entranced. My name and past eluded me as I s...

Jezebel's Magic: Becoming Josephina

by twiddershins on Aug 31, 2017
Fetish

Jeff was just a regular dude when he met Jezebel. They had lived together for a few months and at first they seemed satisfied with each other. They got along fine and would have appeared like any normal couple in public, but that was now long ago. Even then, Jeff had felt lucky to have her because of his tiny penis! One Saturday night, Jezebel came home lat...

Asian Bimbo Sissy Slut Ch. 01

by melltsslut on Sep 14, 2017
Transsexuals & Crossdressers

Soo...where should I start? I'm sitting here now in liquid black leggings, a hot pink crop top, and a carefully teased wig, with D-cup breast forms glued onto my chest. Oh, as well as the special panties my girlfriend designed - for both of us! From the outside, they look like French briefs. On the inside, they're a little more special, if you get my drift....