Sissy Gym Stories

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Orientation
Length
Source
Infinite Scroll

Creating Ginger Ch. 05

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 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 consistent in referr...

Afro Stress Relief Ch. 05

by llts1970 on Aug 1, 2018
Transsexuals & Crossdressers

My alarm went off the next day, my mouth and asshole ached, it was going to be a long day I thought. I had put plenty of grease up my asshole just to ease the soreness but it still felt pretty stretched. I started to remember last night, I couldn't believe I'd taken Baba G's fat black penis in my mouth, or that I'd spoken to the police officer like that! I w...

The Society Ch. 04

by Barno on Sep 13, 2017
Transsexuals & Crossdressers

I have a little explaining and an apology to make. The last installment of The Society, called The Society part 4 was uploaded by mistake. If you are following this story you will find that the first part of this installment is very similar to part 4. Please take this story for what it is, parts 1 through 3 and then followed by this installment, part 5. Sorr...

Caught Relaxing Pt. 01

by StephaniePlayland on Aug 6, 2019
Transgender & Crossdressers

This is going to be a short series of stories. This one really starts the journey out, they won't all be in exact order or have a proper linear flow to them. Just depends on what's has caught my interest that day, and needs to flow out of me. It's Friday night, no plans or anything to do a perfect night to dress up. Hangout have a drink and relax being Ste...

The Society Ch. 05

by Barno on Sep 19, 2017
Transsexuals & Crossdressers

"I don't think that I'm the right person for this. You need someone more experienced. What if I fuck this up? I'll get my balls snatched right out from under my cock!" I was more than a little nervous watching Serena and Corinna rifle through my closet. "Your balls were snipped off quite a while ago my dear and the woman who owns them has given you her orde...

Dark Impassions

by Dragant on May 3, 2018
Interracial

Josh Tylers was a good looking 19-year-old black male with a promising day ahead of him. He was leaving to go on a date with his girlfriend 20-year-old half-Asian bombshell college sophomore Jade Pond. Josh was pretty sure he was going to lose his virginity this time too. She invited him to her dorm room and even threw in some suggestive language to the text...

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Afro Stress Relief Ch. 07

by llts1970 on Sep 23, 2019
Transgender & Crossdressers

Author's Note: - there was a character in the previous chapter called Jane who was working in Tina's company, I realized this was too confusing because of the main character Dr Jane and so I've changed the name from Jane to Monica. I apologize for the delay in getting this chapter out and hope to have more chapters completed sooner. ***** Staci rang and sa...

Made to Obey Ch. 08

by madetoobey on Jul 29, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). Ruth, as a part of my punishment, was setting me tasks until Esther (who'd taken my laptop and mobile phone) could verify I'd never visited such sites before. I'd been forced into a chastity cage and m...

The Sexy Cuckold Couple Pt. 10

by cuckcpl4play on Sep 19, 2017
Fetish

After the crazy collaring weekend, our home life shifted slightly back to some form of normalcy. Master would send us occasional texts, orders, etc., but overall there was nothing significant that was transpiring and in fact Miss Jenny seemed sad that more activity was not taking place. At work it was a bit of a different story...Master was his typical domin...

Back Row Babe

by CarrieQ on Sep 13, 2017
Transsexuals & Crossdressers

When I was young (and far more naïve than I readily care to admit) there was a cinema in the city centre with a certain reputation, where I liked to hang out at weekends. I'd go there wearing a parka and jeans with gym pumps, and take a seat in the very back row of the stalls; the seats where, once the lights were dimmed, it turned as dark as sin. And if t...