Sissy Machine Stories

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Orientation
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Infinite Scroll

It's a Sissyful Life

by sliderx on Aug 23, 2015
Fetish

John sat in the basement, football on the TV, 4chan on his laptop. The game was pretty much a blowout, so he wasn't really paying attention. He was, however, greatly interested in the adult gifs (although 90% of the entries were webms) page he was on. There were a few threads that were catching his eye, girls playing with their asses, deep throat, but he was...

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The Chastity Trap Ch. 02

by slavemalcom on Mar 13, 2018
BDSM

Malcom rushed back through town to his house, all he wanted to do was get to his room and see what could be done about the chastity device trapping his cock. As soon as he opened the door however, Emma came rushing out of her room and looked down from the top of the stairs. "Lott...Oh it's you." She said. She didn't even try to hide the disappointment and d...

Young Master Ch. 02

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

There I was, still impaled on a shemale's cock, one belonging to what was supposed to be my sissy slave, wearing her bra, her cum on my cheek along with my post-fuck smeared make-up, and my cum running down the full length mirror. "I fell" wasn't the best explanation for what happened, but it was all I could think of with my step-father's hulking frame loomi...

Mistress Morgan's Sissy Husband Pt. 03

by corduroysissy on Dec 16, 2017
Transsexuals & Crossdressers

Robin arrived home from work about 5:30 on Thursday, he still felt a little apprehensive about what happened Tuesday night with his sissy friend Patty, and he hoped he might get to talk about it with his wife Morgan. He really enjoyed wearing the corduroy skirt outfit she bought for him, and he loved being a sissy whore for his wife and Patrick, her "boyfrie...

My Wife-His Toy Ch. 01

by wifetoy on Sep 12, 2017
BDSM

The office was quiet as I worked late to finish a project. After all there was no reason to go home to the empty house. Bzzzzzzzt, "Shit" I cried as the jolt of electricity suddenly coursed through the composite fiber chastity device that had imprisoned my touch starved cock for the past six months. This was the master's cruel signal to check the secret em...

The Sissymaiden's Tale Ch. 01

by ppeaks42 on Mar 7, 2018
Transsexuals & Crossdressers

The world was not always this way. Though few remember it, and even fewer choose to speak of it, there was a time when things were different. Before disease ravaged the land. Before the great feminization. Before the influx. Before the Femocracy. It was whispered that once white men had been just that: men. It was nearly impossible to believe, seeming more t...

Subliminal Obsessions Ch. 03

by Sissyhalo on Sep 13, 2017
Transsexuals & Crossdressers

*Before... She shows me our profits and stuff...and stuff meaning gifts with cash transfers and e-notes sent for who. I'm floored, literally floored I've never had this much money in my life. I'm not rich but holy fuck...I can...I just sit and stare and look at the screen. "What are you going to buy first Nikki?" "Bills, bills and some savings but the r...

Revenge?

by magmaman on Sep 15, 2017
Loving Wives

When a young man is barely 19 years old, hormones rage. It's just the way of life. Ricky was that way, having discovered the joys of sex just a few days earlier. He decided he really did like that. That one time had been in his old Chevy Camaro and it was not all that easy to do. The beach party earlier had been a kick, Ricky spent most of the evening dan...

Glory Days Again

by lil_raider on Sep 16, 2017
Transsexuals & Crossdressers

I just couldn't help myself. It had been years since I had a girlfriend and the last time I had gone out in full drag to a gay bar confirmed what I'd been feeling for some time -- a wig and lots of makeup could take 10 years off your age, but not 20. The bar scene was over for me and it had been a while since I'd had any real-life action. I got by with cam...

Falling into Being a Sissy

by Sissyhalo on Dec 12, 2018
Transgender & Crossdressers

My name's Sonny and well life's been pretty damned golden for me. I used to be a hockey jock in high school and was a defenseman so I was kinda big and tough and had all the usual good stuff going for me. Middle classed family, decent money for all of that, lots of high school pussy and even more in college. Being a jock in college doesn't prepare you for...