Sissy Machine Stories

38,061 results
Orientation
Length
Source
Infinite Scroll

New Gurl in Town Pt. 01

by GavinIsaNuisance on Jul 6, 2020
Transgender & Crossdressers

This work is entirely fictitious. Any similarities to actual persons living or dead is purely coincidental and entirely unintentional. All characters portrayed in a naked/sexual nature are 18 and up. *** The city of Los Angeles, California. A place once regarded as the focal point for entertainment and movie stardom now reduced to an over-taxed, grimy, dru...

Our Sissy Slave Ch. 02

by purekink on Sep 25, 2017
Transsexuals & Crossdressers

Would you be our full-time cross-dressing lesbian boislut? Of course you would. I knew that from the moment we'd made you beg to be fucked whilst dressed in a red corset, knickers and stockings ensemble. Your clothes matched those of me and my new student girlfriend, and your makeup was messed only by our juices. It was easy to make you submit after that....

Mistress X 02: Pixie's Predicament

by Long2bLocked on Jan 22, 2019
BDSM

Note to readers: This short story is not part of any series. The setting and characters are based on those from my "Laura's Femdom" stories. My Mistress X stories stand on their own but are best read in order. This particular story describes a predicament bondage session. ***** Mistress Alexis X has a female live in slave named Pixie. She works at Red Ro...

Covid 19 - Pete Turned into Charleigh

by His_fag_wife on May 12, 2020
Fetish

Even with the threat of Covid over everyones life, Pete was still getting on with things whilst he could. It was possible that any day, more restrictions might be placed on the country. They'd already closed the borders, no one knew what would happen next. He had to make the most of the time he had, and he was determined to, today was going to be an amazing...

Cockland Island Pt. 04

by Sissyhalo1 on Dec 16, 2019
Transgender & Crossdressers

It was one of my first lessons as a sissy that I learned on my own. New girl only appealed for some men. And there were all sorts of hotter sissy girls there just working it in the food hall and other places. With real breasts or close enough, with great asses that were getting attention. And as femmed up my brain was there was still this sort of competi...

Trained by My Aunt Ch. 01

by Misslexia on Aug 18, 2017
Fetish

It was my Aunt's suggestion that, when I left home and got a job, I moved in with her. Although my job was a few miles from her house, I had my bike and the renting a flat in the city was not an option. Secretly I was delighted. Aunt Suzy was my mum's younger sister, jokingly described as an 'afterthought' or an 'accident'. Fifteen years younger than my mum...

Cockland Island Pt. 06

by Sissyhalo1 on Jul 6, 2020
Transgender & Crossdressers

I woke up and I was sucking that realistic dildo cock like a soother and it was so weird and right and made me smile as I pulled it out trying to make my lips do the pop you can do sometimes with suckers. I giggled and did it a few more times then pumped it in and out of my mouth trying to get that dick lips feeling going on. That's a sexy sissy trick, all...

A Day at the Fetish Flea

by Tinababy on Jun 11, 2019
Transgender & Crossdressers

I first met Jack at the bar. It was a little uncomfortable for me talking to people there, because not only was it was a drag bar, I was drinking alone and I dreading that I might run into someone who might recognize me. I had been to the Fetish Flea that afternoon, gawking at the outlandish gear. Many booths lined the hall, and hundreds of freaky people st...

Aficionado Gets in Trouble Ch. 02

by His_fag_wife on Jun 12, 2019
Transgender & Crossdressers

Mark cleared the clothes from the table, he wanted a truly clear picture of Pete being used in the stockade, knowing he'd get some great footage for his website selling the stockade frames, it would help sell some more without giving away Pete's identity from the side view. But he'd also get some head on footage for posting on the internet should Pete fail t...

Behavior Modification Institute Ch. 10

by NancyPan on Sep 12, 2017
Fetish

Although I continue to receive some demeaning and aggressive comments, most feedback has been positive. I appreciate all who enjoy this story, as we share similar fetishes. If you are not interested in FemDom, male feminization, and sexual humiliation, do not bother to read this series. ***** I was standing with my petticoat and the skirt of the maid's uni...