Sissy Pony Stories

16,082 results
Orientation
Length
Source
Infinite Scroll

Leaving Silverton Ch. 03

by regina_allen55 on Sep 16, 2017
Transsexuals & Crossdressers

Chapter 03 - Uncle Billy's Girl The truck ground to a halt and Robert opened my door. "Hey Pa," he yelled. "Come meet my new girl." The old man left his chickens and headed toward the truck. "Well Robert." "She is one good looking girl." The old man's eyes roamed my body from head to toe as he held his hand out. "Names Uncle Billy." "Nice to meet yo...

Cinderella - a BDSM Retelling

by MistressMoira on Sep 25, 2017
BDSM

Once upon a time there lived a kinky girl, a very kinky girl indeed, named, well never mind her real name, her chosen nick for play was "Cinderella", for reasons which will become apparent later. Cinderella lived in a polyamorous family with an assortment of bdsm proclivities with her "Daddy" (a switch - top to Cinderella and bottom to his Domme to whom he...

Making Francesca Ch. 07

by Spango on Sep 16, 2017
Transsexuals & Crossdressers

After the glorious sex with Mistress Celia, Frank spent the rest of that day doing housework with Justin. His mind was all awhirl. To all outside appearances, Mistress Celia seemed to be the beautiful woman he had lusted after when she was a waitress at his favorite bar, but now he knew that underneath her clothes she hid a wonderful piece of man-meat. His n...

The English Ranch Pt. 01 Ch. 06

by slave_william on Sep 19, 2017
BDSM

(Warning –this and later chapters describe William's participation in Pony play and describes heavy BDSM and pain scenes which may not be enjoyed by all readers. Do Not Read if you cannot handle this type of fantasy and please remember, it is fantasy. If you do not enjoy this story or any of my writings, I'm certain that there are thousands of other stories...

A Tale of Slavery

by gunnarsub on Sep 17, 2017
BDSM

Once upon a time there was a straight guy who was known by everybody as a well respected fellow. But he had a secret life. Nobody knew that he dreamt to become a feminized slaveslut, seeking an infinite and irrevocable blackmail relationship with a pitiless Mistress who would be prepared to break him with no way out. He wanted the Mistress to torment him n...

Helping Jess Pt. 04

by mski on Sep 25, 2017
BDSM

I got into the house. Jess looked into my eyes and saw I was out of it. "I guess that was quite hard for you John, maybe too much too quickly." I nodded. My head was screwed, I didn't really know where I was. She gave me a kiss on the lips. "OK sleepy head. Let's get to bed. Up the stairs with you, and brush your teeth!" She watched me walk up, then cat-...

The Comic Book

by embarrassednakedmale on Nov 6, 2018
Exhibitionist & Voyeur

Jonathan sat stock-still in his car, his eyes staring blankly ahead into the distant crowd that populated the end of the street where he'd been parked for the last ten minutes. His hands gripped the fake leather of the steering wheel, and he let out a long ragged breath that betrayed the conflict of emotions that were churning away inside him. Outside the...

The Vacation from Hell Pt. 01

by JamesMiehoff on Nov 27, 2018
Erotic Couplings

Copyright (c) 2018 James Miehoff, All Rights Reserved. This work may not be published whether for fee or free without this copyright. --------- This is one of a series of stories set in what I call Universe-J. Universe-J is very much like this universe with a few exceptions. First the people tend to be a little more sexual and less hung up on sex that...

Doctors Orders 2nd Appointment

by Misslexia on Sep 13, 2017
Fetish

The instructions in Dr. Jones' letter were clear, if a little puzzling and I followed them exactly. At a quarter past seven the next morning I rang the bell on the surgery door. Margaret let me in. "Morning Chrissie," she greeted me. "Dr. Jones is in room 3 waiting for you, go right in." I went in. Dr Susan Jones was waiting. She looked stunning again. Her...

Discretion is the Better Part...

by peachesmelba on Sep 17, 2017
Fetish

He'd seen the ad running in the local paper for the past several weeks, and he had to admit, it intrigued him - "Discrete handyman needed for long-term remodel work. One employer, private residence needing significant updates based on owners' personal needs. Rewards commensurate with performance. Contact............" He thought it might be the way it was w...