Sissy Pony Stories

16,082 results
Orientation
Length
Source
Infinite Scroll

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...

Proud To Be A Sissy Ch. 09

by Kary_M on Sep 26, 2017
Transsexuals & Crossdressers

"I hope you like them," daddy stated cheerfully as he lifted the towel from my face while handing me a bra that was laced with trim, matching my panties, "they look great on you sissy." Looking down I saw two flesh toned swells that weren't there before and sitting up I could feel a slight weight pulling down. I jumped off of my bed and stood in front of th...

Training New Couple

by Ponys Master on Sep 17, 2017
BDSM

Master and pony met Jason and Catherine at the nude beach a few years ago and had become fast friends and spent time together when the opportunity presented itself. After some time had passed and over many conversations, drinks and dinner Master and pony became more comfortable about sharing their secrets with their new friends. Master had shown Jason the pa...

Mistress de Sade's Sissy School

by spitzharder on Sep 16, 2017
Transsexuals & Crossdressers

My whole body hurt, everything, both inside and out, the pain had brought me agonisingly awake. I could feel the bars of the cold cage I had been thrown into, it had been my home for several months but the beating was new. The other sissies had turned on me, they might be 'girly' but they were cruel, Mistress Kayne had warned me that to disobey one last ord...

Training Aide Ch. 04

by Angelscuck on Sep 16, 2017
BDSM

Both of my hands were gripped around the base of his huge cock like holding a baseball bat which still left a good six inches available for my lovely wife's waiting cunt. I lay there transfixed at the sight, as her pussy lips opened wide to receive his cock. She slowly lowered herself on to it. It will never fit I thought to myself as she moaned with its...

Jerkboy Life Ch. 01

by stratoblaster on Sep 19, 2017
Exhibitionist & Voyeur

She made me beat off again. I felt like an idiot, kneeling there in the kitchen while my wife and her mother enjoyed their beverages. Pants around my ankles, holding my balls and presenting my hardening dick. "See? He gets off on doing this," my wife said mockingly as my member surged to full erection. The shame was making my heart race. Mrs. Landtree's c...

Stan to Stella Pt. 01

by Maximus_eros on Sep 16, 2017
Transsexuals & Crossdressers

Disclaimer: All persons depicted are 18 or over. The names have been changed to protect identities as this did occur in reality to some degree. ***** Like any story, everything has a beginning and thus we have the day that Stan began his journey of self-discovery at the manly hands of Jason. He like so many was subjected to years of ridicule and shame. Th...

Playing the Part

by Sissysdream on Jan 20, 2020
Transgender & Crossdressers

All people in this story are above 18 or older. This is just a fast story I wrote and don't know if I will do any more on this story. *** My name is Tommy, but these days I go by Tammy. A few weeks ago, I was turned out by my high school bully during summer break and now I am a happy cum drinking sissy. I know I'm getting a bit ahead of myself here so let...

Property of the Master Ch. 02

by BrightTightandWhite on Sep 26, 2017
Transsexuals & Crossdressers

"Wakey wakey sleepy head." The sound of curtains being drawn open was accompanied by a blinding light as my bleary eyes blinked open. "Wha... What? Huh? Hello?" I struggled to come up with coherent words as my brain wasn't fully awake yet. "Good morning Rosie, I hope you slept well," said the same voice as before. "Umm... Yes. Who are you?" I asked. "My...

Girl's Night Pt. 02

by DifferentBreed on Sep 14, 2017
Fetish

Fisher was upstairs, making the bed when he heard the front door opening, signaling Sophie's arrival home. He looked down at the list on her dresser, frowning. He had not completed four tasks. He reapplied his pink lipstick and kissed the paper above the words "make bed with gold satin sheets" as he was instructed. He then scurried downstairs, incomplete lis...