Sissy Pony Stories

16,082 results
Orientation
Length
Source
Infinite Scroll

50 Shades Of Pale Pink Sissy Ch. 02

by davine on Sep 11, 2017
Transsexuals & Crossdressers

All characters are over 18. It's Thursday. Waking up I'm still miserable. I can't bother to look after myself. I'm dirty and bedraggled in old track pants a tee shirt. After I manage a coffee and toast I decide to check my computer. First I check my bank account and I'm astounded to find that there is twenty thousand more than I expected. I check my ema...

Jennifer's New Adventure Ch. 03

by JenniferTaylorTV on Feb 10, 2020
Transgender & Crossdressers

Jayne started easing her dress up over her thighs. They were tanned and muscular but in a very feminine way. With her dress resting on her hips, she reached out and grabbed Jennifer's lead from the fat woman. "Come here Jennifer. I want to see if you like the taste of pussy." And she forced Jennifer's head between her legs. Jennifer could see Jayne was turne...

Papa Knows Best

by justincbenedict on Jun 26, 2018
BDSM

Everyone in this story is over 18. ***** Walking up the path to the house, Tippi knew she looked good in her new riding boots. Would Papa understand? Would he respect her finally as a career woman? Tippi had her own staff and was quite the corporate maven in New York. However, Tippi's family had always ridiculed her, the quick temper and childish pompo...

Young Sissy Ch. 01

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

Author's Note: This is a follow up to The Young Master series. You can start here if you aren't interested in Belle's misadventures as spoiled young man turned out by his own sissy slave and eventually enslaved by his step-father, but it does introduce a lot of characters you'll read about in this series. * I don't know how long I was under...days, weeks....

Girl's Night Pt. 07

by DifferentBreed on Sep 14, 2017
Fetish

This a continuation from an earlier story. It contains fetish themes of forced feminization, public humiliation and other erotic themes that may not be to everyone's taste. If you enjoy these, please read on and leave comments as to how you'd like the story to evolve or what you like. Enjoy. - DB ***** Fisher slid across the passenger seat of his Jeep, man...

Motorcycle Anal Dyke

by magic_tantra on Sep 12, 2017
BDSM

I had a big smile on my face as I drove to the beach because my mistress finally paid some nasty attention to me. I tried to reminisce in my dirty mind the magic moments that just transpired. First I watched Mistress Sandra finish her wine kneeling patiently before her. Handing me the empty glass Sandra bent down, reached into my crotch grabbing my cock with...

A Sissy Saga Ch. 10

by Snurge on Sep 15, 2017
Novels and Novellas

"Disgusting!" exclaimed Miriam Hancock lightly as she examined the photographs Emma Twist handed her. It had taken Hardwick most of the day to produce the prints, but they were well worth waiting for. The headmistress went through them as if shuffling cards, and having glimpsed each one viewed them a second time, more slowly and with greater concentration. "...

The Club Pt. 03

by RubberBudcus on Sep 16, 2017
Transsexuals & Crossdressers

Chapter 4 Training I awoke refreshed. I moved languidly and felt the nightdress move across my warm skin. It was delicious and I lost no time in stroking the fabric under the sheets and feeling my cock rise. I swished back the bedclothes and stood and stretched, my breasts thrusting out against the sheer black fabric. I looked at the nightie for the first t...

A Game within a Game Ch. 02C

by doberinca on Sep 16, 2017
Transsexuals & Crossdressers

Author's Note: This is the second story. I still have sometimes trouble to find the right syntax. I hope you still have fun in reading this second story. A third will be following. The characters involved will appear more 'human', not real good and not real bad, and make sometimes bad decisions. Chapter 2C. Dr. Catherine. The next morning when Rob wake-...

Miss Jennifer's Sissy Housewife

by tiffanyfoxe on Sep 19, 2017
Transsexuals & Crossdressers

My job was much less demanding than my wife's, so she had always "suggested" that I do all the housecleaning, shopping and cooking all week, and of course I never minded because I secretly loved being subservient to her. She loved to tease me when we'd be out somewhere together and she'd see a good looking guy by telling me how attractive she thought he was...