Sissy Pony Stories

16,082 results
Orientation
Length
Source
Infinite Scroll

Casey's Submissive Journey Pt. 08

by corduroysissy on Mar 6, 2018
Transsexuals & Crossdressers

Mistress Betty - Part Two When Karen returned from the kitchen she was holding a drink in each hand and the sight awaiting her not only shocked her, but stopped her dead in her tracks. Betty had her skirt pulled up on her belly and Debbie was between her legs licking her pussy. Betty's face was upturned, her eyes were closed and she had a very contented smi...

Gender Bias

by Goldeniangel on Sep 16, 2017
Reviews & Essays

Blue is for boys, pink is for girls. Boys play with Matchbox cars and G.I. Joe while girls get My Little Pony and Barbie. Boys want to grow up and be astronauts, scientists, firefighters; girls want to be ballerinas, secretaries, and teachers. There are so many stereotypes inundated in society that pertain to gender that it's ridiculous, especially since the...

Covid 19 - Pete Turned into Charleigh Pt. 05

by His_fag_wife on Sep 14, 2020
Transgender & Crossdressers

It was a long night, Charleigh drifted off, but the warmth in her ass, the stretch and lack of comfort as her hands were padlocked together made restful sleep almost impossible. She kept on drinking but in the early hours became aware of an ever increasing need to piss. She thought she'd be able to hold on, but she was getting more and more desperate. By 5...

A Look Into My Mind: Uncle Sissyboy Ch. 04

by rickiee_2002 on Sep 25, 2017
Fetish

I couldn't believe it ... I was finally going to be able to have sex with my niece. She is so gorgeous and sexy. She is everything I could want. Young, thin, tall, beautiful, full pubic busy, sexy ... WOW. I leaned forward and touched the tip of my tongue to her super wet pubic bush and then the tender small lips of her pussy. There was a white liquid oozin...

Mandy Sucks

by LilLindaMelons on Sep 16, 2017
Transsexuals & Crossdressers

I've written this fictional story in a POV style depending on what feedback I receive I may write more like it. I've been chatting to an older man for several ages and finally get up the courage to meet him. I dress up in one of my sexiest outfits and meet him at the appointed time and place. He drives me to a warehouse on an industrial estate before I kn...

New Rules

by skinnysailor on Sep 23, 2019
Transgender & Crossdressers

It began several years ago. Shortly after John’s death. I was out for dinner with my best girlfriend, Margaret. “Donna, honey, it’s been eight months. I know you want to keep working, and stay busy, and you love your job, but really, you should get a maid to do the housework. You could come home and just relax. Keith and I love our Sally. She cooks and clea...

Sissy Downfall Ch. 02

by davine on Sep 26, 2017
Transsexuals & Crossdressers

Revised version. all characters are adults. Part two. All Characters are over 18. * My new life at Mistresses mansion was quite pleasant most of the time. My duties were to be maid to the two mistresses. I helped them bathe and dress; hand washed their delicate garments, cleaned their bedroom and changed the bed clothes daily. Sometimes, if I was really...

Cuckold

by HerLittlePiggy on Sep 18, 2017
Loving Wives

She was a big woman, not fat mind you, but big none the less. She was about 5'11" and probably weighed a muscular 180lbs. Her height garnered attention but not as much as the way she dressed and how she carried herself. She was dressed in a short black leather skirt when I first saw her. A black and red leather corset was tightly laced over her torso to ac...

Fender Bender Ch. 03

by SissyAndi on Sep 14, 2017
Transsexuals & Crossdressers

Author's Note: The following is purely fiction and the property of the author. Any feed back would be greatly appreciated. Susan called me early Monday Morning and asked if I wanted to come over and lay out by the pool with her, she told me that Mark had a business meeting and would be gone most of the day so it would be just us girls. I remembered what h...

St. Andrews College Ch. 06

by Dr_And_Mrs on Dec 2, 2019
BDSM

WARNING: This is a FANTASY story. It may contain themes of consensual non-consent, slavery, dominance/submission, and/or extreme pain. Please do not try any of this at home. Do not try ANY fantasy with ANYONE unless you've discussed it in detail with them beforehand. Informed consent is fucking mandatory. * It was Friday night, and my wife and I had a doub...