Sissy Pony Stories

16,082 results
Orientation
Length
Source
Infinite Scroll

Francis Meets a Black Stud Ch. 02

by FrancisAlba on Sep 14, 2017
Transsexuals & Crossdressers

The first story was easy and this one went by pretty well. If you have any thoughts or suggestions for where Francis should go in installment #3 email me. I will respond to your email and sometimes I will send out previews of what I am working on if you treat me right. Thanks. As I was walking to get the key to my camper I wanted to cum so badly and really...

Jamie's Descent Pt. 02

by nikkiesilk on Sep 18, 2017
Transsexuals & Crossdressers

'That's it, baby,' Vanessa purred as she snaked her hips forwards and back, gently sliding the strapon in and out of my mouth. I could no longer think rationally, as any self control I still had slipped away and trance like, my eyes closed, I sucked the rubber phallus in and out of my lips. 'Baby, you love this don't you?' Vanessa's voice took on a hypnoti...

AliExpress and Sissy Downfall Pt. 07

by His_fag_wife on Apr 9, 2018
Transsexuals & Crossdressers

Please for goodness sake don't read this story if extreme use of submissive males by dominant males and dominant females offends you. This is pure fantasy and at the darker end of the spectrum of stories on Literotica, please do not read if this is not your sort of thing. Otherwise I hope you enjoy the spiral of depravity. ***** Charlie was alone in the ro...

Sissy Auction

by davine on Sep 26, 2017
Transsexuals & Crossdressers

Authors note: this story is a fill in while I get over a block with the fifty shades part three. I also need to revise part two of sissy downfall as Literotica rightly pulled it due to excessive violence. I wish this story was autobiographical. It's not but has some elements of truth in it. I hope you enjoy reading it. I love feedback; even negative. All cha...

The Whore Wife, Sissy CD Husband

by MILF4black on Jul 27, 2020
Transgender & Crossdressers

This story is completely fictional. All characters in the story are over eighteen. Prologue: The Whore wife, Sissy CD Husband "That's it, you little sissy whore, suck that cock." Jennifer told her husband as his head bobbed up and down on the strap on dildo Jennifer was wearing. Her husband, Patrick, lifted his head and the seven inch fake penis slid out...

Cuckold CEO Ch. 07

by drdick69 on Oct 16, 2018
Fetish

I awoke Saturday to the sounds of running water. My wife was already up and in the shower. My head was still swimming from that activities of the night before. Our playful cuckold game had taken us to a different level, with me being submissively used for the pleasure of my wife and her lover. More worryingly, the comment my wife made, before I went to bed,...

A Midnight Swim

by desireethtttv on Sep 16, 2017
Transsexuals & Crossdressers

Relaxing by the apartment's pool one Sunday, I relived the previous evenings midnight swim in nothing more than my long baby blue Eva Picone silk gown. The water had felt so good flowing between the silk and my nude body and the walk back to the apartment even better as I had a raging hard on from the clinging sensation of the silk over my drenched body. I...

Black Licorice

by EROTICbearscribe on Oct 19, 2020
Transgender & Crossdressers

My name is Jamie. I am 19 years old. This is the story of what happened to me Halloween one year ago. It was the last week of October and the leaves had turned brilliant shades of orange, red and yellow. The nights were getting cooler. Everything you could imagine was pumpkin flavored. Usually I get psyched for this time of year but things were different f...

His Sissy Bitch Ch. 07

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

He makes sure they all get a good look at my rear end. He pinned my skirt up in the back, large safety pin holds my skirt up at the top. It's a large baby diaper safety pin, one that women used in the 1950s, pink plastic shows at the top. Kind of cute, the pink plastic matches my ear rings. I could just take my skirt off but he says it's way sexier this way,...

The Sexy Cuckold Couple Pt. 15

by cuckcpl4play on Sep 26, 2017
Fetish

PART 15 POOL 2 As we walked outside, I noticed that our private area was more populated than expected. There were a few more additional males but more than a handful of additional and very attractive females. Sir Jeremy approached my wife quickly and I watched as the other women gawked at her and then began laughing at her as several of them even engaged in...