Sissy Pony Stories

16,082 results
Orientation
Length
Source
Infinite Scroll

Overcoming PTSD

by Justplainjeff on Jul 6, 2020
Romance

Author's note: All characters in this story are entirely fictional. Any similarities to people you might know is pure coincidence. All sexually active people are over 18. Sitting in the discharge room at Walter Reed Medical Center, I was shaking, but far less than the previous day. Each day I was practicing for my release, at the end of this week. I am Ri...

Will my Son be like his Father

by lisablissful on Apr 27, 2020
Loving Wives

Part One 'The Father' I'm Rhonda and this is my story. I'm a small elfin-like woman, 5' 3", very slim, with 32B breasts that sit well with the rest of my body. I have an olive tint to my skin and short dark hair. My best assets are my nipples - they are very dark and grow to about three quarters of an inch in length when I'm sexually aroused. Nothing in lif...

Once Bitten Ch. 01

by HankDolworth on Jul 13, 2020
Sci-Fi & Fantasy

Author's note The muse awoke and I have a new story unwinding in my mind. For this chapter Sci-Fi/Fantasy seems a good place to start. I don't know how many chapters this will take, but I hope to keep a good steady pace of publishing as the story unfolds. Your honest feedback and stars are appreciated. Special thanks to XiraeK for help with editing - Hank...

Linda Loves Lace

by moreandmore on Jul 13, 2020
Erotic Couplings

This short story requires some knowledge of tennis. Skip the next paragraph if you already know the game. For those of you who haven't followed tennis, love means zero. Points are scored as fifteen, thirty, forty, and then game. If tied, at forty, you have what's referred to as 'Deuce'. You must win by two points, so once tied, the next point winner is 'Adv...

One Night Stand Ch. 11

by Tara Cox on Sep 14, 2020
Novels and Novellas

***NOTE*** This story is part of my Trouble Texas Style series that includes Night Walker's Woman (complete), Tight Fittin' Jeans, Goodbye Earl, and Ready to Run. It will be appreciated more when reading in context with those. This chapter is like that review session the teacher gave right before the exam. I am bringing them all together and doing just that...

Journey to Trans Submission Ch. 01

by bluev on Jul 15, 2020
Transgender & Crossdressers

It has been at least thirteen years since I first discovered my kink and one year since I started to think about making it come true. This is a kink I have not shared a word with anyone for a fear of being judged and a fear of being told that it was not right to indulge in such objectification. Finally I came to the point where I said "screw the world, it's...

Finding Ivy Ch. 12

by Lcpce on Oct 5, 2020
Sci-Fi & Fantasy

Ivy pulled into the driveway at her house. It was about 10 am, she noticed Rick was in the yard mowing. Her mother was also in the front yard working on her flowers. Her mother watched her as she pulled in and waved. Ivy sighed, what was she going to say now. She focused on her cock and it disappeared. Her shorts were way to tight her bulge would be obviou...

Slutty Tales Pt. 02: Becky

by AnetteSnow on Nov 2, 2020
Group Sex

Becky and Corey met on one of the many kinky dating apps about a year ago. They both had just gotten out of long and dull relationships and wanted nothing serious. They wanted fuckbuddies for occasional great time. Their chemistry seemed to be a perfect match. Becky liked it rough, fresh and exciting and Corey more than enjoyed giving her what she craved....

The Sissy Mark

by Son_of_Battles on Nov 2, 2020
Transgender & Crossdressers

This is my story submission for the Literotica Halloween 2020 Story Contest. I ask that you forgive any errors you might find, I literally just finished 12 hours before the deadline, and have zero time to get it to my editor before submissions close. As soon as Skye can get a chance to edit for me, I will repost a freshly edited update. Thanks, and don't for...

Winter Project

by Thecsm on Sep 19, 2017
Interracial Love

I want to give thanks to Gentleman With Handcuffs for editing and helping me with this story. My Name is Dale and I'm 18 and in my first year of college. It's in the same town that I grew up in and right now I'm living at home with my Mom (Kathy) and Dad (Paul). They are on the cool side and don't mind me living at home but sometimes it cramps my lifest...