Sissification 101 Stories

2,009 results
Orientation
Length
Source
Infinite Scroll

Felicity Ch. 20

by jjcolejr on Sep 11, 2017
Novels and Novellas

Chapter 20. Paula and Paul She had come to my campsite from hers to thank me for helping her son that morning. "He seems to be a good kid," I said. "Yes, he is, mostly. He is not nearly as helpless with his broken leg as he led you to believe. He had ulterior motives." I nodded but let her statement pass without comment. She understood that I knew what h...

The Roman Gambit Pt. 02

by dtiverson on Apr 13, 2020
Novels and Novellas

FIRST CONTACT We took the Eurostar from St Pancras to Paris Nord. I'd booked Premier class because I wanted the dinner amenities. So, we ate on the train. We got into Paris that evening and took a taxi to the Hotel Lutetia over in the 6th arrondissement. I'd gotten suites for both Mel and me. I wanted my own room to spread out my hacking gear. Mel is tech...

A T-Girl and a Tomboy Pt. 01

by AlexBailey on Jul 14, 2020
Transgender & Crossdressers

Outed by the Cheerleaders _________________________ Hello! This is part one of a full length novel in four parts. It's a gender-fluid, 'what if everything fell into place,' fantasy about self-discovery, coming out and coming of age. It explores pansexuality, cross-dressing and several fetishes -- especially for things like swimsuits and athletic-wear. Som...

There Must Be A Mistake Ch. 20

by Prolonged_Debut10 on Sep 25, 2017
Novels and Novellas

Note: All persons in this novel are fictitious. If you are looking for a great deal of explicit sexual activity, this story is not for you. Those scenes that are included will be evocative rather than just for the sake of sex itself. This story is for your reading pleasure. Its length is undetermined at this time, because I do not know where my mind will tak...

There Must Be a Mistake Ch. 10

by Prolonged_Debut10 on Sep 25, 2017
Novels and Novellas

Note: All persons used in this novel are fictitious. Although the areas used in this novel are real, the streets, buildings, roadways, recreational areas, and other points of interest used to make this interesting reading for you, are neither at the exact heights, or in the location described. If you are looking for a great deal of Explicit Sexual Activity,...

Outsiders Pt. 01

by sycksycko on Sep 13, 2017
Sci-Fi & Fantasy

My D&D group has a tradition where the player with the lowest level character at the end of a successful game has to pay a forfeit to the player with the highest level character. It's to discourage people from missing out on sessions as that causes a delay in leveling up. Unfortunately, I missed a session and ended up with my friend handing me his character...

Naked Portraits Pt. 01

by eagelwolf on Sep 19, 2017
Novels and Novellas

Chapter 1 Gwen After wiping my face free of sweat for the thousandth time with the bottom of my shirt, I grunted in frustration and pulled the shirt all the way off, reducing myself to a dark blue sports bra and paint-smeared jeans. Normally such a bold move would be unthinkable but the heat trumped modesty and besides, I was alone in the sweltering art st...

Mating Rituals Ch. 15

by Scorpius1945 on Sep 25, 2017
Erotic Couplings

Author's notes: 1. This is a work of fiction. The activities and practices described in this story are not necessarily either condoned or recommended. If you choose to do anything described in real life with real people you do so at your own risk. 2. All characters are fictional and any likeness to any living person is purely coincidental. The story is pur...

Breaking Up and Making Up

by nikkiesilk on Sep 14, 2017
Transsexuals & Crossdressers

"Well, Nobody's Perfect!" Joe E. Brown 'Some Like It Hot' Nikkie Silk Chapter One Danny stood at the bar and looked around the pub. It wasn't his usual, but this one had looked bright and warm from the outside on a gray, rainy day. The after work rush wouldn't start for a couple of hours or so yet, so there were only a few old boys who looked like regular...

The Building of Robert G. Holbrook

by Just Plain Bob on Sep 16, 2017
Loving Wives

I sat there in the almost pitch dark room. Almost pitch dark because there was a bit of a glow from the little light on the computer monitor signifying that it was in sleep mode. I sat there with a headful of thoughts that I wished I didn't have. The door opened admitting a shaft of light and my wife came into the room. "What are you doing in here? I've bee...