Sissification 101 Stories

2,009 results
Orientation
Length
Source
Infinite Scroll

Forever Weekend at the Lodge

by JPRichly on Mar 3, 2020
Novels and Novellas

All characters depicted in sexual situations in this novel are over the age of 18 September 2025 It's the final year for the best squad Almington High has produced in decades. The boys a formidable force, undefeatable with the girls electrifying the crowd. As nationals are on their way, the crew are awarded two weeks break for their achievements and decid...

The Beach House

by DreamCloud on Sep 25, 2017
Erotic Couplings

Authors Note: I would like to thank a generous soul who edited my mess. I learned a lot about punctuation in the process. Thank you kind sir! ***** I looked out over the pool to a pristine beach not one hundred steps below the chlorinated water. To the left, I saw trees and a stone fence, to the right, more palm trees and the same stone fence. Both fences...

The Neapolitan Question

by Sara2000Z on Aug 28, 2018
Romance

It takes a while for this story to unfold -- as for most of my stories - but I hope you enjoy reading it. Please leave a comment if you'd like to, as I really appreciate those of you who take the time to write them. Anyone in this story participating in sexual activities is most definitely over the age of 18. +++ 'Jane? Jane McInerney?' 'Yes! Jane McIne...

A Perfect Life

by Wholemanz on Sep 19, 2017
Transsexuals & Crossdressers

DECLARATION: This story is an original literary work. I wrote a story just to stretch my creative muscles. All scientists and Wizards in this work are fictional. Any resemblance to anyone living, dead, or born in the future, is purely coincidental. WARNINGS: Contains transgender themes, Sci-Fi, explicit sex, mild violence, swearing, and strange ideas. It ha...

Devil's Due

by IronDragon on Sep 14, 2017
Loving Wives

Foreword: READ THIS FIRST! First, let me again thank my lovely and talented wife (Black_Dragon_Princess) for her input on and proofreading of this tale. I love you, sweetheart! :) This is probably going to be my last submission to the Loving Wives category, folks. Not saying the ride hasn't been a rollercoaster. In fact, it's been pretty damn fun, someti...

On the Git of Go

by JayDiver on Sep 1, 2017
Group Sex

I hope you enjoy my next story. It's about my favorite sport, skydiving. So some of the terms in here might take a little contemplation to understand. But part of why I wrote this story is to try and give people a more realistic look at skydiving. Some terms are necessary, and I'll try to explain those. Also it's hard to explain the way jumpers use the air c...

Cockroach County

by cowboy109 on Sep 16, 2017
Novels and Novellas

"Hey little brother, this is a good thing. We are starting a new life in West Liberty. Don't feel bad about the broken cup in the kitchen. The doctor said it would take time... months or a year... for both of us." Sandra, the blond around twenty years old, put her arms around Randalf, the slightly younger looking, black hair man. She snuggled her chest arou...

The Jimmy Soul Memorial Party

by YDB95 on Jan 27, 2020
Romance

Derek was back from London, and rumor had it he'd be taking over the room next door to Neil's from that weird Carol chick who'd lived there last semester. Neil hoped so anyway. Fall semester without Derek had been far too tame, and his nerdy and straight-laced neighbor had been a constant reminder of that.. All through the January ritual of another goodbye...

Eager to Please Pt. 01

by Payne_Hall on Dec 14, 2020
BDSM

Author's Note: This one is D/s and Mf/f. While some of my other stories were more about sadism, this one is more for the domination aspect. It's also a romance. Morgan My wife and I almost had the perfect relationship. To give you the idea, I first met Trish when we were in high school together and we were both already balls deep into the fringe edges of t...

The Proper Rules For Strip Poker Ch. 04

by PaulSandarac on Sep 26, 2017
Group Sex

THE PROPER RULES FOR STRIP POKER: THE EPILOGUE Author's Note: To understand the characters in all their dimensions I would recommend reading all of the "Proper Rules" stories; but if a reader doesn't care to do that, this will stand up on its own merits, I hope! A result of some encouragement, I have decided to take the characters out for another spin. This...