Auntie Sissy Stories

8,340 results
Orientation
Length
Source
Infinite Scroll

Killing Daddy Blue

by WickedDrX on Sep 12, 2017
Novels and Novellas

Wednesdays were always boring for Holly, and this one was worse than most. Her usual trade didn't hit the streets until the end of the week when they got paid, or until the welfare checks came. This wasn't the week for the welfare checks. It was cold, and there was a light mist falling that promised to turn into snow very soon. She could move up a few blocks...

Birthday Present Pt. 01

by donnaallure on Sep 18, 2017
Transsexuals & Crossdressers

Birthday Present or (I've Looked at Love from Both Sides Now) Chapter 1 "What would you like for your birthday?" my wife asked. "An unforgettable sex session" I answered, jesting. "Is that right? Well, we'll see" came the reply. I forgot all about the exchange and nothing else was said about my birthday. The day arrived and I got home from work exp...

Flowers in the Heart Pt. 02

by JimBob44 on Sep 15, 2017
Transsexuals & Crossdressers

*Author's Note: Any and all persons engaging in any sexual activity are at least eighteen years of age. **Author's Note: This has an alternate ending to 'Flowers in the Heart.' It read the same as the original posting, until page 4. After posting the story, I realized that Scott was just a little too quick to accept his girlfriend's differences, especially...

The Old House

by l_anonym on Jan 22, 2019
BDSM

Prologue This story is about a group of young people living together in a big old house a bit outside of town. Most of them are students so they enjoy the rather cheap rent and the somewhat secluded place where they can party anytime without having to worry about the neighbours. Don't get me wrong: It's not a place with a nonstop party -- they all have to...

Under the Pure Blood Moon

by MrKnightlyWriter on Mar 17, 2020
NonHuman

Nicolaus's eyes snapped open after a long and deep slumber, something had disturbed him, the sounds of an alarm waking him from his sleep, looking over he found his alarm clock making the most annoying sound possible, effectively waking him, he grumbled, raising from his bed scratching his dark brown hair and yawning loudly. Looking around in his bedroom i...

Chasing The Last Road To Stockholm

by SleeperyJim on Mar 23, 2020
Novels and Novellas

This started out as part of my Conversations universe, but turned out a much longer story than I usually write. I do not apologise for its length, however, having received several emails complaining that I just write flash stories and offer nothing that readers can really get their teeth into. If you're not keen on long stories -- don't read it. If you're...

Awakening: 7 Slutty Blackmail Tasks

by silkstockingslover on Mar 20, 2018
Illustrated

Summary: MILF's sexual awakening by being forced to do 7 slutty tasks. Note 1: This is an April Fool's Day 2018 Contest Story so please vote. Note 2: Thanks to DARKBREEZLY for collaborating with me and creating all the illustrations that bring this story to life. Note 3: Thanks to: Tex Beethoven, thor_p, Robert, and Wayne for editing. Note 4: A warning:...

Heather's Exquisite Map of Tassie

by Thefireflies on Nov 20, 2018
Romance

Dear reader, I've written this story for the inaugural 'In a Sunburned Country Event', for both my enjoyment and yours. I self-edited, and although I've proof-read several times, the time came when I needed to stop playing with it and put it out there. Anyhow, I've found the best way to discover an error is to publish, so apologies for any mistakes. The ev...

Whoremaster (56)

by Cirnhoj on May 15, 2018
Novels and Novellas

Prologue I am ninety-nine years old and tomorrow is my birthday, so I will be a hundred years old in the morning. The big ten-0! I have all my faculties and even my own teeth! What I don't have is all the dear ones I have known in my life. My daughter Polly is now gone and her daughter Jenny too. As for her daughter, my great granddaughter Polly, she is...

Aftermath

by Scorpius1945 on Sep 14, 2017
Erotic Couplings

All characters in this story are fictitious and bear no relationship to any person, living or deceased. The setting for the story is based on historical events but no event reported in the story is based on any specific historical occurrence. The activities described in this story are not necessarily either recommended or condoned by the author. With these c...