Aunt Sissy Stories

18,612 results
Orientation
Length
Source
Infinite Scroll

New school, new you

by HICKSMODE on Nov 15, 2018
Amateur

“Mom why do we have to move so far away, what was wrong with our old town?” I said “I’ve told you already we just have to” mom said Sitting there in a uhaul all you can think of is how shitty your last few months have been, dad up and leaving you and mom in the middle of the night, moving to my stupid aunts house half way across the country, and I had to lea...

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Trapped as a sissy in a fanasy world.

by Duke Montefort on Nov 14, 2019
Fetish

Eugene has an obsession with video games almost shutting out his friends and family. Feeling they have no choice the family begs a videogame company to help them bond with him. The company agrees they test the family can beta test the game, and bond. They even promised that he could not come out until he had properly bonded with each family member seprately....

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Nylon Femdom

by BlkNYLONS on Sep 18, 2017
Fetish

This took place in 1964... A time when the fashion called for women too wear girdles, garters, and shiny ultra sheer reinforced heel and toe stockings, spike heel pumps/mules daily! A time when my fetish for nylons was young and in full bloom! A FANTASY STORY.... As she stood in her bathroom she could almost still feel his presence. Joan would know just...

The New Swim Team Pt. 02

by Doubleganger on Sep 19, 2017
Exhibitionist & Voyeur

Disclaimer: I began writing this story in late 2015. All are over 18 years of age. This story is completely fictional. None of the characters portrayed are real, also none of these sexual encounters ever happened in real life. All the names, places, or events living or dead are purely coincidental. ***** Part 2~ The Teams First Practice. Steven turned of...

A Look Into My Mind: Uncle Sissyboy Ch. 04

by rickiee_2002 on Sep 25, 2017
Fetish

I couldn't believe it ... I was finally going to be able to have sex with my niece. She is so gorgeous and sexy. She is everything I could want. Young, thin, tall, beautiful, full pubic busy, sexy ... WOW. I leaned forward and touched the tip of my tongue to her super wet pubic bush and then the tender small lips of her pussy. There was a white liquid oozin...

Real Life: The RPG

by Katnaace on Nov 25, 2019
Fetish

Having logged in, you get to the biggest question of all - who are you going to play? It's not like this is a big deal. You can just create your character and be on your way.What's next? Danny Hopkins - Dude with a sister Lydia Onava - Widow waking up in an unknown place Claude Rogers - On his way to visit his Aunt Henry Wells - Protesting H20 What's next...

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Going off to College

by Jjjjrsa2 on Dec 5, 2020
Fetish

You are Jess an 18 year old young man who just finished high school and is off to college. After saying goodbye to your mother you made your way to the airport and prepared for the long flight. Hours later after landing and finding your luggage you hear a excited voice in the distance."There you are Jess! It's been so long I hardly recognized you!"...

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It Only Gets Better

by ElderDirt on Sep 14, 2017
Romance

Author's Note: This is a story about how a chance meeting led to a much younger woman becoming an intrinsic part of an older bachelor's life. Readers be warned that if you are looking for raunchy and frequent sex, you will be disappointed. The sex that follows is just the spice added to the meat and potatoes of the love story This is my first venture into...

Discounted Carpet

by Leigh_216 on Jul 31, 2019
Transgender & Crossdressers

My name is Leigh. Well my girl name, I am a cross-dresser. I just feel right to me and I guess that is how I am. All my stories are based on truth; but the places and names have been changed. Friday night and I was ready to hits this clubs but I needed to stop at my Aunt's old house on the east side of town first. Long story short: The family was selling it...

Jason's Secrets Exposed Ch. 11

by jlenil on Sep 14, 2017
BDSM

This chapter will be better appreciated if the reader first experiences the previous 10 chapters. A couple of characters from another work of mine (Ariana) make appearances now in this story. The author will now break the rules of writing and switch from the first person (Alexis) to the third person. This new chapter takes place four years after we left off....