Aunt Sissy Stories

18,612 results
Orientation
Length
Source
Infinite Scroll

A Wild Widow and Widower Ch. 07

by ljprockhard on Apr 22, 2019
BDSM

Editor's note: this story contains scenes of incest or incest content. ***** Participants (all based on people known to the author. Names have been changed and ages have been altered to fit the scenarios.) Len – 64 – widowed 3 years ago (traffic accident) Tammi – Len calls her "T" – 56 - Len's next door neighbor – widowed 18 months ago (pancreatic cancer...

The Garbage Queens

by JimBob44 on Jun 8, 2020
Novels and Novellas

*Author's Note: Any and all persons engaging in any sexual activity are at least eighteen years of age. Disclaimers: This story has been edited by myself, utilizing Microsoft Spell-Check. You have been forewarned. There are mistakes; expect to find many of them. Chapter 20 "Really? REALLY? You'll let that brat put her booger infested hands on you, but I...

Prankster Ch. 08

by Paris Waterman on Sep 15, 2017
Group Sex

Late the next afternoon, Tony met with Barely to set things up for that evening's session at Crazy's place. "You know," Barely said, "I came across something last night when I was editing the tapes." "What was that?" Tony asked. "It's best I show you, then you tell me if you want it back in. It was me, I'd keep it out. I just don't feel comfortable with...

Simply Friends

by puzziboi on Mar 30, 2020
Transgender & Crossdressers

"Hey, Eli," the common law wife and mother of two spoke into her cell phone. She paused a moment then said, "We're around the corner for your place." Valencia Williams ended the call. She looked at her husband, Durrell, who was driving the cash rental car. It was a metallic white gold 2010 Volkswagen Passat station wagon. Durrell, at 34 years of age, was a...

The Society Ch. 02

by Barno on Sep 13, 2017
Transsexuals & Crossdressers

The French maid outfit was just a little loose. I was borrowing Corinna's dresses until I was fitted for my own uniforms and outfits. Actually Corinna and I were close to the same dress size yet our body types were different. I had a more feminine build with flared hips and hard round buttocks while Corinna's more muscular build created a deeper V shaped upp...

Auntie's New Tenant Ch. 03

by BrettJ on Sep 15, 2017
Novels and Novellas

For some young men, hearing that they would have to move in with their aunt might have seemed like a death sentence. For young Daniel Talbot, it had been nothing of the kind. In fact, it was almost the polar opposite - it was the start of an entire new life, one filled with unending joy and incredible sex. Only a short time after moving in with Katrina Pear...

COVID-19 - Campus Closed

by puzziboi on May 12, 2020
Transgender & Crossdressers

"Momma, they're shutting down the campus on Friday," lamented the college junior. "I figured they would. I've been on the phone with Aunt Nettie. You can stay with her for the time being since she's close." "Doesn't she already have a ton of people living with her." "Patrick..I mean, Prisha," she swallowed hard. "There's just not a lot of options right no...

A Sissy Saga Ch. 17

by Snurge on Sep 15, 2017
Novels and Novellas

Titled people were a weakness with Miriam Hancock. She frequently spoke of them with harsh condescension, but the snob in her heart secretly rated them higher than wealthy businessmen, and so it was with some delight she agreed to the visit of the ennobled Marchioness of Wiggleswick. The delight had doubled when she discovered that in both Debrett's Distingu...

Kate's Mom Comes To Visit Ch. 05

by Catytheghost on Sep 16, 2017
Transsexuals & Crossdressers

Part 5 A wedding to plan Carmen OK, dinner was a total surprise for me, that's for sure: Ally and Kate getting married, and Mary putting the fear of the Gods into Maggie. Now that really was a shocker, as Mary gets along with everyone. I even asked her about Lady Jenna using me for her pleasure, and she said, "Honey, you just please her and all will be goo...

A Sissy Saga Ch. 02

by Snurge on Sep 15, 2017
Novels and Novellas

When Jennifer went out onto the terrace William was nervous but relieved to be with someone his own age and gender, even if that person had been sissified just like himself. The two eighteen-year-olds regarded each other and their feminine attire silently for a moment before Archie at last broke the tongue-tied awkwardness. "Better make a start," he said,...