Aunt Sissy Stories

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Sissy Boy Chuck Becomes Just Sissy

by Krazy35 on Sep 14, 2017
Transsexuals & Crossdressers

A long time ago, I realized that I had a thing for women's clothing. I used to sneak into my sister, Jessica's room and get all dolled up in her clothes. She was a year older than me, but we were practically the same size. I got an incredible hard-on looking at myself in her full length mirror. I quickly undressed, put everything back the way I found it, the...

Emery and Alice

by fantaseeboy on Jan 27, 2020
Transgender & Crossdressers

When my uncle, my only living relative, passed away in his sleep from an aneurysm, I returned to settle his estate. I hadn't been in that part of the country for nearly a decade. I had been in middle school when my mother passed and I was forced to move in with my aunt on the opposite coast. My uncle had always been the oddball of my mother's family. But he...

A Sissy is Born Ch. 03

by 0ra11yfix8ed on Sep 16, 2017
Transsexuals & Crossdressers

As the title indicates there are two previous chapters. They are quick reads and even if you've already read them a quick review will enhance the enjoyment of this installment! * When the reality of my situation became clear I began to panic. I was seated in a woman's car dressed as a whore and I had no idea where my regular clothes or car keys were! I be...

A New Way Of Life

by blackdog27 on Sep 14, 2017
Transsexuals & Crossdressers

This story begins as many do. I stared to dress at an early age in my mom's things. Then I started to buy my own things as I got older; panties, bras and high heels. I was always small for my age taking after my mom, she was a small woman with a nice figure and so was I. I was only 5'4 and 110lb, blue eyes and jaw length blond hair. They loved me in high sch...

Sin of Vanity Ch. 01

by Belongs2Beth on Sep 12, 2017
BDSM

Author's Note: This story continues the story of Vance, Marcia's friend introduced in "Marcia Goes Back to School". I have made an effort to make sure that this chaptered story can be read as a stand-alone or as an episode in a continuing series of stories set in the fictional town of Torquay, Connecticut. Readers of my earlier works will be familiar with Mi...

OMG Mom!

by TheSecretlyUnlikelyDuck on Feb 5, 2019
Interracial

You pull into the driveway of 15 Preston Road at around 3pm on a friday afternoon. The light of the late spring sun pours over you as you come to a halt, parked behind the red BMW belonging to Mary Lange. She is a gorgeous blonde, who looks far younger than her actual age of 39, and is unarguably the head of the Lange household. You don't see her husband's c...

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Prankster Ch. 10

by Paris Waterman on Sep 15, 2017
Group Sex

Copyright © 2007 Many thanks to "Techsan" for graciously giving his time and effort to me in editing this and other stories of mine in recent months. As always, I appreciate your excellent support, thanks again, Techsan. Chapter 10 After letting the girls out of the van and escorting them into the warehouse, Tony made a couple of calls to old acquaintan...

Humiliated Sissy Husband Ch. 04

by rik581 on Oct 9, 2017
Transsexuals & Crossdressers

"A Second Helping" "Come along now Max, the guys will be here soon. You still have chores to do first before we are ready," Tonya called out from the open motel room door. The door was wide open as she waited for Max to get out of the car and come in. She had parked in front of the room but across the parking lot. It would be a good 50' walk for him in 6"...

Dry Valley Ch. 20

by RedHairedandFriendly on Sep 18, 2017
Chain Stories

Finishing Touches Three days had gone by since the break-in and attack on Jessica and Bailey. The women had been moved to the Walker Ranch, much to Missus O's soft muttering. But she knew the ranch was the place the girls needed to be to recuperate, she was however out there every day just to ease the burden on her friend Sissy, though Sissy didn't find it...

Aunty's Toys Ch. 03

by novelcriss on Feb 10, 2020
Transgender & Crossdressers

*Thank you for the votes and comments on parts one and two. Sorry I am so slow at this!* *** Simmy slowly came round. A fuzzy recollection of being carried to bed, spending the night half asleep, half aroused, snuggled between the two sexy plump women, hands stroking him throughout the night, feeling the slightly damp sheets where she had ... no he had or...