Auntie Sissy Stories

8,340 results
Orientation
Length
Source
Infinite Scroll

Magic Dress - Veronica

by SlightlyRude on Jun 8, 2020
Transgender & Crossdressers

CHAPTER 1 My name is Vernon. I was 27 years old and I didn't know what to do. It was six o'clock and there was no dinner. Auntie Monica had not come home from work. I can get a drink myself so I had some cola. It got dark and no-one closed the curtains. After not having dinner I went and played on the games console as usual. I wasn't sure if it was allowed,...

Ch. 05 Angela's Confession

by Bushman on Sep 17, 2017
Mature

I ON HAVING A FAMILY I'm Angela, a twenty-nine-year-old college professor with something to confess. I have witnessed a grace and an openness on the part of a seasoned married couple that I envy and would emulate. Granted, my dear step-brother Bill and I each developed a strong physical attraction to both Herb and Lianne; additionally, gaining their friend...

The Humiliation

by justincbenedict on Sep 16, 2017
BDSM

Kourtney, Mary Grace and Caprice crossed Buttermilk Boulevard over to Scarne Avenue, continuing their months long argument about which store is better-Betsy Johnson's or Ann Taylor? "My mom fucking goes to Ann Taylor." Mary Grace said heatedly. "Why would" "Who's that guy, that's Birdie, right?" Kourtney said, staring. "He's kind of cute, BIG." Kourtney s...

Dean returns home

by Lynxbci on May 12, 2020
Fetish

I went home to make sure my mum's old house was all tidy, as it was due to be sold, and I wanted it to be clean, so this could be done quickly. I had grown up at this house with my parents. It was a quiet cul-de-sac where everybody knew everybody and everything, it seems. (I had a good childhood, and, like many who grew up in the seventies, I was spanked at...

The Misadventures of Kate Pt. 02

by Catytheghost on Sep 16, 2017
Transsexuals & Crossdressers

Chapter 3 Kate the lab rat. The rest of the week was spent getting all my paperwork changed over to my new name, and yes, I have a middle name. It's Lucy after my aunt. When I talked to my mom that evening, I asked her if she had already picked out a middle name for me, but she had said no .I told her that it was going to be Lucy after Auntie. She broke out...

Rob Stays with Auntie Serena

by fantasyboy on Sep 12, 2017
Erotic Couplings

I'm 18 years old and I really can look after myself but my mum insisted I went and stayed with some neighbours while she was away for a few days. Mind you I didn't mind as it was with Auntie Serena and Uncle Mark. They weren't really my aunt and uncle but as they were the same age as my parents I was bought up to call them auntie and uncle. You see Serena...

Christmas Cracker

by Tomsparty on Sep 18, 2017
Transsexuals & Crossdressers

It was Christmas 2005. I sat on the lounge floor with my sister surrounded by family and friends. The Christmas tree sparkled and after our dinner we had gathered round the tree to open our presents. As I felt Aunties soft parcel Mum whispered in my ear. 'Be grateful for what ever you receive. We all know Aunties a bit kooky. I've no idea what she's bought y...

Shawn Ch. 01

by Ariel797 on Sep 17, 2017
BDSM

She became vaguely aware of lying on a bed, and movement. The movement, she began to realize, was due to her being in some sort of traveling mobile home, which was currently traveling. The vehicle hit a bump in the road, and she heard the muffled sound of a woman complaining. This was followed by some laughter, then the drone of the wheels on the road took o...

Lady Bird

by N_Deavours on Sep 15, 2017
Fetish

A man is ordered to present his charms to a wealthy woman. "Excuse me Ma'am." "Yes?" Even though he was enormously agitated by the sudden turn of events the strong suppressant still worked efficiently, allowing for only an indistinctly red shade to be visible in his handsome face, noticeable only by the most attentive of aficionados. Only moments ago his...

Auntie Em Ch. 12

by MILFhelper on Sep 15, 2017
Mature

Summertime was over and I was in the middle of my first semester at Parkston Junior College. Carrying a full load didn't give me much time to make the trip back and forth from Auntie Em's so with Mom's and my auntie's financial assistance, I was able to rent a small studio apartment just a couple of blocks from the college. Made for some lonesome nights. I...