Aunt Sissy Stories

1,000 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com

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...

Candy's Day

by daisyboi_sissy on Sep 13, 2017
Transsexuals & Crossdressers

This contains Sissy porn and sex acts. Leave now if you should....everyone here is above 18 years old. Love ya! * I have always loved the feeling of something lacy or sexy on my body. I call it a passion of some sorts, wearing these things made me feel very special and desirable. I was raised by my mom and the closest family we had was my Aunt Trish and h...

Julie and Her Family Ch. 12

by Pretty_Sissy_Julie on May 4, 2020
Transgender & Crossdressers

My sister Becca and I were cuddled together in our nightgowns. Becca is 21 and I am 18. Becca is a beautiful and dominating woman. My name is Julie; I am her submissive sissy "sister." I have been living as a woman for weeks now since my Mum and sis decided I would look better as a woman and not my former life as a very effeminate man. At this point it wou...

A Sissy Saga Ch. 23

by Snurge on Sep 15, 2017
Novels and Novellas

Mrs Pardoe's heart pounded like steam-hammer as she made her way to her room. It had been such a long time since she'd had a young girl to herself, to take command of, to admire and to love, and she knew Mrs Amos's niece Lizzie was a real doll. On the way she passed the Joanna television-person ensconced with Gloria in the stair well of the third floor, bot...

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,...

Keeping My Sissy Secret

by VrijeVogel on Apr 24, 2019
Transgender & Crossdressers

YES! She really won't be home! I thought to myself as I cycled towards my house. My mother's car was missing from the driveway, meaning her plans for visiting a distant aunt hadn't been cancelled after all. Her wardrobe would be all mine for the entire weekend and I couldn't wait to try on her clothes. Aside from everyday clothes fit for a single mom, there...

Aunt Pamela and Leslie Ch. 02

by fantaseeboy on Jun 25, 2019
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** The days passed incredibly slowly after my meeting with Aunt Pamela. She dominated my dreams and fantasies. She often crossed my mind while in class and I would wind up with an erection and squirming in my seat with the memory of the spanking she'd given me and the reward I'd earn...

New Years in New York

by SissyAndi on Sep 13, 2017
Transsexuals & Crossdressers

Disclaimer: The following story contain explicit descriptions of consensual sexual activity and are not suitable for reading by anyone under the age of 18, or anyone offended by reading such material. These acts include bisexuality, cross-dressing and other fetishes and perversions. This story is pure fiction and fantasy. I encourage everyone to practice s...

The Chief Pt. 01

by Aunt_Joanne on Sep 14, 2017
Transsexuals & Crossdressers

When I was 19, I was still trying to figure out what I wanted to do with my life. I had just dropped out of college and was working construction in my home town. Construction work was hard, but I liked it. The guys I worked with were cool. It was honest work and it paid enough for me to keep my head above water. It was also a "manly" pursuit, and that was im...

The Chief Pt. 03

by Aunt_Joanne on Sep 16, 2017
Transsexuals & Crossdressers

Michael drove me into a part of the city on the edge of downtown that I had never visited before. There were lots of small shops, restaurants, and other businesses, mostly housed in older buildings. Some of the structures were a little run down, but the neighborhood was plenty lively. I saw lots of people out on the streets doing their errands and morning sh...