Aunt Sissy Stories

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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...

Sissy Maid to Be... Ch. 03

by missjennymaid on Apr 8, 2019
Transgender & Crossdressers

I would recommend reading the first chapters to get to up to speed on the story, but if you want to start in the middle... Jeremy: A married crossdresser who loves to live out his crossdressing fantasies with his supportive wife. Lizzy: Jeremy's wife who participates in his sissy maid desires every other Friday when they have the place to themselves. Jere...

Auntie's Panties Ch. 02

by EasilyConfused on Sep 14, 2017
Transsexuals & Crossdressers

Jake sat in his bath. The heat from the water made the room feel like a sauna. The main mirror was steamed over and Jake could feel perspiration on his brow. His body tingled from the heat. Pores were opening and cleansing. His body was also tingling from the lotion that his Aunt had added to the water. The lotion was intended to remove his body hair. Not th...

A special Christmas

by Chuveiro on Dec 17, 2018
Fetish

It was already December and I was home alone. Mommy had gone shopping all things she would use on Chiristmas dinner, which would be at our house. I went to my room and got my clothes and toys. I was a sissy, but nobody in my family knew that. The only person who lived with me was mom but she was so old she couldn't notice anything. I dressed up and started t...

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Auntie's Panties Ch. 03

by EasilyConfused on Sep 14, 2017
Transsexuals & Crossdressers

The air in the lounge was filled with both aromatic and visual sexual pleasures as Phoebe continued to enjoy the skill with which Anna ploughed her Mistress's slit with her tongue. Phoebe's hands were on Anna's head ensuring that the penetrations from the latest addition to her brood were deep and long. Anna made muffled sounds as she battled for air whilst...

Trained by My Aunt Ch. 01

by Misslexia on Aug 18, 2017
Fetish

It was my Aunt's suggestion that, when I left home and got a job, I moved in with her. Although my job was a few miles from her house, I had my bike and the renting a flat in the city was not an option. Secretly I was delighted. Aunt Suzy was my mum's younger sister, jokingly described as an 'afterthought' or an 'accident'. Fifteen years younger than my mum...

Sissy Maid Son Pt. 03

by Robyn228 on Oct 21, 2019
Transgender & Crossdressers

Note: This story is entirely a work of fiction, and should only be viewed as a fantasy. Any similarities to actual events or people are entirely coincidental. All characters are over 18. ***** Peter stood there looking at the black stilettos, with so many questions on his mind. He wondered why his brother would ever own stilettos, much less why their mothe...

Vacation with Aunt

by Alice Dragonslayer on Mar 19, 2018
Transsexual

Hello, you are 18, semi long black hair, feminine build, shy and submissive. You visit your Aunt Katy (looks like Katy Perry) for the summer. She may or may not have a daughter. She has a very feminine house and has a pink car. She dresses pretty hot. Her breasts are perfect and she's in her 30's. She doesn't have a husband and stays in an apartment with one...

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The New Swim Team Pt. 06-07

by Doubleganger on Sep 19, 2017
Exhibitionist & Voyeur

Disclaimer: I began writing this seven part saga in late 2015. As the old saying goes; all good things come to an end. Here are parts 6 and 7. I hope you enjoy reading them, as I did writing this chronicle. 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...

My Summer as a Girl Pt. 07

by RightButSexy on Feb 25, 2019
BDSM

Hopefully you will read the earlier stories about how I came to live with my aunt and how I came to dress up as Molly. OK, who am I kidding - How I came to be Molly. But in case you're rushing - I'm a college student who came to live with his aunt. Having no money, we started doing video dates, where I was Molly, a red-headed girl, not Brian, a brown haired...