Auntie Sissy Stories

8,340 results
Orientation
Length
Source
Infinite Scroll

Kinky Dentist Sian And Sissy Rachel Ch. 02

by Sissy Adele Howells on Dec 12, 2018
Fetish

I awoke at 5am on a cold, Saturday morning. Dreaming of my sexy dentist all night made me feel so kinky. The thought of shagging Sian Harris made my cock have a permanent erection. I was surprised to hear the bell on my front door so early. I decided to open the door wearing my pretty, pink dressing gown. It was my cousin Susan Beynon aged 37. Her flaming, r...

Three Old Tarts and a Sissy Ch. 02

by Sissy Adele Howells on Oct 13, 2017
Fetish

We all sat in the living room of Diane Bennett's house. I was proud to be sissy Charlotte Church. My wife to be, Joan Harries sat naked on the sofa next to Sonia White. Joan's body could have done with being ironed over, but for 70 years of age, she had a fantastic figure. Having kinky sex with Joan, two hours earlier was the icing on the cake. For her to ex...

Planet Pretty Sissy

by Hayleykim on Aug 18, 2017
Fetish

Louise ordered her kinky slave to stand naked in front of her. He was in his late forties, about eight years older than the pretty blonde, who had him like putty in her hands. "Welcome to your ultimate fantasy. We don't take passengers on this parallel planet. Is that perfectly understood?" said Louise. "Yes of course, Louise," he replied in a stuttering w...

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 King's Touch Ch. 00

by dragontatto on Sep 19, 2017
Sci-Fi & Fantasy

Thanks to all of those who have been patient with me and the delay for returning to Venus and these wonderful characters. I hope you enjoy and wish me the best during the Nanowrimo contest, which is what I'm writing this story for. * Sandova, Venus, 2108 "Come out child." Clara's gaze was steady on the spot where she was certain she had a little spectator...

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...

Auntie Jean Drummond Lloyd Ch. 2

by Sissy Adele Howells on Aug 31, 2017
Fetish

Auntie Jean sat on a chair behind the bar. She pulled me onto her lap, cuddling me against her orange dress. Kimberley had gone over to her husband. Kevin had his arm around her. They both were kissing, to show they were happily married. Auntie Jean stroked my hair. Karen had left the room, but soon returned wearing a black, lacy dress. Auntie Jean farted qu...

Trapped as a sissy in a fanasy world.

by Duke Montefort on Nov 14, 2019
Fetish

Eugene has an obsession with video games almost shutting out his friends and family. Feeling they have no choice the family begs a videogame company to help them bond with him. The company agrees they test the family can beta test the game, and bond. They even promised that he could not come out until he had properly bonded with each family member seprately....

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Maid in Heaven

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

Many years ago my Mum worked as a bridal consultant for a well-known wedding dress shop. One day to get off College so I could bunk rugby I complained of having a stomachache. The situation was ridiculous. I'm a young man of 19 who had volunteered to continue with my education and study accounts so why the authorities insisted I had to do Rugby as part of th...

A sissy visits the Headmistress

by maturesubmale_for_F on May 12, 2020
Transgender & Crossdressers

1. Miss Stern delivers both punishment and pleasure I knocked timidly on the heavy door and heard Miss Stern's voice from within, commanding me to enter. I slowly opened the door and walked into the presence of my Headmistress. She was in her mid-fifties and sat behind her massive oaken desk as I came in, studying a heavy file. I stood still just inside the...