Auntie Sissy Stories

8,340 results
Orientation
Length
Source
Infinite Scroll

Torrid Lady Victoria Ch. 04

by 123z on Feb 12, 2019
BDSM

Note- Dedicated to Mrs. 123z. Thanks for the ideas. xxx Kent, 1921 x Jeremy Ponsonby Smythe had been delighted to hear that his mother had acquiesced to his wishes that she teach Cynthia how to ride. He was the son of Lord and Lady Henry Ponsonby Smythe of Whitstable in Kent and was hard at work in his attempts to become a Member of Parliament like his f...

Letter from Mount Chapel

by justincbenedict on Aug 20, 2018
BDSM

Dear Shoeblossom, I got into the sweetest deal. I agreed to play femdom games with my geeky male roommate. He owns the house and was renting me one of the rooms, and like so many nerds, he has the hots for us tattooed, embroidered jeans types, I guess. Oscar is the sweetest guy, you know the kind. Comes to try and ask you out when you're smoking in the sch...

The Bad Teddy Bare

by christinecuddlewell on Sep 16, 2017
Fetish

Good neighbours introduced me to Literotica, it's been a useful source of inspiration. As a way of saying thank you I have become a member and collated one of our own stories for you. We do hope that you find it enjoyable. * I'd pulled up the weeds, trimmed the bushes, clipped the hedges and was relaxing in the garden with a book resting on my bosom and a...

Lucy: Speakeasy Visit

by caprine on Aug 18, 2017
First Time

[This is a work of fiction. The story is an unadulterated and unabashed attempt to tickle male fantasies and perhaps some female fantasies as well. As such, the story may or may not totally conform to reality. With some occasional historical exceptions, all other places, events, and persons, are entirely fictitious and any resemblance to actual persons, livi...

Exciting Auntie

by Learningfast on Sep 19, 2017
Fetish

Auntie Barbara had been married briefly many years ago, when I was a child but her husband had left suddenly with the parting shot to my mother and other members of the family, "She's impossible. No man could give her what she wants. Believe me; she'll come to a bad end. One day, some man will do what she wants and it'll kill her." This was reported to me a...

Aunt Matilda to the Rescue

by mollycactus on Sep 15, 2017
Toys & Masturbation

Author's note: I was in a quandary as to what category to use for this one - apologies in advance if anyone feels misled. ***** In this otherwise dismal start to summer, Dick finally saw a tiny bit of happiness. His 'Aunt Matilda' was due for a visit. She wasn't really his aunt, of course - she only had one living relative, her niece Sara. But his mom, Jea...

Leather and Lacy Ch. 03

by mollyj on Sep 14, 2017
BDSM

The pain of the stinging lashes from the light springy whip on her breasts roused her to consciousness. In a state of semi-consciousness, she tried to cover her breasts with her hands, being unable to move her hands brought a moment of panic, bringing her eyes wide open. Ellen was kneeling behind her head smiling down at her, holding her hands in bondage by...

The Vita Tanks

by sarahstone on Sep 14, 2017
Exhibitionist & Voyeur

Background: In the year 2014, the Universal Criminal Reform Act had been ratified as a response to ever growing crime rates around the country. New and unusual punishments had been contrived and the time-consuming court system done away with. Police could arrest without warrants and for various breaches which before would have been considered only minor. Ju...

My Sexy Changes Ch. 04

by TaraJaden on Sep 16, 2017
Transsexuals & Crossdressers

At this point I wasn't the same person I was when At this point I wasn't the same person I was when I first entered the home of Auntie Louise and Alex. I was a person let loose and excited! Auntie Louise straightened my dress and looked me over. "I'm going to give Alex some money and he'll take you wherever you'd like to go." she said. "Your hair looks real...

Aunt Tina Ch. 1

by 4U2njoy on Sep 12, 2017
Mature

I hated the thought of staying with Aunt Tina. She had always seemed so distant and aloof. She was mom's older sister and had been single for over 10 years. Her husband left her for a younger gal and had moved away. She never seemed to date and in fact seemed prudish. Mom was going on a business trip and I was to stay with Tina for a week. Being it was summ...