Sissy Anal Training Stories

79,685 results
Orientation
Length
Source
Infinite Scroll

Submissive Blush Ch. 01

by slutkimmi on Sep 17, 2017
BDSM

A few months ago, Molly accidentally discovered a BDSM website and was incredibly shocked at the pictures that popped onto her computer screen. This website had images of women being used and abused in various positions by various men and women alike. Some would think this website to be degrading and that was Molly's first thought. But, like a train wreck, s...

Pool Passion

by purpledreamweaver on Sep 12, 2017
Group Sex

Jessica stirred as a beam of morning sunshine fell across her sensuous face. As she awoke she stretched her arms, causing the light sheet, which barely covered her naked body, to drift to the floor. Her eyes opened to the sight of her lightly tanned torso reflected in the large ceiling mirror. Her bright green eyes surveyed the taut 36D breasts with the lar...

Intimate Interview

by sarahsucks on Sep 16, 2017
Group Sex

My name's Sarah and I am a twenty two year old nanny. I'd like to tell you about an interview I've just had for a job. I replied to an advert placed by an American couple requiring a nanny for a period of time whilst they will be working in the U.K. I attended the interview held in a meetings room at a hotel in Cardiff. I met the parents Mr and Mrs Richmond...

Dr. Ruark's Problem Ch. 01

by Paris Waterman on Sep 14, 2017
Erotic Couplings

Doctor Robert Ruark peeled off his surgical gloves. The operation had been a difficult one, but after seven hours of grueling work he had succeeded in repairing the damaged heart valve. His brow was deeply furrowed as the tall, lean black man allowed thoughts of Alice to enter his mind for the first time since entering the operating room. 'What the hell is...

An Uncommon Massage

by tension1972 on Sep 1, 2017
Group Sex

I knock on the door and wait for her to answer. I know what I have to do as I look at my watch. I have approximately an hour before my clients come over. She answers, confused, "Can I help you?" "Mrs. Kelly?" I ask already knowing the answer. "Yes," she says. "What can I do for you?" "It's not what you can do for me, but what I can do for you," I smile, u...

Susan's Saturday Night Sex Ch. 03

by SusanJillParker on Sep 26, 2017
Erotic Couplings

There are no characters under the age of 18 in this story. All characters portrayed are over the age of 21. * No excuses and with her actions and inappropriate, sexual behavior already justified, what's good enough for older men to do with younger women is good enough for Susan to do with younger men. Paid to listen to the personal problems of mentally a...

Alyson's Adventures Pt. 06

by ndeavour on Dec 9, 2019
Group Sex

Alyson was at her wits' end. Life in her normal mode was becoming unreal. When she was at work, in her office, more times than not she had her door closed and locked, her skirt hiked up around her waist, her legs spread wide and a black, flesh-like dildo buried deep in her cunt. A window on her computer screen, superimposed over the spreadsheets and the mark...

Butt Fuck College Admissions

by homerdepot on Dec 2, 2019
Anal

Butt Fuck College Admissions Applying for an Ivy League college isn't as easy as it used to be. When John was eighteen all he had to do was get good grades, and play in the high school band. His high school band was a Class A band and won many contests. And playing in the band got him into a good school. Most applicants spend all their time studying, prep...

Poolside Trifecta

by rwcforfun on Jul 31, 2019
Group Sex

(All persons involved in sexual activity in this story are consenting adults, over the age of 18. Any similarities between this story and real life are purely coincidental). *** Faced with a possible layoff, my older brother accepted a sudden transfer to an office in Southern California; about 5 hours. Even with the enticement of a new home near the beach,...

Who a King Must Do Ch. 10

by FanFunatic on Feb 3, 2020
Celebrities & Fan Fiction

With every 'step' Maiev crawled through the streets of Stormwind the expression on her face transformed. More and more the arrogant and vindictive warden gave into her new tendencies, with the blush of an ecstatic exhibitionist getting properly abused by her master appearing on her face. Before she knew it, her tongue hang out like a happily panting dog's. A...