Sissy Babysitter Stories

9,467 results
Orientation
Length
Source
Infinite Scroll

The Babysitter

by Lonedaddy on Sep 18, 2017
First Time

My wife and I live in the valley, just outside of the city. We thought it would be a nice place for a younger couple to raise a family. We bought a two story house with an attached garage. It needed a few minor cosmetic repairs, but nothing major. After some paint and building a new deck out back, it looked really nice. My wife Rose, is the manager of one...

The Director and the Babysitter

by dramatic1 on Sep 14, 2017
Mature

I wouldn't have fucked the hell out of our babysitter if she didn't belong to my gym. See, our babysitter, Stacia, has always been what I would consider "cute." She wears baggy clothes, even in summer, and so I never really got to see her body. Our kids loved her to death. She would come over, my wife dealt with her most of the time, and I just paid her at...

Mrs Andrews Disposes Ch. 03

by lesliejones on Sep 17, 2017
BDSM

Ch. 03—Friday Night Readers will find themselves better equipped to enjoy this story if they have read the first two chapters. This story sometimes deals with bathroom behavior so those offended by that should move on. All characters are 18 or over. By Friday evening, Charlotte Byers had assumed total control over the lives of Karen and Andrea Andrews du...

Sissy and Paul

by slowhand1234 on Apr 22, 2019
Exhibitionist & Voyeur

Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married sev...

Simon Sissy Slave Ch. 04

by Timewarp10 on Aug 20, 2019
BDSM

Simon staggered in for work the day after the slave auction, his body stiff and sore. Mr Berne and the others in the post room were shocked to see the sissy's bruised and lacerated buttocks. Barry's stiff cock betrayed his feelings; whipping and torture excited him. His sadistic nature relished the thought of thrashing Sissy senseless. Sissy was his fuck t...

Sissy Boy Secretary Ch. 07

by Hotenuf4u on Sep 19, 2017
Fetish

Elaine and Tammy had been friends before the unfortunate divorce and still now maintained a good friendship. After all, it was Elaine that helped her get a job as an executive secretary during all of her school breaks, including throughout the summer break. Tammy had known that the company Elaine got her the job at was also Elaine's biggest competitor in the...

Service Day 01: Sissy's Breakfast

by SissyHubbyD on Aug 7, 2019
Transgender & Crossdressers

His alarm goes off at 6 AM that Saturday. On any other Saturday he would ignore the alarm and sleep in until 10 or 11, but not today. Today is Service Day, and he couldn't be happier about it. He gets out of bed quietly, careful not to wake his wife as he does so, and tiptoes out of the room and down the hall to the empty guest room. His outfit for the day...

Simon Sissy Slave Ch. 03

by Timewarp10 on Jul 30, 2019
BDSM

Mr Berne watched with satisfaction as the sissy paraded in the post room. Sissy walked gracefully in high heels. His ballet training made it easy. He knew how to walk like a woman. He had practiced, and he could walk with a book balanced on his head. It gave him poise, and the high heels gave elegance to his calves. The skirt was short enough to look slutty,...

Cockland Island Pt. 05

by Sissyhalo1 on Feb 3, 2020
Transgender & Crossdressers

Waking up like that I think my brain wanted not just more but to place everything that happened to me in an order that I could handle. So deeper into sissyness it was. Playing with my butt plug until I was edging myself and losing myself in it. Abby showed up. Rolled a joint and watched me. "C'mon Nikki, up, let's get you fed and working out." It was h...

Don't Cum in the Babysitter

by Imyourdaddy2nite on Jan 22, 2019
Erotic Couplings

My wife and I were college sweethearts that met our junior year. We took an instant liking to each other and the sexual chemistry was amazing. We had a lot of the same values and morals, but didn't agree with each other on everything, but we could both argue our viewpoints and then agree to disagree. I'm not going to lie; the sex after the more spirited deba...