Sissy Boss Stories

46,032 results
Orientation
Length
Source
Infinite Scroll

Temptations

by Winterfrog on Sep 17, 2017
Loving Wives

Many thanks to Jedbeaker for the editing of this story. It happened on a Friday afternoon at a crowded supermarket. No parking spots were available until I saw a car leaving the lot and a small red Honda waiting for taking it, but as I was in a better position, I quickly took it. Not a polite thing to do and the good-looking young woman in the red Honda o...

A Bubble Bath Warm-up

by Brandy Chase on Sep 12, 2017
Loving Wives

Terri Phillips was going through her normal afternoon routine, preparing for her husband's arrival from work. He always liked her to be waiting for him when he came home. A little kiss to show affection and a martini waiting for him was his idea of wifely duty. She loved Paul so much; she had no problem with this old-fashion idea. So, in her best wifely mann...

Older Than My Mother

by LynnGKS on Sep 15, 2017
Humor & Satire

I'm in bed fucking this bitch and she is older than my mother! Hell! Twenty years older than my mother. Flo claimed to be sixty but I'm sure she shaved a good five, maybe even ten years off her age. The bitch might actually be seventy! Seventy years old and still horny as a mountain goat. Hormones I guess. I just kept pounding away. Her pussy felt okay and...

I Want Your Love

by beautyzdizaster on Sep 13, 2017
Interracial Love

Okay so this is my first time ever posting a story here on literotica. I'm excitedly nervous about this. I don't have an editor yet so I'm sorry for all the errors, I tried to catch them all. I hope you all enjoy this first chapter. Hugz and kisses @--'---,---- beautyzdizaster ****Lalaine's POV**** Yes! My boss decided to let me go early and to enjoy the w...

Life in a Small Town Ch. 01

by The Hungry Eye on Sep 17, 2017
BDSM

It would have been a working class neighborhood, except hardly anyone who lived there worked. It was built in the prosperous early sixties, a suburb of a large Southern city. It was a bedroom community. About ten miles out from the city. The low slung ranch homes didn't look too prosperous now. The trees and shrubs planted by the builders were now tall and o...

What Life Throws at You

by griffin57 on Sep 12, 2017
Transsexuals & Crossdressers

Kind of funny what life throws your way. Some times fate can be a fickle bitch. My name is Rick Tyler and I'm a cop. Well, detective actually. At least I was until 30 seconds ago. I dropped my badge and gun on the desk of the idiot that pretended to be my boss. Baker looked at me with distain. We had disagreed on almost everything and I was tired of his bull...

The Nursing Home

by Mysteria27 on Sep 16, 2017
BDSM

Working in a nursing home sometimes can be very depressing. Most of the residents have long term illnesses and are either bed ridden or are confined to wheel chairs. There are many different kinds of people that work at a nursing home. There are nurses, doctors, aides, dietary aides, maintenance people, and recreation coordinators. The nursing home is usua...

DotCom Ch. 01

by mannytheman on Aug 19, 2017
Exhibitionist & Voyeur

I don't know how I got into this. Well, OK, I know how. I just don't know why. Yeah, I know why, too. It's just the way I am. I guess now's the time to say I couldn't help it, but that wouldn't be true, either. I mean, I don't just strip off my clothes and show my body to anybody. Not that I don't like to; I've been flashing since I was twelve. By now, I gue...

New Straitjacket Tech for '63 Pt. 01

by Piratestan on Sep 17, 2017
BDSM

It was a Wednesday, I think, when my boss asked if he could tie me up. Oh get your mind out of the gutter! It wasn't anything like that, nothing kinky, untoward, or inappropriate. See, I work as a secretary for Globe Publishing, the premiere publisher of detective, real-bondage, and escapology magazines for the contemporary, 1963 newsstand market. We don't...

Atrium of Hell

by MasterforMad on Sep 16, 2017
Sci-Fi & Fantasy

First attempt in English. Hope you enjoy my freakish fantasies. ___________________________________ You are bored. Everything around you appears to be boring. You sit at your desk and wonder whatever you might have done to deserve such a boring time. Your boss is on the light side of the Planet on some boring conference. A meeting with those stuck up angel...