Sissy Boss Stories

46,032 results
Orientation
Length
Source
Infinite Scroll

My Black Beauty

by ianarm on Dec 31, 2019
Erotic Couplings

A few months ago my boss invited me to spend a weekend at his ranch along with the rest of the IT department. His ranch covered almost ten acres and what beauty it was too. I felt so relaxed and even had a room all to myself. In total there were nine of us invited to the ranch and my stay was very refreshing. I got the opportunity to relive some of my childh...

Here Comes the New Boss

by YourObedientServant on Aug 24, 2020
BDSM

I stared worshipfully up at her from where I knelt at her feet. I had hired her six months ago to manage my restaurant, and in three she had tripled my business. In four she had seduced me. In five, she convinced me to let her tie me up... and a month after that I was her slave. Horny and desperate and eager to please. Even in professional contexts, I defer...

Relaxing after Work

by Delilah_Morgan on Dec 23, 2019
Loving Wives

I'm a lucky man, I know that. Been married for twelve years, got two kids, and a job that keeps the roof over our heads and food on the table. Not to brag but I make enough working my stupid cubicle that three years ago my wife could become a stay at home mom. May not seem like much to some but in my family that's huge. Still, on those rough days when your...

Little Man Pretty Girl Ch. 01

by Scribler on Sep 12, 2017
Transsexuals & Crossdressers

Why I went to the club I didn't know. I guess it was for something to do. I had been alone for so long that I needed the company of others. Even if they did treat me with disdain I still needed to socialize with other humans. You see I live alone and I work from home. I do security consultant work for companies that are having trouble with hackers. Recentl...

Little Man and the Stupid Bitch

by Just Plain Bob on Sep 26, 2017
Loving Wives

I guess the first thing you need to know in order to understand what happened is background. My name is Robert Daltry; I'm twenty-seven years old and I work as an aircraft mechanic for a major airline. I'm five foot six, about a hundred and sixty-five pounds and I'm in great shape thanks to daily runs and work outs at the gym. I've always been small – at le...

Frozen Treats

by MistyMorgan on Sep 13, 2017
Loving Wives

Last week James came home from work tired and frustrated. He fixed us some dinner and we sat quietly for about fifteen minutes before he spoke. When he did his voice was low and nervous. "I have to go to Baton Rouge for a week long conference. I would like for you to come with me," he said softly. "When are you going?" I asked. " It's a week and a half aw...

Dragon Clans Bk. 01 Pt. 08

by Vjax on Sep 19, 2017
Novels and Novellas

Nicolas reviewed the photographs for the third time since Selene had emailed them. Pausing on the last one, showing Michael slumped on the ground. Nicolas gave a derisive laugh, 'is this all there is,' he thought as he rose from his desk and walked out onto the balcony. For so many years Nicolas had worked to bring order to the world, his vision of an orde...

Blind, Deaf & Dumb for Erections Ch. 01

by SusanJillParker on Sep 12, 2017
Loving Wives

No longer able to get it up, a man masturbates over sharing his wife and watching. Jim sat in the darkened corner of his bedroom more contemplating his future with his wife, Natalie, than contemplating about masturbating while watching her having sex with yet another man. If only his neighbors knew what was happening behind his closed, bedroom door, he wond...

Moving House

by Sexysarah7 on Sep 26, 2017
BDSM

Author's Note: This story is complete fiction, and is completely unrealistic. It involves some bizarre stunts, which I really enjoyed making up and writing down. If you don't like stories of cuckold husbands being hurt by multiple well endowed lovers, then DON'T READ IT! Last week hubby and I moved house. We went from a very nice house in Surrey, to an even...

Enough Wimps!

by Scorpio44 on Sep 12, 2017
Loving Wives

About a year ago I found a web site filled with erotic stories and since that day I have spent quite a few hours reading the stories. I have been quite impressed with the imagination of some of the writers. I read and enjoyed many of the stories, believing that nothing like the things they described actually happens in the real world. I was wrong. My wife...