Sissy Boss Stories

46,032 results
Orientation
Length
Source
Infinite Scroll

Daily Grind

by darkgoddess2478 on Sep 12, 2017
Illustrated

Every day means the same old thing. I drive to work in a jam of traffic and by the time I get there, my nerves are already clinging for life. I work as a glorified pencil pusher with the nickname of secretary for one of the several CEOs of the company. My day is the same thing day in and day out. First, check company email and respond to each one, making sur...

Fairy Tale in an Ambulance Pt. 04

by KissedAFrog on Aug 30, 2017
Erotic Couplings

It had been days since Hannah had seen Shaun. They had talked almost non-stop since the fire department, but no matter how hard they tried they could never get together. Their other relationships had began becoming more apparent. Her boyfriend had been getting more and more jealous by the day about her constant texting. He had been picking fights and sneakin...

Getting Rid of the Blues Ch. 08

by Realistic Angel on Sep 14, 2017
Erotic Couplings

The saga continues! As always, your thoughts and ideas are appreciated. If you have any situations or types of people that would spice up the story, let me know. Enjoy! * Alex spent the whole day Saturday in funk. She desperately needed her phone, but she was scared of going back to Jake's pub. She was scared of what might happen if she went back there....

The Benefits of 'Overtime'

by ChocolateKisses on Sep 12, 2017
Interracial Love

I am the Accounts Clerk for a small firm where the atmosphere is informal and the staff is pretty much on a first name basis. I generally enjoyed working here, but today wasn't one of those days. It was 6 pm after an already long day. Numbers, numbers and more numbers. They had me in a daze. We were approaching the end of the Company's financial year and not...

Kira's First Errands Ch. 02

by dan57 on Sep 17, 2017
Loving Wives

It had been six months that Dan, Tom and Kira had initiated this bizarre game of part time marriage, at Dan's whim. They had been on vacations in Florida when he made a joke telling Kira she acted as the wife of their close friend Tom. He was still a bachelor and, from time to time, she helped him for his laundry, sewing back buttons, shopping for him or occ...

Blackmailed By My Secretary

by hsvhobbit on Sep 13, 2017
BDSM

My job is pretty much a dream one. I'm one of a team of representatives assigned at one of my company's subcontractors. We smooth out any production problems before they get to the main office. As long as things go smooth, it's as cushy a job as you can get, but if things go bad, we take a lot of heat. We're assigned to a good company, few problems come up...

Making Amends Ch. 02

by Headhuntertales on Sep 13, 2017
Loving Wives

Jim was almost ready to reach out and touch Sally when she danced away and repeated her performance on the other three men. After each man had gotten an eyeful of the naked wife, Sally stopped and took another glass of wine. "Is this just the way it was for my Bill?" Sally asked. The wine, jealously and feeling of betrayal still working on Sally's usual shy...

Skills for the Position

by snobaby22 on Sep 14, 2017
Erotic Couplings

After searching and hunting for a new job, I finally got a call from a man named Mr. Adam Reinhardt, about a month into my search. He owned a small advertising firm, Reinhardt and Associates, and was looking for a secretary to help out around the office with the usual. Considering that I have several years experience with this type of work, I knew there was...

The Client

by Ben Nichols on Sep 12, 2017
Erotic Couplings

Her eyes burned into the back of his head as he walked away. How could any one man be so arrogant, so cocky, such a royal prick? That he had the power and position to get away with it only made it more frustrating. No one had the right to speak to another human being the way he just spoke to her. She was not accustomed to being treated in this fashion, moreo...

The Sisters of Mercy.

by ambiguityperson on Sep 13, 2017
Erotic Couplings

-inspired by the Leonard Cohen song of the same name * The thin line of asphalt stretched into the distance, disappearing at the horizon but still stretching, unseen, into what could possibly be an eternity of dry, dusty desolation. The sun was going down. Soon, he would have to turn off, find a place where he could park, invisible to the cracked, virtuall...