The Boss Stories

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Josie & Gina's City Adventures Ch. 02

by deepemerald on Sep 1, 2017
Group Sex

Chapter 2: Business meetings with the boss Josie and Gina had been in their new job for a month. Gina had to be in the office at 7 a.m. to suck the boss off as he arrived in the morning. She then sat around all morning, bringing the boss his morning coffee and some pussy juice if he asked for it. Josie came in just before the boss’s lunch break at 1. Then h...

Fucking My Boss

by dpingjessie on Sep 11, 2017
Mature

It wasn't right away that I fantasized about my boss. When I was interviewed by her for the job I ended up earning, the thought of having sex with her never remotely entered my mind. Even so, when I did develop those erotic feelings, I never sought anything really passionate or at all romantic. I didn't so much as want to even kiss her. By that point, all I...

Best Boss Ever

by litaz on Aug 19, 2017
Exhibitionist & Voyeur

My name is Donna and I'm an associate in a respectable small-sized law firm in the downtown of a major city. My boss, Larry, is a very charismatic and dominant alpha person that everybody loves and adores. He is very horny and voyeuristic so he hired a young secretary, as horny and voyeuristic as he is. I'm not sure how they found each other, but the firm h...

Chrissy's Mistake

by zbrewster on Sep 17, 2017
BDSM

It was the best of times; it was the worst of times; very much depending on your position in the Chattersby Company hierarchy. From the management point of view, it was the best of times. After 10 years of Republican rule Washington, DC, business practices had run amok. The government worked very hard to favor business and business had taken great advantag...

Job Interview, Anal Intentions

by HeyAll on Dec 9, 2019
Anal

Hannah Chen wore her version of a power suit -- a cute polyester blouse with a pencil office skirt and heels -- as she made her way up the building. This was a nerve wracking experience, despite her outward confidence. Last week she had interviewed with the hiring manager. Today she would be meeting with the boss. When the elevator door opened, a rush of ad...

An Office Surprise

by sexpanthers69 on Sep 14, 2017
Erotic Couplings

You're working for an investment banking company in New York. Your job is to manage business relations with companies abroad - making deals, contracts, etc. You're still pretty new, but experienced and confident that you'll impress your boss. You come to work in a short pencil skirt and a tight blouse. The short skirt is a disciplinary policy, but you're not...

April Fool Office Sissy

by lululuvsblack on Apr 10, 2018
Transsexuals & Crossdressers

"Dear Colleagues This week, in order to help with our efforts to raise money for charitable causes, we have decided to mix up our usual policy of dress down Fridays. This Friday we are instead instigating a "dress up Friday" in which staff are strongly encouraged to come to the office dressed in the office attire of the opposite gender (that's suits and tie...

Blondie Balls My Black Boss

by raven2222 on Sep 13, 2017
Interracial Love

Two years or so after my sexy little blond wife got her first taste of the special eroticism of interracial sex, a significant new turn of events began when my boss flew down south from Chicago to spend some time working with me. I had an idea that the real purpose of his trip was to have an excuse to visit his aunt, which he pronounced ‘awnt’ in his hometow...

Working Hard for Her Job

by fuzzie_writer on Sep 11, 2017
Transsexuals & Crossdressers

Peeta smoothed her skirt down as she sat back at her desk, glancing at the clock in the corner of her monitor. There were only forty-five minutes left until the start of the weekend, and she intended to make the most of it! A chime informing her of a new email interrupted her daydreams about two days off, and she opened outlook to find a message from her bos...

50 Shades of the Grey Mouse Ch. 01

by sarahcoulborn on Sep 13, 2017
Sci-Fi & Fantasy

The orange torchlight flickered as the inn door momentarily opened and then closed once more, the cold air reminding me of the skimpy outfit I was wearing. "Show as much skin as you can, keep them occupied for as long as you can," Mordern had said. I was doing my best but my money was running out fast, Boss Hrarg and his crew were better card players than I'...