My Boss Stories

337,088 results
Orientation
Length
Source
Infinite Scroll

Broken Date

by BackDoorRed on Dec 24, 2019
Toys & Masturbation

Edited by slutkimmi * "What!" Ann snapped in surprise. "Work late again?" "Yeah baby, I'm sorry. I know we had the night planned. I just can't help it!" Terry said knowing full well he just hadn't stood up to his hyperactive boss. "But Terry! This is the third time this month you've called to break our date!" she said in disappointment. Pressing the...

Three is Company Ch. 02

by freeman64 on Sep 15, 2017
Group Sex

Frank and Joe reached the boss's beach house around 11 a.m. wondering what the big man had in mind. One could not turn down the invitation of the boss who was popular, generous and nice. Maybe, the boss would drink and play billiards with them, they thought as they approached the house. A voluptuous woman in her early 30s wearing a blue bikini approached th...

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...

Anna Nicole Smith & Jimbo Bond

by GeorgeTasker on Sep 19, 2017
Celebrities & Fan Fiction

Prelude Anna Nicole Smith walked through the doors into the concert hall. The marquee above read “Megadeth-Live Tonight Only”. Anna wore a pair of form-fitting black leather pants and a Metallica T-shirt that was several sizes too small and clung like shrink wrap to her massive breasts. Beneath the shirt she wore no bra and her nipples clearly poked against...

Smita's Mistake

by madhav on Sep 26, 2017
BDSM

My phone rings. "Hello, Smita here.... Yes sir, I'll be in your office in two minutes." His voice sounds irritated, even slightly angry. I feel nervous as I tread the corridor to his office. It is unlike him. He is always so kind. He never criticizes me and he always understands if I am ill or late. He is the perfect boss and this job is easily the best I ha...

My New Boss

by archyx on Sep 12, 2017
Transsexuals & Crossdressers

Bonjour, this is my first try at writing a story here. As I am french, this is my second language, so please be nice and leave positive comments. ***** I had a really bad week. Actually, bad would be an understatement, shitty would be more appropriate. Problems after problems had punctuated my Days. I managed to get a new job as an assistant executive at a...

Bound

by Ashson on Sep 17, 2017
BDSM

Finding a decent job in the current economic climate is not an easy task. That's the reason for my current job, working as a receptionist/ secretary for this small firm and it was a firm that wasn't going to get any bigger. My boss, who was also the owner, was a sleazy scumbag. I worked for him because he paid me but if anything else came up, anything at all...

Olivia's Revenge Ch. 02

by OliviaFantasy on Sep 13, 2017
Erotic Couplings

My first story, Olivia's Revenge, needed a sequel. People pointed out rightly, that the revenge hadn't happened yet by the end. And I think the characters had other parts of their story that needed to be told. This is the sequel (some of the details are based on an old conversation with an old friend when I first had this fantasy so they aren't easy to expla...

Exhibition Addict

by maksut on Sep 5, 2017
Exhibitionist & Voyeur

Sorry for my English. But you'll enjoy this factual story. Every thing started a very hot summer day ten months ago. It was almost my home arrival time. My wife had just come out from the shower. So she was naked. The doorbell rang. She thought it was I. She opened the door. Surprise!!! It was not I. He was the teenager son of our neighbor. Both of them w...

Manipulating Jenny Ch. 04

by BeamMeUp on Sep 18, 2017
Exhibitionist & Voyeur

Summary: Voluptuous 18 year-old office flirt Jenny in stockings and garter belt, helps her boss make a decision, and she learns of another woman wanting to meet her for a lesbian encounter. Tuesday arrives a week after Jenny's 55 year-old grey haired boss says he will discuss giving her a substantial pay rise. He gives her the day off so the staff will not...