Gay Boss Stories

2,300 results
Orientation
Length
Source
Infinite Scroll

The Boss

by Jatku on Sep 27, 2020
Gay

You are Jake. A normal guy in his early 30's. You spend your time split between work and home. Nothing too much of a social life to speak of, but that's never been an issue for you. You like to be alone, but every once in a while you do enjoy the company of another man. At least, that is the way you used to feel. Lately you have been feeling extremely horny...

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My Kind of Taxi

by FadeEstates on Aug 18, 2017
Gay Male

I was a tourist staying in New York for a week, I was having fun with friends and all, but it came down with me wanting more then friends. I took a taxi from Hamilton Heights down to Central Park, not knowing that I only had seven dollars in my pocket. I was in the taxi with a man born in Saudi Arabia, he was a nice man, maybe thirty years old by looking a...

Box Shaped Heart Ch. 10

by laurasfox on Dec 19, 2018
Gay Male

Chapter Ten - Let's Make A Salad All right, at least he had managed to make the leather chair look decent after the online BDSM groups had supplied him with useful information on how to clean cum off leather. The best part was that he hadn't needed to call Mark to the rescue, and a tissue and some rubbing alcohol that he had luckily found in the small vanit...

The Customer (Dexter's Saga) Ch. 21

by JoyStick56 on Sep 14, 2017
Gay Male

Disclaimer: This story is a work of pure fiction. Names, characters, places, and incidents are either the product of the author's imagination or are used fictitiously, and any resemblance to actual persons, living or dead, events, or locales is entirely coincidental, and no harm or slanderous intent is implied or intentional. Other than that, the usual discl...

And In The End Ch. 02

by BabyJamesBoy on Aug 18, 2017
Gay Male

I wish I could say we all lived happily ever after...but I'd be lying. James had decided to move on with his love life, and I was not invited for the ride. Oh, we had a friendship of sorts. Or we were working on it, but it was awkward at best. I tried to find someone of my own, but failed miserably. It was all because I kept comparing the new men to him. H...

One Night in San Francisco

by KeithD on May 15, 2019
Gay Male

[One Night in XXX Story Event] The shock set it on how stupid I'd been. Pete Parnell hadn't hired me for his Chicago investment firm despite what I had disclosed at my job interview with him about what I'd done in college but because of what I'd admitted I had done in college. It wasn't just that I went with other men, but it was that I had been promiscuous...

Trying to Keep My Job

by tomguy12345 on Sep 23, 2019
Gay Male

I took a job in a supermarket after my company downsized. I wasn't happy to be doing it at 42 but I was genuinely desperate. My girlfriend was working too, and it just wasn't enough. If we missed any more rent payments I'd be out of my apartment. Even worse than taking a shit job was the selection of 20-something supervisors I now had, all of whom enjoyed...

We Meet Eventually Ch. 08

by 1suitedbi on Sep 23, 2019
Gay Male

Chapter 8 - Early morning riser Alex and Will experience the ultimate alarm call. I was woken the next morning, not by my alarm but by Will's hands slowly massaging my hard cock, thru my silk pyjamas, slowly, my senses coming back to life I could feel his hardness against my silk clad butt, reaching back I slowly ran my hand over his thigh, moving it slowl...

The Hapless Detective

by idsweaterguy on Sep 16, 2017
Gay Male

Chapter 1: I parked my car four houses down from the house the man I was following had parked in front. I watched the middle-aged man who was about six-two and wearing a brown fleece jacket, jeans and a brown baseball cap get out of his car, throw a backpack over his shoulder and walk up to the front door of the non-descript but rather large house in a newe...

Putting the Boss in His Place

by Harristi on Sep 25, 2017
Gay Male

Working for Kevin sucked. His branch office was one of the insurance company's most productive, but he got those results by being a hard-ass to the people who worked under him. His reputation as a tyrant was well known, so I was not pleased when I learned that I was being transferred to his unit. It's not that Kevin intimidated me—he didn't. I knew I was go...