Gay Boss Stories

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Boss's Older Boy Toy

by fidofashion on Oct 11, 2017
Gay Male

I had just returned to the office from my workout I usually did on my Friday lunch hour, when I was called and told to report to Mr. Kohn's office up on the Penthouse floor. My heart hammered in my chest, and I had a cold knot in my stomach. This couldn't be good news. It was Friday, the company had been laying off staff, and I was older. I hadn't even see...

Boss Likes Hypnosis Pt. 01

by Oddballs on Oct 19, 2020
Gay Male

Jack looks over the HYPNO-APP on his phone; with sunglasses, of course. The mid-aged and handsome silver fox looks at his very old pocket watch that he USUALLY uses for hypnosis. Jack has been practicing kinky hypnosis for years, and it's been his favorite fetish since he was a teenager. But hypnosis hasn't always been easy at all; just getting a guy into a...

Boss Likes Hypnosis Pt. 02

by Oddballs on Oct 19, 2020
Gay Male

"Now John. When I say 'wake'." Jack says as he gets close, "You are going to confess to me that not only are you a straight, married man like you always have been. But you will also believe you are in devastating love with my genitals." "Yes Jack..." "Right then." Jack takes a step back and snaps his fingers "Wake!" SNAP! Jack blinks awake and glances do...

Camera Time

by Bossanova001 on Mar 18, 2020
Gay Male

I was cleaning out the closet when I found a camera that looks expensive. I don't remember buying him this so where is it from. I walked into the bedroom passing boxes and bubble wrap on the way. "Where the hell did this come from?" Bassir was sitting on the floor grabbing a box. I've never seen that box before. It was all black with a lock on it. "Hold th...

Birthday fun

by Bossanova001 on Apr 1, 2020
Gay Male

*These two characters have a bigger story that I'll publish later* "Tyrell I told you no gifts," Bassir groaned when he saw me walk in with two horribly wrapped presents. I've never wrapped presents before especially for somebody else but I tried. "Shut up. You knew I was going to buy you presents." I sat next to him on the bed. He was wearing my favorite...

Night out

by Bossanova001 on May 12, 2020
Gay Male

*This is the last short of them before I publish the actual story. It's language in this short that's offensive. Sorry in advance.* * Tonight both me and Tyrell were able to chill together without work. He was watching a show called 'House' and I was reading a book. He had his head on my lap with his hair tied into a high ponytail. Like usual I had on shor...

My Boss and Master Ch. 03

by MitchCapslock on Sep 14, 2017
Gay Male

All comments and criticism welcome. My Boss, My Master: Losing it I kept up my office routine, even though I knew Mr. Compton was out of town and might not be back for the rest of the week. Each morning, I would stop in the lobby restroom, change into a pair of panties and then head to my office. I quickly found that I liked the feel of women's underw...

My Boss and Master Ch. 02

by MitchCapslock on Sep 14, 2017
Gay Male

All comments or criticism welcome. New rules, new life The message light was already blinking when I got to my desk Tuesday morning. "Mitch, this is Wendy. Mr. Compton asked that I remind you of your 4 p.m. meeting this afternoon in his office." Forget? It was all I had thought of since I left his office, the taste of his cum coating my throat. It was...

My Boss and Master Ch. 01

by MitchCapslock on Sep 14, 2017
Gay Male

All comments and criticism welcome/ The words from my boss snapped me back to reality. I'd lost myself for the past 10 minutes on his cock, using my mouth and tongue to make long, slow strokes along his shaft. He was perched against his desk, naked from the waist down, as I knelt before him. His pants were folded neatly across the back of the chair, while...

The Boss's Pleasure

by Universal_Thirst on Aug 28, 2017
Gay Male

Being the boss doesn't come with as many advantages as people tend to think. Yes, I make the most of all my employees but I also work the most hours and do the most in those hours. I have to coordinate, train, exhort, hire and fire people all the time. And while I can hire or promote someone just for being hot, if I'm careful to have more work appropriate re...