Gay Gay Boss Stories

22,838 results
Orientation
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Infinite Scroll

The Intern Ch. 01

by horniboy on Aug 17, 2017
Gay Male

It was my first summer out of college and I was really struggling to find a job. I was only just 18 and was supposed to spend my weekends partying with all my friends. But no job meant no money. Still, it wasn't all bad. As an 18 year old with a taste for older men, I could usually rely on a generous man to buy me a drink or two on a Friday night down at the...

Tied Down and Made Up Ch. 02

by Thlipsi on Sep 14, 2017
Gay Male

"He's not merchandise. I'm buying him." Mr Baxter stated firmly. My breath hitched and I stared, wide-eyed at him. The Boss laughed. "We haven't even discussed price!" "30,000." Came the immediate reply. I choked on my spit and Mr Baxter looked at me out of the corner of his eye. "Worth every dollar." He muttered, and I blushed fiercely. The Boss seemed a...

Working It Out: Wife Finds Porn

by Baron_Cumhausen on Jan 16, 2019
Gay Male

Like a lot of folks, my boss lets me work at home one day a week. I enjoy it, not only for the two hours commute time it saves me, but for what it allows me to do with that free time. My work at home day is Wednesday, which is perfect because my wife's is Friday. Because she has a similar awful commute as mine and similar work hours, on Wednesday's I have an...

Ken's Sex Toy

by SlimTim_86 on Aug 18, 2017
Gay Male

My phone rang; it was the Accounts department manager Ken. "Afternoon Ken, how are you?" "I'm fine Jim, can you come to my office at 17:00, we need to discuss your secondment?" Dam! I thought as I put the phone down. Not only do I finish work at 16:30 I really don't want to go on a secondment to the Accounts department. It had been discussed with my boss...

Something To Remember Me By

by timmywells on Aug 18, 2017
Gay Male

It was time to pack my things and leave the dorm room that I called home for my freshman year at Hobart, having done very well in the classroom and more surprisingly having survived sharing the cramped quarters with a roommate who was the exact opposite of me in many ways. It had been a shaky start for us, with him always suspecting that I was gay from the...

God's Angel Ch. 02

by dagan732 on Sep 14, 2017
Gay Male

Gabriel worked the rest of the week and volunteered some lunch and a few hours after work. He enjoyed volunteering and feeling like he was making a difference in someone's life, helping them with a few pieces of food so that maybe they'd be able to help themselves. He also loved his new job. It was challenging making sense of what Ethan had done to the recor...

Fucked Up Ch. 03

by ruggerjocklad on Sep 14, 2017
Gay Male

The first thing that occurred to me, as the door of the huge master bedroom was locked shut behind me, was how totally fucked I was. Followed shortly thereafter by the realisation that I was almost certainly going to have my arse fucked - for the first time in my entire 37 years on Earth - by some perverse, voyeuristic sadist, in about twenty minutes' time....

Zack's Toys

by JimBob44 on Aug 17, 2017
Gay Male

*Author's Note: Any and all persons engaging in any sexual activity are at least eighteen years of age. ***** Derek Boudreaux checked his mailbox. Three banks down, one of the numerous tenants that lived in the apartment complex likewise checked their mailbox. Derek had tried once to engage the neighbor in conversation. The neighbor had claimed not to spe...

Failing Upward

by el_wing on Sep 14, 2017
Gay Male

Chapter 1: Tabula Rasa Shock works that way. A person runs on automatic. I read that once. Like an old movie projection camera rolling in slow motion. Click, click, click. The film sticks. Celluloid melts. My fate-- part of the mangled frames. I never believed in fate until now. "Wes, you make your fate," my father used to say. Tabula rasa. Blank sla...

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...