Gay Boss Stories

2,300 results
Orientation
Length
Source
Infinite Scroll

Stripping the Boss Naked

by TheShyGay on May 10, 2019
Gay

Steve was just a young college guy looking for a summer job between semesters. When he got called in for an interview at the chicken place his friends worked at, he was thrilled! They all said the boss, Nelson, was incredibly hot, but sadly had a wife. Still, Steve was excited and hopeful that he would get the job. When Steve walked into the restaurant, he l...

Open in Reader

Loser Takes All

by trashcan44 on Aug 18, 2017
Gay Male

It was my first job out of college and I was determined to make good. I felt I was on the "fast track" when the owner of the company invited me to join him and two important clients on a sport fishing trip to the Louisiana gulf coast. It was made clear that I was to be a "go-fer" with benefits, that is my job was to see that everything went smoothly and do a...

Spark & Stone - Ch. 16

by laurasfox on Dec 9, 2019
Gay Male

Chapter Sixteen - #TGIM Aidan sat at his desk, fired up his computer, and began browsing through his e-mails. Leaving aside the spam that seemed to find him no matter how hard he tried to keep it his inbox crap-free, a few social media notifications that he ignored since they just showed how happy some people were, and newsletters from online shops he only...

Great Meeting Ch. 07

by CandPS on Aug 17, 2017
Gay Male

I wake up in the morning and can't believe how happy I am. After months of fantasizing about Rob, I'm wide awake in his bed and feeling absolutely wonderful. We greet each other with a kiss and immediately my cock is at attention, as is his. It appears that we are hopelessly aroused by each other and our lust is evident. I look in his eyes and they appear t...

The Quarry Ch. 02

by the_apocalypse on Aug 22, 2017
Gay Male

The rest of the day dragged by with nothing to do but read the handbook, eat the food that was brought and lay in the cell. None of us even got let out for a couple of hours exercise, and eventually the lights were all switched off and the wing descended into complete darkness. I dropped the hand book, stripped my jeans and vest top off and climbed into my b...

Everybody Does It: Day Four

by timmywells on Aug 29, 2017
Gay Male

Just a reminder that this story contains graphic sex between dominant and submissive categories, although the sex is not completely gay in nature, and there is a degree of humiliation involved. At this point, reading the previous installments would seem to be helpful in understanding the story. ... Paul Lombardo felt empty as he packed up his briefcase be...

Killer Sex Ch. 01

by willbass1331 on Aug 18, 2017
Gay Male

Chapter 1 - My Boss I hate my fucking boss. He casually strolls through the cubicles glancing over everyone's shoulders making some asinine comments. So pretentious, pompous, and touchy. Walking with a gorgeous douchey smile showcasing his bright white teeth. His brown hair is combed over without any gel. When I would look at him, his green eyes would l...

Avenging Angel Ch. 02

by BabyJamesBoy on Aug 18, 2017
Gay Male

The memories kept coming to me in the form of dreams, or I guess nightmares would be more accurate. In the dark the feeling of being helpless and used like a blow up sex doll would wake me from a sound sleep. My girlfriend blamed my lack of interest in her usually charming ways on the stress of building up my career in music; I knew that my problems ran dee...

Spark & Stone - Ch. 29

by laurasfox on Apr 21, 2020
Gay Male

Chapter Twenty-Nine -- Don't Say You've Never Done Anything For Me Heathcliff felt like an automaton as he moved through the house. First things first, he needed to sort out what the hell was going on with those so-called healthy drinks Aidan's company was selling. If there was something bad in them, that was bad for him, too. At least, that was a topic he...

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...