Gay My Boss Stories

22,166 results
Orientation
Length
Source
Infinite Scroll

A Hike with the Boss

by timmywells on Aug 18, 2017
Gay Male

For 19 year old Randy Davidson, the intern position at the printing company had begun as something to keep him busy until college resumed in the fall, but after the owner of the firm took a liking to the lad things changed. Maybe it was because George Beck sensed that the young man had similar feelings toward him, despite the fact that at 64 he was more tha...

Cum Dump Trump

by Cumalittlecloser on Aug 18, 2017
Gay Male

This is a story of fiction, any similarities to real people or events is merely coincidental. In British slang "to trump" means to expel gas through the anus often in a highly audible way. I guess there are other things that one can "trump" out of their ass. * When I got out of college, my aspirations were to be the best political candidate the nation wou...

Homesick for the Holidays

by BabyJamesBoy on Aug 18, 2017
Gay Male

It had been a long year. My first album was a smashing success and the touring to support it started in January and here it was almost Christmas and it was just winding down. The nightly parties had become more necessary than I cared to admit, the high of performing needing to be tamped down by as many substances, some legal, some not as I could get a hold...

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...

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Demands on Him Ch. 02

by secretkkisses on May 15, 2019
Gay Male

Again, this story thread was previously published under my old username, latenightkiss, which I no longer have access to. Once the old thread has been published I will add new chapters! ***** "Will, honey, will you make sure there's plenty of ice in the cooler?" Jenna called from the kitchen. I checked my watch and saw that it was almost time for our gue...

Demands on Him Ch. 02

by latenightkiss on Aug 30, 2017
Gay Male

"Will, honey, will you make sure there's plenty of ice in the cooler?" Jenna called from the kitchen. I checked my watch and saw that it was almost time for our guests to arrive. The New Year's Eve party had been Jenna's idea three years ago when we'd first moved in together, and it had evolved into a tradition. Jenna had spent the last two days cleaning an...

Spark & Stone - Ch. 09

by laurasfox on Nov 4, 2019
Gay Male

Chapter Nine - When Will You Be Home? "So, was no one else available to take care of all these?" Aidan questioned while pointing with a pen at the huge stack of folders on his desk. One of the promises he had made to himself was to be more assertive. At least, that was one of the things the motivation audio books he was listening to on his way to work ever...

Everybody Does It : Day Two

by timmywells on Sep 15, 2017
Gay Male

This is the second part of a story involving a boss and his subordinate. It would greatly help the reader to check out the first part before reading this. Please note that like the first part, this story involves coerced sex along with dominant and submissive characters. Those not interested in such situations would probably not enjoy this story. *** The...

Outed and Married

by keptsissy on Sep 26, 2017
Gay Male

He always threatened me with being exposed to my coworkers, to the world as the sissy I am to him. Usually it was part of what I thought was his dirty talk, sex talk. He'd tease me with it. He'd be deep inside of me, slow fucking me, talking dirty into my ear. Or he'd have me restrained and be masturbating me as part of 'my reward', as he called it, and woul...

The Foreman Ch. 01

by HannahSavannah on Aug 18, 2017
Gay Male

I work as night foreman at a San Francisco warehouse operation. Sounds like a dumb job and in some ways it is. However, it’s easygoing and has its moments. . . plenty of moments. I was 32 and just a year or so back from overseas--somewhat brain dead--so the easy pace gave me time to heal. It wasn’t rocket science. It was basic intelligence, initiative and a...