Gay Boss Stories

2,300 results
Orientation
Length
Source
Infinite Scroll

Not the Best Idea

by KeithD on May 15, 2019
Gay Male

"Why were you down in that neighborhood at all, Aaron?" I didn't want to sound judgmental under the circumstances—my little brother, Aaron, had dragged himself to my downtown Philadelphia apartment in the middle of the night with a tale of woe of having been dosed with a date rape drug in a bar down by the naval shipyard on the rough south end of Philly and...

Mel Takes My Manhood Pt. 05

by RSchwuler on Apr 13, 2020
Gay Male

Standard disclaimer: this story is a very over the top work of fantasy, and it contains extreme humiliation, blackmail, and unsafe, non-consensual sex practices. If that's not your thing, please don't read it. Otherwise, enjoy! - This strange new state of affairs continued. Everyday I would report to the gym, strip to my jockstrap, and Cliff, my self-appoi...

Unexpected Ch. 08

by BNDMTL on Sep 25, 2017
Gay Male

I feel another kick to the guts. I need to keep my wits about me long enough to leave with my dignity intact. Everything is different. I've walked into a different world. Jase seems to be the guardian of Cory or is helping his mother out. Alex has a kid who calls him Daddy. Benny leans toward me with his arms out. "I want Poppy." I bring my arms up for hi...

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...

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...

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...

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...

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...

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...