Gay Boss Stories

2,300 results
Orientation
Length
Source
Infinite Scroll

Getting Ahead

by wimpywelshwilly on Aug 18, 2017
Gay Male

My phone buzzed on the desk, and I made the mistake of looking at it. "GET IN!!" Read the text message from my friend Ben. "ONE-NIL!" I let out a small groan of disappointment, I couldn't believe I was missing the semi-final. City had never got this far and I was stuck in the office. I looked at the clock, thinking if I could get home in time to watch the...

Workplace Behaviour

by CynicalLion on Mar 30, 2020
Gay Male

A sharp crack rang out in the otherwise quiet office, the sound followed immediately by muffled sounds of pain. Cyrus Fears was sitting at his desk, going over some numbers, and nearly snapped his pen in half when another crack rang out far too soon after the first one and more pained noises followed. Sighing lightly, Cyrus set his pen aside and calmly stood...

Everybody Does It : The Beginning

by timmywells on Sep 15, 2017
Gay Male

This story's theme is partly non-violent domination, and contains scenes of humiliation and submission. ****** For Paul Lombardo, Wednesday was just another day. A day closer to Saturday and the weekend, and when he arrived for work that morning, Paul had no idea how much is life was about to change. What began as a quiet day, yet another in a series of s...

Pecker Order

by sr71plt on Aug 18, 2017
Gay Male

Some clients thought the "Bull" in the Bull Thorne Financial Services name related to Wall Street symbols, but those who had known Jim "Bull" Thorne the longest knew he had that nickname because he had the longest, thickest dick in Texas. Of course, it could just as well have been an acknowledgment that he also had the biggest pair of balls in Houston, based...

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...

College Fund Ch. 04

by bjmichaels on Sep 14, 2017
Gay Male

The two guys who Ally had told me to watch, slid out of their booth and I saw them walk out the back door of the bar. One was short, maybe my size, about forty-years old; the other was older, bald and quite fat. Earlier, I had witnessed the fat guy push a twenty-dollar bill to the younger man. "The younger guy is Eddie," said Ally. "He used to work at the f...

My New Lover Ch. 02

by silverace1 on Aug 18, 2017
Gay Male

You are sitting at your desk concentrating on the job at hand. The phone rings and you swing around with your back to your desk to gaze out the window as your boss starts to tell you the problems of his day. You don't hear your office door opening and closing or the lock snicking close. I quickly doff my clothes and get down on my hands and knees to crawl u...

The Indian Doctor Ch. 02

by KeithD on Jul 17, 2019
Gay Male

It had been weeks since I'd seen the Indian doctor. I'd been propositioned by my boss, a Swede fifteen years older than me. And, basking in the new world the doctor had opened up for me, I'd let him fuck me in his room and then on his boat off the beach in Phattaya, a seaside resort for the super rich Thai and expatriates not more than a two-hour drive from...

Paying Back The Boss

by jim_mcd on Sep 1, 2017
Gay Male

This is my first attempt at fiction. Hope you like it. Post any feedback through the link below. Paying back the Boss My heart was still pounding and my face burning as I walked into the office toilets. I'd just dropped my boss in it during a conference call with a client, potentially costing the business thousands of pounds. My boss, Steve, ended the c...

My New Daddy Ch. 03

by sissytoy20 on Mar 6, 2018
Gay Male

The buttplug that Sam had unceremoniously forced inside my tight asscunt had hurt like hell, but I'd enjoyed the feeling of being forced open with no warning. The little, pink butt plug wasn't very large, but it had felt like a giant donkey dick in my ass. It had flashed by in Sam's hand so quickly, maybe it was larger than I thought. It felt huge in my butt...