Gay Boss Stories

2,300 results
Orientation
Length
Source
Infinite Scroll

Spark & Stone - Ch. 07

by laurasfox on Sep 23, 2019
Gay Male

Chapter Seven -- Who's This Nice Guy? Okay, okay, so he had to be completely out of his frigging mind to go through that and live to tell the tale. Well, that was definitely an exaggeration, but Aidan felt the need to do precisely that. Because as soon as he had gotten home, he had slipped under the covers, in bed, and ... Sort of jerked off furiously whil...

Cock-Crazed

by mmgo on Aug 18, 2017
Gay Male

This is the second part of a three-part series. As with the part one, this is a true story. This part is called Cock-Crazed. I had become familiar with man to man sex, but suddenly I seemed to find it everywhere. One day, I was on a business trip in a city several hours from home. I had completed my business day and impulsively stopped at an adult bookstore...

My New Daddy Ch. 02

by sissytoy20 on Feb 13, 2018
Gay Male

I went home and slept well after my session with my new Daddy. My asspussy ached and that aching made me smile. I knew that his cum was still deep inside me and that meant I belonged to him. I couldn't wait to be on my knees for Ted again very soon. I had college classes the next day but I couldn't keep my mind on my studies. All I could think of was Ted po...

Miss Ivy's Boy

by CynicalLion on Mar 10, 2020
Gay Male

Proper summary cuz the character limit on here is just a tad stifling: Roy Winters is the cashier of Miss Ivy's Botany and has a thing for some of Miss Ivy's regulars. When one of them catches him staring, Roy gets exactly what he's been wanting for awhile. It was early morning in the downtown area of Silverstream where an unassuming plant shop sat just off...

What Happens in Vegas

by randomlyrandom on Oct 6, 2020
Gay Male

I wasn't sure if I was really going to do this. I had fantasized about hooking up with a man for years, but now that the opportunity was really here, could I actually go through with it? I'm in Vegas, and what happens in Vegas stays in Vegas, right? With a deep breath, I stood up, pulled my jeans on, tied my shoes, and I was out the door. He checked all my...

Outted by the Boss

by BmthAdmirer on Sep 14, 2017
Gay Male

As a professional guy working in a professional job I had always kept quiet about my sexuality knowing that one or two of my colleagues were exceptionally homophobic and the only release of the hatred was my boss Neil. Neil was a decent guy who I had known of for some time on the company but when I was forced into my new role and told Neil would be my boss I...

Gentlemen's Club Ch. 14

by Ywashere on Sep 14, 2017
Gay Male

Hi, everybody! I'd like to thank kevinmd & cookieaddict (don't have your Usernames, so I'm calling you by the first parts of your email addresses) for bringing me out of retirement – it's feedback like yours that makes writing for this site so rewarding :-) Y All characters engaged in sexual activities are at least 18 years old. Max Bruhner, ace investi...

Spark & Stone - Ch. 28

by laurasfox on Apr 14, 2020
Gay Male

Chapter Twenty-Eight - Drinks And Trolls Won't Break My Bones "What is it, son?" Heathcliff drew one deep breath. Aidan was upset, and he needed someone with real-life experience to help him deal with this. Rushing after Aidan felt like a bad idea, and he needed to have someone look at the situation and tell him where he had gone wrong. "I got into a fig...

Catching the Eye of a Mob Boss Ch. 02

by Her11 on Mar 21, 2018
Gay Male

Jace: I was eating my microwaved dinner when my phone started ringing, I checked caller ID and saw an unfamiliar number. Weird, I answered in case it was work. "Hello?" I answered. "Hello is this Jace Ederson?" asked a hauntingly familiar beautiful voice and I froze. "This is Diego Salvatore, we met earlier today, you ran into my body guard." "I...I.. r....

College Fund Ch. 03

by bjmichaels on Sep 14, 2017
Gay Male

It was on my fifth day of work Ally informed me someone would be coming in at 2pm for a hot-oil massage. Not only that, but he wanted the 'Deluxe' package too. "What's the 'Deluxe' package?" I asked while wiping my sperm and semen off the floor of Ally's office. I'd only heard of package numbers 'one' and 'two.' He came out of the uniform room and handed...