Gay Supervisor Stories

214 results
Orientation
Length
Source
Infinite Scroll

Saturday with Chris

by orvette1 on Aug 18, 2017
Gay Male

I am a salesman and have a regular route. Along that route I found the best fuck buddy I have ever had. There is nothing but a sexual relationship between us, so things aren't complicated. I met Chris at one of my stops. At the time he was a supervisor. He's average height and build, but there's something about him that attracted me. It didn't hurt he kept...

Rock-a-Bye Ch. 01

by emoboi on Aug 18, 2017
Gay Male

*All names have been changed to protect the innocent, namely me. * "…W-what?" "I said," he began, that fuckin' lopsided grin of his slowly and, oh, so seductively, turning into a sneer. "I know you like me." "I-- heh, Walking Wet Dream, come on now," I stammered, the heat from the embarrassment of being found out creeping up my face at an awfully...

Border Guard CMNM

by movieye on Aug 31, 2017
Gay Male

My godson and I were returning to Laredo after a weekend in Nuevo Leon, Mexico. Cheap booze, cheap steaks, probably the best part of my weekend was when I hired a senorita to show Devin a good time! You see, Devin, had just turned 18 and had been accepted in the University of Texas so he wanted to party with his favorite gay "uncle" one last time before sc...

Jono's Journey Home Ch. 06

by Shy_Bottom69 on Sep 19, 2017
Gay Male

Chapter 6 - Jono & The Gilded Cage We finished our meal and walked out to the Range Rover. Reza climbed in the back with me. When Tam put the key in the ignition there was an odd sound a funny electronic warning tone. He swore colorfully as he picked up a handset. He called the mobile operator to retrieve his message then dialed the number. "Benjamin I have...

Romantic Evening for Two Pt. 04

by keptbyfather on Jul 17, 2018
Gay Male

Editor's note: this story contains scenes of incest or incest content. ***** I sat in my parents' living room, waiting for Dad to finish getting ready for dinner at the Fountain Rock. On the way home, Dad said it was a date. I couldn't stop my head from spinning. All of this seemed to be a bit too easy. Or, was I over thinking things? Just last night, Dad...

Taking One for the Team

by blklthrjkt on Sep 1, 2017
Gay Male

I've always been a big fan of football, not so much the game but the players. I think it all started when I was 18 and a senior in high school when I became intimately familiar with the football team. I was a bit of a nerd in high school. I ran around with the bookish crowd, but was not the most intellectual of the bunch. In my black plastic rimmed glasses...

Story of a Girlie Boy Ch. 02

by August74 on Oct 6, 2020
Gay Male

I was now fitting into my new life as Tyrone's whore. It's been two months since I began my transition from a functioning and boring man into a sexy girlie boy. My pimp, Tyrone, is my master. He is my everything. He has taught me so many ways to service real men and now I feel confident of my skills. I have done it all. Fucking, and sucking is just the begin...

But I'm Not Gay Sir!

by August74 on Oct 12, 2020
Gay Male

My name is Tommy B. I had just turned 18 and I had a lot to be thankful for. I recently graduated from high school with excellent grades. My family was very supportive and accepted my decision to take a year off from beginning college. I secured a part time job working in a local trucking company processing bills from 6pm to 10pm. The pay was pretty good and...

Imprisonment Ch. 02

by AgentK on Oct 9, 2017
Gay Male

Friday morning came too early for Justin MacDowell, who looked the picture of misery as he sat working at his desk in his small office at the prison. He'd barely been able to sleep since Wednesday, when the warden had discovered he'd been skimming money from the sales of prisoners' belongings to auction houses. The only way he'd been able to keep his job, an...

ENM Intertwined - Jack Pt. 08

by SpecialtyM3 on Mar 31, 2020
Gay Male

[Zayne's POV] Not for the first time today, I had to stop myself from laughing as Jack ran his incredibly nice ass towards the dressing room. He tried to slam the door shut behind him but it only bounced back open leaving his bare backside open to the crowd. Jack just stood there facing the wall as he let his guard down under the belief that he was out of s...