Gay My Boss Stories

22,166 results
Orientation
Length
Source
Infinite Scroll

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...

Flower Shop

by newbitime on Sep 16, 2017
Gay Male

I was broke! Broke and bi curious. I'm a good looking, in good shape 27 year old that was plain and simply, down on his luck. With too much time on my hands, due to lack of work, I was spending more and more time surfing online personals... from women looking for men, to men looking for men, and even a few trannies looking for men! Regardless of which secti...

Forced Ch. 02

by nickymartin on Sep 25, 2017
Gay Male

Just as I thought the massage would remain the same, simply stroking my ass, I suddenly felt pressure of a finger rubbing around my anus. The sensation was divine and I sighed a bit. I felt more oil drip onto the crack of my ass and then a finger returned and slowly pushed into me. I have done that to myself but had never been fingered by anyone else before....

Straight Cop Loses Control

by Coxswain on Oct 22, 2019
Gay Male

Straight Cop Loses Control Gulf Coast Trooper craves the bottom Most folks passing a State Trooper cruiser parked beside a county road will slow down and hope they're not doing anything illegal. If they're in southern Alabama, none suspect what waits inside that patrol car, champing at the bit, restless, growling, eager get out, to go wild. Ever been to G...

My Boss and Master Ch. 03

by MitchCapslock on Sep 14, 2017
Gay Male

All comments and criticism welcome. My Boss, My Master: Losing it I kept up my office routine, even though I knew Mr. Compton was out of town and might not be back for the rest of the week. Each morning, I would stop in the lobby restroom, change into a pair of panties and then head to my office. I quickly found that I liked the feel of women's underw...

The Vacation House Ch. 28

by 1Puck1 on Oct 11, 2017
Gay Male

I'm finally able to let loose and have some fun here in Burlington. It has been little more than work upon more work and stress ever since the building site was set up a few weeks ago. It was a bitch driving the trailer up here but Tag and I managed to get it on solid ground. The utilities are all hooked up and most importantly we have WiFi and running hot a...

The Indian Doctor Ch. 03

by KeithD on Jul 17, 2019
Gay Male

The Indian doctor's second summons came during a business lunch with my boss at the Bangkok club rooms in the Montien Hotel of the Royal Phattaya Yacht Club. It came as somewhat of a surprise as it was more than a month after the last time I'd been at the doctor's office. My boss was sponsoring me for membership in the club even though I had yet to buy so mu...

Command Performance, the Next Day

by BabyJamesBoy on Aug 18, 2017
Gay Male

It had been a pretty wild night; I woke up parched and hungry. I only half remembered the private show I had done, parts of it came back in flashes like someone flipping through the channels while all hopped up on Red Bull. I found the guys in my band sitting down to breakfast, so I joined them. The smell of their food turned my stomach. Normally I'm a toas...

Spark & Stone - Ch. 19

by laurasfox on Jan 21, 2020
Gay Male

Chapter Nineteen - A Bit Of Trouble Aidan was in deep, deep trouble. What was he to do about Heathcliff's direct confession? At least, he believed it to be a confession, and it wasn't right to think it so. For some reason, Heathcliff continued his game of driving Aidan nuts and seemed utterly oblivious to how that made his bed partner of convenience feel....

Bad Luck for Me

by Triplebottom on Aug 18, 2017
Gay Male

I wasn't very happy. My boss made me take a vacation because I hadn't taken one in years. Ever since I divorced my wife, I simply drowned myself with work. I didn't want to date or even look at another woman. I was just so damn heart broken. Heather was perfect to me. I guess she didn't feel that way about me since she had an affair with her old crush from h...