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Tag Archives: obey
Flashback Friday: The Hitchhiker
This story, originally written in fall of 2020, was originally for Patrons only and is now available for all as part of Flashback Fridays, the first Friday of the month.
Jakob was spoiled, yet lonely. A trust fund baby, he had grown up learning how to manipulate others to his own advantage. Some might even call it covert hypnosis, the way he could seemingly charm anyone to do anything.
During the shutdown, he could only spend so much time out by the pool, so he went online and began to truly study the artform and how he might be able to better use it to his advantage. He knew too many would be with him solely for the money, so as lonely as he was, he wanted someone who could truly be part of his life.
As restrictions began to ease, the privileged young man decided to go for a drive.
On his drive, he spotted a young man hitchiking, a considerable ways away from a broken down vehicle that had been on the side of the road.
As the sweaty hithchiker introduced himself as Breckin, he also explained that few cars had gone by and the few that had were not willing to stop for a man they feared.
Little did Breckin know it was Jakob that should have been feared; then again, perhaps Jakob was exactly what the lost soul needed. Either way he was grateful as Jakob pushed play and the music helped his body, sore from walking, to really relax.
As he dozed off, he had strange dreams about being a poolboy.
Continue reading Flashback Friday: The Hitchhiker
Sir’s Trophy Poolboy
A Change in Hierarchy
The Birthday Jockslave
His Friend’s Son, the College Intern
Under His Co-Worker’s Wing
Maturing Attraction
A New Poolboy
Looking impressive there, jock.
“I’m flattered, Coach, but most days I’m already working an internship that might help me land a job after college.”
“Thanks, Coach, I just wish I had time to play more. What brings you to the park today?”
Well, one of My buddies is looking for a new poolboy… and I think I just found him.
“I’m flattered, Coach, but most days I’m already working an internship that might help me land a job after college.”
Is that so, jock? Do you like it?
“I guess so, Coach, though they are working me pretty hard.”
You could have a much more relaxed schedule that lets you come out here much more often.
“I mean it’s hard work now, but someday it’ll be worth it, right? And wouldn’t I have to do work as a poolboy too?”
There will be plenty of times when My buddy is working his own job, and your duties won’t take that long. And working out is part of what will be expected of you in your free time, and this is some great cardio out here the way you play.
“What industry is he in? Maybe it would be worth checking out if it helps me make connections, Coach.”
Well, I want you to think right about this for a moment. Is such a career where you are left working long hours and stressing right out really how you want to be left spending the rest of your life? Or would you rather be left being able to enjoy the simple pleasures you crave deep down, such as time spent right outdoors playing frisbee or anything else you are left loving to do. And deep down, you know this would not have to be left permanent but you could be left how you are left enjoying it for a summer, all you have to do is let me train you right for the position that I think you already are beginning to desire deep down.
“Yes, Coach. A session with you would be good.”
