Tag Archives: poolboy

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.


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Sir’s Trophy Poolboy

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Relaxation at the Pool; Relaxation Into a Poolboy

That’s it, jock. Just relax. It feels so good to relax out there on the raft, out on the pool where you belong. And you do belong in or beside the pool, for deep down you know you have longed to be a poolboy. You have been working so hard to transform that body or Coach, and you have built and sculpted it into a physique worthy of being seen. It feels so good to think of getting to wear barely anything – and sometimes nothing at all – as you do find yourself so ready to be that poolboy that loves having his body admired. That muscle looks so good wet, and you love how your wet muscle makes other men get wet. As your desire to become a poolboy grows stronger, you realize that being a poolboy is such a nice simple life for a simple jock like you. That’s right.

You are simply a jock, and it’s so simple for jocks to be so simple, so simply keep letting go of all other thoughts right now. There’s no need to think about anything else except that poolboy body. A body that is meant to be seen, and you love showing it off more and more. You grow to love showing off just how athletic and muscular you are becoming. You love working to make that physique even fitter and stronger.The thought of that hard muscle starts to make your dick hard. You can feel it getting harder in your swimsuit even now. Feel it strain, and realize it will soon need release. But first, you can simply release any of that unneeded intelligence and all unnecessary inhibitions. Simply keep letting them go as you simply keep becoming more and more simple – and that simply feels so good.
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Loving That Pool Life

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A New Poolboy

Looking impressive there, jock.

“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.”

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From Bully to Bulldog

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New Year, New (Simple) You

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Get Away From It All

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Dripping

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Poolboy Evaluation

This story was previously available only for Patrons and is now available for all as part of Flashback Fridays. Enjoy!

All that poolboy training these last few months is taking over more and more. Being here next to the pool, going so deep as you wear a swimsuit, makes you feel completely like that poolboy. He has been in your subconscious, slowly changing you. He has been pushing you to work out more, training harder and harder for that lean poolboy muscle. He has been pushing you to eat the right foods at the right time. 

Most importantly, he has been pushing you to think more and more with that dick, all other unneeded thoughts and intelligence just draining away. You don’t need it. Thinking is hard – your dick is hard … why not just think with your dick? You just need to follow that dick as it fills up with pleasure anytime you please a guest. That’s right. When you’re not on lifeguard duty, you’ll be available to service the needs of any of our visitors, and this means you need to be ready for any role. And as you let go of all inhibitions, you find yourself so ready to strip out of that swimsuit and so ready to satisfy our guests in any way that does not harm you beyond agreed upon impact pay. Because a poolboy like you is always so horned up, you are so ready to make sure every guest is left completely satisfied.


“Hey Coach, is this the newest poolboy?”

Sure is, Arturo. I was just putting the finishing touches on Jamaal here and as you can see, he’s very horned up and ready to serve the guests. Although, perhaps you can help me double-check that.

“Double-check? You mean act as if I’m one of the guests here ready for some service?”

Exactly. Why don’t you  help me break him in? He’s obviously ready and rearing to go. 

“It’d be my honor, Coach.”

Very good. Let me help you both get in the mindset. GOOD POOLBOYS OBEY. Jamaal, all your poolboy training is fresh in your mind and you’re ready to service your first guest, Arturo. Remember that his pleasure is your pleasure. Arturo, you in turn will feel as if you are a guest, entitled to all the perks and privileges of this resort. You will feel this way until you have orgasmed, at which point you will return to being a fellow poolboy who is so grateful Coach rewarded his service with this opportunity.

While you will both end up platonic co-workers after this, with your sexual energies turned to our guests, you will find yourselves extremely attracted to each other right now.


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