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The boy jack bailey Chapter 1: the grooming

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November 18, 2021 | Full Length Video : 32min 34sec

Not everyone is made to be a master. For many it’s something you’re born with or you’re not. And even if it’s in your family legacy, sometimes that quality can skip a generation.

I adore my grandson, Jack. He’s beautiful and intelligent and perfectly capable of deciding his own path. When I introduced him to the buyer’s club, giving him a taste of power and privilege, I was surprised when he told me he felt off. Not that he was uncomfortable with the idea of men owning boys, but he found himself fantasizing about being one of the boys himself.

It had ...More

It had never occurred to me that Jack would see himself as submissive, or that being owned would be something he would want or need. But I could tell he was sincere, and I couldn’t deny him the satisfaction I know many of the boys had felt before him.

I told him it wasn’t easy. The demands of a slave can be intense, even scary at times. That different masters require different things, and it’s not his place to question it once he's properly sold. He said he understood, but I had to be sure.

As my grandson, I wanted to be the one who brought him in for his grooming and initial assessment. I told him I would treat him like any other boy, giving him the true, authentic, unbiased experience. He said this was exactly what he wanted, so I let my feelings go and allowed Jack to become a slave, and for me to become Master Charger.

As soon as I got Jack up on the presentation block, I was delighted with how well he took to his new position. He was obedient, compliant, and took to my direction and tone very well. Perhaps it was that he trusted me and knew that I wouldn’t harm him. Or perhaps it was our own sexual history that made him eager to serve. Or it was his true nature… the nature of a sub… finally feeling at home…

When I took off his clothes, I began to think of him more as a product and less as my flesh and blood. I could see what attracted me to him, yes, but I began to see him as something the buyers would love too. Smooth, soft skin. Occasional freckles. A round bubble butt without an imperfection. I knew how it tasted, but it didn’t stop me from feeling it and licking it like it was the first time.

It was good for Jack to see me taking full control of his body. Smacking his balls, fingering his hole, and stroking his cock. He needed to learn that being a slave meant that his body, his pleasure, and his pain were no longer his to control.

As I took off my shirt and tie, I planted his face right into my crotch. He stayed put as I began to undress, training him to sniff the scent of my hairy crotch through the fine fabric of my suit. Every boy needs to know his master’s scent. Learn it, embrace it, crave it, and know it’s the sign of their superior. Jack has tasted me before, but he needed to inhale me. And as I looked down at this sweet, innocent face, I couldn’t believe how well he took to it.

It took everything in my power not to fuck him right then and there. I wetted my fingers and toyed with his hole, feeling the familiar sensation of his soft, stretchy sphincter around my digit. It fit like a ring, tight but smooth. I knew he would make someone very happy.

As I continued to open his hole, tasting it, sniffing it, and feeling it relax on the end of my tongue, I could see Jack playing with his rock hard cock, turned on beyond expectation. He had never been treated like this before. He’d never been with a man who would use him, dominate him, and make him feel like what he is: a slave.

I was so happy that I could be the one to deliver this moment to him. To give him this opportunity to learn his true nature and give up control. How lucky is he, I thought to myself. Of all the men who would bring him in, to have his loving, caring, nurturing, and powerful grandfather to be the one.

I knew I was going to have to open him up. Really stretch the limits of his hole. It was just the way of it. Not just because I love him, but because he needed to know what it’s like to be taken by a man of my position: a master.

It would be rough, and a little scary, but it would be the ultimate test of potential. If he could handle that, he’d be well on his way to being someone’s prize possession...

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THE BOY JACK BAILEY

Jack comes from a long line of powerful men. Everyone before him has shown incredible promise, excelling in their chosen fields and becoming pillars of the community and the family. It’s a big, cold shadow to have to live in, striving to be like his father and grandfather. When he became aware of the world of buyers, masters, and slaves, he felt he’d found a unique answer to a problem he didn’t know he had. He knew he’d never be like the men in his family, but he found himself drawn to the idea of serving men like them. He fantasized about being submissive, taking care of their needs in every way, even taking their hard, deep, bareback breeding. Luckily, Jack’s grandfather happens to be a master and was happy to show him what life is like on the other side of the power dynamic.

Played by Jack Bailey
MASTER CHARGER

Master Charger is brought in to appraise the merchandise of the collective, inspecting the young men to give their owners honest, impartial value for resale purposes as well as to feel secure in their investments. A prized specimen in his own right, Master Charger is a stunningly handsome mature daddy with salt and pepper hair, a trimmed beard, a bodybuilder’s physique, and a powerful, insatiable desire to breed. Whether on the auction block, up for assessment, or the property of the dom, boys tremble and quiver at the thought of being under foot to the powerful daddy, making him an impressive presence among the buyer society.

Played by Lance Charger
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The Boy Jack Bailey series cover

The Boy Jack Bailey

The Boy Jack Bailey: Chapters
1. The Grooming 33mn
Not everyone is made to be a master. For many it’s something you’re born with or you’re not. And even if it’s in your family legacy, sometimes that quality can skip a generation. I adore my grandson, Jack. He’s beautiful and intelligent and perfectly capable of deciding his own path. When I introduced him to the buyer’s club, giving him a taste of power and privilege, I was surprised when he told me he felt off. Not that he was uncomfortable with the idea of men owning boys, but he found himself fantasizing about being one of the boys himself. It had never occurred to me that Jack would see himself as submissive, or that being owned would be something he would want or need. But I could tell he was sincere, and I couldn’t deny him the satisfaction I know many of the boys had felt before him. I told him it wasn’t easy. The demands of a slave can be intense, even scary at times. That different masters require different things, and it’s not his place to question it once he's properly sold. He said he understood, but I had to be sure. As my grandson, I wanted to be the one who brought him in for his grooming and initial assessment. I told him I would treat him like any other boy, giving him the true, authentic, unbiased experience. He said this was exactly what he wanted, so I let my feelings go and allowed Jack to become a slave, and for me to become Master Charger. As soon as I got Jack up on the presentation block, I was delighted with how well he took to his new position. He was obedient, compliant, and took to my direction and tone very well. Perhaps it was that he trusted me and knew that I wouldn’t harm him. Or perhaps it was our own sexual history that made him eager to serve. Or it was his true nature… the nature of a sub… finally feeling at home… When I took off his clothes, I began to think of him more as a product and less as my flesh and blood. I could see what attracted me to him, yes, but I began to see him as something the buyers would love too. Smooth, soft skin. Occasional freckles. A round bubble butt without an imperfection. I knew how it tasted, but it didn’t stop me from feeling it and licking it like it was the first time. It was good for Jack to see me taking full control of his body. Smacking his balls, fingering his hole, and stroking his cock. He needed to learn that being a slave meant that his body, his pleasure, and his pain were no longer his to control. As I took off my shirt and tie, I planted his face right into my crotch. He stayed put as I began to undress, training him to sniff the scent of my hairy crotch through the fine fabric of my suit. Every boy needs to know his master’s scent. Learn it, embrace it, crave it, and know it’s the sign of their superior. Jack has tasted me before, but he needed to inhale me. And as I looked down at this sweet, innocent face, I couldn’t believe how well he took to it. It took everything in my power not to fuck him right then and there. I wetted my fingers and toyed with his hole, feeling the familiar sensation of his soft, stretchy sphincter around my digit. It fit like a ring, tight but smooth. I knew he would make someone very happy. As I continued to open his hole, tasting it, sniffing it, and feeling it relax on the end of my tongue, I could see Jack playing with his rock hard cock, turned on beyond expectation. He had never been treated like this before. He’d never been with a man who would use him, dominate him, and make him feel like what he is: a slave. I was so happy that I could be the one to deliver this moment to him. To give him this opportunity to learn his true nature and give up control. How lucky is he, I thought to myself. Of all the men who would bring him in, to have his loving, caring, nurturing, and powerful grandfather to be the one. I knew I was going to have to open him up. Really stretch the limits of his hole. It was just the way of it. Not just because I love him, but because he needed to know what it’s like to be taken by a man of my position: a master. It would be rough, and a little scary, but it would be the ultimate test of potential. If he could handle that, he’d be well on his way to being someone’s prize possession...
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