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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 ... [Read more]

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.

Latest updates for The Boy Jack Bailey
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Master Charger and The Boy Jack Bailey

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... [read more]

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Master Charger, Master Houser, Master Legrand, The Boy Cole, The Boy Jack Bailey, The Boy Marcus and The Boy Troye

The holidays represent a special time for the buyers. As they’re spending time with their families, seeing the work from their... [read more]

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Master Charger, The Boy Cole and The Boy Jack Bailey

Becoming a man isn’t about age. It’s not about a birthday or losing your virginity or getting a job. It’s none of the things... [read more]

Series with The Boy Jack Bailey