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jack bailey

Ever since he burst onto the scene in 2020, Jack Bailey has been raising temperatures as the nation’s twink sensation every man desires.

This gorgeous young stud from Missouri stands tall at 5'10, with striking blue eyes, a smooth and sexy body, a thick 7-inch cock, and a bubble butt that’s practically begging to be filled. In short, Jack is the kind of twink who knows exactly what he wants—and that’s to be fucked and dominated in the dirtiest ways imaginable.

Known for his insatiable sex drive and love of bondage, Jack is a bottom who thrives on being pushed to his limits. Whether he’s tied up, gagged, or taking a gangbang, his nympho energy is off the charts, and you can see it in every wild performance.

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Latest Updates Series
Catching Scoutmaster | TROOP TIME | Chapter 15 Jack Bailey Lance Charger Troye Jacobs
Catching Scoutmaster | TROOP TIME | Chapter 15 Jack Bailey Lance Charger Troye Jacobs
Catching Scoutmaster | TROOP TIME | Chapter 15 Jack Bailey Lance Charger Troye Jacobs
Catching Scoutmaster | TROOP TIME | Chapter 15 Jack Bailey Lance Charger Troye Jacobs
Catching Scoutmaster | TROOP TIME | Chapter 15 Jack Bailey Lance Charger Troye Jacobs
Catching Scoutmaster | TROOP TIME | Chapter 15 Jack Bailey Lance Charger Troye Jacobs
Catching Scoutmaster | TROOP TIME | Chapter 15 Jack Bailey Lance Charger Troye Jacobs

It can get quite difficult to find a few minutes of alone time when you’re in the great outdoors looking after a few dozen over-excited... [read more]

After Camping | TROOP TIME | Chapter 14 Jack Bailey Marcus Rivers Patriarch Smith Troye Jacobs
After Camping | TROOP TIME | Chapter 14 Jack Bailey Marcus Rivers Patriarch Smith Troye Jacobs
After Camping | TROOP TIME | Chapter 14 Jack Bailey Marcus Rivers Patriarch Smith Troye Jacobs
After Camping | TROOP TIME | Chapter 14 Jack Bailey Marcus Rivers Patriarch Smith Troye Jacobs
After Camping | TROOP TIME | Chapter 14 Jack Bailey Marcus Rivers Patriarch Smith Troye Jacobs
After Camping | TROOP TIME | Chapter 14 Jack Bailey Marcus Rivers Patriarch Smith Troye Jacobs
After Camping | TROOP TIME | Chapter 14 Jack Bailey Marcus Rivers Patriarch Smith Troye Jacobs

The boys got back to base camp in the middle of the afternoon. The three of them had been on an unsupervised, mini-expedition... [read more]

Scout boys Cole and Jack have returned early from their hike. If truth be known, they were dawdling behind the others and so deep... [read more]

Boys Will be Boys | TROOP TIME | Chapter 11 Jack Bailey Legrand Wolf Marcus Rivers
Boys Will be Boys | TROOP TIME | Chapter 11 Jack Bailey Legrand Wolf Marcus Rivers
Boys Will be Boys | TROOP TIME | Chapter 11 Jack Bailey Legrand Wolf Marcus Rivers
Boys Will be Boys | TROOP TIME | Chapter 11 Jack Bailey Legrand Wolf Marcus Rivers
Boys Will be Boys | TROOP TIME | Chapter 11 Jack Bailey Legrand Wolf Marcus Rivers
Boys Will be Boys | TROOP TIME | Chapter 11 Jack Bailey Legrand Wolf Marcus Rivers
Boys Will be Boys | TROOP TIME | Chapter 11 Jack Bailey Legrand Wolf Marcus Rivers

I’ve been messing about with Jack for quite a while now. We slip away from everyone else as often as we can. We’ve certainly... [read more]

The Master’s Grandson | THE BUYER'S GROUP | Chapter 9 Cole Blue Jack Bailey Lance Charger
The Master’s Grandson | THE BUYER'S GROUP | Chapter 9 Cole Blue Jack Bailey Lance Charger
The Master’s Grandson | THE BUYER'S GROUP | Chapter 9 Cole Blue Jack Bailey Lance Charger
The Master’s Grandson | THE BUYER'S GROUP | Chapter 9 Cole Blue Jack Bailey Lance Charger
The Master’s Grandson | THE BUYER'S GROUP | Chapter 9 Cole Blue Jack Bailey Lance Charger
The Master’s Grandson | THE BUYER'S GROUP | Chapter 9 Cole Blue Jack Bailey Lance Charger
The Master’s Grandson | THE BUYER'S GROUP | Chapter 9 Cole Blue Jack Bailey Lance Charger

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]

The Master’s Grandson | TEACHING MY GRANDSON | Tape 4 Cole Blue Jack Bailey Lance Charger
The Master’s Grandson | TEACHING MY GRANDSON | Tape 4 Cole Blue Jack Bailey Lance Charger
The Master’s Grandson | TEACHING MY GRANDSON | Tape 4 Cole Blue Jack Bailey Lance Charger
The Master’s Grandson | TEACHING MY GRANDSON | Tape 4 Cole Blue Jack Bailey Lance Charger
The Master’s Grandson | TEACHING MY GRANDSON | Tape 4 Cole Blue Jack Bailey Lance Charger
The Master’s Grandson | TEACHING MY GRANDSON | Tape 4 Cole Blue Jack Bailey Lance Charger
The Master’s Grandson | TEACHING MY GRANDSON | Tape 4 Cole Blue Jack Bailey Lance Charger

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]

Dolf looks like a badass, but he’s really a big softy at heart. He’s got the energy of a supportive big brother that motivates... [read more]

Party Favor | THE BUYER'S GROUP | Chapter 8 Cole Blue Jack Bailey Lance Charger Legrand Wolf Marcus Ryan Patriarch Smith Troye Jacobs
Party Favor | THE BUYER'S GROUP | Chapter 8 Cole Blue Jack Bailey Lance Charger Legrand Wolf Marcus Ryan Patriarch Smith Troye Jacobs
Party Favor | THE BUYER'S GROUP | Chapter 8 Cole Blue Jack Bailey Lance Charger Legrand Wolf Marcus Ryan Patriarch Smith Troye Jacobs
Party Favor | THE BUYER'S GROUP | Chapter 8 Cole Blue Jack Bailey Lance Charger Legrand Wolf Marcus Ryan Patriarch Smith Troye Jacobs
Party Favor | THE BUYER'S GROUP | Chapter 8 Cole Blue Jack Bailey Lance Charger Legrand Wolf Marcus Ryan Patriarch Smith Troye Jacobs
Party Favor | THE BUYER'S GROUP | Chapter 8 Cole Blue Jack Bailey Lance Charger Legrand Wolf Marcus Ryan Patriarch Smith Troye Jacobs
Party Favor | THE BUYER'S GROUP | Chapter 8 Cole Blue Jack Bailey Lance Charger Legrand Wolf Marcus Ryan Patriarch Smith Troye Jacobs

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

Jack was pretty gutted when he didn’t get the job he’d hoped for. He’d worked so hard to prepare and present himself as... [read more]

My name is Mr. Smith, and I’ve been a scoutmaster for more years than I care to admit to. I recently took early retirement from... [read more]

The Grooming | THE BOY JACK BAILEY | Chapter 1 Jack Bailey Lance Charger
The Grooming | THE BOY JACK BAILEY | Chapter 1 Jack Bailey Lance Charger
The Grooming | THE BOY JACK BAILEY | Chapter 1 Jack Bailey Lance Charger
The Grooming | THE BOY JACK BAILEY | Chapter 1 Jack Bailey Lance Charger
The Grooming | THE BOY JACK BAILEY | Chapter 1 Jack Bailey Lance Charger
The Grooming | THE BOY JACK BAILEY | Chapter 1 Jack Bailey Lance Charger
The Grooming | THE BOY JACK BAILEY | Chapter 1 Jack Bailey Lance Charger

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]

I sometimes wonder whether becoming a scout leader was the right thing to do. It felt amazing at first. I was back out there,... [read more]

Interview Prep | TEACHING MY GRANDSON | Tape 2 Jack Bailey Lance Charger
Interview Prep | TEACHING MY GRANDSON | Tape 2 Jack Bailey Lance Charger
Interview Prep | TEACHING MY GRANDSON | Tape 2 Jack Bailey Lance Charger
Interview Prep | TEACHING MY GRANDSON | Tape 2 Jack Bailey Lance Charger
Interview Prep | TEACHING MY GRANDSON | Tape 2 Jack Bailey Lance Charger
Interview Prep | TEACHING MY GRANDSON | Tape 2 Jack Bailey Lance Charger
Interview Prep | TEACHING MY GRANDSON | Tape 2 Jack Bailey Lance Charger

Jack is lucky to have a grandpa as attentive and caring as Lance. The older man is not only handsome and charming, but he knows... [read more]

Top Training | TEACHING MY GRANDSON | Tape 1 Jack Bailey Lance Charger
Top Training | TEACHING MY GRANDSON | Tape 1 Jack Bailey Lance Charger
Top Training | TEACHING MY GRANDSON | Tape 1 Jack Bailey Lance Charger
Top Training | TEACHING MY GRANDSON | Tape 1 Jack Bailey Lance Charger
Top Training | TEACHING MY GRANDSON | Tape 1 Jack Bailey Lance Charger
Top Training | TEACHING MY GRANDSON | Tape 1 Jack Bailey Lance Charger
Top Training | TEACHING MY GRANDSON | Tape 1 Jack Bailey Lance Charger

From the outside, Jack’s household seems perfectly ordinary. Close-knit, loving family with a handsome, all-star athlete boy.... [read more]

From the outside, Jack’s household seems perfectly ordinary. Close-knit, loving family with a handsome, all-star athlete boy.... [read more]

I haven’t been a scout for very long. Being honest, it took me forever to pluck up the courage to join. My mom always tells... [read more]

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* All models on this website were 18 years of age or older at the time of filming.
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