Shot entirely on HD, Jack’s Teen America 18 parodies beauty pageants and Jack’s lovely contestants all compete for the crown. They take off their clothes, they masturbate, they suck, they…

Teagan Presley & ANAL ” does the rest of this description even matter? Jack is really busy casting big, bouncing, beautiful butts for music videos. They shake, they roll and…

Shot entirely on HD, Jack’s Teen America 21 features Digital Playground’s lovely contract star, Lacie Heart in a slam-min’ romp with Scott Nails, Poppy Morgan & Renae Cruz in decadent…

Jack is really busy casting for music videos and now he’s landed Digital Playground’s super fine contract star, Jesse Jane®. She fucks Ben English every which way in true gonzo…

Don’t miss Digital Playground’s Exclusive Contract Stars, Teagan Presley and Jana Cova in a very personal, off the hook sexual experience! All the screamin’ hot sex in Digital Playground’s award…

Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful boobies. They bounce, and they shake. There’s more than a mouthful, more than…

Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful boobies. They bounce, and they shake. There’s more than a mouthful, more than…

Don’t miss Digital Playground’s Exclusive Contract Star, Stoya in her debut boy / girl scene. Jack’s POV 9 is off the hook sex! All the screamin’ hot sex in Digital…

Jack is really busy casting for music videos and now he’s landed Digital Playground’s super fine contract star, Sophia Santi alongside Selina Draagen, Alyssa Chase, Carli Banks, Marlena, Christina Brooks…

Jack is really busy casting for music videos and now he’s landed Digital Playground’s super fine contract star, Sophia Santi alongside Selina Draagen, Alyssa Chase, Carli Banks, Marlena, Christina Brooks…

Shot entirely on HD, Jack’s Teen America 19 features Jesse Jane and Sophia Santi in intimate and seductive hardcore action! The Jack’s Teen America series arodies beauty pageants and Jack’s…

Jack’s casting again! This time he’s looking for leg models… sexy, leggy vixens who want to be in fresh, up and coming music videos. In volume 3, Digital Playground’s contract…

All the screamin’ hot sex in Digital Playground’s award winning Jack’s Playground series are now shot in POV perspective for your ultimate enjoyment. In Jack’s POV Playground, YOU will get…

Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful butts. They bounce, they roll and they shake and Jack finds pleasure deep…

Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful butts. They bounce, they roll and they shake and Robby finds pleasure deep…

All the screamin’ hot sex in Digital Playground’s award winning Jack’s Playground series are now shot in POV perspective for your ultimate enjoyment. In Jack’s POV Playground, YOU will get…

All the screamin’ hot sex in Digital Playground’s award winning Jack’s Playground series are now shot in POV perspective for your ultimate enjoyment. In Jack’s POV Playground, YOU will get…

Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful butts. They bounce, they roll and they shake and Jack finds pleasure deep…

Master Robby D. delivers more hot pussy pounding and intense orgasmic blow jobs. This time he turns his attention to some sexy ass mothers we’d all like to fuck. Some…

With five lovely ladies competing for the same title, it’s a tight race to the finish and Tiffany is off to a succulent start. She charms the judges and Scott…

With five lovely ladies competing for the same title, it’s a tight race to the finish and Tiffany is off to a succulent start. She charms the judges and Scott…

All the screamin’ hot sex in Digital Playground’s award winning Jack’s Playground series are now shot in POV perspective for your ultimate enjoyment. In Jack’s POV Playground, YOU will get…

All the screamin’ hot sex in Digital Playground’s award winning Jack’s Playground series are now shot in POV perspective for your ultimate enjoyment. In Jack’s POV Playground, YOU will get…

Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful boobies. They bounce, and they shake. In volume 3 of this delicious show,…

Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful boobies. They bounce, and they shake. In volume 3 of this delicious show,…

Jack’s Playground 32, features Digital Playground’s contract babe, Sophia Santi, eager to make it in the music video scene. She shows her distinct talents and raw, exquisite beauty in two…

Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful butts. They bounce, they roll and they shake and Robby finds pleasure deep…

Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful butts. They bounce, they roll and they shake and Robby finds pleasure deep…

Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful boobies. They bounce, and they shake. In volume 2 of this delicious show,…

Jack’s at it again! In his playground, Jack is busy casting for music videos. The delicious girls will do ANYTHING for stardom! Some suck, some fuck, some masturbate but they…

Jack’s at it again! In his playground, Jack is busy casting for music videos. The delicious girls will do ANYTHING for stardom! Some suck, some fuck, some masturbate but they…

Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful boobies. They bounce, and they shake. In volume 2 of this delicious show,…

Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful boobies. They bounce, and they shake. In volume 2 of this delicious show,…

Jack’s at it again! But this time, it’s professional… and even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack’s answer to getting a…

Jack’s at it again! But this time, it’s professional… and even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack’s answer to getting a…

Jack’s at it again! But this time, he’s focusing in on hot babes with BIG, FUN ASSED… It’s more cushion for the pushin’…. Forget professional… this volume is all about…

Jack’s at it again! But this time, it’s professional… and even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack’s answer to getting a…

Jack’s Playground is a collection of Jack’s personal videos, homemade in Santa Monica, California showcasing his uncanny ability to persuade girls to perform sexual acts in front of his camera….

Jack’s Playground is a collection of Jack’s personal videos, homemade in Santa Monica, California showcasing his uncanny ability to persuade girls to perform sexual acts in front of his camera….

Jack’s Playground is a collection of Jack’s personal videos, homemade in Santa Monica, California showcasing his uncanny ability to persuade girls to perform sexual acts in front of his camera….