Jack`s at it again. This time, it`s even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack`s answer to getting a f*ckin` job!

Jack`s at it again. This time, it`s even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack`s answer to getting a f*ckin` job!

Shot in High Definition. With six lovely ladies competing for the same title, it`s a tight race to the finish and Digital Playground contract stars, Jana Cova and Lacie Heart, are off to a succulent start. Lacie calls Scott her bitch before she takes his huge c*ck in her wet mouth and tight littl...

Jack`s at it again. This time, it`s even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack`s answer to getting a f*ckin` job!

Jack turns what he knows best into a career. Welcome to Jack`s answer to getting a f*ckin` job!

Shot entirely on HD, JACK`S TEEN AMERICA 20 features Digital Playground contract stars, Shay Jordan, Sophia Santi, and Jana Cova with industry babes Hillary Scott, Holly Morgan, and Sue Diamond. This horny hardcore action line parodies beauty pageants and Jack`s lovely contestants all compete fo...

Jack`s at it again. This time, it`s even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack`s answer to getting a f*ckin` job!

Jack`s at it again. This time, it`s even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack`s answer to getting a f*ckin` job!

Jack turns what he knows best into a career. Welcome to Jack`s answer to getting a f*ckin` job!

Shot in High Definition. This latest release from Digital Playground features Jesse Jane and Sophia Santi in intimate and seductive hardcore action! The Jack`s Teen America series parodies beauty pageants and Jack`s lovely contestants all compete for the crown. They take off their clothes, they m...

Jack`s at it again. This time, it`s even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack`s answer to getting a f*ckin` job!

With five lovely ladies competing for the same title, which girl will take the honors? Will Brooke or Jamie get to deliver their acceptance speech? Did Jack vote for one of their amazingly anal delights? Does Sara stand a chance of winning with her delectable titty-f*ck offering? Is the slippery,...

Jack`s at it again. This time, it`s even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack`s answer to getting a f*ckin` job!

Jack`s at it again. This time, it`s even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack`s answer to getting a f*ckin` job!

Jack`s at it again. This time, it`s even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack`s answer to getting a f*ckin` job!

Shot in High Definition. 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 Nails when she swallows his ENTIRE c*ck, up to his balls, in a decadent and sloppy blowjob before she lets him f*...

Five horny teens. Two sound guys with equipment. One contest. One winner. Sound familiar? It is. It`s JACK`S TEEN AMERICA. Put it in and cast your vote! 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 Ja...

Shot in High Definition. Jack`s at it again. This time, it`s even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack`s answer to getting a f*ckin` job!

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. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he imme...

Shot in High Definition. JACK`S TEEN AMERICA 21 features Digital Playgrounds lovely contract star, Lacie Heart, in a slammin romp with Scott Nails, Poppy Morgan, and Renae Cruzin decadent anal scenes plus sexy Tricia Oaks and the oh-so-hot Rebeca Linares. This horny hardcore action line parodies ...

Shot in HD. With five lovely ladies competing for the same title, it`s a tight race to the finish and Bree is off to a succulent start. She charms the judges and Scott Nails with her amazing body and gorgeous face. Alicia shows she`s got the stamina to go the distance as she works the treadmill, ...

See real girls uncensored. Winner of AVN`s Venus Awards, Nightmoves for Best Gonzo Series. Playful, powerful, and supremely sexual - a revolutionary sex comedy... One of the most original series in years! -- AVN magazine

The My First Porn series is a comical sex-spectacle of Jack directing his first porn movie. Volume 7 features the lovely and sweet Gianna in a tempestuous f*ck scene with Scott Nails and his massive c*ck. Then the gorgeous Kinzie Kenner, one of the hottest babes alive, shows up on set. She lets C...

MY FIRST PORN is a comical sex-spectacle of Jack directing his first porn movie. In Volume 3, watch Teagan Presley doing what she does best. Add Austin Kincaid and Faith to the mix and this installment sells itself. Don`t miss it!

Shot in High Definition. The MY FIRST PORN series is a comical sex-spectacle of Jack directing his first porn movie. Volume 9 is over 2 hours and features Teagan Presley in a brand-new, amazingly ass-a-liscious anal scene. With juicy boy/girl f*ck sessions, anal, tons of tease and titty, MY FIRST...

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. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he imme...

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. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he imme...

Jonni Darkko turns his unique vision loose in the inspired sequel to his Evil Angel debut. Five nasty angels showcase their sexy craft for the man with the camera. The DVD version contains an additional 51 minutes of interviews and other behind-the-scenes footage.

This latest release from Digital Playground features Riley Steele and Stoya in intimate and seductive hardcore action! The Jacks Teen America series parodies beauty pageants and Jacks lovely contestants all compete for the crown. They take off their clothes, they masturbate, they suck, they fuck ...

The MY FIRST PORN series is a comical sex-spectacle of Jack directing his first porn movie. Volume 11 is over two hours and features Shay Jordan as she`s worked into a frenzy. With juicy boy/girl romps and tons of tease and titty, MY FIRST PORN 11 has it all. Enjoy some first-class humor interlac...

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. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he imme...

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. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he imme...

Jack`s busy in his playground casting big-ass babes for leading roles in his yet-to-be-seen music videos. The delicious girls will do ANYTHING for stardom! Some suck, some f*ck, and some take it up the ass, but they ALL get naked and show their big beautiful, bouncing butts for the camera. There`...

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. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he imme...

Jack is really busy casting for music videos and now hes on the hunt for big, beautiful boobies. They bounce and they shake. Theres more than a mouthful, more than a handful plenty of big boobies bursting out of their bras. Forget professional... This volume is all about big, hot, bouncing boobs...

Lawyer by day, nympho by night From the creator of Busty Beauties comes De-Briefed, the XXX legal soap opera of all-time! Hustler's contract girl Jessica Jaymes is an attorney at an outrageous law firm where the way to get ahead is to give head...and give up your ass, too. This is a Hustler fe...

Shot in HD Widescreen. Jack is really busy casting for music videos and now he`s landed Digital Playground`s super fine contract star Sophie Santi. True to Jack`s good sense, there`s a lot of tease and a lot of action and it`s all entertaining! Forget professional... This volume is all about tota...

There`s nothing better than f*cking a p*ssy or ass that`s wet!!! These whores are all horny and looking to make your big c*ck their pet. So don`t be left high and dry, because these sluts are WETTER THE BETTER every day!

Shot in High Definition. The MY FIRST PORN series is a comical sex-spectacle of Jack directing his first porn movie. Volume 8 is three fullhours and features Digital Playground contract stars Sophia Santi and Lacie Heart, alongside industry babes Sasha Grey and Kinzie Kenner. With buttloads of sl...

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. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he imme...

Jack is really busy casting for music videos and now he`s landed Digital Playground`s super fine contract star, Teagan Presley. She takes a big c*ck in the butt and we KNOW Scott Nails found some SWEET ASS pleasure deep in her crack. True to Jack`s good sense, there`s a lot of tease and a lot of ...

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. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he imme...

See six of your favorite f*ck fantasies! More rectal-wrecking ass sex, sperm-drenched semen soakings, and wild wet dreams lensed in stunning twat-twinkling detail. Enjoy!!!

Intense boy/girl and anal scenes.

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. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he imme...

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. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he imme...

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. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he imme...

P.O.V. with a twist! See twisted fantasies turned into reality.

Jack`s Playground 31, the superstar edition, stars the lovely Jana Cova in two delectable scenes, Devon in all her naked splendor and DP`s original contract star, Rocki Roads in brand new, never-before-seen footage. She lets Vince Vouyer spin her around and pleasure her all over. Jasmine Byrne do...

Prime Young Girls 7 young fuck-sluts with the freshest pussies are waiting for you! Once again Hustler brings you the hottest young sluts and all the dirty details of what they've been up to this summer. Featuring hardcore Kama Sutra lessons that rewrite the ancient art of ass-banging, hot ...