Blu-Ray Version. 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 between their crevices. True to Jack`s good sense, there`s a lot of tease and a lot of action and it`s all entertaini...

Blu-Ray Version. Jack is really busy casting big, bouncing, beautiful butts for music videos. They shake, they roll, and they swallow fat c*cks whole! True to Jacks good sense, theres a lot of tease and a lot of action and its all entertaining! Forget professional... This volume is all about big,...

Blu-Ray Version. Shot entirely on HD, JACK`S TEEN AMERICA #4 features Katsuni 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 masturbate, they suck, they f...

Blu-Ray Version. 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...

Special Contract UnitbrbruJack's Checklist/ubrbrliShitty Shitty Bang Bang liAnal Pipe Cleaning liAnal Bubble Blowing liLee Stone Throwing liBlind Demolition liPaddle Discipline liGag and Swallow liDiapers liSwallow the Roman Soldier liDid we mention Anal?

Blu-Ray Version. JACK`S BIG ASS SHOW is now available in high-definition on Blu-Ray Disc with Super Fine Asses EVERYWHERE! Jacks at it again! But this time, hes focusing in on hot babes with BIG, FUN ASSES. With Digital Playgrounds contract stars, Lacie Heart and Jana Cova, its more cushion for ...

Playful, powerful and supremely sexual - a revolutionary sex comedy...One of the most original series in years! Real girls uncensored, an explosion of sexual frenzy and desire. Big tits are more than a handful, they`re two!!!

Blu-Ray. Dont miss Lauren Phoenix, Rachel Rotten, Meagan, Sativa Rose, and Harmony in insanely 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 f*...

Blu-Ray Version. 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!

Blu-Ray Version. 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 between their crevices. In volume 5 of this ASS-A-LISCIOUS show, Jack shows some good judgment as he enlists Katja Ka...

Blu-Ray Version. 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, 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, the weights ...

Blu-Ray Version. All the screaming hot sex in Digital Playgrounds award winning Jacks Playground series are now shot in POV perspective for your ultimate enjoyment. In Jacks POV Playground, YOU will get the BEST action, the most delicious tease, and pure comedy IN YOUR FACE. Pretend YOU are casti...

Blu-Ray Version. In volume 4 of this ASS-A-LISCIOUS show, Jack shows some good old-fashioned nepotism as he enlists the hard-bodied Naomi to devirginize his cousin for an 18th birthday surprise. Naomi does the job, turns up the heat, and gives the young lads` future lovers stiff competition! Sexy...

Blu-Ray Version. 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!

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 new POV Playground, YOU will get the BEST action, the most delicious tease and pure comedy IN YOUR FACE. Pretend YOU are casting for musi...

Blu-Ray Version. With its unique camera work, JACK`S POV 13 brings you into the action and doesn`t loosen its grip until you`re completely drained. It puts you in the driver`s seat and gives you the best action, the most delicious teases, and pure in-your-face comedy. It`s your job to cast sexy, ...

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

Blu-Ray Version. This DVD stars the lovely Teagan Presley with Audrey Bitoni, Kapri Styles, Alexis Love, and Maya Hills. Plus, their luscious legs, fantastic feet, and tantalizing toes!!

Blu-Ray Version. Jack knows ambitious chicks will do anything to win first place in a beauty pageant. JACK`S TEEN AMERICA 22 features Jack and his crew interviewing lovely contestants Teagan Presley, Sasha Grey, and Adrianna Lynn to find out why they are qualified to be the next Teen America. The...

Blu-Ray Version. With its unique camera work, JACK`S POV 14 brings you into the action and doesn`t loosen its grip until you`re completely drained. It puts you in the driver`s seat and gives you the best action, the most delicious teases, and pure in-your-face comedy. It`s your job to cast sexy, ...

Blu-Ray Version. 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. You will get the best action, the most delicious tease, and pure comedy in your face. Pretend you are casting for music videos as ...

Blu-Ray Version. Let Jack`s cameras tease and tempt you, offering the finest bush on the planet, all in first hand perspective. In volume 6, Digital Playground`s ultra-hot, super fresh and amazingly gorgeous, Shay Jordan takes on super stud, Scott Nails delivering an invigorating blow job and an ...

Blu-Ray Version. 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-fuck offering? Is the slipp...

Blu-Ray Version. Jack is really busy casting for music videos and now hes on the hunt for big, beautiful butts. They bounce, they roll, and they shake and Jack finds pleasure deep between their crevices. True to Jacks good sense, theres a lot of tease and a lot of action and its all entertaining!...

Starring Jesse Jane! Smoking Hot Jesse Rocks Till It Rolls! 'Playful, powerful and supremely sexual - a revolutionary sex comedy... One of the most original series in years!' The New Jack Is Harder Deeper Faster Than Ever Before! Jack is really busy casting for music videos and now he'...

Blu-Ray Version. 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 fuck scene with Scott Nails and his massive cock. Then the gorgeous Kinzie Kenner, one of the hottest babes alive, shows up o...

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 cock, up to his balls, in a deca-dent and sloppy blow job before she lets him fuck her tight little ass...

Blu-Ray Version. 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 a handful... Plenty of big boobies bursting out of their bras. Forget professional... This volume is all about bi...

Blu-Ray Version. This new release stars Katsumi in her panty hose with More Anal and Lots of Fun Jack TV and Fine Ass Chicks, Titty-Fucking, Cock-Sucking and Banging Their Way Into Music Video Stardom! This title is HOT HOT HOT!!!

Make A Wish, Now Blow Me! Babe Got Cock Attitude! Vitamin C Wanted! 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 the best action, the most delicious...

Blu-Ray Version. Jacks casting again! This time hes looking for leg models... sexy, leggy vixens who want to be in fresh, up and coming music videos. In Volume 3, Digital Playgrounds contract super stars, Sophia Santi and Lacie Heart show they are PERFECT from HEAD to TOE! Join them and an all-st...

Blu-Ray Version. 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 ...

Blu-Ray Version. Directed by Robby D., JACK`S PLAYGROUND #30 is an incredibly insatiable, sexy installment of the multi-award winning Jack`s Playground line. This Robby D. series has been named Best Gonzo Series (AVN), Best All-Sex Series (Nightmoves), and Best Comedy Series (AFWG), and that`s ju...

Blu-Ray Version. 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, ho...

Blu-Ray Version. This series chronicles the life of Jack, a porn director, and the many comical mishaps of his uber job. This first installment features the lovely Teagan Presley in a succulent and decadent f*ck fantasy. The volume is ripe with anal, boy/girl and, of course, a plethora of gooey,...

Blu-Ray Version. MY FIRST PORN is a comical sex-spectacle of Jack directing his first porn movie. In Volume 2, Devon gets down and she gets dirty. Its hot, its messy and you dont want to miss this.

Blu-Ray Version. The camera starts at her petite ankle and slowly travels up the milky skin of her calf and around her toned hamstring on a journey to the pink treasure nestled between her two long legs. Welcome to JACK`S LEG SHOW 4, where leg aficionados are introduced to the slender limbs of St...

Blu-Ray Version. Robby D jumps head first into the interracial anal market with A JUNGLE STORY. Featuring mixed ethnicities ranging from Asian to Spanish, African-American and Caucasian, this anal f*ck-fest details the complex and compromising tale of a black couple that moves into a white subur...

Blu-Ray Version. Jacks at it again! In his playground, Jack is busy casting for music videos. The delicious girls will do ANYTHING for stardom! Some suck, some f*ck, some masturbate, but they ALL get naked and show big beautiful, bouncing titties for the camera. Theres more than a mouthful, more ...

Blu-Ray Version. 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 fuck and some take it up the ass but they ALL get naked and show their big beautiful, bouncing butts for th...

Blu-Ray Version. 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 between their crevices. In Volume 3 of this delicious show, Digital Playground`s amazing contract superstar, Jana C...

Blu-Ray Version. When Jack puts his mind to something, the filthy possibilities are endless! In Jacks Asian Adventure 2, Jack rounds up the most exotic Asians he can find for a wild time of fun and games. These horny girls love you long time and they most definitely sucky, sucky. Digital Playgrou...

Blu-Ray Version. 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!

Blu-Ray Version. Shot entirely on HD, CONTROL 10 features almost three amazing hours of pure c*ck tease featuring the insatiable Jenna Haze in a mind-blowing anal performance with Scott Nails. Director Robby D. captures sexy in every girl. His amazingly delicious and f*ckable cast also includes e...

Blu-Ray Version. 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-cla...

Blu-Ray Version. Robby D`s BLACK C*CK SLUT plays on your every fantasy. Watch the biggest and blackest c*cks drill the hottest starlets in the business. The girls love every inch they`re given and so will you. BLACK C*CK SLUT embraces every kinky taboo you`ve dreamt of. It`s superbly cut with you...

Blu-Ray Version. 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 care...

Blu-Ray Version. High-end, hot gonzo featuring plenty of anal and the biggest asses.