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. 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!

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. 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 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!!!

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 fuckin` job!

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. 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. 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...

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. JACK`S PLAYGROUND #33 stars Devon in a scandalous scene with Scott Nails, plus gorgeous babes titty-f*cking, c*cksucking, and banging their way into music video stardom. This title is HOT HOT HOT!!!

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 ...

The award-winning, best-selling, and highly acclaimed JACK`S PLAYGROUND is now available on Blu-Ray. Jack is really busy casting for music videos, and the girls in volume 27 will do anything for a shot at fame. True to Jack`s good sense, there`s a lot of tease and a lot of action and its all ente...

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. 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`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....

Blu-Ray Version. 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 delectable scenes. Then Michelle Maylene proves she will do anything for fame too. Flower Tu...

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 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. 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 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. 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...

Real Girls Uncensored! Starring Sophia Saint ! 'Playful, powerful and supremely sexual- a revolutionary sex comedy... One of the most original series in years!' The New Jack Is Deeper Faster Than Ever Before!

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. 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 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. Jack is really busy casting for music videos and hes scored some super fine ass for volume 38. Digital Playgrounds amazing contract super stars Teagan Presley and Lacie Heart join an all-star cast that includes blowjob maven Audrey Bitoni plus Leah Luv, Neveah, and Roxy Deville. ...

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, ...

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. 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!!

Jack is really busy casting for music videos and now hes landed Digital Playgrounds super fine contract star, Teagan Presley. She takes a big cock in the butt, and we KNOW Scott Nails found some SWEET ASS pleasure deep in her crack. True to Jacks good sense, theres a lot of tease and a lot of act...

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 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. TITLICIOUS 2 is packed with ANAL, tease, masturbation, and tons of titty fucking! Mick Blue kicks off the film with a slammin scene and explodes on Alanahs jugs as Scott gives Mason more than a mouthful of cock. A fantastic fuck fest, this disc is the first place to look for 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. Don`t miss this all-star cast that includes Hannah Harper, Lacey Maguire, Annette Schwarz, Rachel Roxxx, and Britney Stevens in a very personal, off the hook sexual experience! All the screamin` hot sex in Digital Playground`s award winning Jack`s Playground series are now shot i...

Blu-Ray Version. 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. Dont miss it!

Blu-Ray Version. Its better than a fortune cookie, fried ice cream, pad Thai and sushi! Director Robby D. mastered the art of high-def porn and now hes created a whole new breed of gonzo eye candy. This deliciously perverse title will satisfy your Asian craving for at least a week. In the first s...

Blu-Ray Version. The MY FIRST PORN series is a comical sex-spectacle of Jack directing his first porn movie. Volume 6 features the amazing anal queen, Delilah Strong, in a butt scene with Scott Nails that rocked the whole damn house! Next up you`ll find the lovely and sweet Riley Shy engaged in a...

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 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 b...

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. 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 ...

Blu-Ray Version. Director Robby D. delivers the genuine goods in this fresh tribute to natural redheads. The amazingly gorgeous, red-haired, mostly freckled cast sucks, f*cks, and takes it in the ass. The carpets match the drapes in this sexy, funny adventure. A spin-off of the best selling and m...

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. 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`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. 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. Everybody knows that bad girls have more fun, and the Digital Playground girls are the baddest on the block. Digital Playground`s BAD GIRLS 2 is the new, kinky gonzo from acclaimed director Robby D. Contract stars Riley Steele and Angelina Armani are naughty and begging to be pun...