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...

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 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...

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. 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 ...

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`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. 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. 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,...

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...

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. 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...

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!!!

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. 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...

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`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. The MY FIRST PORN series is a comical sex-spectacle of Jack directing his first porn movie. Volume 10 is over two hours and features Stoya in a brand-new, amazingly ass-a-liscious anal scene. The A-list cast includes sensational f*ck stars Sophia Santi, Kortni Kiss, Sabrina Rose,...

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. 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. With its unique camera work, JACK`S POV 12 brings you into the action and doesn`t loosen its grip until you`re completely drained. It puts you in the driver seat and gives you the best action, the most delicious teases, and pure in-your-face comedy. It`s your job to cast sexy, yo...

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. 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. POSH KITTEN plays tribute to the days of pin-ups and high-heeled honeys. The A-list cast pours sexuality across the screen with smoldering glances and steamy seductions resulting in mind blowing, screaming orgasms. With boy / girl, girl / girl, solo, and anal scenes throughout, t...

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

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 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 the second volume, Digital Playground`s contract superstar, Shay Jordan, shows she is perfect from head to toe. Jack`s gorgeous babes deliver ...

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 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. STOYA: PERFECT PICTURE is an expression of Stoya`s exploration of love by Digital Playground`s celebrated director Celeste. Contract star Stoya takes on life`s trials and tribulations with her succulent pussy and tight ass in this moving sexual drama! As she explores the secrets ...

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. 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 MY FIRST PORN series is a comical sex-spectacle of Jack directing his first porn movie. Volume 4 rocks the house with Scott Nails and Jasmine Byrne in a Viagra induced, titillating anal scene, plus Charmane gets a bad case of Turet`s syndrome and Eric Masterson takes full adv...

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. 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!

Sumptuous Lela Star is Club Jenna`s most nefarious nympho yet, with appetites that range from posh to profane. Flanked by an energetic cast with an array of creative cravings, Lela draws you deep into the murky darkness of her most intimate obsessions. With her hooks buried deep in your willing f...

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. TEAGAN`S JUICE features Teagan Presley in six lascivious scenes. Rich with innuendo, Celeste uses ripe fruits and juices intertwined with passionate sex in each seductive scene. Teagan unleashes her desire in three provocative boy/girl scenes with Jerry, Marco Banderas, and a hea...

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...

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 ASS ADDICTION is the newest incarnation from acclaimed director, Robby D. Volume 1 features Kinzie Kenner in her very first anal orgy with Scott Nails, Jean Val Jean, and Marco Banderas! Shyla Styles gets an anal tag teaming she`ll never forget and Katja enjoys a B/B/G that ends w...

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. 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 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 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. 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 ...