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 massive melons bursting out of their bras. JACK`S BIG TIT SHOW 9 is all about the tantalizing titties of Gia...

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 massive melons bursting out of their bras. JACK`S BIG TIT SHOW 8 is all about the tantalizing titties of Gin...

Shot in High Definition. 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 abo...

Real girls uncensored! Guaranteed big! Back dat ass up!

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, round, gorgeous ...

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!!!

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...

Shot in High Definition. 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, the amazingly talented, Kinzie Kenner takes over with a scrumptious f*ck and suck spectacle and her fine boob...

Ruby aspires to be a better actress, so when she`s accepted as the leading lady in a wrestling-themed show, she jumps on it! Sadly, the director prefers Ruby`s rival when she also arrives for try-outs, enraging Ruby, and motivates her to be a better actress and a better fuck!

Shot in High Definition. 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 ...

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! 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. There`s more than a mouthful, more than a handful ...

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 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, the amazingly beautiful, Krystal Steal takes over with a scrumptious f*ck and suck spectacle and her fine boobs on display. Then Rebec...

Jack is really busy casting for music videos, and now hes landed Digital Playgrounds super fine contract star, Jesse Jane. She f*cks Ben English every which way in true gonzo style. Throughout JACK`S PLAYGROUND 37, you will enjoy similar sexcapades with Kelsey, Roxy, Jelena, Sue, and Valentina. T...

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. 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 vi...

While most young girls dream of white picket fences and getting happily married when they grow up, Peyton (Stormy Daniels) always had other plans. At the age of 20, she meets Charles (Randy Spears), an older man of wealth and status. After seducing him into marrying her, she deviously begins putt...

Shot in High Definition. 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 winning Jack`s Playground series are now shot in POV perspective for your ult...

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. 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 ...

LACIE: SEXUAL FREAK is a visual palette of equally sexy, erotic, and naughty delights. Shay Jordan joins Lacie Heart to tease and toy with the men they desire, working them over to their own satisfaction and delight, releasing them from duty only after they have satisfied them fully. Their co-sta...

3 Ways! Facials! Anal!

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!

There`s a reason everyone loves a bad girl. Bad Girls 4 is packed with more scandalous and naughty sex than ever before. These girls know that being this bad has never been so good.

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...

4 amazing hours of huge heaving breasts! All of the giant jugs and hot sex you can handle!

Who needs to be clean when you have dirty girls doing oh so filthy things? Hot, nasty sluts get so foul that you will explode with an ecstasy filled howl!!!

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 ...

The Young Harlots want to reveal their dirtiest secrets for you..... So pull on their pigtails, lift their pleated skirts, spread their legs wide, grab those hot little asses, spit into their tight pussies and fuck them hard.... and the dirty little sluts will reveal everything.

Shot in High Definition. It`s ass good ass anal gets!

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

Shot in High Definition. DEEPER #7 takes you deep inside Digital Playground`s lovely and exotic Katsumi. She captivates the screen in sensational ANAL scenes with Steve Holmes and Chris Charming. Featuring insane intros, state-of-the-art editing, masterful direction and a delightful foray of fles...

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 at it again! But this time, he`s focusing in on hot babes with BIG, FUN ASSES. It`s more cushion for the pushin`. Forget professional... This volume is all about ASS. It`s hot and kinky and Jack`s found a new niche.

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 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. 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!

Beginning with the first frame and continuing until the final credits roll, DEEPER 10 is an intense sexual experience. It embarks on a journey, deep inside Digital Playgrounds own Shay Jordan and Lacie Heart. This blockbuster series showcases Shay in all her beauty. She captivates the screen in a...

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. 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...

Shot in High Definition. 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 e...

Shot in High Definition. 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 competiti...

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*...

INSTANT LESBIAN is the dosage called for when wanting to see two gorgeous woman exploring each others bodies. These girls got so wet with excitement we couldn`t stop there. Just when you thought a guy wasn`t needed, a couple of these lovely ladies even let us bring in a STUD to finish things off.

Special Edition 2-Disc Set Shot in HD Widescreen. L.A. Faces with Oakland Booty. Rita Faltoyano Has A Farewell Pooper Party! Everything is Bigger On Texas Alexis! Rebeca Linares is Proof... Just Say No To Drugs! Big Ass Fashion Sense! Tourist Maria Bellucci Bows To The Darkside! Rachel StarrMarin...

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,...

Deaf and dumb Jodie escapes from her city pimp to the haven of Ashby Stables, where she discovers that she can ride for life.

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, young women in musi...