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`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. 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*...

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`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. 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. 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. 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. 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...

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!

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 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. 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!!!

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...

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 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 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. 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`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. 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 #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`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. 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. 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 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. 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. 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. 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. 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. 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 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 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 fuck and suck spectacle and her fine boobs on dis...

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 ...

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. 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. 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,...

Double Contract Stars Edition! Sexy! Horny! Hot Gilrls Loves Masturbating! My Ass Will Take Boy & Toy! White Boy 'N Tha Hood! The My First Porn series is a comical sex-spectacle of Jack directing his first porn movie. Volume 8 is 3 full hours and features Digital Playground contract stars...

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 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 fuck and suck spectacle and her fine boobs on di...

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. 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...

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 Version. Raven Alexis arrives in the land of opportunity eager to escape her disparaging past. Her innocence and girl-next-door looks prove dichotomous as she quickly loses her inhibitions. In this light hearted feature film, Raven finds redemption in her powerful sex appeal. As the story...

Blu-Ray Version. Asian sensation, Shay Jordan is back with an eager-to-please cast of exotic nymphs. Jack`s Asian Adventure 4 will surely satiate because these young hotties were born to satisfy your every need.

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. GABRIELLA FOX: NUDE is Digital Playground`s masterful new offering of the luscious contract star Gabriella Fox. Acclaimed director Robby D. explores ways to heighten one`s sexual experience by restraining vital senses like sight, taste, and touch. The cast of horny vixens and stu...

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...