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Jack's Playground 7
Digital Playground (SKU: 62629)
No Listings Currently Available
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 immedia...
Jack's Playground
Digital Playground (SKU: 57295)
No Listings Currently Available
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 immedia...
Jack's Playground 13
Digital Playground (SKU: 76880)
No Listings Currently Available
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 immedia...
Jack's Playground 2
Digital Playground (SKU: 57957)
No Listings Currently Available
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 immedia...
Jack's Playground 3
Digital Playground (SKU: 59293)
No Listings Currently Available
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 immedia...
Jack's Playground 15
Digital Playground (SKU: 78524)
No Listings Currently Available
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 immedia...
Jack's Playground 26
Digital Playground (SKU: 100464)
No Listings Currently Available
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 immedia...
Jack's Playground 8
Digital Playground (SKU: 63638)
No Listings Currently Available
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 immedia...
Jack's Playground 14
Digital Playground (SKU: 77725)
No Listings Currently Available
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 immedia...
Jack's Playground 20
Digital Playground (SKU: 87103)
No Listings Currently Available
See real girls uncensored. Winner of AVN`s Venus Awards, Nightmoves for Best Gonzo Series. Playful, powerful, and supremely sexual - a revolutionary sex comedy... One of the most original series in years! -- AVN magazine
Jack's Playground 17
Digital Playground (SKU: 83011)
No Listings Currently Available
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 immedia...
Jack's Playground 31
Digital Playground (SKU: 110825)
No Listings Currently Available
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. Jasmine Byrne does...
Jack's Playground 11
Digital Playground (SKU: 73102)
No Listings Currently Available
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 immedia...
Jack's Playground 19
Digital Playground (SKU: 85602)
No Listings Currently Available
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 immedia...
Jack's Playground 23
Digital Playground (SKU: 92271)
No Listings Currently Available
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 immedia...
Jack's Playground, 6
Digital Playground (SKU: 61436)
No Listings Currently Available
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 immedia...
Jack's Playground 36
Digital Playground (SKU: 145154)
No Listings Currently Available
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 totally...
Jack's Playground 10
Digital Playground (SKU: 71500)
No Listings Currently Available
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 immedia...
Jack's Playground 21
Digital Playground (SKU: 88895)
No Listings Currently Available
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 immedia...
Jack's Playground 4
Digital Playground (SKU: 59660)
No Listings Currently Available
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 immedia...
Jack's Playground 25
Digital Playground (SKU: 96160)
No Listings Currently Available
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 immed...
Jack's Playground 12
Digital Playground (SKU: 75073)
No Listings Currently Available
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 immedia...
Jack's Playground 9
Digital Playground (SKU: 69671)
No Listings Currently Available
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 immedia...
Jack's Playground 18
Digital Playground (SKU: 84365)
No Listings Currently Available
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 immedia...
Jack's Teen America: Mission 4
Digital Playground (SKU: 86472)
No Listings Currently Available
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!
Jack's Playground 16
Digital Playground (SKU: 81282)
No Listings Currently Available
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 immedia...
Jack's Playground 24
Digital Playground (SKU: 93876)
No Listings Currently Available
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 immedia...
Jack's Playground 22
Digital Playground (SKU: 89499)
No Listings Currently Available
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 immedia...
Jack's Teen America: Mission 14
Digital Playground (SKU: 109692)
No Listings Currently Available
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, we...
Barely Legal 58
Hustler (SKU: 111487)
No Listings Currently Available
These young cheerleader whores are full of team spirit and big throbbing c*cks! They feverishly practice their oral skills on each other`s p*ssies and sport f*ck to stay in shape. These young sluts know how to take one for the team!
Jack's Playground 34
Digital Playground (SKU: 131760)
No Listings Currently Available
Shot in High Definition. This new release stars Katsumi in her panty hose with More Anal and Lots of Fun Jack TV and Fine Ass Chicks, Titty-F*cking, C*ck-Sucking and Banging Their Way Into Music Video Stardom! This title is HOT HOT HOT!!!
M.I.L.F. Money 6
Legend (SKU: 80126)
No Listings Currently Available
Welcome to another scorching edition of M.I.L.F. MONEY, the only reality programming for your c*ck. Did you know that 90% of single parents are women. 54% of those women have stroke-value, and an impressive 90% of those women lack common sense and good judgement. What do these numbers mean to you, t...
Jack's Teen America: Mission 11
Digital Playground (SKU: 103731)
No Listings Currently Available
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!
Jack's Leg Show 3
Digital Playground (SKU: 142809)
No Listings Currently Available
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 Volume 3, Digital Playgrond`s contract super stars, Sophia Santi and Lacie Heart show they are PERFECT from HEAD to TOE! Join them and an...
Jack's POV 8
Digital Playground (SKU: 140915)
No Listings Currently Available
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 video...
Jack's Teen America: Mission 17
Digital Playground (SKU: 123192)
No Listings Currently Available
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 little p...
Teen Hitchhikers 14
Cinema Play (SKU: 139708)
No Listings Currently Available
These girls need a real hard ride!
Jack's Playground 35
Digital Playground (SKU: 140161)
No Listings Currently Available
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 act...
Jack's Playground 27
Digital Playground (SKU: 101292)
No Listings Currently Available
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 immedia...
Jack's Teen America: Mission 6
Digital Playground (SKU: 95571)
No Listings Currently Available
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!
Jack's Playground 28
Digital Playground (SKU: 102910)
No Listings Currently Available
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 immedia...
Jack's Teen America: Mission 3
Digital Playground (SKU: 84653)
No Listings Currently Available
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!
Jack's Teen America: Mission 8
Digital Playground (SKU: 99308)
No Listings Currently Available
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!
Jack's Playground 30
Digital Playground (SKU: 107406)
No Listings Currently Available
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 just a few of the acco...
MILF Money 3
Legend (SKU: 64265)
No Listings Currently Available
REAL MOMS WITH REAL STROKE-VALUE!Since its inception, the M.I.L.F. Money Series has:Paid for a year of hot, nutritious lunches for one childAllowed 6 children to get Christmas presents for the first time everPaid for a mother of two to get her tubes tied to avoid future unwanted nuisancesPaid of Cra...
Jack's Playground 33
Digital Playground (SKU: 118948)
No Listings Currently Available
Shot in High Definition. 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!!!
Jack's POV 2
Digital Playground (SKU: 112868)
No Listings Currently Available
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 music v...
Jack's POV
Digital Playground (SKU: 109345)
No Listings Currently Available
Digital Playground is proud to announce the release of a brand ne line by Director Robby D. 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...
Jack's Teen America: Mission 1
Digital Playground (SKU: 77761)
No Listings Currently Available
Jack turns what he knows best into a career. Welcome to Jack`s answer to getting a f*ckin` job!
Jack's Teen America: Mission 15
Digital Playground (SKU: 114266)
No Listings Currently Available
Shot in HD. 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...