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`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 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!

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 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,...

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...

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...

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

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

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*...

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 ...

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 career. Welcome to Ja...

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...

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 Robby finds pleasure deep between their crevices. In Volume 3 of this delicious show, Digital Playground`s amazing contract superstar, Jana Cova proves she is...

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 f*ck scene with Scott Nails and his massive c*ck. Then the gorgeous Kinzie Kenner, one of the hottest babes alive, shows up on set. She lets C...

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 suck, they fuck ...

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...

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...

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 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...

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 do...

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. 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!!!

Britney Rears is back for a third installment of pop star spoofing, singing and screwing!

There`s nothing fishy in these nets... just prime teen p*ssy ready for the reamin` and creamin`! Bag `em and bang `em any way you like... in nets, stockings, tights, knee-highs or hose, it doesn`t matter as long as they`re wrapped! Manicured toes, perfectly arched soles, and leggy lovelies deli...

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 Stoya as she wraps ...

Lexi Belle hates her new job cleaning house, but a big hard cock poppin` out of our Horny Susan Spinning Sex Table made her a happy bitch! Sindee is a wacky slut that struts, sucks and fucks for the Sexy Maid Service! Give her a Spin! Jynx is a sexy Latina who bounces and spins on Lee`s rod like ...

An all-new assortment of European lovelies gets the Rocco business in this latest in the DIRTY DREAMS series. Includes behind-the-scene footage and photo galleries.

At the Russian Institute, a smart boarding school reserved for girls descended from wealthy muscovite families, it is the effervescence. Here are holidays! The young ladies are going to escape the severe discipline of the instate and give free expression to their pleasure. With Sofia and Natalia,...

Dirty f*cking, messy blowjobs, and nasty 3-ways break out on the set of Britney`s television show as one lick of a Britney Pop turns gorgeous babes into gonzo sex freaks! America`s tabloid princess loses her mind, rips off her clothes, and gets f*cked in the ass, and when Britney`s little sister ...

HUSTLER brings you two anal intensive adventures sure to drain your ball sack dry! These sluts are cock hungry, and won`t rest until they are properly butt-fucked!

Shot in High Definition. All the screaming 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 POV Playground, YOU will get the BEST action, the most delicious tease, and pure comedy IN YOUR FACE. Pretend YO...

Tight, wet, and willing! Angel Valentine`s p*ssy is an acrobatic wonder! Bree Olson is a simple girl who loves a good old fashioned facial! Stephanie Cane is an innocent girl with a tiny twat!

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...

7 Delicious ass scenes!!!

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...

Starring Heather Summers! 6 Bra Bustin' Scenes! Hot Office Sex! Big Tits, Tight Holes! Huge Tits! Cum Guzzler! Up The Ass! Sloppy Facials! Cum On My Face! Big Tits Boss is a focus on powerful women with big tits in the professional environment. Enjoy the hot and steamy hardcore actio...

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...

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...

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...

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.

Perfect posteriors.. beautiful backsides.. tantalizing tails. Call 'em what you will, we've got the roundest and rockin'-est rears in the known universe. Bent over and prepared to be pounded, we proved once again that there are asses.. and then there are fine asses.

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...