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 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, hot, bouncing boobs...

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 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. 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 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...

Shot in High Definition. Jana Cova is a sexual freak and she wants you to watch. For the first time in her life, Jana takes it in her sweet p*ssy and tight bum all at the same time and she loves it. Discover your own desires in this delicious movie starring DP`s amazing Jana Cova in her wettest t...

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 Tucci goes with the...

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 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 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 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...

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. Digital Playground`s sexy and elusive contract star, Sophia Santi plays a sex-inspired MADEMOISELLE in this lofty production by Robby D. Sophia appears in various states of undress and desire as she pleasures herself in front of the television.

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 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 ...

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 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 ...

Jack is really busy casting for music videos and hes scored some super fine ass for volume 38. Digital Playgrounds amazing contract super stars Teagan Presley and Lacie Heart join an all-star cast that includes blowjob maven Audrey Bitoni plus Leah Luv, Neveah, and Roxy Deville. This is gonzo f*c...

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...

Shot in High Definition. In Digital Playground`s JANA COVA IN BLUE, contract superstar Jana Cova makes good on her promise to become a perfect slut. With the help of contract sister Sophia Santi and a breathtaking all-star cast, Jana is redefined in her hardest film to date. Director Celeste dict...

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. 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!!!

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!

HELL HATH NO FURY!Years ago, Eric Jones sold his soul to the Devil so he could be a player. Now, he feels there`s a technicality, and he wants to renegotiate. Well, it`s not that easy. It seems that Satan likes a good wager.

Shot in High Definition. You`ve loved Hannah in everything and now you can enjoy her work as you never have before, with all the production values Digital Playground is famous for. Hannah Harper is a sexual freak and she wants you to watch as she turns up the heat. Throughout Digital Playground`s...

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...

Shot in High Definition. DEEPER #3 is beautiful, erotic, and cinematic homage to the greatest horror movies ever made. Starring Digital Playground`s contract superstar, Jesse Jane in two twisted and mind-blowing f*ck scenes, DEEPER #3 delivers a multitude of flesh fantasies. Anal queen, Hillary S...

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 ...

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!!!

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 ...

Shot in High Definition. JACK`S MILF SHOW delivers more hot p*ssy pounding and intense orgasmic blowjobs with some mothers, aunts, and top executives that are all super hot and horny for a real good c*ck.

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!

Shot in HD! The product of fine parenting. Ashley needs lunch money. Daddy`s broke... and feeds her pig-sauce instead! Lela Star`s beachside bang out! Mia Rose`s hopscotch hijinks! The painters come to Chelsie`s house... they leave her face spackled! Patty cake, patty cake baker`s man, suc...

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...

Staying out of trouble requires a little dirty work! Acclaimed writer/director Robby D., gives newmeaning to `sexual, dark comedy` with Repo Girl! In a strange twist of fate, Repo Girl is a fun story about a girl who has to steal cars to stay out of jail, only this time it`s legal! Can she do it?

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 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...

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*...

HARDCORE XXX SEX ACTION!A showcase for the sexuality and sensuality of Jesse Jane. -- AVN MagazineThere are few masterpieces in the porn world. This is one of them. Visually stunning! -- Adult DVD EmpireA passionate and visionary tour de force! -- Propaganda MagazineThe perfect title for this mas...

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

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 a...

Directed by Celeste, WAY OF THE DRAGON is a surreal journey through a sensual dreamscape of Asian customs, fantasies, and sexual delights. Watch a beautiful young cast as they create an artistic masterpiece of pain and pleasure. With ropes and kimonos, Celeste casts a vibrant, sexy light on Asia`...