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.

Teagan Wants More! 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 Jack’s answer…

Five horny teens. 2 sound guys with equipment. 1 contest. 1 winner. Sound familiar? It is. It’s Jack’s Teen America. Put it in and cast your vote! Jack’s at it…

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 Jack’s answer to gettin a fuckin…

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 Jack’s answer to gettin a fuckin…

Special Contract Unit 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 Jack’s answer…

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 Jack’s answer to getting a…

Eva, Sandra, Gia and Melissa are all willing to do whatever it takes to win “Miss Teen America”. So they show off their particular tlaents on the crew interviewing them….

Teagan Is Back! 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 Jack’s answer…

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…

A FantASStic Show Are you ready for some extreme bubble bursting butts?

Teagan Presley & ANAL, does the rest of this description even matter? Jack is really busy casting big, bouncing, beautiful butts for music videos. They shake, they roll and they…

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…

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 Jack’s Playground: Leg Show 3,…

The camera starts at her petite ankle and slowly travels up the milky skin of her calve and around her toned hamstring on a journey to the pink treasure nestled…

Fuck Me Silly Vol. 2 Seven of today’s hottest stars brought together in one collection to show off exactly what makes them so special! There’s nothing funny about how sexy…

Jana Cova is a sexual freak and she wants you to watch. The oh-so-lovely Carli Banks fills her up perfectly in this superbly erotic fuck film. For the first time…

BiBi gets her fill! Bubbly beauty BiBi Jones wants to get pregnant but her guy Tommy Gunn, is running on empty. Turning to her close friends for semen samples doesn’t…

James is a masseuse with a demanding clientele, handling everyone from horny MILFs to naughty girlfriends. As his business grows, he enlists the help of his amateur buddies to service…

Mega Packed with Juicy Crack “Check out these packs with juicy crack presented by Jack”

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 fuck and some…

Big, Hot and Kinky! “More Cushin For the Pushin”

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…

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…

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…

Janine’s First Interraical and No Condom Scene! See Janine gulp all the frosting from the double stuffed oreo.

Sisters Chanel, Eva and Keisha are used to stealing clothes – and boyfriends. But when Chanel leaves husband Xander for good, she sets her sights on sister Eva’s husband Michael,…

Sexual Freak 3 Shot entirely on HD, Sexual Freak 3 features Digital Playground’s newest contract star, the lovely Shay Jordan, in a plethora of deviant and mischievous erotic play. Sexual…

Sexual Freak In Sexual Freak, Jesse Jane is at an all time high. Her insatiable lust and her pure power are exploited and showcased under Robby’s artful direction. Watch her…

Sexual Freak 7 Digital Playground’s contract superstar Stoya is a sexual freak and she proves it in this erotic masterpiece. With Celeste at the helm, the Sexual Freak series just…

What would you do to save your sex life? For four desperate couples, they’ll try anything – even a kinky couples retreat! But when the couples take their sexual swapping…

Digital Playground’s contract superstar, Sophia Santi is a sexual freak and she proves it in this erotic masterpiece. With new direction and casting by Celeste, the Sexual Freak series has…

Enjoy the lovely Hannah Harper, as you’ve never seen her before, in a mesmerizing and remarkable Digital Playground production. Directed by Celeste and boasting 9 scenes, Hannah Erotique is a…

Return To Paradise Relax. Take a deep breath. Acclaimed director Joone immerses you in an island paradise where all your senses are stimulated to new erotic heights as beautiful, highly…

Dick and Jane are a happy couple until Jane starts to neglect Dick. Jane’s sister immediately steps in and the situation gets sticky. See how Dick blows off his steam…

The teens in this series taunt, tease, and get exactly what they asked for. Their eager mouths are hungry and their tight peaches are ready for exploring!

Celeste unleashes her dirty side in Teagan Video Nasty. Superstars Teagan Presley and Jenna Haze set the tone for the filthy, nasty ride of pleasure. Teagan and Jenna tap every…

Stoya Video Nasty Stoya makes crazy-sex in three scintillating scenes in Digital Playground’s third installment of Video Nasty. She proves her pure deliciousness in a sexually charged three-way with Alektra…

It’s no secret that Kagney Linn Karter loves to pleasure herself, and in this film she shows off at her own hand. Scott Nails enters the room and clearly provides…

Enjoy Digital Playground contract star Shay Jordan in this wonderful and sexy horror spoof. Set in another era, 6 erotic stories unfold in an eerie mansion. It’s delightfully wicked and…