Jack’s POV 14 With its unique camera work, Jack’s POV 14 brings you into the action and doesn’t loosen its grip until you’re completely drained. Jack’s POV 14, starring Digital…
Jack’s POV 12 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. Jack’s POV 12 puts you…
Real Girls Uncensored You don’t know Jack until you’ve seen through his eyes. Don’t miss this all-star cast that includes Hannah Harper, Lacey Maguire, Annette Schwarz, Rachel Roxxx & Britney…
Jack’s POV 10 Don’t miss Digital Playground’s Exclusive Contract Stars, Teagan Presley and Jana Cova in a very personal, off the hook sexual experience. All the screamin’ hot sex in…
Ride The Curves With Reckless Abandon Jack is really busy casting for music videos and he’s scored some super fine ass for volume 38. Digital Playground’s amazing contract super stars…
The Comedy is in the Commentary 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…
Jack’s MILF Show Master Robby D. delivers more hot pussy pounding and intense orgasmic blow jobs. This time he turns his attention to some sexy ass mothers we’d all like…
Jack’s Playground: Big Ass Show 9 Jack’s busy in his playground casting big-ass babes for leading roles in his “music videos”. This time he gets Alexis Texas and Shyla Stylez…
A FantASStic Show Jack’s Big Ass Show is back with another episode, and although Jack isn’t getting anything once again it seems like where ever he goes there’s girls with…
Jack’s Playground: Big Ass Show 4 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…
“Eastside Connection” Starring Digital Playground’s newest sensation, Shay Jordan and an entire cast of young, gorgeous, almond eyed beauties, Jack’s Asian Adventure will please your pallet. Jack uses the tried…
Jack’s Playground: Asian Adventure 4 Digital Playground’s Asian sensation, Shay Jordan is back for more… with a cast of eager-to-please, exotic nymphs, Jack’s Playground: Asian Adventure 4 will surely satiate…
Icon Celeste’s Icon features an amazingly beautiful, all-star cast in some of the hardest scenes they’ve ever shot. Digital Playground’s contract superstar, Teagan Presley leads the way, down a revealing…
Hush Hush features Jesse Jane and Shay Jordan, two of Digital Playground’s hottest babes, alongside an amazingly gorgeous, all-star cast in well over 2 hours of hot erotic exploits. With…
Tryst In Tryst, director Celeste delves into the NY fetish scene, featuring Sophia Santi in 6 full scenes and her first interracial violation. Also starring Faith, Gia Paloma, Clara G.,…
Teenlicious There’s nothing more delicious than the dripping clear morning dew on fresh barely fucked teen pussy. The fountain of youth is literally a liquid from a youthful teen. The…
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…
Teen America: Mission #8 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…
Teen America: Mission #4 Jack’s at it again with Jack’s Teen America Mission #4. This time, it`s even kinkier than before. Jack’s checklist: Backdoor Bonanza, Whip the Pony, Racquetball Rectal,…
Teen America: Mission #23 Jack knows ambitious chicks will do anything to win first place in a beauty pageant. Jack’s Teen America: Mission #23 features Jack and his crew interviewing…
Teen America: Mission #14 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…
Teen America: Mission #13 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…
Teagan’s Juice Shot entirely on HD, Teagan’s Juice features Teagan Presley in 6 lascivious scenes. Rich with innuendo, Celeste uses ripe fruits and juices intertwined with passionate sex in each…
The best “A” girl ever. Teagan: All-American Girl is a heartwarming tribute to youth, with slow, steamy glances at innocent rites of passage. Watch a beautiful young cast as they…
Extra credit never felt so good. Everyone remembers their academic life; textbooks, homework, detention, lube, dildos…another typical day at Filmore Bush Academy, where Sex-Ed is a hands-on class. Digital Playground’s…
She’s busted. Angie is a girl seeking pleasure in her work, ready to use her best features to draw thick membered, horny men right into her delicious plan. She’s adventurous…
Once she logs on, you’ll never want to log off. Once she logs on, you’ll never want to log off. Gorgeous and sinful Stoya slips under the spell of lust,…
Stoya Perfect Picture Stoya Perfect Picture is an expression of Stoya’s exploration of love by Digital Playground’s celebrated director Celeste. Contract star Stoya takes on life’s trials and tribulations with…
Sticky Sweet Internationally acclaimed and multi-award winning director, Robby D. offers fans a raw and unapologetic tribute to the kind of hardcore sex that will keep minds racing at night….
Shay: All-American Girl Shay: All-American Girl is a heartwarming and sexy tribute to youth growing up in America. Scott presents Shay with a lovely birthday cake, only to have his…
Sexual Freak In Jesse Jane: 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….
Sexual Freak 8 Digital Playground’s best selling Sexual Freak line is proud to offer up Audrey Bitoni in all of her gorgeous, freaky splendor. This exotic brunette delivers her best…
Sexual Freak 5 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….
Riley Steele So Fine Digital Playground contract star Riley Steele is the finest birthday present ever in another unforgettably hot boy/girl/girl scene. Some of the hottest pleasure providers in town…
Riley Steele Roommates Riley Steele lives in a house filled with lust, seduction, bribery and manipulation. Her impulsive roommates push their sexual desires to a dangerous edge, exposing their obsessions,…
Riley Steele Lights Out Riley Steele has suffered a heartbreak that sends her in a tailspin of degradation to find the love and lust she’s been longing for. After dating…
Riley Steele Chic Riley Steele: Chic is straight from the mind of the most acclaimed female director in adult entertainment and showcases one of the hottest new stars. Celeste directs…
Porcelain Jana Cova is Porcelain. This intimate and artful production shines new light on Digital Playground’s exclusive contract super star, Jana Cova. In this glamorous and smart vignette, director Celeste…
Pirates 2006 AVN Award Winner – Best Video Feature 2006 AVN Award Winner -Best Director – Joone Quick. Batten down the hatches and get ready to set sail on an…
Hannah Erotique 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…
