Jack’s Redhead Adventure These Gingers are ripe and ready to show the world that redheads are much more fun in the sack. They’re known for their mercurial tempers; but did…
Jack’s POV You don’t know Jack until you’ve seen it like this. All the screamin’ hot sex in Digital Playground’s award winning Jack’s Playground series are now shot in POV…
Jack’s POV 8 You don’t know jack until you’ve seen through his eyes. Sweet. One-of-a-kind P.O.V. Super hot semen slurpers. Pretty tight fresh box. Sexy dark haired babe Honey DeJour…
Jack’s POV 6 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 POV Playground,…
Jack’s POV 2 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…
Starring BiBi Jones in her first POV. Beautiful BiBi Jones drips her young, sweet juices all over thick rods and long, hard members. Sliding and pumping on the giant cock…
Real girls uncensored Imagine what it would be like to date your favorite porn star. Imagine waking up next to a naked Kayden Kross and having hot morning sex with…
Jack’s POV 17 You think you know Jack? These bitches are sucking up his dick and swallowing it deep in their pussies… I think they know a little more about…
Jack’s POV 16 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,…
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…
Real girls uncensored. Jack is really busy casting for music videos and now he’s landed Digital Playground’s super fine contract star, Jesse Jane. She fucks Ben English every which way…
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: Leg Show 4 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…
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…
Jack’s Playground: Big Ass Show 2 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….
“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…
Jack’s Asian Adventure 2 Always A Happee Ending! You like partay?’Playful, powerful and supremely sexual – a revolutionary sex comedy. . . One of the most original series in years!…
Do you believe in the power of hypnosis? Seductive Selena Rose does! As a recent graduate of Mick Blue`s hypnotherapy class, she is convinced by Mick that she has the…
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…
Hot Rod For Sinners Set in the days of 50’s pin up stars, Jesse and Jana get down and dirty while they get you off in Celeste’s greatest masterpiece to…
Lust is in the eye of the beholder. The power of love can survive anything, except the spell of a very off and mysterious watch that latches itself on to…
Her deepest desires. Seductress Jesse Jane sizzles with desire as a woman on the verge of marriage, haunted by a mysterious engagement gift. Overcome by explicit visions of naughty past…
You can never escape your past or your future. Sexy, seductive Riley Steele discovers a weak link in her marriage as perverted visions and dreams continue to haunt her, even…
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.,…
The bad girls are in charge. Vicki Chase and Riley Reid hook up with guys at work. After Vicki’s sex session with James Deen, the girls get busted for their…
This Time It’s Personal. AVN Top 500 2005 AVN Award Winner for Best Film 2005 AVN Award Winner for Best Director 2005 AVN Award Winner for Best Actor 2005 AVN…
Paradise… they’re taking it all in… with a smile. Hardcore fucking that will bring you to your knees. This cockold gonzo release starring Jesse Jane and Riley Steele is aimed…
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 #3 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 #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…
