Open The Fuck Box Legendary porn shooter John Leslie serves up four sizzling variations on how to wax that ass in Crack Her Jack 10, the master’s latest collection of…
With 20 extra minutes that are not found on the original VHS version and featuring a full linear transfer, this is the definitive version of this classic fuck-for-all!
Crack Her Jack 1 Maestro John Leslie makes a stylistic departure in his brand-new series, using the camera in a more seductively straightforward manner than before, but still with more…
Crack Her Jack 11 The masterful John Leslie returns with Crack Her Jack 11, featuring a perfect blend of sizzling new sluts and tried and true fan favorites. The mix…
John Leslie focuses his perverted eye on the world of the three-way in five smokin’ scenes! Check out mocha goddesses Adriena and Kapri Styles teaming up on Mr. Pete, or…
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,…
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 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…
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…
Vegas Rooftop Nights: Milf Jackie Hoff vs SoloTheBull At our Flourish Vegas Penthouse Jackie Hoff wanted to get some BBC Meat. So she called over SoloTheBull to fill up her…
You Don’t Know Jack Until You’ve Seen Through His Eyes. All the screamin’ hot sex in Digital Playground’s award winning Jack’s Playground series are now shot in POV perspective for…
You Don’t Know Jack Until You’ve Seen Through His Eyes. All the screamin’ hot sex in Digital Playground’s award winning Jack’s Playground series are now shot in POV perspective for…
Jack’s POV 9 Don’t miss Digital Playground’s exclusive contract star, Stoya in her debut boy/girl scene. Jack’s POV 9 is off the hook sex! All the screamin’ hot sex in…
Jack’s POV 15 With its unique camera work, Jack’s POV 15 brings you into the action and doesn’t loosen its grip until you’re completely drained. Jack’s POV 15, features Digital…
Jack Attack Vol. 6 From Digital Playground comes Jack Attack 6, featuring six scenes of couples filming their private moments for your viewing pleasure. Starring Selena Rose, Adrianna Luna, Anikka…
Jack Attack Vol. 5 Beautiful women get fucked in the most sensual and lustful way possible. The rules are changed. Worlds are rocked. Desks are defiled and it doesn’t make…
Save the best for last. In the ninth installment of Jack’s Big Tit Show, Jack is on the hunt for big, beautiful boobies, using his trusty music video ploy to…
Jack’s Playground: Big Tit Show 6 Call Jack “The Titty Hunter”. He’s hunting for trophy titties, and will only settle for his favorites; big, beautiful boobies. They bounce, and they…
The One and Only 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…
Jack’s Playground: Big Tit Show 4 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…
Jack’s Playground: Big Tit Show 7 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…
Got D’s? Some More Juice For You To Squeeze. Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful boobies. They bounce, and…
Jack Says, “Big Tits Are More Nutritious.” Jack’s at it again. In his playground, Jack is busy casting for music videos. The delicious girls will do anything for stardom. Some…
