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….

When Alina West gets busted for breaking and entering, she shows her chump friends just how hardcore she can be, promising Mark Ashley the ride of his life if he’ll…

Bad girl Riley Evans and her boyfriend have to take summer courses. They hate their teacher for it so they decide to trash his office. Once there, they figure out…

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 Jack vote for one…

Not everyone who visits this hotel has an innocent motive. After another type of getaway, Gabbie Carter and Xander Corvus let themselves into their room with a bag of stolen…

Sadie Pop is hanging out at a friend’s house. She gets bored and starts snapping some naked pics of herself. This starts to turn her on, so she decides to…

Jasmine Jae came all the way from England to experience American dick. She was the bad girl growing up and went to Catholic school – where she also got fingered…

In an attempt to get some street-cred Candy Apples had each of her tits tattooed. It didn’t work and she still hungered for some respect from the neighborhood. Finally she…

Emily Norman was caught trying to shoplift lingerie and she couldn’t call her parents for help, so she calls her friend’s dad instead. Her friend’s dad, Will, picks Emily up…

Sarai Minx is here with us today for a brand new scene! She has the nicest pair of big tits! She starts off by teasing us in the shower!. She…

Jack’s Playground 33, features Digital Playground’s one and only insatiable and sexy Devon. She’s eager to make the music video cut and demonstrates her distinct talents on Scott Nails’ throbbing…

Sarah Vandella’s neatly trimmed bush glimmers with wet juices when she starts making out! But the action only gets sloppier as Sarah helps herself to a big dick balls deep…

In her earlier performance, webcam model Myu Tsubaki masturbated for us. In this episode, watch her interaction with a new lover. From baring her full breasts, to taking a few…

Nick was in a hurry but doctor Starr wasn’t ready to let him go in till she found his symptom. She was pretty sure it was because Nick barely relaxed…

Valentina Nappi stars in the steamy and provocative Rocco’s Perverted Secretaries #8. This 46-minute video, produced by Rocco Siffredi, showcases Valentina’s exceptional skills as a secretary and her insatiable appetite…

Blonde bombshell Dolly Leigh has always been willing to go to great lengths to get the cock she wants, and taking a job as a nanny to get close to…

Trent’s family is in the business of distributing libations. So when Cindy Sterling strolls into his dorm room with a Sorority Bash invite, he’s suspicious. But it’s not long before…

Jackie Hoff is a big titted slut who has one request. To fuck in public! She asked us to make that dream come true and we got her a big…

After wrapping up in the shower, Abbey Brooks went off in search of lotion to moisturize her skin, including her big boobs and thick booty. As Abbey tore her house…

Haley Reed might be a kinky little voyeur, but at least she’s organized! When her 9 o’clock alarm goes off, the blonde spinner bounces into action, tiptoeing into Nat Turner’s…

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Being such a bad-ass around school landed Xander Corvus in Detention. Since the hard-ball teacher Mr. Ferguson said no talking, Dillion Carter was prepare to ride out the session in…

Looking like she just stepped off the golf course, this Japanese babe is ready for some hole in one fun! Watch as her partner squeezes her hard nipples then plays…

Nothing sends a shiver racing up Catie’s back to the small hairs of her neck like the sensitive caresses of her girlfriend Raven. When she glides her fingertips down Catie’s…

Renee Pornero is back again! Are you fucking with me?! How does a girl get up after having her body testd by a bunch of thugz in scene one and…

Ivy Rose is a posh, spoiled brat who gets whatever she wants whenever she wants it! What does she want today? Champagne, caviar, jewels… oh, and a big juicy cock…