It doesn’t get much hotter than this! Madison Ivy is absolutely smokin’ in strappy red lingerie and thigh-high boots, and Small Hands is the lucky man who has the pleasure…
Riley Reid’s private shows are among the most sought after, because she gives 110% – to the right client. Jessy Jones knew what he was getting himself into, full body…
Star’s new neighborhood seems pretty boring – until she spots a local creep checking her out. Lucky for her Jordi will do anything to get closer to that sweet teen…
Taylor sits at the desk thumbing through a book, her 36DD breasts stunning in a black and white lace bra. Mira, standing behind her can’t keep her hands off Taylor’s…
Teal Conrad and her man are spending the day in bed making the most beautiful music together. Giovanni knows just how to play Teal’s supple body like a viola, and…
“Jack’s Playground 31,” the superstar edition, stars the lovely Jana Cova in two delectable scenes, Devon in all her naked splendor and DP’s original contract star, Rocki Roads in brand…
Tattooed hottie Aubrey Kate slowly introduces her new lover to the whole concept of her being a shemale. They’ve talked about it enough, but he’s still not ready to play…
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…
Kawaii Boku, the sweet little Asian brunette, invites her boyfriend up to play with her at her parents’ house. He plays with her cunt hard and then she sucks his…
The boys haven’t had a model on the casting couch they’ve liked as much as Nickey Huntsman in a while. She has three holes that are equally equipped to take…
The My First Porn series is a comical sex-spectacle of Jack directing his first porn movie. Volume 9 is over 2 hours and features Teagan Presley in a brand-new, amazingly…
Britney Amber would like to sell her 3-wheeler to her boyfriend’s son Billy, but he laughs when she tells him the asking price of $100,000. Britney learns from Billy that…
Just when you thought Luna Star couldn’t possibly look any more stunning, the beautiful bombshell drapes her big tits and pussy in pearls and blows us all away with another…
Chris Diamond sits in class, bored out of his mind. He begins fantasizing about his sexy, busty bookworm of a classmate Nekane. While taking notes during the lecture, Chris tries…
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….
Brandi revisits her award winning character Jen Hanlon from ‘The Candidate’, when she and Judge Beth Pellegrino (played by Julia Ann) fell in love.The scene is very tender, as Beth…
Danny is the only student to show up to the new substitute teacher’s class. Everyone skipped except him, and sub Ms. Bardot is very grateful. She tells him she wants…
Charles Dera trains London River in her home gym. He has her workout to her max, but can’t help showing off his muscles in an attempt to impress her. Luckily…
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. Hannah Harper is…
