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 to getting a…

All alone at home with nothing more to keep her company than her horny thoughts and desires for hot sex, Olive Bell got so turned on she had to drop…

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…

It’s Dean and Adriana’s anniversary, and they’ve decided to celebrate at the hottest restaurant in the city. The thing is Adriana doesn’t exactly go for the chocolates and the roses,…

Aiko Nagai leaves no need for a towel, because even if she lets some jizz drip out of her mouth at the end of the session, she’s just doing it…

It’s hard to believe Tyler’s lasted so long at his job, given how his bitch of a boss finds new ways to make his life a living hell. After working…

Not every girl worked out well, Alexxxis thought she was a lot hotter than she actually was so we used her in this clip and got everything we could out…

Thieving ain’t easy. Jasmine learns that the hard way when Luke, her lover and partner in crime, betrays her to the cops to land her behind bars. With the help…

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….