Tiffany’s birthday surprise for her boyfriend, Alex, isn’t quite ready when he rings the doorbell, so she asks her stepmom, Christiana, to entertain him for a few minutes while she…

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….

Gracie Gates was at a job interview and her car got towed. She’s been out of a job for a while and has been relying on her boyfriend to pay…

Star athlete Johnny Sins got the scare of his life when Audrey Show threatened to throw him off of the team, but fortunately for him, all she really wanted was…

Jack’s Playground 34 features Digital Playground’s exotic contract superstar, Katsumi. She’s a panty hose model by trade but she’s eager to make the switch to music video queen. She demonstrates…

Duncan Saint wants to borrow his fathers car but he hasn’t finished all of his chores. When his father refuses to give him the keys, Duncan asks his new step…

It’s race day, and the girls of the track team are getting pumped, especially petite, purple-haired Spiraling Spirit! Spirit is full of energy, pulling down her track pants to show…

Everyone has a favorite sexual fantasy for their alone time. For Johnny Sins, it’s watching his neighbor, that sexy Latina Chloe Amour, swimming around in her little skimpy red bikini…

Samantha Sin and Claire Dames have been swinging for as long as they’ve been married. They love swapping their spouses, but they didn’t know the guys were getting to know…