A playful game of tennis gets rigged, because Natalia Starr’s big tits keep bouncing in her sports bra! She’s distracting the competition and he’s clearly hard and horny. She wins…
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….
Charles Dera heads to the hospital with a boner that just won’t quit. Lucky for him Nurse Karlee is on duty and ready to tame that dick into submission. Charles…
Disorder In The Court! All rise! Court is in session, and dysfunctional couple Mick Blue and Kylie Rocket have a financial dispute to settle. Mick was left with a hefty…
Van Wylde’s seemingly conservative stepmom, Dana DeArmond, likes to keep her house pristine, but it turns out she also has a raunchier side hidden underneath her model housewife attire. As…
Marc’s latest obsession is a sexy webcam model named Taylor Sands, and he couldn’t be more psyched to go meet her. So after an enthusiastic blowjob from his hot and…
School Valedictorian Kylie Page is starting to realize she’s spent more time with her head in the book than giving head, she’s got one last chance at a full college…
Busty beauty Skyla Novea hates studying for exams. So, when she misses one of her finals, she pleads to her professor, Sean Lawless, to let her write a make-up. Mr….
Bad girl mechanic, Katrina Jade has been working hard to get a black mustang working again, but it’s no fun if she can’t play. The owner of the vehicle arrives…
Being blindfolded and stimulated with a big vibrating want is almost enough to put this little Asian cutie over the edge, and just when she thinks that’s a lot, one…
Memphis Monroe is feeling sexually neglected by her husband who is constantly working and not listening to her. When she suggests him to hire a male sex therapist, he accepts…
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…
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…
Kitty Lynn surprises her favorite professor with a cupcake, but she has something special planned with it. She decides that the best way for her professor to eat said cupcake…
When Blanche Bradburry offers to help stepdaughter Claudia Macc and her beau Charlie Dean with their math homework, she’s secretly hoping to give a hand with another hard problem. The…
The “My First Porn” series is a comical sex-spectacle of Jack directing his first porn movie. Volume 4 rocks the house with Scott Nails & Jasmine Byrne in a Viagra…
