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….
Bill Bailey is watching his sexy stepsister Kylie sunbathe by the pool. She looks so good, but he could never fuck her – that would be wrong. Kylie’s dad asks…
Kimmy’s teacher Mr. Sins has come over to her house to talk some sense into the wayward teen. It seems her parents are concerned about their daughter skipping class, causing…
Christmas morning is supposed to be a time for family and holiday cheer, but Lena can’t stop thinking about all sexual escapades she’s witnessed and taken part in at her…
Lilith Moaningstar gets tricked in an epic scenario! Lilith’s boyfriend is busy playing cards with his boys when his brother comes around the house. Lilith didn’t get a chance to…
All Natural Threesome Hailey Rose and Lily Starfire are a pair of absolute stunners with some big natural titties! So, we thought: why not get these two together in cute…
August and Eva are free-spirited hotties who love a good joyride. They’re having so much fun they catch they attention of an off-duty cop, who pulls them over for speeding….
Kenta thinks a part-time job at a beach hotel, surrounded by gorgeous women, is the perfect opportunity to prove that his newfound success with the female sex isn’t all because…
Cruising with Cash Derek Savage and his buddy are cruising the streets of LA looking for some hotties for another exciting livestream, and they find even more than they bargained…
Once she is assigned her position within the firm, Ai Mizushima is introduced to her direct supervisor. He wastes no time instructing Ai on the daily duty he expects her…
Mischievous Kimmy Granger is the beautiful daughter of a rich entrepreneur and she gets everything she wants… including men! Seth Gamble, the family doctor, is a particular slippery fish to…
Keisha has been waiting all day for her boyfriend to come over. She decided to keep herself busy with a little phone sex session, teasing her clit while he tells…
It seems like Mikey Butders has just stopped caring about school because he knows that he’s about to receive a football scholarship. However his teacher, Mrs. West, is angry with…
Sean wants to be cured of his pussy eating addiction. Dr. Riley Reid, his psychiatrist, decides that the only way to cure him is to show him that getting could…
Suburban couple Keisha Grey and Keiran Lee want to spice up their marriage, so they meet legendary pornstar Kendra Lust! Carnal shenanigans ensue as Kendra helps Keisha and Keisha realizes…
Shy Ella has never received a professional massage before, so she asks for a female masseuse. Horny masseuse Jillian wants to introduce Ella to the benefits of mixing milking tables…
The only thing better than one huge Latina bubble booty is two, so double your pleasure with Lela Star and Rose Monroe as they twerk their big asses and jiggle…
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…
Chris Lockwood can’t get his pants to zip. His stepsister, Scarlett Alexis, comes in to tell him they’re going to be late and winds up crouched before him to help….
All the screamin’ hot sex in Digital Playground’s award winning Jack’s Playground series are now shot in POV perspective for your ultimate enjoyment. In Jack’s POV Playground, YOU will get…
Luna is the second fan to win a spot as a guest on Jean Val Jean’s cooking show. Things are going great until Aria, filled with jealousy, interrupts them just…
Behind enemy lines and at the mercy of her ex, Nikki Ransom (Kira Noir) tries to keep Joe Riggs (Alex Jones) talking while she waits for rescue. Riggs assures her…
She smiles before the session starts because she’s excited to finally get her pussy rubbed. She’s tired of doing it herself, so being able to lay back and relax while…
Parker Ambrose and Ricky Spanish are playing chess as Ricky’s stepsis Scarlett Alexis makes a snack in the kitchen. Scarlett flashes her goods at Parker, prompting him to join her…
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….
