Jenna Ashley knows that her teacher is married, but she doesn’t care. She’s going to teach you how to steal anyone’s man! Leaning in and being willing to talk about…

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….

When burnout slacker Rina Ellis greens out during a 90s movie marathon, she has some seriously fucked up dreams. Santanico Pandemonium has taken over an alternative 90s dystopia and It’s…

Ricky Spanish may be an adult, but his mom doesn’t trust him home alone. The last time he was home alone, Ricky masturbated in the living room and the neighbors…

Phoenix Marie likes to dominate men. Of course she gives them the ultimate pleasure when she lets them fuck her pussy and she sucks their cock, but they have to…

Alexis is called into her manager’s office because she is just not working out as a waitress. Danny says she’s getting any better and her work outfit is too revealing….

Mai Mizusawa is on the phone, arranging an important meeting for her boss. But he is more interested in rewarding her for the new contract she just secured with her…

Busty beauty Cassidy Banks shows up at a massage place she’s read about online and is surprised to discover her masseur, Sean Lawless, operates out of his own home. Under…

Starring Digital Playground’s newest sensation, Shay Jordan and an entire cast of young, gorgeous, almond eyed beauties, Jack’s Asian Adventure will please your pallet. Jack uses the tried and true…

Teagan Presley & ANAL ” does the rest of this description even matter? Jack is really busy casting big, bouncing, beautiful butts for music videos. They shake, they roll and…

Sharon Lee is an exceptionally beautiful Asian woman, cast against a background of warm textures and sweeping violins that lend this scene a serene and sensual quality that’s impossible to…

Jay Romero gets to decide his new stepsister from two candidates: Lexi Lore and Chanel Camryn. They begin the day in the pool, where Chanel comes on strong. Lexi goes…

After spending years in love with Miwa only to see his older brother, Satoshi, marry her, Takashi is finally taking his revenge, making his sister-in-law crave his cock more than…

Jun Kusanagi is a real life Japanese whore in bright red lingerie who only wants to please the men she’s servicing. She sucks off a few different dicks and offers…

The My First Porn series is a comical sex-spectacle of Jack directing his first porn movie. Volume 8 is 3 full hours and features Digital Playground contract stars Sophia Santi…

Parallel Lust is an anthology series exploring the dark side of sexual desires and urges that lurk beneath the surface of seemingly normal individuals, offering a dark examination of the…

Xander Corvus bust in through his girl Teanna’s bedroom window and buried his face right in that juicy ass. Teanna tried to focus on her homework, but there was no…

Shy Sister Cheats With Her Brother-In-Law Conservative, sweet Sadie Rose has always had a bit of a flirty but ultimately innocent relationship with her sister’s husband, Manuel Ferrara. She never…

Who needs a bikini bottom when you have an ass as fine and juicy as Missy Martinez’s? This bodacious babe spent a sunny summer day catching sun on the sumptuous…

Chanel Preston’s new butler, Chad White, is in for a treat on his first day of work. Chanel puts her goods on display at every opportunity, but Chad remains professional….

Sarai Minx is here with us today for a brand new scene! She has the nicest pair of big tits! She starts off by teasing us in the shower!. She…