The My First Porn series is a comical sex-spectacle of Jack directing his first porn movie. Volume 10 is over 2 hours and features Stoya in a brand-new, amazingly ass-a-liscious…
When Elsa’s friend ropes her into pool hopping at a neighbor’s house, she’s hesitant – she’s not even wearing a swimsuit! And what happens if they get caught? Elsa’s friend…
Busty Kendall Karson is the new, sexy weather reporter who is starting her first day on the job. Sensing her nervousness, all horny Markus Dupree wants to do is make…
Angel Youngs thought she had the house to herself, so she started masturbating in the kitchen. Little did she know, her roommate’s boyfriend was in the house. He couldn’t believe…
Big-titted Yola Flimes is making a surprise treat with whipped cream for her man, Robin Heart. Robin, however, would rather be treated to Yola’s voluptuous body, spanking her big ass…
In Part 2 of The Loophole, devious Kimmy Granger hangs back to ask her teacher, Brad Newman, a few more questions about sex and marriage. Brad quickly gets nervous when…
James is a retired hit man, enjoying his continuous bedroom romps with his horny wife, Abigail Mac. In the middle of the night, intruders kidnap his wife as they beat…
Sometimes Susie gets really horny working all day as a nurse, so she changes into some more comfortable clothes during her lunch breaks, and follows the doctors to a secret…
It’s Ricky Spanish’s birthday and his stepsister Theodora Day is so excited. She bounces into Ricky’s bedroom with a card and then brings him breakfast in bed. She wants to…
Codi Carmichael was lead blindfolded to her very, very special birthday party. She was surprised by her friends and by the cake, but the cumshot just blew her right the…
When Nelly finds herself in a tight spot (financially speaking), she turns to the wrong kind of people (local bad boy Luke Hotrod) and ends up even more heavily in…
Danny D overhears his sister and her friend, Amber Nevada, having a sex talk. Big booty Amber, having just lost her virginity, realizes that she’s a real nympho and loves…
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….
Alana Cruise is a gorgeous brunette that has her eyes set on getting two cocks to fill her pussy. This petite hottie bends her perfect figure and sucks cock and…
Thinking that Liam Salvatore is unable to see anything, petite babe Matty Mila Perez cheekily strips down to her thong and flashes him her small, natural tits! When she notices…
“Deeper 3” is beautiful, erotic and cinematic homage to the greatest horror movies ever made. Starring Digital Playground’s contract superstar, Jesse Jane® in 2 twisted and mind-blowing fuck scenes, Deeper…
What would happen if four families each contributed one member to create a new family? In this episode of Family Swap, Serena Hill and her swap mom Jessica Ryan have…
Jack’s casting again! This time he’s looking for leg models… sexy, leggy vixens who want to be in fresh, up and coming music videos. In volume 3, Digital Playground’s contract…
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…
