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…
Alaina Dawson has only had sex one time before, so this is a big stretch for her. Adventure has always been her thing, however, so when she was approached by…
Hot and classy Lenina Crowne is taking an exciting trip with her husband; the only problem is that he bought them the cheapest, ugliest hotel room possible and this won’t…
Gia Derza is on set for a mainstream photoshoot but the photographer has taken a keen interest in her “assets”. She changes into her lingerie right in front of him…
Grind Bar is the type of establishment mothers warn their sons about. Despite its location off the beaten path, the dive bar has been drawing in young men from nearby…
The newest busty beauty to show up at ZZ headquarters in search of big cock is Devyn Cole, who specifically asked to get fucked by one of the best dick-slingers…
It’s just another boring night at home for Mia Lelani. She’s stuck watching TV with her slobby husband until his bad boy brother Scott Nails arrives. Mia and Scott have…
Little Humper Jordi has an extra funny prank for his new stepmom, Jada Sparks: a trick bathing suit that dissolves in water! He leaves it on her bed, making it…
Codi Vore has ordered a suction dildo for her shower, and it seems like she’s done it right under the nose of her blind husband. However, it’s just a ruse…
Martina Gold got more than she bargained for with her massage appointment, hands-on attention from a skillful masseur that got her so horny she couldn’t stand it. When Luke started…
Alex Legend surprises his wife Abigail Mac with a special gift; Brazzibot Nicolette Shea! Abigail’s less than pleased he blew so much money on a robot; that is until Nicolette…
Kenta just can’t seem to get lucky, and even his best friend Saiki is spending all his time fucking Wakaba instead of hanging out with him. When Kenta prays for…
Digital Playground’s Katsuni was the inspiration for this passionate film. Written and directed by Celeste, Minx is based entirely around Katsuni’s own dominant sexual persona and many fantasies she dreamt…
Shot entirely on HD, Jack’s Teen America 18 parodies beauty pageants and Jack’s lovely contestants all compete for the crown. They take off their clothes, they masturbate, they suck, they…
Kenzie Reeves’ grades aren’t doing so hot and there’s a good chance she’ll be losing her scholarship! Dean Kyle Mason has seen this before, hot blonde students thinking they can…
All she wanted was a massage, but this man went extra lengths to make sure she left the massage table feeling better than ever before. He removes her shoes and…
When nature calls…sometimes you WILL use the ladies bathroom. And when you get caught with your pants down by a sexy stewardess…a deep dicking always speaks louder than words…and maybe…
It’s Charlie Dean’s first night at the Caribbean resort when he bumps into the most beautiful blonde he’s ever seen, Vinna Reed. As luck would have it, her hotel room…
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…
Danny gets a job as a production assistant on a porn set, thinking it’ll be fun to get a behind-the-scenes glimpse of how the work is done. He can’t believe…
Abella Danger spends her days playing video games and her girlfriend Kimmy Granger is sick of it! Determined to have Abella get off her ass, Kimmy gets rid of Abella’s…
After marrying a family man, Reagan decides she’s going to be a hands-on stepmom – instead of treating her husband’s son and daughter as an afterthought, she’s going to be…
The stern new warden at the ZZ Prison has a special disdain for notorious inmate AJ Applegate, who he’s locked in solitary confinement with Markus Dupree as her personal guard….
Alyssia Kent and her boyfriend are trying to spice things up, so Alyssa buys herself a remote controlled vibrator, which Alyssia decide to try out in the changing room Jay…
