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…
Things get hot and heavy in the 1-800-Phone-Sex office when newbie Sierra shows up to cover a shift. Isis volunteers to teach the wide-eyed blonde a lesson in proper pussy…
Christen Courtney has a crush on her boss Pablo, but he’s so darn dedicated to work that he never notices her advances! After trying desperately to give him a clue…
Kenzie Madison is fooling around with her girlfriend when she unveils her new strap-on, but her girlfriend wants nothing to do with it! Kenzie’s pissed off; her girlfriend never wants…
Chanel Preston is used to her intern’s incompetence, but today Jordi has outdone himself. Miss Preston speaks so quickly that Jordi only catches every third word, and he genuinely thought…
Gia and Alina are best friends. They have known each other for years; they have dated the same guy for months. It should come as no surprise that they wanted…
A seedy motel provides the backdrop for a crumbling affair whose end triggers a night-long series of events that span espionage, and the ruining of two public figures. Pro-environment politician…
Nathaly Cherie would never try and explain her love of the bad boys. She just goes with what she likes, in this case, studs like Angelo who flood her pussy…
Valentina Nappi’s voluptuous ass is Xander Corvus’ for the taking! Valentina flaunts her sexy body before she lets Xander stick his big cock in her mouth, pussy, and asshole, ending…
Jasmine Jae came all the way from England to experience American dick. She was the bad girl growing up and went to Catholic school – where she also got fingered…
Sexy redhead Lacy Lennon is preparing dinner for her boyfriend, only for him to call and cancel their date over the phone! Worse than that, the no-good boyfriend wants to…
Amber and Janet are at the gym waiting for their training appointment but Linda, the gym’s owner, cancels on them to continue flirting with new customers. The girls are furious…
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…
RoccoSiffredi – Tarra White, Aletta Ocean And Donna Bell – Rocco’s Bitches In Uniform 2 S02RoccoSiffredi – Tarra White, Aletta Ocean And Donna Bell – Rocco’s Bitches In Uniform 2…
Casca Akashova has her nephew and his friend’s staying with her for a while, but she’s finally had it. Between the loud video games and the moaning from the girl’s…
John wants to hire Kimber James as his babysitter, but first he needs to understand what a transsexual is. The only way Kimber knows how to explain that she’s a…
Dani hates doing the call-in portion of the radio show more than anything. She has to put up with a bunch of local yokels yammering on about whatever’s on their…
Luna Star’s boyfriend Carmello forgets it’s Valentine’s Day, and although she appears to keep her cool when he shows up with his buddies Xander Corvus and Mick Blue, you can…
Holy shit look who it is!!!! Gianna Michaels!! This top notch bitch loves getting her juggs fucked and ravaged!!The best part is her tits are fucking perfect and ALL NATURAL!!!…
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…
French cutie Alice Fabre hasn’t gotten laid in a month, so when Danny D starts asking her about a book she’s readying, this schoolgirl decides she’s gotta fuck this older…
The “My First Porn” series is a comical sex-spectacle of Jack directing his first porn movie. Volume 6 features the amazing anal queen, Delilah Strong in a butt scene with…
