At this years office christmas party, Jack’s boss Brittany Andrews took him into her office to exchange gifts. Jack was pretty dissapointed, however, because he didn’t have anything to give…
How anyone could ever leave Eva Karera is beyond her new boyfriend’s belief. Still super sexy, this MILF has some serious sex skills that put younger women’s to shame. She…
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…
Zoey Monroe wants to let her boyfriend fuck her ass, but her virgin asshole is so tight that she’s worried she won’t be able to handle it! Lucky for her,…
After being featured in a TV commercial, sexy Sheridan Love has let it get to her head, now considering herself a starlet of sorts. While her son is annoyed by…
Jennifer White just got traded for a deal two syndicates made. She’s going to show these homies how to treat a whore the way she learned before. They were going…
Bianca Bangs sits in the kitchen asking the magic ball about her sex life. When her stepbrother, Jodie Johnson, joins her, Bianca switches her questions to Jodie’s sex life. Jodie…
Keiran Lee has somehow found himself at the doorstep of a cult, courtesy of his best friend. Now there’s crazy, and then there’s cult crazy, but there’s something different about…
Brazilian beauty Luna Corazon got together with her best friend Rina Ellis to talk about the man she’s been dating, but Rina’s cold response only got her more confused. Their…
Takaki Hijiriryo just got out of the nail salon, and she’s finally all ready for her big night at the hotel with her new male friend. She’s excited to meet…
Takashi is enjoying his job as gardener much more now that he can use the power of the enchanted dollhouse to have cute maid, Maria, suck his cock and give…
“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…
Luna Star is all set to binge some TV in her tight little onesie, but her boyfriend Xander Corvus won’t let her choose the show, AGAIN. So, she grabs the…
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….
Julie Cash has been getting complaints about her bedside manner. Her patient satisfaction surveys say that she’s too focused on boring things like health and wellness and not enough on…
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…
Destiny Dixon just broke up with her boyfriend, and she’s none too pleased about it. When her taxi shows up, it’s obvious that she’s furious at her ex, so taxi…
Erica Lauren needs to get her divorcee daughter out of the house, so she sets her up on date. But when Michael Vegas arrives, he mistakes Erica for her daughter….
Stefanie’s father has stood her step-mother Cathy up, claiming that he has to work late. Feeling sorry for her, Stephanie invites her to join her and her boyfriend on their…
The sexy Halle Hayes and Scott Nails are working late tonight, to look over their bad numbers for the month. Both of them turn out to be more interested in…
You’ve seen Kendra Sunderland in fancy outfits, far away photoshoots, in the news, or just on social media. But what do you really know about her? Her personality, interests, friends?…
It’s Johnny’s wedding day, and after fucking his bride’s little sister he thinks he’s ready to get hitched. But Anya Ivy has something else in mind. This maid of honor…
