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….

Yui Shimizu is wearing the fishnet body stocking her master prefers her to wear. She has already been bound at the wrists on the sex chair, and she wets her…

Lucy Mendez is a cute petite girl who just wants a big dick inside of her. She gets told by her friends that Bang Bros has the biggest cocks and…

In this self-shot sex documentary series from some of the biggest names in the business, Digital Playground gets up close and personal, offering you a behind-the-scenes look at what it’s…

Secret Crush is as down to fuck as they come. She wants to test the limits of her public sex life, so she finds a secluded beach to get railed…

Janet is new to town and her car broke down on the wrong side of the road! This spicy latina has a fiery personality and can’t pay for the expensive…

Renato is working hard at his desk for the good of his relationship with sultry blonde Angelika Grays. Feeling playful, Angelika brings him a beverage dressed in white stockings and…

Sweet girlfriend Amber spends her day off with the love of her life, Billy. The two are almost inseparable… and in the brief moments when they aren’t together, Amber transforms…

Brooklyn and Bill are getting ready to go out when their hot young neighbor Katy comes over to "borrow a cup of sugar." Lucky for horny Katy, both husband and…

Karma RX’s boyfriend surprises her with a spa day, but it’s not what she expected. Thankfully, the masseuse Johnny Sins is super hot. Johnny places crystals on Karma’s boyfriend’s eyes…

Katsuni makes crazy-sex and delivers superb anal scenes throughout Digital Playground’s fourth installment of Video Nasty. She proves her pure and delicious nastiness in a sexually charged three-way and in…

Tiffany Mason has already gone on to become quite a superstar but all of the superstars had to start somewhere. Her very first scene was this one with TT Boy….

Mr Hardwood gets caught off guard when Dr. Vanessa tells him that she needs to check his prostate. He refuses to get a finger up his ass so Dr. Vanessa…

Ashton Blake is a tattooed babe with giant pierced tits that she can’t keep in her red hot dress. She has a pierced clit to match and she wants to…

Mama in all her glory, just like her smaller counterpart! What’s the best way to spend your time with cum sprays and loud moans? So what if someone refused to…

When Matt Ice bumped into his girlfriend’s stepmother doing yoga in the living room, he couldn’t help but feast his eyes on Lili D’s juicy ass as she moved through…

What Kyra Hot wants, Kyra gets. When her co-worker Pablo’s rugged good looks caught her eye, Kyra decided to do whatever it took to seduce him. After sabotaging the photocopier,…

Van Wylde has come to stay at Raven Hart’s quaint B&B, but he’s not quite prepared for how this sexy MILF likes to tease her guests. Fortunately for Raven, Van…

Blonde MILF Zlata Shine is trying to get some work done when her computer starts misbehaving, so she calls a repair service. She’s still in her silky pink robe with…

Emma and Athena arrive at their old friend’s place while passing through town, and Lucas can’t keep his eyes off them! When his girlfriend patiently waits in bed, Lucas sneaks…

Teena puts on her little kitty collar and her wristband because she knows that they are good early warning devices. She is obviously afraid that Brandon Iron is going to…

Hot brunette whore gets her Japanese slit pleasured with a pink vibrator. She mews and coos like all the Japanese sluts do when they are embarrassed about receiving so much…

Angel Allwood is a busty MILF who likes to work up a sweat, keeping her body nice and tight with extra-long workouts. When she got home from a jog one…

Sasha Pearl is hanging out, getting a little sun, when her boyfriend’s son stops by. Like always, he’s upset that Sasha does nothing while his dad works his ass off…

Teenage virgin Bailey Brooke has just started attending college and is quite the prude. She’s hardly even kissed a guy and has never seen a cock before. So imagine her…

Tyler Nixon doesn’t like to lose, so when Audrey Bitoni starts pulling ahead of him in sales, he’s furious! Lo and behold, as he’s coming out of the washroom one…

Graduate student Abella has a problem: she’s supposed to meet with her doctoral advisor Professor Holmes every week, but she just can’t seem to focus when she’s alone with him….