Even some of the most powerful men have their insecurities. In this series of vignettes, we follow John, Mick, James and Keiran as they explore and deal with the challenges…
Josephine Jackson gets out of bed and heads to the bathroom, stripping out of her PJs and freshening up in the tub when her roommate’s boyfriend, Angelo Godshack, accidentally walks…
Angela White is a renowned medical practitioner and the envy of all her peers. Having successfully completed over ten thousand procedures, it’s clear to say that there is no patient…
La Sirena has a pair of huge, natural tits! This babe loves to get her throat fucked by dick. She only has one perfect nipple pierced and her natural titties…
Baby Got Boobs Vol. 20 Ashley is a wild cowgirl working the mechanical bull, but she’d rather take Robby for a ride. There’s nothing quite like getting bucked and fucked….
Bill Bailey is looking forward to yet another lazy day in his brand new inflatable pool when he is magically whisked away to somewhere else entirely. Stunned to find himself…
There’s much more than meets the eye at The Red Viper, a strip club where the sexy entertainment is as dirty as the ulterior motives of its patrons and staff.
Hailey and her husband’s car breaks down on the highway. Luckily for them, Tony DiSergio happens to be riding his brand new ride and offers his help. Hailey has to…
After angsty Chloe gets roped into a dinner date with her mom and Keiran, her mom’s conservative new boyfriend, she decides to have a little fun with him. Though her…
Hot waitress Mandy Waters wants to make Kai Jaxon a regular, so she offers him a special off-menu treat, flashing him her boob and then sucking his cock at his…
In the early 20th Century, suave genius scientist Victor Frankenstein works with a grown up Peter and Wendy to open a portal to another dimension. When a sexy hooked handed…
Kimmy Kimm looks really cute in her cosplay costume and stockings. This brunette babe is thanking the doctor for taking care of her during her internship when she suddenly feels…
18 is a great age to start getting her pussy played with. This little whore loves all the attention she can get in “Amaenbou 10.” Watch her get toyed, fingered,…
Jack is really busy casting for music videos and now he’s landed Digital Playground’s super fine contract star, Teagan Presley. She takes a big cock in the butt and we…
Payton Preslee meets her boyfriend’s son Kyle for the first time and it’s turning her on because Kyle is a lot hotter than his dad. Payton is so hot and…
Scarlett needed a shopping partner, so she convinced Criss to go shopping with her by promising to buy him some jeans. She had no idea Criss had such a huge…
Rachael Madori’s got the sweetest, most scrumptious ass around and boy does she ever love getting fucked in it. All she needs is a little bit of lube a whole…
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…
