So you filled out the paperwork incorrectly and now you ended up in the wrong dorm room. As you walk in you discover that you’ll be sharing dorms with a…
Michelle was keen on getting the attention of the hot young cable guy who had come over to fix the cable (which was convieniently not working). She got a lot…
When Roger goes over to his blind old professor’s house for help with his English Lit thesis, he’s not expecting to get educated by the professor’s wife.
Sophia is sick and tired of her annoying landlord Johnny pestering her for rent money. After three months of non-payment, Johnny is finally fed up – he lets himself into…
Mae and Seth are both pretty young and innocent, Seth has invited Mae to his families place in the country for that romantic “first time”. Styled with plush crimsons and…
“Jack’s Playground 31,” the superstar edition, stars the lovely Jana Cova in two delectable scenes, Devon in all her naked splendor and DP’s original contract star, Rocki Roads in brand…
Robby is over at his girlfriend Bailey’s house as they prepare to study for their college midterm exams. Reagan, Bailey’s stepmom, really wants her stepdaughter to focus on her studies…
The lovely Purple Bitch is using some alone time to stretch out her asshole with a big dildo and making herself gape. Her horny boyfriend starts spying on her though…
Busty Asian MILF Kianna Dior just moved into the neighborhood and she’s desperate for a cup of sugar, so she heads over to her neighbor‘s house. Turns out her neighbor…
Riley Reid is slowly being introduced to bondage. Her lover, and future Master, instructs her to put on her banded leather body-strap, and to meet him in the bathroom. Leaning…
London River’s husband is a sports nut, and he’s been dragging her through every athletics outlet looking for some kind of special football. But the only balls this busty blonde…
Jessie can’t wait to rush right into the bedroom and put the perfect ending on a romantic evening out with her husband. Feeling his manly body engulf her completely, as…
Savana Styles tends to get a little carried away when she’s pitching a product she’s passionate about. Luckily for her, client Keiran Lee appreciates that kind of passion, even if…
Keiran has got himself into a mess. His new hookup app keeps matching him up with beautiful women, but he can’t keep track of them all. When he’s out for…
Back in 2013, Riley Jenner was an awkward mess at the school talent show, and the only person to be nice to her about the whole embarrassing ordeal was principal…
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….
Zoe Parker loves spending time out doors and meeting new friends on the dock, but today the dude she met is more horny than usual. She’s feeling a little frisky…
The sexy Hime Marie and boyfriend Kyle Mason are messing around before bedtime. Hime wants to get fucked, but Kyle is being a total nerd and wants to rest. When…
When nurse Isis Love’s patients aren’t comfortable, she knows the best medicine to change their minds is a sip on her big fat titties and a hang on their boners….
Peta Jensen has made an appointment at an underground black market spa and she has no idea what to expect. Luckily for her, she’s in for the fucking of a…
Mischievous Kimmy Granger is the beautiful daughter of a rich entrepreneur and she gets everything she wants… including men! Seth Gamble, the family doctor, is a particular slippery fish to…
Damon Dice is a private eye hired by Anna Morna’s husband – he wants to know her every move. Damon begins photographing Anna in secret through the window, but soon…
For the first time in Digital Playground history, we will be hosting a nationwide search to find the next DP Star. We were accepting video submissions for the entire month…
