Oh man! Mike and I went MILF hunting around our neighborhood last night and we were so lucky to knock on Jaylyn Rose’s door! Because this sexy big titted mommy…

Jack’s Playground 33, features Digital Playground’s one and only insatiable and sexy Devon. She’s eager to make the music video cut and demonstrates her distinct talents on Scott Nails’ throbbing…

Slutty Jessie Volt was giving a random guy a blowjob in the parking lot, but she discovers a voyeur filming the entire thing! She tracks the guy down, and demands…

She may be young but what she lacks in experience she makes up for sheer exuberance. This eager cock-jockey gets on her man’s meat like a cowgirl aboard a mechanical…

Lacy Lennon seems like a perfectly innocent college student on the surface, but she has a serious thing for Steve Holmes, who she’s renting a room from. In fact, Lacy’s…

This cute Japanese nympho is getting a massage when the guy rubbing her down pulls aside her sports gear and starts fingering her pussy. It feels good for her and…

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….

Kelly has been going to raves for many years, so she enjoys the atmosphere achieved with glowing lights. She even puts a pink light up toy in between her awesome…

Stevie Shae is married to Kendra Lust’s ex husband, and as a result, they’ve never exactly been best friends. But when Stevie’s sex life dries up, she has no one…

On a Tuesday afternoon, in a high rise building, a conference room is heating up with some tense negotiations. One company wants to buy out the other and everyone wants…

Graycee Baybee just gets word that her friend can’t take her to the airport so her friend’s dad, Mr. Mason, offers to take her. While conversing, Graycee tells him about…

Russian minx Katrin Tequila never needs to pad her lackluster resume. It’s more her style to distract her potential employer with what she really excels at: sexy flirting, sloppy blowjobs,…

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 new POV Playground, YOU will…

Uploaded: 2024.02.13 2024.02.13 Show more…

Danny has decided to take his relationship to the next level and finally move in with his girlfriend. The one thing he isn’t quite ready for is meeting her daughter,…

This girl loves dressing up in traditional Japanese clothing and going for a walk down the path under her cute blue umbrella. Her hairy pussy gets played with in the…

From the makers of 2007’s Best Release “Babysitters”, 2008’s Best Seller & Best Release “Cheerleaders”, and 2009’s 1 hit “Nurses”, comes the bigger, sexier “Teachers”! Textbooks, homework, detention, lube, dildos…another…

Ria Sunn found the Bangbros House. Here all Dick dreams can become true. She was horny. One dick was not enough. She wanted two dicks at the same time. Luckily…

Khloe Kapri has some badass ideas that she is able to portray on set for Pretty & Raw. She wants to feel used and taken advantage of in complete submission…

Nubiles – Angela Wild – Ecstasy

“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…

Wearing her sexiest pink lingerie including a ruffly bra, tight and tiny pink plaid skirt and pink lacy panties, a Japanese whore gives a blowjob outside. She gets fucked on…

Uploaded: 2024.02.17 2024 Show more…

Brandy is sick of her stepdaughter Darcie always sneaking in past curfew and wearing slutty clothes that show off her big tits and round ass. But Brandy was once Darcie’s…

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….

Essie Got Back is getting ready to fly home after spending a great time with her friend and friend’s husband. She is sad to leave because she wanted to get…

Lily has hired handsome private chef Mike to cater her party. When she checks on him in the kitchen before the guests arrive, the food isn’t the only thing that…

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…