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….

Uploaded: 2024.02.24 2024.02.24 Show more…

Sexy neighbor River Lynn just got home, and she notices that the front door doesn’t creek anymore, and her smoke detectors are not chirping too, but the best surprise comes…

Xander Corvus bust in through his girl Teanna’s bedroom window and buried his face right in that juicy ass. Teanna tried to focus on her homework, but there was no…

The only time Corinna Blake and her stepbrother Jessy Jones can ever manage to stop arguing is when they’re fucking. So when Corinna won’t stop talking during the news, Jessy…

Secretary Giselle has a run in her stockings – during a very important client meeting. When she’s caught changing her pantyhose in the company conference room, she must be disciplined…

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…

My new camera needs new footage, and today I started filming my girlfriend like a voyeur. She knew what was happening, and gave me the best blowjob and more. Good…

Sabina Rouge is the whole package, and those big, pouty lips are the cherry on top. She teases the camera and shows off her tongue – a little glimpse into…

Jayden Lee will only cum if you fuck her hard. Judging from the smile on her face our stud is giving it to her just right. See her beg or…

Meeting guys in hotel rooms for group sex isn’t something this beautiful long haired brunette Asian girl does often, but she really loves the feeling of six hands on her…

Abigail can’t believe she had to find out about Felicity’s wedding through friends. That’s no way to treat an ex-girlfriend! Abigail crashes the party to show Felicity just what she’ll…

A little flirtation goes a long way with shy beauty Melissa Moore, and her black beau Isiah Maxwell knows exactly which buttons to push to get Melissa undressed! Surprising his…

The soft glow of twilight streaming through Cara’s bedroom window has put her into a fanciful mood. Stretched out elegantly on her feather duvet, she marvels at the beauty of…

When Danny stops in at his mother-in-law’s house, he’s in for a dirty surprise. Ashley is covered in cum and hungry for more! She’s shocked to see Danny, and doesn’t…

Blonde Dylan Moore decides to surprise her girlfriend, Vanessa Sky, during her sweaty home workout with a vibrator against her pussy! Dylan rips open Vanessa’s sheer leggings so her GF…

Shot entirely on HD, Shay: Sexual Freak 3 features Digital Playground’s newest contract star, the lovely Shay Jordan, in a plethora of deviant and mischievous erotic play. Sexual Freak 3…

Busty blonde Miss Jackson is at the health spa waiting for her next massage appointment. She passes the time by taking a dip in the jacuzzi pool and as the…

When a visiting nurse Mea Malone set up shop in Leny’s office giving quick check-ups, he just had to check it out for himself. After peeking in the office and…

Manuel Ferrara could snuggle into Marta La Croft’s full figure all day long! Her big breasts are just right for soft pillows, but Marta’s in the mood to fuck. She…

Not only did her new stepson leave an egg in her boot, he hides and puts one on the bed right where she sits down! That’s the last straw for…

Terrible, Cum-Sucking Employees Cheerleader Kait, newly employed, is in a work training session with Kelsey Kane. Things seem “business casual” when suddenly, Alex Jones (the boss!) waltzes in, bends Kelsey…

LegalPorno – Tina Fire – Busty Slut Tina Fire Gets Fucked 4on1 And Pissed All Over SZ2826LegalPorno – Tina Fire – Busty Slut Tina Fire Gets Fucked 4on1 And Pissed…

Nikki is a travelling-hippy-type, hitch-hiking her way to the next great adventure. When she stumbles upon an orchard looking to hire workers, she’s a welcome sight and hired immediately. For…

At a café, Lily meets up with Janet and Amber after an afternoon delight with the grocery boy to start drafting their own gym ideas. Meanwhile, Linda is quietly eavesdropping…

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…