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….

Nina’s had a thing for her best friend’s hot dad for a long time, and she’s picked the perfect day to make her move. The cute teen knocks on his…

Enjoy Digital Playground contract star Jesse Jane® in this wonderful and sexy horror spoof. Set in another era, 6 erotic stories unfold in an eerie mansion. It’s delightfully wicked and…

Kendall shows up to her friend’s house, but her friend isn’t there yet! Who opens the door? Her friend’s hot dad. Does he mind if she waits? Not at all….

Uploaded: 2024.02.17 2024.02.17 Show more…

Danielle Foxxx is a hot tranny MILF who’s bi-sexual babysitter has asked for a raise. Danielle will give him a raise, that’s for sure. This super busy pornstar treats her…

Having a bossy stepsister is annoying, especially when she is hot. This is exactly what happens to Johnny Love with his sexy stepsister Dixie Lynn. She wants chores done and…

Candy gets very bored and lonely when her husband goes to work. She has her close friend Savannah come over to pleasure her and have fun. On this day her…

Italian beauty Valentina Nappi oils herself up over and under her bangin’ full bodysuit, spread out on a massage table, ready for Kyle Mason’s warm hands and hard cock to…

Summer’s heating up so Aidra is selling ice cold ZZ Lemonade to the public. While her customers cool off she heats up with Jordi, who licks her her round ass…

Tiny babysitter gets fucked by her boss’ huge cock and takes his load all over her face.Tiny babysitter gets fucked by her boss’ huge cock and takes his load all…

Are you ready for a beautiful, bouncy, big booty blonde to arch and twerk, to tease and flaunt, to crawl across your screen? She’s played the cutesy friend, the oblivious…

Angie Miller was doing a photo shoot for Only Fans in a forbidden place. The manager took her to a more suitable place and fucked her.

Coming home from a long day of shopping, it was just Goldie’s luck to drop one of her bags in the driveway. But when her neighbor Jax spotted it walking…

Andi Avalon is new in the neighborhood and she already has a new cock to fuck. While her neighbor’s wife is out, Andi stops by his house in sexy lingerie…

Brandi and Alexis leave their husbands – for each other. But is there something missing from this wet lesbian paradise? With two stepsons on the loose, forgetting about the dick…

Uploaded: 2024.02.09 2024 Show more…

Bridgette invites Ariana and Xander to a business meeting on her husband’s yacht to celebrate the business deal between families; little does Ariana know that Bridgette’s real plan is to…

Brandi and Alexis leave their husbands – for each other. But is there something missing from this wet lesbian paradise? With two stepsons on the loose, forgetting about the dick…

Sommer Isabella is an ebony babe who wants nothing more than to become Mick Blue’s best dance student. There’s just one problem; she’s top heavy! Her gorgeous natural tits are…

Mona Wales is recently single and she can’t wait to get out and fuck like a whore again. This MILF gives you a great peek at her pussy when her…

Paige Owens has just moved into the house of her dreams. There’s just one problem: the old tenant hasn’t moved out! Skinny ebony stunner Chanel Skye hides in the furniture…

No Time For Fuckery Alexis has a busy schedule, and wished her stepson Brad did too. He chooses to lollygag around instead of getting done like finding a job and…

Parker Sims is trying to make his bed when his stepsister Jojo Austin jumps onto it and begins wrinkling the sheets. They argue, with Jojo insisting that she wants to…

August Skye has her friend’s husband, Brad, stop by since she’s heard he’s great at massages. Brad didn’t expect to be massaging August’s ass and tits though, but he can’t…

Uploaded: 2024.02.15 2024.02.15 Show more…

Bubbly Desiree Dulce blows bubbles and bounces on an exercise ball, teasing her perky tits and juicy pussy lips before Xander Corvus enters and gives this sexy vixen the cock…

Gabbie Carter thinks she’s about to surprise her boyfriend in the shower, stripping out of her skimpy clothes before she enters, only for her to be shocked when she finds…

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 POV Playground, YOU will get…