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….
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…
Welcome to The Sessions, a sexy series that allows you into one of the most intimate spaces known to man—the therapist’s office. Be a fly on the wall as patients…
Maggie Green make look like a sweet stepmom, but looks can be deceptive! Maggie’s stepdaughter has her date, Johnny The Kid, over at the house, but Maggie keeps butting in…
This stunning beauty was alone at the laundry mat, angrily throwing her clothes in the dryer. Turns out her boyfriend is a complete jerk and what better way for revenge…
Lia Taylor’s craving the sweet release of a long, lazy stretch masturbating on her sofa. No one else knows her body the way she does, all her sweet spots and…
Art student Natty may be shy and quiet, but she’s managed to seduce her beautiful model Veronica without saying a word! Over their sessions together, Veronica has fallen in love…
Veruca James hasn’t ever done anything like this before, but her dreams of becoming a porn star are going to require some double penetration and toe sucking. She’s totally prepared…
Nataly Porkman just turned 18 years old and is ready to get her pussy absolutely destroyed. They go through a series of different stages where we watch her masturbate, suck…
Ashley might look like a sweet girly girl, but she knows a thing or two about cars. She works hard for her money and gets sweaty doing it. But bending…
Kendra Sunderland looks stunning in a shiny little bikini that barely covers her big natural tits. As great as she looks in her swimsuit, Kendra can’t wait to be stripped…
Keiran’s got a bit of an embarrassing problem he’s got to deal with at the Doctor’s office today. He hasn’t ejaculated or had sex for over a month, and is…
Reagan will do anything to get the perfect sexy picture off to her husband. She’s trying her best to up her selfie game, but still could use a little help….
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…
Lexi went in the bathroom and saw her boyfriend’s brother, Criss, coming out of the shower. Seeing Criss’ huge cock made her so horny, that she just wanted to fuck…
