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…
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…
Misty Stone has a surprise for Isiah Maxwell that she knows he’s going to like, but first he has to put on a blindfold and follow her lead. Misty stealthily…
Shot entirely on HD, Jack’s Teen America 21 features Digital Playground’s lovely contract star, Lacie Heart in a slam-min’ romp with Scott Nails, Poppy Morgan & Renae Cruz in decadent…
It’s time yet again for another public bang! We have with us for another round, the lovely Samantha Cruz and her banging body. We talk for a bit with her…
As Riley slips into a tiny thong and a tight, little black dress, her mind runs over what her boyfriend Jonathan might have planned for the Valentine’s Day surprise he…
Live streaming hotties Chanel Camryn and Lily Starfire are sure their cosplay collab is going to be very popular with fans. The babes help each other change into their schoolgirl…
Whitney Wright lands a job interview at a recruiting firm and shows up in a sexy outfit that would seduce any hiring manager! What she doesn’t know is that the…
Paige Owens is a wild cumslut! This babe loves to get oiled up, slick and she is ready to get her holes destroyed! She dances around and plays with her…
This Asian girl loves wearing her glamorous jewelry and posing against the crushed red velvet cloth. It feels luxurious against her soft skin and inspires her to stick her butt…
Lacy Lennon is a smoking hot redhead that has an amazing bush to match her stunning hair color. She dances around and shows off her seductive sexual energy, all while…
Jack is really busy casting for music videos and he’s scored some super fine ass for volume 38. Digital Playground’s amazing contract super stars Teagan Presley and Lacie Heart join…
Jill Kassidy has been spending some time at her friend’s house and she swears that her friend is moaning very loudly during sex so that Jill will get jealous. The…
Every perfect princess needs to be rescued – in this case, from a chastity belt. Good thing her hunger for cock is heroic…our princess won’t quit until she gets the…
Roma Amor is hanging poolside and streaming live with Jordi El Nino, the lifeguard, who is loving looking at all her assets. Katerina Moreno arrives with her derp of a…
Katie makes herself fully available for Donnie. She lights candles near the bedside, adorns herself in black lacy lingerie, and blindfolds herself. This isn’t just another typical romp in the…
Wow check out Britanny Oneil, this big titted mommy is amazing! In the following adventure, you will see busty mom Britanny banged by a young man working in pool maintenance….
To replenish the gene pool, the Amish have hired an outsider to impregnate their daughter. In order to ensure a repeat performance, she decides to take it deep in the…
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…
