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….
Dee Williams arrives home and discovers her house stinks of cologne. She follows the scent upstairs to her stepson Justin Hunt’s bedroom. Dee bursts into his room and catches Justin…
When you’re a horny slut like Alby Rydes, sometimes you just need to get your ass fucked. So Alby called up Bill Bailey, who she knows loves a woman in…
Joanna Angel is all dressed up in her perfect lingerie and she is ready to get down and dirty. This fun-sized babe has a pair of perfect perky tits and…
The best thing to ever happen to Jacky Joy, Sophia Grace and Jenny Jett’s pussies was to join the So Cal Swingers club. You see on swing night no cock…
Sexy car thief Veronica is watching as Kai parks his luxury car and leaves his garage door wide open as if in invitation. The stealthy beauty climbs into the hatchback,…
The My First Porn series is a comical sex-spectacle of Jack directing his first porn movie. Volume 8 is 3 full hours and features Digital Playground contract stars Sophia Santi…
The French Secret Service has sent in their most seasoned spy, Liza Del Sierra, posing as a maid to infiltrate Danny D’s mansion. Holding on to British intelligence documents has…
With the sun setting and darkness shrouding them in mystery, Mia Malkova and her man wandered in from the wilderness outside of their cabin to explore their passion further. Once…
The sexy Sybil is mid-blowjob on her boyfriend (Scott Nails) when her fitness trainer Tiffany Watson shows up for an at-home workout session.The session begins and it seems anything but…
Jennifer White wants to get with her stepson Parker Ambrose. She takes every chance she gets to wear tight outfits that highlight her big tits and ass. Today, Jennifer is…
Spring is in the air, and ebony babe Ashley Aleigh is doing some deep cleaning when she comes across a box of forgotten sex toys. Ashley takes a break from…
Phoenix Marie is a busty school nurse who is constantly getting hit on by the horny dudes at ZZ University. So imagine her surprise when the sexy, petite, and fantastically…
John wants to hire Kimber James as his babysitter, but first he needs to understand what a transsexual is. The only way Kimber knows how to explain that she’s a…
Watching Aidra’s ass slowly swallow up her gym shorts as she worked out on the elliptical caught Reena’s attention hard! Creeping on the booty made it impossible for her think…
Nicolette Shea is the dealer at shady a backroom poker game. Scott Nails and Alex Legend join the game one evening and lose every round. They are both skeptical, watching…
Astrid comes home and finds a video camera set up in the living room. Thinking her husband left it out, she decides to put on a little show. Little does…
Katrina met the perfect man: thoughtful, giving, who knows what she wants before she does. And tonight he’s giving her to someone else… Uploaded: 2024.02.18 2024.02.17 Show more…
Aubrey Black is the slutty MILf next door who just loves to offer a helping hand. And when Markus Dupree returns home from school, Aubrey is happy to give him…
Struck by Cupid’s arrow of love, Christina Shine is planning a very special surprise for boyfriend George Lee. With Valentine’s Day peaking around the corner, the gorgeous blonde wraps up…
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…
After inspecting Mr. Sins new place, Insurance Agent Bitoni determined the house was at risk. Johnny figured it would be very costly to insure the house so he tried to…
