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….

Katie Kinz has requested that she get two hot buff guys to fuck her at the same time! Her request video was a perfect tease, so we set up the…

Teagan Erotique is an erotic feast starring Digital Playground’s Teagan Presley with Jesse Jane and Jamie Lynn, Sativa Rose, Nautica Thorn, Jayna Oso, Sandra Shine and Keri Sable. Directed by…

If she wants to be dirty then I’ll treat her dirty. Watch me teach this chick a lesson.

Notorious fuck ups Charles Dera and Ramon have been tasked with an important clinical study to determine once and for all which is more pleasurable – vaginal or anal sex….

Maren was all set to have her rectum piped out by our black dudes but when one of them pulled free long enough to shaft her throat you will be…

We shot this scene staring Allison Moore and Trillium in black and white because we felt like it an because it made their sexy lingerie really pop. Speaking of pop,…

Amber Jayne is feeling hot and confident after her divorce. After years of matrimony this milf wants cock, even if it’s attached to her daughter’s husband. She loves knowing that…

A girl experiencing strange intense sexual dreams is watched over by doctors who monitor her as she falls into a deep slumber. In her dream we see the sexual depths…

This hot scene starts with sexy Payton Preslee teasing you in her hot one-piece outfit. Once Payton gets herself worked up, Quinton James shows up to pour oil all over…

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…