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….

They wanted to get into the gang but these OGs aren’t interested in letting white bitches be a part of their crew. When it comes time to jump them in,…

Ohana Petite is texting obnoxiously while her tutor Michael Fly tries to help her learn. Eventually Michael relents and lets Ohana take a break. He goes to the fridge and…

Tori Montana and Harmonie Marquise are bickering sisters who are always getting on each other’s nerves. One day while they are fighting over clothes, their mom’s boyfriend, Duncan Saint, breaks…

I found this video of my daughter’s eighteenth birthday in the basement. That was a memorable day because my girl was leaving home for college and I got to bone…

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…

A group of seven close-knit friends plan what might be their last big blowout weekend getaway together. The only single member of the bunch, Sarah (Paige Owens), has a plan…