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….

Crystal Greenvelle got lonely waiting for Angelo Godshack to come home. She was wearing the cobalt-blue lingerie he bought her, but soon needed to free her nubile body. As she…

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Spencer (Stirling Cooper) and Julia (Katana Kombat) are a married couple in a rut. To get their relationship back on track for Valentine’s Day, Spencer sets them up with a…

Jack is really busy casting for music videos and now he’s landed Digital Playground’s super fine contract star, Teagan Presley. She takes a big cock in the butt and we…

Sexy Taylor Lynn introduces herself to this hardcore group of dark dudes, she doesn’t even get to ask what their names are before they toss her to the ground and…