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….

Charles Dera and Elsa Jean are a seemingly normal, perfectly happy couple. Thinking his wife is out for the day, taking part in one of her many “housewife hobbies”, Charles…

Jack’s Playground 34 features Digital Playground’s exotic contract superstar, Katsumi. She’s a panty hose model by trade but she’s eager to make the switch to music video queen. She demonstrates…

Abigail Mac loves being wifed-up, but she missed her sluttier days, days filled with her ex-boyfriend’s big dick. Keiran Lee is fine with Abigail moving on because deep down he…

Keiran Lee enters the kitchen to find his son’s sexy teen girlfriend, Lana Rhoades, cooking breakfast in her pink panties. Lana wanted to surprise her boyfriend, but he’s already left…

Professor Brittany Andrews notices one of her bright students struggling and wants to help. She knows some people on staff that can help him but in order to get him…

Any first year law student would be able to tell you that breaking and entering Ashley Long’s pussy without her permission would be illegal. However, for reasons unknown to us…

Kaylani is a bit dry when the clip starts, she should have shown up pre-lubed but that is a typical rookie mistake. What matters most is that she works through…