Will has a sweet thing going on. He lives in LA and scored one hell of a housing find when he came across a cougar who has several rental properties…

Jack’s Playground 33, features Digital Playground’s one and only insatiable and sexy Devon. She’s eager to make the music video cut and demonstrates her distinct talents on Scott Nails’ throbbing…

Mick Blue wakes up next to smoking hot Mona Azar the morning after a big party. Though he went to bed alone, he’s not exactly upset about spending the morning…

Uploaded: 2024.02.20 2024.01.06 Show more…

One morning, Ike receives a call from his stepdaughter Athena’s school. She has a real attitude problem, her grades are at an all-time low and, to make things worse, she…

Tiffany Watson gets hit on by a chick on the street and she expertly denies her saying that she only likes dicks. The girl goes back to her place and…

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….