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….

Check out this video of this blonde beauty alone outside. She caught me filming but was so friendly, probably because I was the first cock she’s played with all day!

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…

Chanel Camryn was making out with her husband Brian Omally as his buddy Jax Slayher walked in to pick up hard drives. Chanel asked her husband Brian if she could…

Studious college senior Luna Luxe tries to convince her boyfriend to take his studies a little more seriously when he’s bored in the library. But there are two sides to…

Smoldering hot European brunette Heather Harris needs a place to stay, but the rent her new roommate, Jordi, is demanding, is too high. Heather tries negotiating with Jordi, but her…

Leanna Lass just graduated at the top of her class from this little farming town in Michigan, and she’s ready to spread her wings and go out into the real…

Octavia Red misplaced some important papers for her boss. She got them mixed up with other files so she had to go to her boss’s home and pick them up….