Jack’s Playground: Big Tit Show 6. Big tits are more than a handful. They’re two..

Montel’s back in da house! What’s da assfuckathon?

Jack is really busy casting for music videos and now he’s landed Digital Playground’s super fine contract star, Sophia Santi alongside Selina Draagen, Alyssa Chase, Carli Banks, Marlena, Christina Brooks…

Farmer Joe sayez: “Dangnabit, I ain’t seen girleez this cute since my sisters.”

Lets take a moment and give thanks for the sweet teens in Jack’s Playground 16.

Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful butts. They bounce, they roll and they shake and Jack finds pleasure deep…

All the screaming 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, get the BEST…

6th Annual Tranny Awards: The Winners. 6th Annual Tranny Awards: The Winners is directed by Blackula. The performers in this movie won awards at the most recent Tranny Awards in…