“Lets listen to these cummentators discuss their thoughts on Jack’s bitches.” And cut the farting.

Jack’s Playground 30 is packed full of the dirtiest chicks enjoying giving awe-inspiring blow jobs, masturbation, ball-bustin’ tease, and pussy lovin’ action. Featuring busty, brunette superstar Jenaveve Jolie, Jack’s Playground…

Jack’s Playground 31, the superstar edition, stars the lovely Jana Cova in two delectable scenes, Devon in all her naked splendor and DP’s original contract star, Rocki Roads in brand…

“The playground keeps getting better with new hot pussy. This could be the sexiest of the series! Just load up, and get ready for the wet target!”

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…

“Exotic waves of molten cum erupt into timid young glesh in this amazing exploitation of carnal voracity”

Juicy Cheeks Meets Juicy Peaks

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…

Smoking hot Jesse rocks ’till it rolls! The new Jack is harder, deeper, faster than ever before!

Jack be Nimble. Jack be Quick. Jack be Back Muthafucka.

Fuck dat Jack muthafucka… Dis be Montel’s International hayose o’ Poontang! Jack thinks dis be Jack TV but I calls it Montel-a-vision.

We be on numba Foh, and dis be Montel’s Wah so deal wit dat you muthafucka!

Montel n’ Dirty say if ya can’t adap, den you muss let me tippity tap dat izass.

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

Montel the Stunt Cock sez: “Dis one gots loads of juicy treats fo all y’allz.” I will survive!!!

Montel sez: “Don’t make me angry, I’ll get cockzilla on yo ass.”

Numba nine, numba nine, nine titties, nine inches, nine pussies…I said nine mutha fucka! Oh yeah…and nine money shots!

Thugs seek a stiff $1,000,000 ransom in exchange for afro-american penis (aka Montel).

Tired of getting fucked?! Let the Law Offices of Cody Law help you fuck back!

Jack turns 1!…and there’s a whole lotta frosting on deez cakes!

Dr. Hienrich Shizen sez, “Zarez nutting unlucky about zee numba 13…unless you’re zee one taking zee 13 eenchez.”

“Dis one be off da hinges wit lots of titayz and all kinds of juicy young ass.”

“Trick o’ treat… Jack wants to lick some pretty meat. And Montel ain’t got nuttin’ to say ’bout dat!”

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

Jack’s Playground is a brand new reality series featuring Jack, a trust fund child and aspiring music video director who happens to have a knack for persuading real girls to…

Ten lipstick lesbians are strapped for gash! An exclusive girls-only club where your everyday lesbian need not apply. The Underground Lesbian Strap-On Club is a place where the most hard-core…

A FantASStic Show Are you ready for some extreme bubble bursting butts?

Teagan Presley & ANAL, does the rest of this description even matter? Jack is really busy casting big, bouncing, beautiful butts for music videos. They shake, they roll and they…

Jack’s casting again! This time he’s looking for leg models… sexy, leggy vixens who want to be in fresh, up and coming music videos. In the second volume, Digital Playground’s…

Jack’s casting again! This time he’s looking for leg models… sexy, leggy vixens who want to be in fresh, up and coming music videos. In Jack’s Playground: Leg Show 3,…

The camera starts at her petite ankle and slowly travels up the milky skin of her calve and around her toned hamstring on a journey to the pink treasure nestled…

Mega Packed with Juicy Crack “Check out these packs with juicy crack presented by Jack”

Jack’s busy in his playground casting big-ass babes for leading roles in his yet-to-be-seen music videos. The delicious girls will do ANYTHING for stardom! Some suck, some fuck and some…

Big, Hot and Kinky! “More Cushin For the Pushin”

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 Robby finds pleasure deep…

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…

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…

Come and play with us. Again Seventeen’s most beautiful models are invited to play. The misbehave themselves in all kind of places making usa of sex toys, their horny girlfriends…

When Jack puts his mind to something, the filthy possibilities are endless! In Jack’s Playground: Asian Adventure, Jack rounds up the most kinky, exotic Asians to give him a happy…