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…

Crack Her Jack 1 Maestro John Leslie makes a stylistic departure in his brand-new series, using the camera in a more seductively straightforward manner than before, but still with more…

Crack Her Jack 11 The masterful John Leslie returns with Crack Her Jack 11, featuring a perfect blend of sizzling new sluts and tried and true fan favorites. The mix…

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…

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

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

“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.

In over two decades working in both Europe and the U.S., Italian-born porn legend Rocco Siffredi has come to truly treasure American girls. The director/stud gets to exercise this passion…

Master Robby D. delivers more hot pussy pounding and intense orgasmic blow jobs. This time he turns his attention to some sexy ass mothers we’d all like to fuck. Some…

Men of the World: Paris (Jack Jones, Men Of The World. Alphamales Studio, Eurocreme Group) [2013, WEB-DL, 720p]

100% Pure Amateur! Jack isn’t the only one who gets dull after a day of all work and no play! These frisky kitties can’t wait to unwind after a long…

We all know the Miss Teen America pageant is full of flaws. You can’t judge a beautiful young woman based solely on a few simple tasks. Jack sets out to…

Jack’s at it again! But this time, it’s professional and even kinkier than before. Jack turns what he knows best into a career.

Teagan Wants More! Jack’s at it again! But this time, it’s professional… and even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack’s answer…

Five horny teens. 2 sound guys with equipment. 1 contest. 1 winner. Sound familiar? It is. It’s Jack’s Teen America. Put it in and cast your vote! Jack’s at it…

Jack’s at it again. But this time, it’s professional…and even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack’s answer to gettin a fuckin…

Jack’s at it again. But this time, it’s professional…and even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack’s answer to gettin a fuckin…

Special Contract Unit Jack’s at it again! But this time, it’s professional… and even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack’s answer…

Jack’s at it again! But this time, it’s professional… and even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack’s answer to getting a…

Teagan Is Back! Jack’s at it again! But this time, it’s professional… and even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack’s answer…

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…

The father of modern trans porn, Joey Silvera, compiles seven gender-bent scenes with one big thing in common: gigantic she-dicks! TS Mega Cocks packs femme, functional, super-hung T-girls from the…

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…

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…

Emma Luvgood and Liliana Moreno receive 122 loads to the face! They love to entertain themselves and it quickly becomes a mind over matter situation. Emma and Liliana are suddenly…

Six-babe, Double-D, double-disc edition! Six hot girls and six big, long scenes… all in the tease and please style that only B. Skow delivers! But this time the emphasis is…

With its unique camera work, Jack’s POV 12 brings you into the action and doesn’t loosen its grip until you’re completely drained. Jack’s POV 12 puts you in the driver…

With its unique camera work, Jack’s POV 14 brings you into the action and doesn’t loosen its grip until you’re completely drained. Jack’s POV 14, starring Digital Playground’s beautiful contract…

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…