“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.

Evan Says, ” He who throweth the first Stone, must be ready to bone.”

Arrrrrgh!!! Thar be pirates hittin’ this here booty! Captain Evan returns, “Time to walk my plank, my prettees.”

That’s right!… Best gonzo series muthafuckas!!! To celebrate, we added a bootylicious sista to commemorate da festiviteez.

Sorry about Jack’s 20, folks. I bitchslapped Jack to make sure that won’t happen again.

Give To The Yummypie.com Telethon

Cousin Nick P., Ph.D., drops knowledge on what it’s like to cut these muthafuckas.

Choc full o’ fun and flavor!

Watch Tera take the double Buda! See Rocki take it in the… barn… and will Tommy ever pop?

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

Analizar Esto Maricon … Did I just speak Spanish?

“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!

Squirt Bang Eleven super sexy babes get soaked! These chicks are cumming so hard everyone’s going to feel it! Get slick and splash around at the Squirt Bang!

Porn star Tasha Reign is the hottest crossover star to hit the Hollywood scene. Paired with her best friends and fellow porn stars, Anna Morna and Mia Malkova, as well…

In a world where fantasy meets reality, anything is possible. Turn on the fun in this gonzo style film where everything is your POV. Watch as hot, young, sexy girls…

Settle in boys and girls. We’re going to tell you a story of how your mother got fucked by all the men you don’t call daddy…

Dark Obsession A man’s ex-wife comes back to haunt him — even with a second wife now in the picture. Some people just can’t let go. And her stranglehold will…

They’ll do anything to get their man. The hunt is on! Digital Playground contract superstars Jesse Jane® and Riley Steele are locked, cocked and ready to rock! These blonde babes…

The Dirtiest Teens In America

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…

A Lesbian Compilation These luscious ladies have desires that need fulfilled! They can’t help but explore the nethers of other sexy women! They’re Passionate For Pussy! They can’t get enough!

Kissing Buddies (Digitalplayground)

Jasmine Jae is a pretty girl who plays ugly games – starting with clueless airline CEO Marcus London. After bankrupting his airline, Jasmine plans to flee the country. Until she…

Smut, is exactly what this sexy title entails. 6 hardcore scenes each depicting an erotic story full of raw, filthy desires! One of the raunchy tales follows businessman Kieran Lee,…

What do you do when you want to dump your husband AND get a plump divorce settlement? Set him up with another woman and catch him cheating! Unless he already…

BiBi gets her fill! Bubbly beauty BiBi Jones wants to get pregnant but her guy Tommy Gunn, is running on empty. Turning to her close friends for semen samples doesn’t…

James is a masseuse with a demanding clientele, handling everyone from horny MILFs to naughty girlfriends. As his business grows, he enlists the help of his amateur buddies to service…

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…

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…