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…

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…

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

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.”

Directed by Celeste, Shay Jordan’s Juice is a dizzying frenzy of tantalizing flesh and mouthwatering fucks, starring Digital Playground’s contract superstar, Shay Jordan alongside a beautiful and elite cast that…

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

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…

The Dirtiest Teens In America

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…

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)

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…

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,…

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…

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…

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.

Fuck Me Silly Vol. 2 Seven of today’s hottest stars brought together in one collection to show off exactly what makes them so special! There’s nothing funny about how sexy…

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…