What’s that peekin’ out her dress? It’s her crack ready from some punishment. Step right up and crack her jack because if you do it right, she’s guaranteed to come…

Jack’s Playground: Leg Show 4 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…

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…

With 20 extra minutes that are not found on the original VHS version and featuring a full linear transfer, this is the definitive version of this classic fuck-for-all!

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 3 “It Must Be Ass Day!”

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!

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”

Choc full o’ fun and flavor!

Give To The Yummypie.com Telethon

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

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.

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

“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.

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.”

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).

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…

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

Jack on Moms He has a soft spot (or a hard spot!) for MILFs, and in Jack On Moms you will see why!

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…

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…

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,…