Cumless: A Digital Playground XXX Parody Charlotte is not your average college student – she’s rich, she’s popular, and she’s the hottest virgin in town. After her best friend Deena…

Fast and furious. The need a deep, hard drilling and power fucking is the only way to go! Beautiful Jesse Jane and sultry, sexy Stoya gear up for an explosive…

In the desert, no one can hear you scream. Each year, students from the local colleges congregate at this deserted motel to blow off steam from finals with hedonistic partying…

Meet The Fuckers – A Digital Playground XXX Parody It’s been a while since he visited his parents, and after some pressure from the wife, they set out for their…

“Montel’s War” Jack’s Playground is a collection of Jack’s personal videos, homemade in Santa Monica, California showcasing his uncanny ability to persuade girls to perform sexual acts in front of…

Hot Babes, Bangin’ Sex, And Nasty Jack… 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…

Ride The Curves With Reckless Abandon Jack is really busy casting for music videos and he’s scored some super fine ass for volume 38. Digital Playground’s amazing contract super stars…

Real girls uncensored. Jack is really busy casting for music videos and now he’s landed Digital Playground’s super fine contract star, Jesse Jane. She fucks Ben English every which way…

The Comedy is in the Commentary Jack’s Playground is a collection of Jack’s personal videos, homemade in Santa Monica, California showcasing his uncanny ability to persuade girls to perform sexual…

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…

Jack’s Playground: Big Ass Show 9 Jack’s busy in his playground casting big-ass babes for leading roles in his “music videos”. This time he gets Alexis Texas and Shyla Stylez…

A FantASStic Show Jack’s Big Ass Show is back with another episode, and although Jack isn’t getting anything once again it seems like where ever he goes there’s girls with…

Jack’s Playground: Big Ass Show 4 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…

Jack’s Playground: Big Ass Show 2 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….

“Eastside Connection” Starring Digital Playground’s newest sensation, Shay Jordan and an entire cast of young, gorgeous, almond eyed beauties, Jack’s Asian Adventure will please your pallet. Jack uses the tried…

Jack’s Playground: Asian Adventure 4 Digital Playground’s Asian sensation, Shay Jordan is back for more… with a cast of eager-to-please, exotic nymphs, Jack’s Playground: Asian Adventure 4 will surely satiate…

Save the best for last. In the ninth installment of Jack’s Big Tit Show, Jack is on the hunt for big, beautiful boobies, using his trusty music video ploy to…

The One and Only Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful boobies. They bounce, and they shake. There’s more than…

Jack’s Playground: Big Tit Show 4 Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful boobies. They bounce, and they shake. There’s…

Jack’s Playground: Big Tit Show 7 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…

Got D’s? Some More Juice For You To Squeeze. Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful boobies. They bounce, and…

Oops…Jack Did It Again! More D-Cups Are Waiting For You To Unload On! Jack is back and he’s ready to give you more of what you really care about… big…

Jack Says, “Big Tits Are More Nutritious.” Jack’s at it again. In his playground, Jack is busy casting for music videos. The delicious girls will do anything for stardom. Some…

Jack’s Playground: Big Tit Show 8 Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful boobies. They bounce, and they shake. There’s…

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…

Save the best for last! Jack says dee cups will surely keep you up!

2 seconds will be deducted from your Pay-Per-Minute time for every second watched.Premium PPM allows us to bring you the best Adult content from the hottest studios.Playground HillsBehind their white…

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…

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.

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.

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.

Give To The Yummypie.com Telethon

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

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.

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.”