Public sex at its best! Tera & I “Meat” at the mall…construction crews have never been so happy! Valentina & me out in the woods…she found some “wood” there! Alena’s…

Some Family Trees Are So Confusing. Dearest Ashley, as you know things got pretty confusing with the family over the holidays. I stayed at my brothers a few months and…

Sonia, a young working class Hungarian girl has just won the jackpot by getting married to Eric, an upper class Frenchman who showers her with gifts. A modern Don Juan,…

Pour Charlotte (de Castille), Jackie et Michel ont amené un espagnol bien plus jeune qu’elle. La puma s’affaire à le branler et le piper et c’est parti pour une enculade…

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…

Unshaggables, The Lucia comes to Angel’s Unshaggable Agency with a problem – She’s too shy to ask guys for anal sex! Luckily for her, Antonio is obsessed with anal sex….

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.”

Give To The Yummypie.com Telethon

“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…

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 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…

Montel n’ Dirty say if ya can’t adap, den you muss let me tippity tap dat izass.

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

Tired of getting fucked?! Let the Law Offices of Cody Law help you fuck back!

“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.

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…

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…

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…

Hookup Hotshot: Cruising The Internet You might think of Bryan Gozzling as a Romeo for the Millennial age – his online dating savvy and rude sexuality entice fashionably nasty waifs…

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…

You don’t know Jack until you’ve seen through his eyes. Don’t miss this all-star cast that includes Hannah Harper, Lacey Maguire, Annette Schwarz, Rachel Roxxx & Britney Stevens in a…

You don’t know Jack until you’ve seen through his eyes. Naughty Teagan – whack it again! Sienna West – Yo Quiero Soft Taco! Jana Cova – Bring it on Jana-101!…

Beautiful BiBi Jones drips her young, sweet juices all over thick rods and long, hard members. She shows off her naughty skills as the youngest new nasty girl. She and…

When Jack puts his mind to something, the filthy possibilities are endless! In Jack’s Playground: Asian Adventure, Jack rounds up the most kinky, exotic Asians to give him a happy…