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…

Pretty Eye’d Cock Sucker Jackie Ohh. Jackie Ohh is a newbie to the industry but not to sucking cock, this pretty eye’d cock sucker really knows how to please a…

The House Slave Gia Dimarco Brings Mason Lear Out to Play. The legendary beauty Isis Love is back and she brought a friend, the sexy Gia DiMarco. These two hot…

Shut Up and Serve Ryan Keely Makes Dom Jack Hammer Her Sub. Jack Hammer is a dom, who rarely subs. But today is one of those days. And who wouldn’t…

Alina Belle Sucks My Big Load Out of Me. I love getting a nice blowjob, I especially love it when it’s from a hot Latina like Alina Belle. Today I…

Busty Babes Say “No Pain No Gain!” When They See Huge Cocks!!. Carolyn was feeling sore and decided to relax in the Jacuzzi. Little did she know that her pussy…

Without Limits 2. Davis is a very successful young businessman. His life evolves around and between two important women; his lover Helen (Claudia Jackson) and Peggy (Sandra Iron), who is…

Jack Parties in Vegas!. Jack parties in Vegas! Two horny housewives take on Jack. Sativa wants to know how big Jack really is. Special Bonus Scene: Find out if Mr….

Sexy Scouts Are On The Hunt For Their Next Creampie!. Petite blonde cutie Coco Lovecock earned her creampie badge by letting an older guy blow his load inside her sweet…

Black Out #4. Lights… camera… Blackout! For over 2 hours, come check out the hottest African princesses get de-throned and big-boned into submission. Vanessa Monet gets her pussy painted and…

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…

William, a clown whose career is taking off with difficulty sees his future darken. Because in a video filmed without his knowledge where he reveals his premature ejaculation problems, he…

Chad White Is The Jackoffanator Chad’s a photographer whose favorite subjects seem to come alive as he processes the film. His imagination carries him into these teen pussies, living out…

Sister Jacked Carolina Cortez – “You can’t leave me out here in the middle of nowhere! You’re my stepbrother! You just don’t throw your family out of the car! I’ll…

Outdoor Sins There is nothing sinful about outdoor sex in fact, it’s some of the best fucking you’ll ever have! The warm sun on your naked body, a toned fuck…

Girls Night Out is back with a vengeance! Tanner, Penny and the girls take the party bus out on the town. After loading up on some cocktails, they head to…

Six naughty little anal sluts are about to shake your beanstalk like never before, spreading their sweet little ass cheeks and taking on giant size c*cks deep up their quivering…

2008 AVN nominee VAN STYLES is back with the hotly anticipated sequel to his acclaimed interracial epic SOULED OUT! This three hour fuck marathon pairs beautiful white vixens up with…

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…

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

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…

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 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…

Dr. Hienrich Shizen sez, “Zarez nutting unlucky about zee numba 13…unless you’re zee one taking zee 13 eenchez.”

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

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…

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…

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…

Scene 1. Noname Jane, Alec Metro Scene 2. Topanga, Jack Hammer Scene 3. Dru Berrymore, Rafe Scene 4. Kristy Love, Billy Glide, Julian St. Jox

Beautiful superstar Kayden Kross comes up close, right in the palm of your hands, with lusty POV action. Kayden invites you to reach out and touch her as she and…

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 to bend over for him. These…

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…

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…

John Leslie focuses his perverted eye on the world of the three-way in five smokin’ scenes! Check out mocha goddesses Adriena and Kapri Styles teaming up on Mr. Pete, or…

“Amanda Bryant – My niece came by demanding I give her the BJ part in a scene. Well, you can’t just send someone out to do a job taking their…