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…
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…
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…
She’s on the fly. Erik Everhard and Scott Nails are sneaky, perverted gym rats who have a dirty, lusty contest going; scamming on hot girls who come to work out….
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…
Jack’s Playground: Big Tit Show 6 Call Jack “The Titty Hunter”. He’s hunting for trophy titties, and will only settle for his favorites; big, beautiful boobies. They bounce, and they…
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…
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…
Tremendous Latina Blondie Fesser Fucking Only in the Ass with Her Round Ass Few scenes can be seen in our country with a purely “made in the USA” style, and…
Whorin’ Round the House Real People, real sex. This hot wife loves to be her hubby’s dirty little whore. These sluts enjoy Whorin’ Round The House. . Whorin’ Round the…
Round White Asses Get lost in some round white asses with this exquisite selection of hot girls. There’s no better way to appreciate a bubble butt than to squeeze your…
Includes 2 bonus scenes! 2013 AVN Award Nominee for Best POV Release. 2013 AVN Award Nominee for Best POV Series. It’s pound the round time again and we’re on a…
Pound The Round P.O.V. #7 2011 AVN Award Nominee for Best Big Butt Series. We hope you’re ready, because you’re about to witness over three hours of serious pussy and…
Pound The Round P.O.V. #8 This item comes in a sleeve. All you lovers of fine booties…unite. It’s pound the round time again, and we’re about to take you on…
Pound The Round P.O.V. #6 Get ready for the plump round asses of Sadie West, Bridgette B, Capri Cavalli, Gracie Glam, and Katie St Ives. All these girls are dripping…
Pound The Round P.O.V. 2010 AVN Award Winner for Best POV Sex Scene. Come and pound some plump round asses, POV style. Isis Taylor, Madison Parker, Kagney Linn Karter, Alexis…
My Sister Has A Big Round Ass The second these guys saw their new stepmoms, they had a pretty good feeling their new stepsisters would have massive asses to match….
Pound The Round P.O.V. #3 Join Aliz, Micah Moore, Cindy Hope, Juelz Ventura, and Aletta Ocean on this p.o.v. adventure that’s full of tits, ass, and all the p.o.v. pounding…
It’s time to pound some plump round asses, POV style. Director/performer Mike Adriano has brought together five booty-ful babes that can’t wait to get pumped full of cock. Join Amy…
Pound The Round P.O.V. #4 It’s Pound The Round time again… P.O.V. stylez. Cum and join Angelica Saige, Charlotte Vale, Mackenzee Pierce, Bailey Lane, and Alanah Rae as they give…
All Star Edition It’s time for some ass pounding, POV style. This is the all-star edition, so Alexis Texas, Shyla Stylez, Jayden Jaymes, Ashli Orion, and Rachel Starr are here…
Round The Back Sometimes it’s all about the ass. Get ready for over 7 hours and 40 minutes of hardcore ass pounding. Featuring Jessie Rogers, Ashli Orion, Alanah Rae, Sadie…
