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…
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…
Sweethearts Playground #10 Again Sweethearts most beautiful models are invited to play. They misbehave themselves in all kinds of places making use of sex toys, their horny girlfriends and willing…
Anal Playground Get ready for playtime in one of women’s most erotic zones… her butt! They’ve got your dick hard and their little assholes are gaping… it’s time for some…
Philippine Underground: Manila Asia Bootleg has gathered together a group of hot and sexy Pilipino girls ready to get down and dirty in a classic tale of east meets west….
Ground And Pound It’s pussy fucking time, and these bitches are about to get pounded to the ground. Check out Carla Cox and Liza del Sierra getting an injection of…
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…
Ronda ArouseMe: Grounded And Pounded In this inspiring and moving parody film, Ronda ArouseMe (Kleio Valentien), the Olympic medalist in Kama Sutra and reigning UPC (Ultimate Porno Championship) women’s bantamweight…
Interracial Playground The stage is set for all around interracial fucking! Sexy white girls are overwhelmed with engorged black cocks all around! Sexy white chicks are filled to the brim…
Stuck In Groundhog Day Loop – Anal Is the Only way Out – Fucktacular E64It happened again. We thought it was just another normal morning and decided to have a…
