Starring Jesse Jane!
Smoking Hot Jesse Rocks Till It Rolls!
'Playful, powerful and supremely sexual - a revolutionary sex comedy... One of the most original series in years!'
The New Jack Is Harder Deeper Faster Than Ever Before! ...
Real Girls Uncensored!
Starring Sophia Saint!
'Playful, powerful and supremely sexual- a revolutionary sex comedy... One of the most original series in years!'
The New Jack Is Deeper And Faster Than Ever ...
Starring Teagan Presley And Katsuni!
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 his camera. As soon as Robby D ...
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 his camera. As soon as Robby D saw a few video clips of real girls so thirsty for fame, ...
The New Jack Is Harder , Deeper, Faster Than Ever Before!
Jack is really busy casting for music videos and hes scored some super fine ass for volume 38. Digital Playgrounds amazing contract super stars Teagan Presley and Lacie Heart join an all-star cast that ...
Jack is really busy casting for music videos and hes scored some super fine ass for volume 38. Digital Playgrounds amazing contract super stars Teagan Presley and Lacie Heart join an all-star cast that includes blowjob maven Audrey Bitoni plus Leah Luv, Neveah, and Roxy ...
Starring Jesse Jane!
Smoking Hot Jesse Rocks Till It Rolls!
'Playful, powerful and supremely sexual - a revolutionary sex comedy... One of the most original series in years!'
The New Jack Is Harder Deeper Faster Than Ever Before! ...
Analizar Esto Maricon did I just speak Spanish?
Stop hitting me asshole!
I can't believe Montel is a short Black-Xican, but I like him!
'Playful, powerful and supremely sexual - a revolutionary series in ...
Real Girls Uncensored!
Starring Sophia Saint!
'Playful, powerful and supremely sexual- a revolutionary sex comedy... One of the most original series in years!'
The New Jack Is Deeper Faster Than Ever ...
Real Girls Uncensored!
Starring Teagan Presley!
Jack is really busy casting for music videos and now he's landed Digital Playground's super fine contract star, Teagan Presley. She takes a big cock in the butt and we know Scott Nails found some sweet ...
Real Girls Uncensored!
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 ...
Special XXX Superstar Edition
This volume is all about the hottest, nastiest, and screamin' sex you'll ever see!
Jack's Playground 31, the superstar edition, star the lovely Jana Cova in two delectable scenes, Devon in all her naked splendor and DP's ...
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 his camera. As soon as Robby D saw a few video clips of real girls so thirsty for fame, ...
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 his camera. As soon as Robby D saw a few video clips of real girls so thirsty for fame, ...
Starring Teagan Presley And Katsuni!
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 his camera. As soon as Robby D ...
Watch Tera take the double buda!
See Rocki take it in the...barn...
This brand new, never-been-seen footage showcases Tera Patrick, pre-boob job, in a smoking hot, fuck sandwich with two European horse cocks. She loved it and so will you. Jack also found ...
Starring Jesse Jane!
Smoking Hot Jesse Rocks Till It Rolls!
'Playful, powerful and supremely sexual - a revolutionary sex comedy... One of the most original series in years!'
The New Jack Is Harder Deeper Faster Than Ever Before! ...
Cast:
Jesse Jane, Jelena Jensen, Kelsey Michaels, Roxy Deville, Diana Doll, Valentina Vaughn, Ben English, Chris Charming, Eric Masterson, Scott Nails
Studio:
Digital Playground
Series:
Jack's Playground
Director:
Robby D
Categories:
Gonzo, Blu-Ray
Rating:
Average Rating Not Yet Available
close
Jack's Playground #33
'The Playground returns hotter and hotter! This is the visual feast of sexual energy that you are craving. Prepare yourself for sweet, carnal ...
Cast:
Devon, Celeste Star, Devaun, Renee Richards, Riley Mason, Bree, Sara Stone, Scott Nails, Tommy Gunn, Jerry
Studio:
Digital Playground
Series:
Jack's Playground
Director:
Jack
Categories:
Gonzo, Blu-Ray
Rating:
Average Rating Not Yet Available
close
Jack's Playground #36
Real Girls Uncensored!
Starring Sophia Saint!
'Playful, powerful and supremely sexual- a revolutionary sex comedy... One of the most original series in years!'
The New Jack Is Deeper And Faster Than Ever ...
Cast:
Sophia Santi, Alyssa Chase, Carli Banks, Holly Wellin, Christina Brooks, Marlena, Selina Draagen, Scott Nails, Ben English
Studio:
Digital Playground
Series:
Jack's Playground
Director:
Robby D
Categories:
Gonzo, Blu-Ray
Rating:
Average Rating Not Yet Available
close
Jack's Playground #28
Starring Teagan Presley And Katsuni!
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 his camera. As soon as Robby D ...
Cast:
Teagan Presley, Katsuni, McKenzie Lee, Poppy Morgan, Terri Summers, Scott Nails, Eric Masterson, Marco Duato
Studio:
Digital Playground
Series:
Jack's Playground
Director:
Jack
Categories:
Gonzo, Blu-Ray
Rating:
Average Rating Not Yet Available
close
Jack's Playground #29
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 his camera. As soon as Robby D saw a few video clips of real girls so thirsty for fame, ...
Cast:
Julia Ann, Delilah Strong, Tiffany Hopkins, Isabella, Taryn Thomas, Zoe Britton, Chase Dasani, Chris, Eric, Lee, Nacho Vidal
Studio:
Digital Playground
Series:
Jack's Playground
Director:
Jack
Categories:
Gonzo, Blu-Ray
Rating:
Average Rating Not Yet Available
close
Jack's Playground #38
The New Jack Is Harder , Deeper, Faster Than Ever Before!
Jack is really busy casting for music videos and hes scored some super fine ass for volume 38. Digital Playgrounds amazing contract super stars Teagan Presley and Lacie Heart join an all-star cast that ...
Cast:
Lacie Heart, Teagan Presley, Audrey Bitoni, Leah Luv, Nevaeh, Roxy Deville, Eric Masterson, Scott Nails
Studio:
Digital Playground
Series:
Jack's Playground
Director:
Robby D
Categories:
Gonzo
Rating:
Avg. Rating of 4.75 stars over 38 ratings
close
Jack's Playground #38
Jack is really busy casting for music videos and hes scored some super fine ass for volume 38. Digital Playgrounds amazing contract super stars Teagan Presley and Lacie Heart join an all-star cast that includes blowjob maven Audrey Bitoni plus Leah Luv, Neveah, and Roxy ...
Cast:
Teagan Presley, Audrey Bitoni, Lacie Heart, Leah Luv, Nevaeh, Roxy Deville, Eric Masterson, Scott Nails
Studio:
Digital Playground
Series:
Jack's Playground
Director:
Robby D
Categories:
Gonzo, Blu-Ray
Rating:
Average Rating Not Yet Available
close
Jack's Playground #37
Starring Jesse Jane!
Smoking Hot Jesse Rocks Till It Rolls!
'Playful, powerful and supremely sexual - a revolutionary sex comedy... One of the most original series in years!'
The New Jack Is Harder Deeper Faster Than Ever Before! ...
Cast:
Jesse Jane, Jelena Jensen, Kelsey Michaels, Roxy Deville, Diana Doll, Valentina Vaughn, Sue Diamond, Ben English, Chris Charming, Eric Masterson, Scott Nails
Studio:
Digital Playground
Series:
Jack's Playground
Director:
Robby D
Categories:
Gonzo
Rating:
Avg. Rating of 3.25 stars over 46 ratings
close
Jack's Playground #27
Analizar Esto Maricon did I just speak Spanish?
Stop hitting me asshole!
I can't believe Montel is a short Black-Xican, but I like him!
'Playful, powerful and supremely sexual - a revolutionary series in ...
Cast:
Austin Kincaid, McKenzie Lee, Aidan Layne, Annmarie Michelle, Tory Lane, Sofie Paris, Scott Nails, Kevin Kline, Richard Raymond
Studio:
Digital Playground
Series:
Jack's Playground
Director:
Jack
Categories:
Gonzo, Blu-Ray
Rating:
Average Rating Not Yet Available
close
Jack's Playground #36
Real Girls Uncensored!
Starring Sophia Saint!
'Playful, powerful and supremely sexual- a revolutionary sex comedy... One of the most original series in years!'
The New Jack Is Deeper Faster Than Ever ...
Cast:
Sophia Santi, Alyssa Chase, Carli Banks, Holly Wellin, Christina Brooks, Marlena, Selina Draagen, Scott Nails, Ben English
Studio:
Digital Playground
Series:
Jack's Playground
Director:
Jack
Categories:
Gonzo
Rating:
Avg. Rating of 4 stars over 32 ratings
close
Jack's Playground #35
Real Girls Uncensored!
Starring Teagan Presley!
Jack is really busy casting for music videos and now he's landed Digital Playground's super fine contract star, Teagan Presley. She takes a big cock in the butt and we know Scott Nails found some sweet ...
Cast:
Teagan Presley, Candy Manson, Karlie Montana, Lexi Love, Lexxi Tyler, Myah Monroe, Ruby, Chris Charming, Scott Nails
Studio:
Digital Playground
Series:
Jack's Playground
Director:
Jack
Categories:
Gonzo
Rating:
Avg. Rating of 4 stars over 41 ratings
close
Jack's Playground #34
Exotic waves of molten cum erupt onto timid young flesh in this amazing exploitation of carnal voracity!
Cast:
Katsuni, Alicia Alighatti, Alicia Angel, Tiffany Rayne, Kelly Kline, Courtney Cummz, Chris Charming, Eric Masterson, Jerry, Marco Banderas, Tommy Gunn
Studio:
Digital Playground
Series:
Jack's Playground
Director:
Jack
Categories:
Gonzo
Rating:
Avg. Rating of 4.25 stars over 39 ratings
close
Jack's Playground #33
'The Playground returns hotter and hotter! This is the visual feast of sexual energy that you are craving. Prepare yourself for sweet, carnal ...
Cast:
Devon, Celeste Star, Devaun, Renee Richards, Riley Mason, Bree, Sara Stone, Scott Nails, Tommy Gunn, Jerry
Studio:
Digital Playground
Series:
Jack's Playground
Director:
Jack
Categories:
Gonzo
Rating:
Avg. Rating of 3.75 stars over 40 ratings
close
Jack's Playground #32
Real Girls Uncensored!
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 ...
Cast:
Sophia Santi, Jelena Jensen, Alexis Silver, Brooke Haven, Flower Tucci, Michelle Maylene, Chris Charming, Scott Nails, Jerry
Studio:
Digital Playground
Series:
Jack's Playground
Director:
Jack
Categories:
Gonzo
Rating:
Avg. Rating of 3.5 stars over 41 ratings
close
Jack's Playground #31
Special XXX Superstar Edition
This volume is all about the hottest, nastiest, and screamin' sex you'll ever see!
Jack's Playground 31, the superstar edition, star the lovely Jana Cova in two delectable scenes, Devon in all her naked splendor and DP's ...
Cast:
Jana Cova, Devon, Rocki Roads, Isabella, Jasmine Byrne, Bianca Pureheart, Taryn Thomas, Eric, Scott Nails, Tommy Gunn, Vince Vouyer
Studio:
Digital Playground
Series:
Jack's Playground
Director:
Jack
Categories:
Gonzo
Rating:
Avg. Rating of 3.5 stars over 59 ratings
close
Jack's Playground #30
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 his camera. As soon as Robby D saw a few video clips of real girls so thirsty for fame, ...
Cast:
Jelena Jensen, Jenaveve Jolie, Rita Faltoyano, Taryn Thomas, Marlena, Renee Richards, Chris Charming, Scott Nails, Marco Duato
Studio:
Digital Playground
Series:
Jack's Playground
Director:
Jack
Categories:
Gonzo
Rating:
Avg. Rating of 3 stars over 38 ratings
close
Jack's Playground #29
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 his camera. As soon as Robby D saw a few video clips of real girls so thirsty for fame, ...
Cast:
Julia Ann, Delilah Strong, Tiffany Hopkins, Isabella, Taryn Thomas, Zoe Britton, Chase Dasani, Chris, Eric, Lee, Nacho Vidal
Studio:
Digital Playground
Series:
Jack's Playground
Director:
Jack
Categories:
Gonzo
Rating:
Avg. Rating of 3.25 stars over 39 ratings
close
Jack's Playground #28
Starring Teagan Presley And Katsuni!
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 his camera. As soon as Robby D ...
Cast:
Teagan Presley, Katsuni, McKenzie Lee, Poppy Morgan, Terri Summers, Scott Nails, Eric Masterson, Marco Duato
Studio:
Digital Playground
Series:
Jack's Playground
Director:
Jack
Categories:
Gonzo
Rating:
Avg. Rating of 3.5 stars over 63 ratings
close
Jack's Playground #27
Analizar esto maricon Did I just speak Spanish?
I can't believe Montel is a short Black-Xican, but I like him
Cast:
Austin Kincaid, McKenzie Lee, Aidan Layne, Annmarie Michelle, Tory Lane, Sofie Paris, Scott Nails, Kevin Kline, Richard Raymond
Studio:
Digital Playground
Series:
Jack's Playground
Director:
Jack
Categories:
Gonzo
Rating:
Avg. Rating of 4.25 stars over 42 ratings
close
Jack's Playground #26
Montel's Back In Da House
Jayna Does Anal It's Guaranteed Analicious!
What's Da Assfuckathon
Cast:
Jana Cova, Nautica Thorn, Jayna Oso, Marie Luv, Paola Rey, Sintia Stone, Chris Charming, Jean Val Jean, Mick Blue
Studio:
Digital Playground
Series:
Jack's Playground
Director:
Jack
Categories:
Gonzo
Rating:
Avg. Rating of 3.75 stars over 44 ratings
close
Jack's Playground #25
Watch Tera take the double buda!
See Rocki take it in the...barn...
This brand new, never-been-seen footage showcases Tera Patrick, pre-boob job, in a smoking hot, fuck sandwich with two European horse cocks. She loved it and so will you. Jack also found ...
Cast:
Tera Patrick, Rocki Roads, Nikki Benz, Kelli Tyler, Melanie Jagger, Sandra Romain, Randi Wright, John Decker, Selrahc Renard, Dale DaBone, Joey Ray, Mark Ashley, Tommy Gunn, Aramas Feldina
Studio:
Digital Playground
Series:
Jack's Playground
Director:
Jack
Categories:
Gonzo
Rating:
Avg. Rating of 3.5 stars over 161 ratings
close
Jack's Playground #24
New Juicy Flavor! Longer Lasting Anal!
Choc Full O' Fun And Flavor!
Cast:
Jennifer Luv, Jazmin, Sabina, Sarah Blake, Reina Leone, Evan, Eric, Tommy, Lee
Studio:
Digital Playground
Series:
Jack's Playground
Director:
Jack
Categories:
Gonzo
Rating:
Avg. Rating of 3.75 stars over 48 ratings
close
Jack's Playground #23
Nick P Gets Snippy, Cuttin 23 of these ain't easy damnit!
Cousin Nick P, Ph.D., drops knowledge on what it's like to cut these ...
Cast:
Jenaveve Jolie, Montana Rae, Naudia Nyce, Smokie Flame, Venus, Joey Ray, Tommy Gunn, Tony T, Pascal
Studio:
Digital Playground
Series:
Jack's Playground
Director:
Jack
Categories:
Gonzo
Rating:
Avg. Rating of 3.75 stars over 63 ratings
close
Jack's Playground #22
Cast:
Jenaveve Jolie, Jade Hsu, Harmony, Jacqueline, Nicole, Melody Daily, Jackie Ashe, Tony T, Tommy Gunn, Pascal
Studio:
Digital Playground
Series:
Jack's Playground
Director:
Jack
Categories:
Gonzo
Rating:
Avg. Rating of 3.25 stars over 50 ratings
close
Jack's Playground #21
Sorry about Jack's 20, folks, I bitch slapped Jack to make sure that won't happen again.
Montel's back bitches!
Cody Law Fights For The ...
Certificate of Compliance: The graphic images contained within this website are exempt from the requirements of 18 U.S.C. S2257 of Title 18, United States Code and the regulations of 75 C.F.R. §75 because they were produced prior to July 3, 1995 or have model releases available for inspection through their respective publishers. Date of Declaration: January 1, 2010.
Jack's Playground #37
