With five lovely ladies competing for the same title, it's a tight race to the finish and Tiffany is off to a succulent start. She charms the judges and Scott Nails when she swallows his entire cock, up to his balls, in a deca-dent and sloppy blow job before she lets him ...
With five lovely ladies competing for the same title, it's a tight race to the finish and Bree is off to a succulent start. She charms the judges and Scott Nails with her amazing body and gorgeous face. Alicia shows she's got the stamina to go the distance as she works the ...
With five lovely ladies competing for the same title, which girl will take the honors? Will Brooke or Jamie get to deliver their acceptance speech? Did Jack vote for one of their amazingly anal delights? Does Sara stand a chance of winning with her delectable titty-fuck ...
Jack knows ambitious chicks will do anything to win first place in a beauty pageant. 'Jack's Teen America 8' features Jack and his crew interviewing lovely contestants including Eva Angelina and Melissa Lauren. Jack wants to know what special 'talents' they possess in order ...
Starring Riley Steele And Stoya!
Jack knows ambitious chicks will do anything to win first place in a beauty pageant. 'Jack's Teen America 23' features Jack and his crew interviewing lovely contestants including Digital Playground's scintillating ...
Starring Riley Steele And Stoya!
Jack knows ambitious chicks will do anything to win first place in a beauty pageant. 'Jack's Teen America 23' features Jack and his crew interviewing lovely contestants including Digital Playground's scintillating ...
Jack's at it again! But this time it's professional...and even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack's answer to getting a fuckin' ...
Jack's at it again! But this time, it's professional... and even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack's answer to getting a fuckin' ...
Jack's Checklist:
Backdoor Bonanza, Whip the Pony, Racquetball Rectal, Strapped Submission, Icing Special, Asian Anal, Blindfolded BJ, Bring Mic, WAY up the down ...
Starring Lacie Heart!
Shot entirely on HD, Jack's Teen America 21 features Digital Playground's lovely contract star, Lacie Heart in a slam-min' romp with Scott Nails, Poppy Morgan & Renae Cruz in decadent anal scenes plus sexy Tricia Oaks and the oh-so-hot ...
Jack's at it again! But this time, it's professional... and even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack's answer to getting a fuckin' ...
Special Contract Starvaganza!
Pop In My Eye! Up The Poop Shoot! Double Pussy Lick!
Tuna Sandwich! Goldilick! Butt Bubbles! Femme Frolic!
Shot entirely on HD, Jack's Teen America 20 features Digital Playground contract stars, Shay Jordan, ...
Shot in High Definition. With six lovely ladies competing for the same title, it's a tight race to the finish and Digital Playground contract stars, Jana Cova and Lacie Heart, are off to a succulent start. Lacie calls Scott her bitch before she takes his huge cock in her wet ...
With five lovely ladies competing for the same title, it's a tight race to the finish and Tiffany is off to a succulent start. She charms the judges and Scott Nails when she swallows his entire cock, up to his balls, in a deca-dent and sloppy blow job before she lets him ...
With five lovely ladies competing for the same title, it's a tight race to the finish and Bree is off to a succulent start. She charms the judges and Scott Nails with her amazing body and gorgeous face. Alicia shows she's got the stamina to go the distance as she works the ...
With five lovely ladies competing for the same title, which girl will take the honors? Will Brooke or Jamie get to deliver their acceptance speech? Did Jack vote for one of their amazingly anal delights? Does Sara stand a chance of winning with her delectable titty-fuck ...
Five horny teens. 2 sound guys with equipment. 1 contest. 1 winner. Sound familiar? It is. It's Jack's Teen America. Put it in and cast your vote! Jack's at it again! But this time, it's professional... and even kinkier than before. Jack turns what he knows best ...
With five lovely ladies competing for the same title, it's a tight race to the finish and Tiffany is off to a succulent start. She charms the judges and Scott Nails when she swallows his entire cock, up to his balls, in a deca-dent and sloppy blow job before she lets him ...
Cast:
Tiffany Rayne, Riley Mason, Texas Presley, Katja Kassin, Alicia Angel, Chris Charming, Tommy Gunn, Scott Nails
Studio:
Digital Playground
Series:
Jack's Teen America Mission
Director:
Jack
Categories:
Just Legal, Blu-Ray
Rating:
Average Rating Not Yet Available
close
Jack's Teen America Mission #9
Teagan is Back!
Cast:
Teagan Presley, McKenzie Lee, Carmen, Tiffany Hopkins, Jazmin, Chris Charming, Jean Val Jean, Kurt Lockwood, Marco Duato, Scott Nails
Studio:
Digital Playground
Series:
Jack's Teen America Mission
Director:
Jack
Categories:
Just Legal, Blu-Ray
Rating:
Average Rating Not Yet Available
close
Jack's Teen America Mission #15
With five lovely ladies competing for the same title, it's a tight race to the finish and Bree is off to a succulent start. She charms the judges and Scott Nails with her amazing body and gorgeous face. Alicia shows she's got the stamina to go the distance as she works the ...
Cast:
Courtney Cummz, Bree, Taryn Thomas, Veronica Lynn, Alicia Alighatti, Ben English, Scott Nails, Tommy Gunn
Studio:
Digital Playground
Series:
Jack's Teen America Mission
Director:
Jack
Categories:
Just Legal, Blu-Ray
Rating:
Average Rating Not Yet Available
close
Jack's Teen America Mission #14
With five lovely ladies competing for the same title, which girl will take the honors? Will Brooke or Jamie get to deliver their acceptance speech? Did Jack vote for one of their amazingly anal delights? Does Sara stand a chance of winning with her delectable titty-fuck ...
Cast:
Brooke Haven, Jamie Elle, Michelle Maylene, Brandy Talore, Sara Stone, Chris Charming, Scott Nails, Evan Stone
Studio:
Digital Playground
Series:
Jack's Teen America Mission
Director:
Jack
Categories:
Just Legal, Blu-Ray
Rating:
Average Rating Not Yet Available
close
Jack's Teen America Mission #8
Jack knows ambitious chicks will do anything to win first place in a beauty pageant. 'Jack's Teen America 8' features Jack and his crew interviewing lovely contestants including Eva Angelina and Melissa Lauren. Jack wants to know what special 'talents' they possess in order ...
Cast:
Eva Angelina, Gia Paloma, Melissa Lauren, Sandra Romain, Aidan Layne, Sascha, Scott Nails, Tommy Gunn, Chris Charming
Studio:
Digital Playground
Series:
Jack's Teen America Mission
Director:
Jack
Categories:
Just Legal, Blu-Ray
Rating:
Average Rating Not Yet Available
close
Jack's Teen America Mission #23
Starring Riley Steele And Stoya!
Jack knows ambitious chicks will do anything to win first place in a beauty pageant. 'Jack's Teen America 23' features Jack and his crew interviewing lovely contestants including Digital Playground's scintillating ...
Cast:
Riley Steele, Stoya, Ariel Summers, Angelina Valentine, Emy Reyes, Erik Everhard, James Deen, Mick Blue, Scott Nails
Studio:
Digital Playground
Series:
Jack's Teen America Mission
Director:
Robby D
Categories:
Just Legal
Rating:
Avg. Rating of 3 stars over 29 ratings
close
Jack's Teen America Mission #23
Starring Riley Steele And Stoya!
Jack knows ambitious chicks will do anything to win first place in a beauty pageant. 'Jack's Teen America 23' features Jack and his crew interviewing lovely contestants including Digital Playground's scintillating ...
Cast:
Riley Steele, Stoya, Ariel Summers, Angelina Valentine, Emy Reyes, Erik Everhard, James Deen, Mick Blue, Scott Nails
Studio:
Digital Playground
Series:
Jack's Teen America Mission
Director:
Robby D
Categories:
Just Legal, Blu-Ray
Rating:
Average Rating Not Yet Available
close
Jack's Teen America Mission #7
Jack's at it again! But this time it's professional...and even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack's answer to getting a fuckin' ...
Cast:
Vanessa Lane, Katja Kassin, Austin Kincaid, Tiffany Holiday, Marie Luv, Chris Charming, Jean Val Jean, Scott Nails, Richard Raymond
Studio:
Digital Playground
Series:
Jack's Teen America Mission
Director:
Jack
Categories:
Just Legal, Blu-Ray
Rating:
Average Rating Not Yet Available
close
Jack's Teen America Mission #6
Jack's at it again! But this time, it's professional... and even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack's answer to getting a fuckin' ...
Cast:
Dascha, Eva Angelina, Kinzie Kenner, Tory Lane, Avena Lee, Chris Charming, Christian, Tommy Gunn
Studio:
Digital Playground
Series:
Jack's Teen America Mission
Director:
Robby D
Categories:
Just Legal, Blu-Ray
Rating:
Average Rating Not Yet Available
close
Jack's Teen America Mission #22
Cast:
Teagan Presley, Sasha Grey, Adrianna Lynn, Annette Schwarz, Jenny Hendrix, Mick Blue, Scott Nails, Tommy Gunn, Tyler Durden, Ethan Hunt
Studio:
Digital Playground
Series:
Jack's Teen America Mission
Director:
Robby D
Categories:
Just Legal
Rating:
Avg. Rating of 5 stars over 55 ratings
close
Jack's Teen America Mission #4
Jack's Checklist:
Backdoor Bonanza, Whip the Pony, Racquetball Rectal, Strapped Submission, Icing Special, Asian Anal, Blindfolded BJ, Bring Mic, WAY up the down ...
Cast:
Jasmin, Haley Paige, Katsuni, Gianna, Jean Val Jean, Scott Nails, Tommy Gunn, Tyla Wynn
Studio:
Digital Playground
Series:
Jack's Teen America Mission
Categories:
Just Legal, Blu-Ray
Rating:
Average Rating Not Yet Available
close
Jack's Teen America Mission #21
Starring Lacie Heart!
Shot entirely on HD, Jack's Teen America 21 features Digital Playground's lovely contract star, Lacie Heart in a slam-min' romp with Scott Nails, Poppy Morgan & Renae Cruz in decadent anal scenes plus sexy Tricia Oaks and the oh-so-hot ...
Cast:
Lacie Heart, Tricia Oaks, Poppy Morgan, Rebeca Linares, Renae Cruz, Christian XXX, Scott Nails, Tony de Sergio, Jay Lassiter
Studio:
Digital Playground
Series:
Jack's Teen America Mission
Director:
Jack
Categories:
Just Legal
Rating:
Avg. Rating of 3.25 stars over 37 ratings
close
Jack's Teen America Mission #3
Jack's at it again! But this time, it's professional... and even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack's answer to getting a fuckin' ...
Cast:
Lauren Phoenix, Harmony, Sativa Rose, Rachel Rotten, Megan, Christian, Mark Ashley, Tommy Gunn, Rob Rotten
Studio:
Digital Playground
Series:
Jack's Teen America Mission
Director:
Robby D
Categories:
Just Legal, Blu-Ray
Rating:
Average Rating Not Yet Available
close
Jack's Teen America Mission #20
Special Contract Starvaganza!
Pop In My Eye! Up The Poop Shoot! Double Pussy Lick!
Tuna Sandwich! Goldilick! Butt Bubbles! Femme Frolic!
Shot entirely on HD, Jack's Teen America 20 features Digital Playground contract stars, Shay Jordan, ...
Cast:
Shay Jordan, Sophia Santi, Jana Cova, Hillary Scott, Holly Morgan, Diana Doll, Marco Banderas, Mick Blue
Studio:
Digital Playground
Series:
Jack's Teen America Mission
Director:
Robby D
Categories:
Just Legal
Rating:
Avg. Rating of 4 stars over 31 ratings
close
Jack's Teen America Mission #19
Jack's Checklist!
Make-Up Box!
Bustiful Babes!
Jesse's Bodyguard!
Sophia's Best Friend!
Hand Cuffs!
Butt Plug!
Cream Pie Orgy!
Mr. ...
Cast:
Jesse Jane, Sophia Santi, Kelsey Michaels, Nadia Styles, Carmella Bing, Jelena Jensen, Jerry, Scott Nails, Anthony Hardwood, Eric Masterson
Studio:
Digital Playground
Series:
Jack's Teen America Mission
Director:
Jack
Categories:
Just Legal
Rating:
Avg. Rating of 3 stars over 47 ratings
close
Jack's Teen America Mission #18
Cast:
Sophia Santi, Gianna Michaels, Marlena, Roxy Deville, Alyssa Chase, Tiger, Nick Jacobs, Scott Nails
Studio:
Digital Playground
Series:
Jack's Teen America Mission
Director:
Jack
Categories:
Just Legal
Rating:
Avg. Rating of 4.25 stars over 35 ratings
close
Jack's Teen America Mission #17
Shot in High Definition. With six lovely ladies competing for the same title, it's a tight race to the finish and Digital Playground contract stars, Jana Cova and Lacie Heart, are off to a succulent start. Lacie calls Scott her bitch before she takes his huge cock in her wet ...
Cast:
Jana Cova, Michelle B, Holly Morgan, Holly Wellin, Lacie Heart, Riley Mason, Scott Nails, Jerry
Studio:
Digital Playground
Series:
Jack's Teen America Mission
Director:
Jack
Categories:
Just Legal
Rating:
Avg. Rating of 3.5 stars over 43 ratings
close
Jack's Teen America Mission #16
With five lovely ladies competing for the same title, it's a tight race to the finish and Tiffany is off to a succulent start. She charms the judges and Scott Nails when she swallows his entire cock, up to his balls, in a deca-dent and sloppy blow job before she lets him ...
Cast:
Tiffany Rayne, Riley Mason, Texas Presley, Katja Kassin, Alicia Angel, Chris Charming, Tommy Gunn, Scott Nails
Studio:
Digital Playground
Series:
Jack's Teen America Mission
Director:
Jack
Categories:
Just Legal
Rating:
Avg. Rating of 4 stars over 47 ratings
close
Jack's Teen America Mission #15
With five lovely ladies competing for the same title, it's a tight race to the finish and Bree is off to a succulent start. She charms the judges and Scott Nails with her amazing body and gorgeous face. Alicia shows she's got the stamina to go the distance as she works the ...
Cast:
Courtney Cummz, Bree, Taryn Thomas, Veronica Lynn, Alicia Alighatti, Ben English, Scott Nails, Tommy Gunn
Studio:
Digital Playground
Series:
Jack's Teen America Mission
Director:
Jack
Categories:
Just Legal
Rating:
Avg. Rating of 4.25 stars over 38 ratings
close
Jack's Teen America Mission #14
With five lovely ladies competing for the same title, which girl will take the honors? Will Brooke or Jamie get to deliver their acceptance speech? Did Jack vote for one of their amazingly anal delights? Does Sara stand a chance of winning with her delectable titty-fuck ...
Cast:
Brooke Haven, Jamie Elle, Michelle Maylene, Brandy Talore, Sara Stone, Chris Charming, Scott Nails, Evan Stone
Studio:
Digital Playground
Series:
Jack's Teen America Mission
Director:
Jack
Categories:
Just Legal
Rating:
Avg. Rating of 3.5 stars over 51 ratings
close
Jack's Teen America Mission #13
Five horny teens. 2 sound guys with equipment. 1 contest. 1 winner. Sound familiar? It is. It's Jack's Teen America. Put it in and cast your vote! Jack's at it again! But this time, it's professional... and even kinkier than before. Jack turns what he knows best ...
Cast:
Sativa Rose, Claire Robbins, Bianca Pureheart, Jasmine Byrne, Jamie Huxley, Chris Charming, Scott Nails
Studio:
Digital Playground
Series:
Jack's Teen America Mission
Director:
Jack
Categories:
Gonzo
Rating:
Avg. Rating of 4 stars over 41 ratings
close
Jack's Teen America Mission #12
Cast:
Jenaveve Jolie, Jaime Elle, Gigi, Yasmine Vega, Candy Manson, Scott Nails, Richard Kline, Eric Masterson
Studio:
Digital Playground
Series:
Jack's Teen America Mission
Director:
Jack
Categories:
Just Legal
Rating:
Avg. Rating of 4 stars over 57 ratings
close
Jack's Teen America Mission #11
Teagan Wants More
Cast:
Teagan Presley, Austin Kincaid, Renee Richards, Tory Lane, Teena Fine, Jon Dough, Scott Nails, Marco Duato, Tommy Gunn, Chris Charming
Studio:
Digital Playground
Series:
Jack's Teen America Mission
Director:
Jack
Categories:
Just Legal
Rating:
Avg. Rating of 3.75 stars over 80 ratings
close
Jack's Teen America Mission #10
Cast:
Taryn Thomas, Carmen, Trinity, Terri Summers, Kelly Kline, Eric Masterson, Scott Nails, Marco Duato
Studio:
Digital Playground
Series:
Jack's Teen America Mission
Director:
Jack
Categories:
Just Legal
Rating:
Avg. Rating of 3.5 stars over 64 ratings
close
Jack's Teen America Mission #9
Teagan is Back!
Cast:
Teagan Presley, McKenzie Lee, Carmen, Tiffany Hopkins, Jazmin, Chris Charming, Jean Val Jean, Kurt Lockwood, Marco Duato, Scott Nails
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 Teen America Mission #16
