Jack's Teen America Mission
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Cast:
- Taryn Thomas,
- Carmen,
- Trinity,
- Terri Summers,
- Kelly Kline,
- Eric Masterson,
- Scott Nails,
- Marco Duato
Studio: Series: Jack's Teen America Mission Director:
Category:
All models were 18 years or older at the time photos or videos were taken.
 Teagan is Back!
Cast:
- Teagan Presley,
- McKenzie Lee,
- Carmen,
- Tiffany Hopkins,
- Jazmin,
- Chris Charming,
- Jean Val Jean,
- Kurt Lockwood,
- Marco Duato,
- Scott Nails
Studio: Series: Jack's Teen America Mission Director:
Category:
All models were 18 years or older at the time photos or videos were taken.
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: Series: Jack's Teen America Mission Director:
Category:
All models were 18 years or older at the time photos or videos were taken.
Digital Playground and contract director Robby D. are thrilled to release the video trailer for Jack's Teen America 2, the second installment in their brand new, revolutionary, hard-core fetish series. Jack's Teen America 2 contains 6 scenes and over 3 hours of the hottest, ...
Cast:
- Jennifer Luv,
- Katja Kassin,
- Kelly Kline,
- Nautica Thorn,
- Nikki Benz,
- Roxy Jezel,
- Tommy Gunn
Studio: Series: Jack's Teen America Mission
Category:
All models were 18 years or older at the time photos or videos were taken.
 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: Series: Jack's Teen America Mission Director:
Category:
All models were 18 years or older at the time photos or videos were taken.
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: Series: Jack's Teen America Mission Director:
Category:
All models were 18 years or older at the time photos or videos were taken.
 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: Series: Jack's Teen America Mission Director:
Category:
All models were 18 years or older at the time photos or videos were taken.
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: Series: Jack's Teen America Mission Director:
Category:
All models were 18 years or older at the time photos or videos were taken.
Cast:
- Jenaveve Jolie,
- Jaime Elle,
- Gigi,
- Yasmine Vega,
- Candy Manson,
- Scott Nails,
- Richard Kline,
- Eric Masterson
Studio: Series: Jack's Teen America Mission Director:
Category:
All models were 18 years or older at the time photos or videos were taken.
 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: Series: Jack's Teen America Mission Director:
Category:
All models were 18 years or older at the time photos or videos were taken.
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: Series: Jack's Teen America Mission Director:
Category:
All models were 18 years or older at the time photos or videos were taken.
Cast:
- Sophia Santi,
- Gianna Michaels,
- Marlena,
- Roxy Deville,
- Alyssa Chase,
- Tiger,
- Nick Jacobs,
- Scott Nails
Studio: Series: Jack's Teen America Mission Director:
Category:
All models were 18 years or older at the time photos or videos were taken.
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: Series: Jack's Teen America Mission Director:
Category:
All models were 18 years or older at the time photos or videos were taken.
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: Series: Jack's Teen America Mission Director:
Category:
All models were 18 years or older at the time photos or videos were taken.
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
Studio: Series: Jack's Teen America Mission
Category:
All models were 18 years or older at the time photos or videos were taken.
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