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' job.

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' job!

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' job!

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' job!

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' job!

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' job!

"Jack" interviews girls hoping to compete in a teen America pageant...but somehow ends up having sex with them.

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' job!

Jack is back baby! But this time around, it's professional... and ten times kinkier than last time! Jack has an eye for the hottest teen sluts on the streets, and he's turned it into a career of capturing them on film! Let that be a lesson; don't want a real job? Learn to be a professional pervert instead!

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 into a career. Welcome to Jack's answer to getting a fuckin' job!

Sara Stone, Brooke Haven, Brandy Talore and Jamie Elle are all trying to win the title of Teen America and they are ready to fuck anyone, and everyone to get it.

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Which aspiring starlet will be named Jack's Teen America in Mission 16? Jack will walk you through the competition, taking time to savor each of the beautiful contenders. They're young, they're hot and they all want to win. Put it in now and help Jack decide who will get the crown!

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 mouth and tight little pussy. Jana Cova uses her sexy accent and top-model looks to manipulate and seduce young, gorgeous Holly Morgan. Michelle B. shows she's a worthy contestant as she eagerly participates in a mind blowing anal with Jerry. Tasty Riley lets Scott delve into her delicious box for a shot at the trophy and insatiable anal nymph, Holly Wellin takes a crazy butt pummeling for the grand prize. Which aspiring starlet will be named "Jack's Teen America" in Mission 17 Jack will walk you through the competition, taking time to savor each of the beautiful contenders. They're young, they're hot and they all want to win. Put it in now and help Jack decide who will get the crown!

Jack's lovely contestants all compete for the crown. They take their clothes off, they masturbate, they suck, fuck and they take it in the ass. Don't miss this spectacular hardcore erotic action!

Shot entirely on HD, Jack's Teen America 19 features Jesse Jane and Sophia Santi in intimate and seductive hardcore action! The Jack's Teen America series parodies beauty pageants and Jack's lovely contestants all compete for the crown. They take off their clothes, they masturbate, they suck, they fuck and they take it in the ass. With an entirely all-star cast, Volume 19 is spectacularly hard-core and erotic. Don't miss it!

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 Rebeca Linares, This horny hard-core action line parodies beauty pageants and Jack's lovely contestants all compete for the crown. They take off their clothes, they masturbate, they suck, they fuck and they take it in the ass. Jack's Teen America 21 delivers horny fucks, hot chicks, fine asses and big titties. Don't miss it!

Jack knows ambitious chicks will do ANYTHING to win first place in a beauty pageant. Jack's Teen America 22 features Jack and his crew interviewing lovely contestants Teagan Presley, Sasha Grey, and Adrianna Lynn to find out why they are qualified to be the next Teen America. The girls are quite adept at coaxing out Jack's vote, but it's Teagan who really gets it in the end. Literally. Jenny Hendrix and Annette Schwarz join the hot sucking, fucking and anal action. Jack's Teen America 22 is full of horny girls who won't settle for second place!

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 contract stars Riley Steele™ and Stoya. Jack wants to know what special "talents" they possess in order to become the next Teen America. Riley and Stoya studied long and hard for the oral portion of the competition, and they both are willing to twirl Jack's ten-inch baton. All the girls are quite adept at coaxing out Jack's... vote. Angelina Valentine, Ariel Summers and Emy Reyes join the hot sucking, fucking and anal action. "Jack's Teen America 23" is full of horny girls who won't settle for second place!

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' job! Over 2 1/2 hrs Long.