Teen America: Mission #12. 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…

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…

Teen America: Mission #22. Jack knows ambitious chicks will do anything to win first place in a beauty pageant. Jack’s Teen America: Mission #22 features Jack and his crew interviewing…

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…

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…

Teagan Is Back! 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…

Eva, Sandra, Gia and Melissa are all willing to do whatever it takes to win “Miss Teen America”. So they show off their particular tlaents on the crew interviewing them….

Special Contract Unit 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…

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 gettin 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 gettin a fuckin…

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…

Teagan Wants More! 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…

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.

We all know the Miss Teen America pageant is full of flaws. You can’t judge a beautiful young woman based solely on a few simple tasks. Jack sets out to…

Slutty Neighborhood Teens 3. 2021 AVN Award Nominee for Best Ingenue Movie. If you’ve ever been in the mood for some nice whorish fun without leaving your neighborhood, then go…

“When sexy teenagers equip themselves with menacing dildos, no man’s ass is safe! The sassy young lovelies of director Joey Silvera’s “Miss Teen Strap America 2” are strapped and ready…

Perv City’s Anal Creampies Vol. 5. First Anal for Blonde Beauty Kate Kennedy: What better way to kick off summer holidays than a sweltering scene starring all-American blonde beauty queen…

Ass Trained By An Older Guy 3. Squirting superslut Paige Owens knows how to combine a sexy outfit to get PervCity’s attention. Rebel black and electric pink mirror her hairy…