Jack turns 1!…and there’s a whole lotta frosting on deez cakes!

Dr. Hienrich Shizen sez, “Zarez nutting unlucky about zee numba 13…unless you’re zee one taking zee 13 eenchez.”

“Dis one be off da hinges wit lots of titayz and all kinds of juicy young ass.”

“Trick o’ treat… Jack wants to lick some pretty meat. And Montel ain’t got nuttin’ to say ’bout dat!”

Lets take a moment and give thanks for the sweet teens in Jack’s Playground 16.

Jack’s Playground is a brand new reality series featuring Jack, a trust fund child and aspiring music video director who happens to have a knack for persuading real girls to…

Jack on Moms He has a soft spot (or a hard spot!) for MILFs, and in Jack On Moms you will see why!

Teagan Presley & ANAL, does the rest of this description even matter? Jack is really busy casting big, bouncing, beautiful butts for music videos. They shake, they roll and they…

Jack’s casting again! This time he’s looking for leg models… sexy, leggy vixens who want to be in fresh, up and coming music videos. In the second volume, Digital Playground’s…

Jack’s casting again! This time he’s looking for leg models… sexy, leggy vixens who want to be in fresh, up and coming music videos. In Jack’s Playground: Leg Show 3,…

Mega Packed with Juicy Crack “Check out these packs with juicy crack presented by Jack”

Big, Hot and Kinky! “More Cushin For the Pushin”

Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful butts. They bounce, they roll and they shake and Jack finds pleasure deep…

Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful butts. They bounce, they roll and they shake and Jack finds pleasure deep…

Six-babe, Double-D, double-disc edition! Six hot girls and six big, long scenes… all in the tease and please style that only B. Skow delivers! But this time the emphasis is…

All the screamin’ hot sex in Digital Playground’s award winning Jack’s Playground series are now shot in POV perspective for your ultimate enjoyment. In Jack’s POV Playground, YOU will get…

All the screamin’ hot sex in Digital Playground’s award winning Jack’s Playground series are now shot in POV perspective for your ultimate enjoyment. In Jack’s POV Playground, YOU will get…

All the screamin’ hot sex in Digital Playground’s award winning Jack’s Playground series are now shot in POV perspective for your ultimate enjoyment. In Jack’s POV Playground, YOU will get…

John Leslie focuses his perverted eye on the world of the three-way in five smokin’ scenes! Check out mocha goddesses Adriena and Kapri Styles teaming up on Mr. Pete, or…

If sex is your disease, she is the antidote! Fuck my pussy! Cock sucking hospital staff! Sex that makes me drool!

A Modern Day Fairy Tale They Did a Lot More Than Go Up a Hill! Kira is looking for love in all the wrong ads. Dating services, internet, newspapers, all…

“Amanda Bryant – My niece came by demanding I give her the BJ part in a scene. Well, you can’t just send someone out to do a job taking their…

Booty Jackin’

I might like getting a blow job or sticking my cock deep in your snatch, but when I want to finish I want your hand wrapped firmly around my shaft….

Blu-Ray Version. 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…

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…

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…

Jack’s back and he’s on the prowl for some new slutty girls ready to get raunchy on camera. Join the adventure as he devours and conquers each one of their…

Got Long Legs? Just Wait Until It Opens! Jack’s casting again! This time he’s looking for leg models… sexy, leggy vixens who want to be in fresh, up and coming…

When Jack puts his mind to something, the filthy possibilities are endless! In JACK`S ASIAN ADVENTURE 3, Jack rounds up the most exotic Asians he can find for a wild…

Facials, creampies, natural tits, and five hot anal scenes… this one has it all. If you like your sex ass-up and wall to wall, this is your DVD. It’s the…

Starring Chanell Heart! Includes Bonus Scene! Booty Jackin’! All Black! Sweet Buns! Nasty Lil’ Mama! Big Butts! Huge Dicks!

Special Jack Napier Benefit DVD All Proceeds From The Sale Of This DVD Go To Help Jack Napier’s Recovery And Medical Expenses These horny girls give their all for Dog…

Busty Grannies Vol. 2 Get ready for some hardcore fucking with these naughty big-tit Busty Grannies. . Scene 1 – Duration: 21 min – Starring:  RayVeness  Shorty Mac  Scene 2…

Hailey Rose Is Titwoman Elegant Angel proudly presents “Hailey Rose is Titwoman”, a glamorous showcase that’s just as luxurious as Hailey’s perfect, natural breasts. Hailey invites you to spend one…

Not My Grandpa! 10 Being one of Grandpa’s favorites means she gets a big inheritance, and there is no way she’s missing out on his savings! This cute blonde minx…

A pact must be kept and a secret must never be revealed . . . Confused by her overwhelming attraction to her stepson, Cameron (Lucas Frost), Gina (Dana Vespoli) posts…

Hot College POV Action A hard, young collegiate cock. A wet, tight, coed pussy. And a camera with a fully charged battery that’s ready to capture all the scorching hot…

Young, Hung & BiCurious Vol. 2 These all-American young, hung, ripped, and horny college jocks got it going on. They’ve arrived on campus overflowing with hormones, eager to get their…

Asia’s Cum Quest Asia Lee, the petite and irresistible Asian teen, steps into the sperm clinic with a sparkle in her eye and a craving she can’t ignore. Eager to…