When Jack puts his mind to something, the filthy possibilities are endless! In Jack’s Playground: Asian Adventure 2, Jack rounds up the most exotic Asians he can find for a…

Jack’s busy in his playground casting big-ass babes for leading roles in his music videos. This time he gets Alexis Texas and Shyla Stylez to bend over for him. These…

You don’t know Jack until you’ve seen it like this! All the screamin’ hot sex in Digital Playground’s award winning Jack’s Playground series are now shot in POV perspective for…

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 new POV Playground, YOU will…

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…

Save the best for last! Jack says dee cups will surely keep you up!

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…

Digital Playground’s Asian sensation, Shay Jordan is back for more… with a cast of eager-to-please, exotic nymphs, Jack’s Playground: Asian Adventure 4 will surely satiate because these young hotties were…

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…

Uncle Jack Is Always There For His Nieces!

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…

Jack’s POV 13 With its unique camera work, Jack’s POV 13 brings viewers into the action and face to face with the lovely Stoya. Jack’s POV 13 puts anyone in…

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…

Jack’s POV 5

When they go to see Jack or one of his friends, they know what to expect but they don’t know what will happen… They know they will be on their…

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…

Dizzying AnalA jackhammer cock devastates the asses of two girls who scream with pleasure….

Sit On Her CockJulia is an enchanting, black-haired, tattooed, transsexual stunner, with a killer body, and a big, fat dick. Having electrical problems, she calls on a handyman, who gets…

Connie Has the Tastiest AssholeCarl visits Connie for his weekly massage. She’s lying on the bed with her legs open and spreads her pussy lips. Carl has to get a…

DAP First-Timer JuliaJulia is a raven-haired, tattooed, transsexual hottie, with a toned, tanned, womanly body, and a stiff, stout shaft. Being the hungry slut that she is, it takes two…

So You Like ShemalesNataly is a stunning, raven-haired, tattooed, transsexual siren, with a firm, fit womanly body, and a nice, beefy tongue depressor. In this scene, Nataly is playing a…

Trans Maid Fucks a Pervert in His Hotel RoomMelissa is a hot trans hotel maid. After straightening a room, she cleans the bathroom. When the guest returns, he thinks he’s…

She Loves Anal SexDaniele is a sultry, irresistible, raven-haired, tattooed, transsexual knock-out, with a toned, tanned body, and a stiff, stout, beef stick. As a masseur sensually strokes her back…

Temp Maid, TheCarl’s wife is heading out of town for a month, and she tells Carl he should get a Temp Maid to help keep up with things. Carl agrees…

Fucking Her AssExciting young Asian Mona has a lithe body and long legs. Her tight, red dress doesnt stay on long, of course, and neither does her sphincter stay empty:…

Hot ShowerJackeline Teen and Susy Gala want to show the world that the shower can be a very naughty place to get naughty with their bodies. Their stunning bodies glisten…

Ass PoundedTempting youngster Sofie always seems to be horny, so she doesn’t need much convincing to wriggle out of her slinky dress and begin rubbing her clitoris with her fingers….

SandwichedBruna and Estela are a pair of ravishing, tall, brunette, transsexual sirens, with stiff, stout cocks. The girls amorously kiss, and caress, while a voyeuristic stud jacks off. They move…

Sit Your Ass DownStacy is eighteen and cute as a button, so she does a slow striptease for the cameraman and displays every inch of her young, nubile body. She…