Jacky William, a clown whose career is taking off with difficulty sees his future darken. Because in a video filmed without his knowledge where he reveals his premature ejaculation problems,…
Divine Bitches – Featuring January Seraph And Jack Hammer Mistress January Seraph teaches Jack to be a better slave by teasing him with denial, trying to stop his thinking with…
Josephine Jackson Sexy Spinner W Super Size Tits Tag Teamed Dean Van Damme bends over pretty PAWG Josephine Jackson so the inked-up Englishman can drill her in doggystyle. Dean fucks…
EveTheSexyFairy and CherryBomb Double Jack Up Mr. Flourish EveTheSexyFairy and Cherry Bomb Bomb double jack up MrFlourish in double blowjob, rimming, fingering or half fisting his ass and more slutiness…
Jack’s Redhead Adventure These Gingers are ripe and ready to show the world that redheads are much more fun in the sack. They’re known for their mercurial tempers; but did…
Jack’s POV 17 You think you know Jack? These bitches are sucking up his dick and swallowing it deep in their pussies… I think they know a little more about…
Jack’s POV 12 With its unique camera work, Jack’s POV 12 brings you into the action and doesn’t loosen its grip until you’re completely drained. Jack’s POV 12 puts you…
“Montel’s War” 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…
Hot Babes, Bangin’ Sex, And Nasty Jack… Jack’s Playground 31, the superstar edition, stars the lovely Jana Cova in two delectable scenes, Devon in all her naked splendor and DP’s…
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…
Jack’s POV 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…
Jack’s POV 8 You don’t know jack until you’ve seen through his eyes. Sweet. One-of-a-kind P.O.V. Super hot semen slurpers. Pretty tight fresh box. Sexy dark haired babe Honey DeJour…
Jack’s POV 6 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,…
Jack’s POV 2 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…
Starring BiBi Jones in her first POV. Beautiful BiBi Jones drips her young, sweet juices all over thick rods and long, hard members. Sliding and pumping on the giant cock…
Real girls uncensored Imagine what it would be like to date your favorite porn star. Imagine waking up next to a naked Kayden Kross and having hot morning sex with…
Jack’s POV 16 All the screaming 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,…
Jack’s POV 14 With its unique camera work, Jack’s POV 14 brings you into the action and doesn’t loosen its grip until you’re completely drained. Jack’s POV 14, starring Digital…
Real Girls Uncensored You don’t know Jack until you’ve seen through his eyes. Don’t miss this all-star cast that includes Hannah Harper, Lacey Maguire, Annette Schwarz, Rachel Roxxx & Britney…
Jack’s POV 10 Don’t miss Digital Playground’s Exclusive Contract Stars, Teagan Presley and Jana Cova in a very personal, off the hook sexual experience. All the screamin’ hot sex in…
Ride The Curves With Reckless Abandon Jack is really busy casting for music videos and he’s scored some super fine ass for volume 38. Digital Playground’s amazing contract super stars…
Real girls uncensored. Jack is really busy casting for music videos and now he’s landed Digital Playground’s super fine contract star, Jesse Jane. She fucks Ben English every which way…
The Comedy is in the Commentary 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…
Jack’s MILF Show Master Robby D. delivers more hot pussy pounding and intense orgasmic blow jobs. This time he turns his attention to some sexy ass mothers we’d all like…
Jack’s Playground: Leg Show 4 The camera starts at her petite ankle and slowly travels up the milky skin of her calve and around her toned hamstring on a journey…
Jack’s Playground: Big Ass Show 9 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…
A FantASStic Show Jack’s Big Ass Show is back with another episode, and although Jack isn’t getting anything once again it seems like where ever he goes there’s girls with…
Jack’s Playground: Big Ass Show 4 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…
Jack’s Playground: Big Ass Show 2 Jack’s busy in his playground casting big-ass babes for leading roles in his yet-to-be-seen music videos. The delicious girls will do anything for stardom….
“Eastside Connection” Starring Digital Playground’s newest sensation, Shay Jordan and an entire cast of young, gorgeous, almond eyed beauties, Jack’s Asian Adventure will please your pallet. Jack uses the tried…
Jack’s Playground: Asian Adventure 4 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…
Jack’s Asian Adventure 2 Always A Happee Ending! You like partay?’Playful, powerful and supremely sexual – a revolutionary sex comedy. . . One of the most original series in years!…
Vegas Rooftop Nights: Milf Jackie Hoff vs SoloTheBull At our Flourish Vegas Penthouse Jackie Hoff wanted to get some BBC Meat. So she called over SoloTheBull to fill up her…
You Don’t Know Jack Until You’ve Seen Through His Eyes. All the screamin’ hot sex in Digital Playground’s award winning Jack’s Playground series are now shot in POV perspective for…
You Don’t Know Jack Until You’ve Seen Through His Eyes. All the screamin’ hot sex in Digital Playground’s award winning Jack’s Playground series are now shot in POV perspective for…
Jack’s POV 9 Don’t miss Digital Playground’s exclusive contract star, Stoya in her debut boy/girl scene. Jack’s POV 9 is off the hook sex! All the screamin’ hot sex in…
