Teen America: Mission #8 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 #4 Jack’s at it again with Jack’s Teen America Mission #4. This time, it`s even kinkier than before. Jack’s checklist: Backdoor Bonanza, Whip the Pony, Racquetball Rectal,…
Teen America: Mission #3 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 #23 Jack knows ambitious chicks will do anything to win first place in a beauty pageant. Jack’s Teen America: Mission #23 features Jack and his crew interviewing…
Teen America: Mission #14 With five lovely ladies competing for the same title, which girl will take the honors? Will Brooke or Jamie get to deliver their acceptance speech? Did…
Teen America: Mission #13 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…
Meine geile Nachbarin 17 Milf Da Cada is unpacking her groceries when her neighbor Freddy excitedly rings the doorbell. For an evening invitation, the sex fiend desperately needs company and…
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…
Watch Me Sodomize Your Girlfriend! Kira is a sweet, young, blonde European heartthrob with tasty, tiny tits and a firm little body. After her boyfriend leaves to relieve himself, she…
Boy Meats Girl #2 One on one. Face to face. Big cocks fill tight slots in the latest volume of Axel Braun’s pussy spearing xxxtravaganza. This is just good old…
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…
Teen America: Mission #5 Jack’s Teen America 5 includes the divine bodies of contract superstars Teagan Presley and Devon, along with industry babes Dascha, Sandra Shine, Jayna Oso, and Keri…
Jack’s POV 15 With its unique camera work, Jack’s POV 15 brings you into the action and doesn’t loosen its grip until you’re completely drained. Jack’s POV 15, features Digital…
XXX Super-Stars Jacky Lawless Part 1 With her two arguments in her blouse that require a license, Jacky Lawless really drives every guy crazy. In order to get her hands…
Fuck Me Outside 1 To celebrate 20 years of filmmaking we are proud to present the Joy Collection…definitive moments from our award-winning catalogue. Transport yourself to nature’s bedroom where sweet-smelling…
Jack Attack Vol. 6 From Digital Playground comes Jack Attack 6, featuring six scenes of couples filming their private moments for your viewing pleasure. Starring Selena Rose, Adrianna Luna, Anikka…
Jack Attack Vol. 5 Beautiful women get fucked in the most sensual and lustful way possible. The rules are changed. Worlds are rocked. Desks are defiled and it doesn’t make…
Save the best for last. In the ninth installment of Jack’s Big Tit Show, Jack is on the hunt for big, beautiful boobies, using his trusty music video ploy to…
Jack’s Playground: Big Tit Show 6 Call Jack “The Titty Hunter”. He’s hunting for trophy titties, and will only settle for his favorites; big, beautiful boobies. They bounce, and they…
The One and Only Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful boobies. They bounce, and they shake. There’s more than…
Jack’s Playground: Big Tit Show 4 Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful boobies. They bounce, and they shake. There’s…
Jack’s Playground: Big Tit Show 7 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…
Got D’s? Some More Juice For You To Squeeze. Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful boobies. They bounce, and…
Jack Says, “Big Tits Are More Nutritious.” Jack’s at it again. In his playground, Jack is busy casting for music videos. The delicious girls will do anything for stardom. Some…
Teen America: Mission #12 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…
Jack Attack Vol. 4 Get ready for the 4th installment of your favorite series ? Jack Attack. These cock hungry babes know just how to handle a huge, throbbing cock…
Jack’s back. Jack Attack is here showing off the hottest porn stars today. Directed by the prodigious Robby D., Jack Attack is plain, no-frills, no-bullshit classic porn star fucking. Had…
Jack’s Playground: Big Tit Show 8 Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful boobies. They bounce, and they shake. There’s…
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 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…
Monster Meat 8 It’s Monster Meat like you’ve never seen it before as we’ve put together ten scenes of huge dicks plowing through little chicks. Watch Shane Diesel, Biggz, Mr….
Monster Meat We’ve got more than enough meat in this monster edition of the biggest fattest cocks ever known to man. With Shane Diesel, Mandingo, Sledge Hammer, Lexington Steele, Jack…
Anal Redhead Josephine H Fucks & Milks Jack H & Friend! Slutty redhead looks so sexy – look at that fat ass and nice tits. Josephine H takes that hard…
Cum On My Toes Cuck Husband While This Hot Stud Fucks Me! Bella Rossi’s husband sets her up with a day of pampering complete with a fashion photo shoot with…
