The Stakes are high for Kayden Sexy superstar Kayden Kross is in trouble. Her man, James Deen, has a gambling problem that even her persuasion of pleasure cannot curb. James…

The naughtiest one goes to bed first. Sexy, seductive Riley Steele sucks down juicy pussy as hungrily as she pumps hard on thick cocks. She and her naughty little sister…

Jesse Jane has gotten herself into a mess. Looking to make life with husband Manuel Ferrara more comfortable, Jesse Jane welcomes new house keeper Vicki Chase into her world. But…

Kissing Cousins Sara and Chris are a monogamous married couple. They’re both become victims of the daily grind, and somehow, their sex has become… typical. Sara’s cousin Jessica comes for…

A salacious battle of love and lust. Pretty Riley Steele is a very jealous daughter, and her naughty mother Francesca Le, laps it up, knowing she’s one hot pieceof MILF…

Jesse Jane Online Exclusive Digital Playground contract star Jesse Jane finds herself infatuated with a budding online relationship, but as the requests become kinkier and stranger, she begins to worry…

Jesse Jane Image Jesse Jane: Image explores the famous and undeniably sexy image of Digital Playground superstar, Jesse Jane. Her playful fantasies are fulfilled in 4 amazingly provocative scenes. Watch…

This assignment will leave you begging for more. Jesse Jane Homework gets an A+. Another class act from Robby D. and the Digital Playground girls. Jesse Jane leads an ensemble…

Jesse Jane Fuck Fantasy Digital Playground’s Jesse Jane Fuck Fantasy is an ultra-horny, wall-to-wall sex montage. Each fantastic scene depicts a tangible, true to life fantasy with amazing heat and…

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!…

Lust is in the eye of the beholder. The power of love can survive anything, except the spell of a very off and mysterious watch that latches itself on to…

Her deepest desires. Seductress Jesse Jane sizzles with desire as a woman on the verge of marriage, haunted by a mysterious engagement gift. Overcome by explicit visions of naughty past…

You can never escape your past or your future. Sexy, seductive Riley Steele discovers a weak link in her marriage as perverted visions and dreams continue to haunt her, even…

When lust becomes an addiction Stoya thought house sitting would be a great get away from her ex-boyfriend Erik Everhard. But when Erik follows her to a new location, he’s…

The bad girls are in charge. Vicki Chase and Riley Reid hook up with guys at work. After Vicki’s sex session with James Deen, the girls get busted for their…

Out with the old, in with the new. Kayden Kross is every man’s dream girl. So, when the stunningly beautiful babe is left by her knuckle headed boyfriend, the super…

She never imagined anything so deep. Sultry Kayden Kross hungrily devours the new hung studs she comes upon, in desperation for sexual healing since her marriage to bad boy Erik…

Temptation finds Riley Riley Steele is Manuel Ferrera’s girlfriend…who may not be his for long after he loses a bet and has to change girlfriends with his buddy, Erik Everhard….

Paradise… they’re taking it all in… with a smile. Hardcore fucking that will bring you to your knees. This cockold gonzo release starring Jesse Jane and Riley Steele is aimed…

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…

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…

Extra credit never felt so good. Everyone remembers their academic life; textbooks, homework, detention, lube, dildos…another typical day at Filmore Bush Academy, where Sex-Ed is a hands-on class. Digital Playground’s…