Zsur Cummings and his buddy are tormenting their big-titted neighbor, Rachael Cavalli, with a series of pranks, angering her to no end! When they drop off a surprise package for…
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 vote! Jack’s at it…
Busty MILF Ariella Ferrera can’t find a single pair of panties anywhere in the house, it’s like they’ve all disappeared – or got stolen! Turns out her new stepson Kyle…
New Stepdaugther Juliana is anxious to get a breast reduction. Thing is she has to convince her stepdad to let her go through with it. Once she gets a chance…
Jenna Reid sets up a kissing booth on the corner of the street to try and raise money for her cheerleading squad to go to nationals. She stands there in…
Chanel Camryn caught her step dad Jay Bangher jacking off on camera. He explained he made his living making videos for Sheer.com. Chanel was intrigued. Could she make money with…
Hiking can be a great way to exercise but what this couple quickly learns is that the only cardio they need is sex! They head home to start their thrusting…
As a secretary for lawyer Xander Corvus, Madison Ivy is disillusioned by conservative office life. She wants excitement, and so eavesdrops when she patches a phone call through to her…
Sol Raven’s band is requesting a new drummer. She will audition him. In addition to being a good musician, he will have to demonstrate the attitude of a rock star,…
When Blanche discovers her husband is cheating on her by uncovering emails from his mistress, she’s furious! But you know what they say – why get mad when you can…
Paige Owens looks like the girl next door but she is a dirty cumslut! Her mum’s new boyfriend has twins and she can’t help but want to fuck them both!…
A couple finds a vintage black & white film in the attic of the home that they just moved into. When they press play, they’re propelled back in time to…
Ana Foxxx feels a little betrayed when she discovers her boyfriend’s stash of online porn. The one thing they all have in common, though, is the bush. Seems like the…
Logan is the only one who knows how to treat Natalie’s feet right – other guys fake it but Logan is honestly and completely obsessed with her perfect feet! Gorgeous…
Showing off everything she got, this dumb white bitch Jodie Taylor gets what’s cumming to her when three big black cocks come at her. She’s sucking and fucking, trying to…
Jordi is new to America and he already has an American girlfriend! However, when his girlfriend brings Jordi to her mother Julia’s 4th of July BBQ, all of Julia’s friends…
“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 original contract star, Rocki Roads in brand…
Mr. Dera is giving Savannah one last chance to pass her woodwork class. Her last assignment is to make an object which can be used at home. Only one thing…
Before joining her girlfriend in bed, Tess had it in her mind to put on a little show and tease Foxies Gold to the fever pitch of desire. After slipping…
Even some of the most powerful men have their insecurities. In this series of vignettes, we follow John, Mick, James and Keiran as they explore and deal with the challenges…
The skies are a whole lot friendlier when a group of the world’s most beautiful stars pose as slutty flight attendants and sneak onto a plane to shoot a reality…
Piper and Carolina show up to decorate their friend’s house for a party, but quickly realize that their friend’s parents, Phoenix and Johnny, never left town at all and are…
The My First Porn series is a comical sex-spectacle of Jack directing his first porn movie. Volume 8 is 3 full hours and features Digital Playground contract stars Sophia Santi…
