Immersion Therapy Erin (Jay Taylor)’s body language is nervous and uncomfortable, while her therapist, Daniella (Angela White), talks to her. But Erin isn’t listening. She’s more engrossed in her own…

Chad White Is The Jackoffanator Chad’s a photographer whose favorite subjects seem to come alive as he processes the film. His imagination carries him into these teen pussies, living out…

Jack the Tickler Jack’s back! This time his trusty scalpel has been replaced by an even more fiendish instrument. The feather of doom! Now fearful females who walk the night…

Sister Jacked Carolina Cortez – “You can’t leave me out here in the middle of nowhere! You’re my stepbrother! You just don’t throw your family out of the car! I’ll…

Jackies schärfste Nummer SD HD Trotz zahlreicher Liebschaften hat Traumfrau Jackie den Mann fürs Leben immer noch nicht gefunden. Deshalb beschließt die kesse Blondine, sich unter ihren Ex-Lovern umzusehen, ob…

Cherie DeVille Is Evil Gorgeous face, curvaceous body and adventurous personality make stylish blonde MILF Cherie DeVille a favorite of fans and XXX directors. The six-hour Cherie DeVille Is Evil…

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…

Arrrrrgh!!! Thar be pirates hittin’ this here booty! Captain Evan returns, “Time to walk my plank, my prettees.”

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…

Jack’s Playground 33, features Digital Playground’s one and only insatiable and sexy Devon. She’s eager to make the music video cut and demonstrates her distinct talents on Scott Nails’ throbbing…

Jack is really busy casting for music videos and now he’s landed Digital Playground’s super fine contract star, Sophia Santi alongside Selina Draagen, Alyssa Chase, Carli Banks, Marlena, Christina Brooks…

Jack turns 1!…and there’s a whole lotta frosting on deez cakes!

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 to fuck. Some…

Teagan Presley & ANAL, does the rest of this description even matter? Jack is really busy casting big, bouncing, beautiful butts for music videos. They shake, they roll and they…

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 to the pink treasure nestled…

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! Some suck, some fuck and some…

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 shake and Robby finds pleasure deep…

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 shake and Jack finds pleasure deep…

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 shake and Jack finds pleasure deep…

Mother Fucking Anal Mayhem When the husband’s away, the whores will play. Six sexy housewives are ready to get down and dirty on anyone in their neighborhood with a had…

Six-babe, Double-D, double-disc edition! Six hot girls and six big, long scenes… all in the tease and please style that only B. Skow delivers! But this time the emphasis is…

Beautiful superstar Kayden Kross comes up close, right in the palm of your hands, with lusty POV action. Kayden invites you to reach out and touch her as she and…

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 Digital Playground’s award…

Beautiful BiBi Jones drips her young, sweet juices all over thick rods and long, hard members. She shows off her naughty skills as the youngest new nasty girl. She and…

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 POV Playground, YOU will get…

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…

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…

Watch super slut Amy Fisher do what she does best! No one is quite the whore she is, and here you will see exactly why! Watch her take on the…

“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!

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…

The Road To Sisterhood – This week’s Haze submission comes from the lovely girls at ***, These sisters put their pledges through some serious shit. At first they had every…

Kora Angel 5 “Monster Clit Masturbation”After a short hiatus, hot bodybuilder MILF Kora Angel is back with a vengeance! Watch her jack off her huge clit to multiple, body jerking,…

Fucking His Ass And Sucking His DickLias a bewitching, foxy, transsexual wonderment, with jet black hair, a killer body, and a humongous, demon cock. When a guy notices her jacking…

Playtime Nudes: Pink And Juicy 2Heather Vandeven is applying her make up in the mirror preparing to film this hot sexy video for you. She drops her jacket and reveals…

Cum Loving MILFSKarina and Melody Pleasure are having finally a meet up again after almost seven years! They both havent changed! Melody is dominating Karina and the male slaves are…

Wild French Muscle DommeMuscled up Maryse Manios is having some plumbing work done on her home, but when she finds out she doesn’t have enough money to pay for the…

Toy Time for Fany’s FannyFanys a horny, redheaded T-girl, with natural breasts and a cock. She dances, imagining her man watching her. After peeing, she lies face down on the…