Devon puts in long, hard hours working at a secretary for multiple businessmen. She brings them coffee, answers their phones, lets them play with her huge tits, and sucks their…

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 his camera….

After soaking in a flower petal milk bath and taking a steamy shower in her lingerie, a very wet Tru Kait is taken to the bedroom, where Michael Vegas fucks…

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…

When Heather (Demi Sutra) and Sam (Scarlit Scandal) discover their best friend Vanessa (Demi Sutra) is getting married to a guy they absolutely can’t stand (Xander Corvus), they set out…

Occasional workplace fuck buddies, Candy Alexa and Raul Costa, are both working hard at the office. Candy is bored and in the mood to get fucked, but Raul brushes her…

Ri-Ai Saotome is a new Japanese slut who wants to be in the movies. She sits on the casting couch and answers a few questions before she takes off her…

After her late great auntie’s tragic death, Desiree Dulce is fixated on getting her hands on Aunt Gladys’ secret inheritance. Desiree makes her way to her aunt’s house and finds…

After another long night of partying during Spring Break, all she wants to do is sleep the day away! Her partying roomies, however, just wanna get their rocks off, but…

Doctor Shimohei’s campaign to reform the girls of Mitsushi Private School seems to be going well, until an entire class boycotts his lesson! Shimohei and the handpicked students who’ve already…

When Athena comes home to find a bed covered in red rose petals, she strips off and enjoys the luxury of playing in them. Featuring a slow striptease and lots…

When Shay Sights learns that her daughter is getting bullied by the neighborhood jerk she decides to take matters into her own hands and pay the bully a visit! Shay…

Roxy Ryder is an adventurous young teen that likes to spend her time outdoors. She is also a raging slut that can barely keep her clothes on! They go to…

Jade Baker has just been enrolled in an all-girls Ivy League school; however, she’s having a little trouble fitting in… Jade’s been caught vandalizing, skipping class and even having sex…

After being followed down the street by a car full of catcallers, Lexi decides to give the guys exactly what they wished for – as expected, Lexi’s offer to fuck…

Elisa greets us by announcing that this is her first abbywinters solo scene “in a little while” (the last one was nine years ago!), so “I’m really looking forward to…

After a rousing robot sex romp with her step-daughter, Missy is revved up and ready for more. While she’s promised her husband a taste of anal action on their upcoming…

Alanah is looking for her friend to go shopping for a new outfit to wear to the rodeo. She finds her friend’s cute brother and tries him on for size…

Kendra Spade in black lingerie; have we got your attention yet? Feast your eyes on Kendra’s sexy body while she plays with herself, awaiting Xander Corvus and his hard cock…

Sexy assassin Romi Rain has blown and shot her way out of two sticky situations in one night, and now she wants a reward from her boss Stallion. He wants…

High school senior Shigeki forgot there was a day off today, and now it’s too late for him to find a date. Things are looking bleak until his friend Kei…

Jill (Gigi Allens) is the finest, most diligent secretary that Brad has ever had. Even when she’s not at her desk, she’s underneath his, working long hours to get her…

Kate (Halle Hayes) and Rick (Small Hands) look like a perfectly dull married couple, but someone from Kate’s past is about to change everything. One day, Jen (Aila Donovan) shows…

Shot entirely on HD, Jack’s Teen America 18 parodies beauty pageants and Jack’s lovely contestants all compete for the crown. They take off their clothes, they masturbate, they suck, they…

Cherry Kiss has wanted to size up the new ad executive for a while now and by size up we mean she wants to see how big his cock is….

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…

Halle Von is having a really hard time dealing with her girlfriend’s mom. Bianca Breeze just doesn’t approve of her for some reason, and Halle can’t guess why. To try…