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…

Johnny has a very embarrassing situation; he needs to use a big boy diaper because he pees when he sleeps, and just about when he is going to nap, his…

Charles Dera can’t believe his ears when Tiffany Watson confesses that being tickled makes her squirt, and he can’t believe his eyes when she proves his doubts wrong! Looking to…

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…

Hot sex is about to get hotter! Smoking hot big tit babe Skylar Snow is ready to fuck and suck! Deep poundings and cumfilled orgasms are about to get hotter!…

Cindy Joss wants to attend her annual high school reunion, but her jealous husband doesn’t let her go. Her step-mother-in-law, Gali Diva, offers to accompany her to protect her and…

Ariana’s best friend is always bragging about her boyfriend’s dick. Curious, horny, and armed with cash, Ariana is determined to find out just what makes Ryan’s cock so legendary.

Krissy Lynn’s son has had some trouble making friends, but he seems to have connected with Ricky Spanish, who has come over to hang out and is staying for dinner….

Melissa Stratton is a hot busty MILF that any red-blooded guy that comes across her is sure to have wet dreams of, just as pool boy Lucky Fate does in…

Alexa Payne got locked out but she is so used to it already that she gave her friend a key to the house if it ever happened again. Unfortunately her…

When Bill Bailey woke up on a hospital stretcher without any memories of how he got there, he was pretty worried. But Dr. Ho and the lovely nurse Rio Lee…

Monique Alexander comes across an old dildo stuck between the cushions in her couch. As she rubs it clean she thinks about how she’d love some pie for dessert. Suddenly…

Ri-Ai Saotome is a horny slutty Japanese newbie with big round tits and an extra hairy cunt. She wants to make a good impression with her first time on camera…

When Richelle Ryan got cat-called by some asshole construction workers, she decided to call their bluffs by hiking up her skirt, shaking her thick booty, and telling them to whip…

Evelin Stone is a public flashing daredevil! She grabs a scooter and flashes around town and gets honked at from a passing boat in the marina! She gets straight to…

Jack’s at it again! But this time, he’s focusing in on hot babes with BIG, FUN ASSED… It’s more cushion for the pushin’…. Forget professional… this volume is all about…

The Gang’s been solving mysteries all month and there’s been some really close calls! There’s been crazy clowns, gruesome ghosts, wily witch doctors, and freaky phantoms! Fred broke his arm…

Last time on Prom Whore Wars, we saw Raven Bay fuck principal Johnny Sins to get a chance to rig the votes for prom queen. Well, that didn’t go over…

Felicity Feline’s terrific drumming skills, and her banging body, are put on display in a scene that’ll will have you bopping your head along to the beat while she hits…

The My First Porn series is a comical sex-spectacle of Jack directing his first porn movie. Volume 9 is over 2 hours and features Teagan Presley in a brand-new, amazingly…

Sex siren McKenzie Lee struts and stretches, putting her banging bod on display for Kerian Lee before getting a good, hard pounding in her tight, wet pussy.

Curiosity and the appeal of quick cash draws Alina Lopez to a pharmaceutical trial for a promising new “pill for horniness” run by Dr. Scott Nails. Will Alina prove herself…

Kimber’s husband can’t seem to get anything done while his new assistant, Lilly, flirts with him at their home office. When Lilly asks for a raise, she learns that Kimber…

Kaylani Lei thinks she’s the queen of the neighborhood, and with the upcoming election for Neighborhood Spokeswoman she just might be. But first, she’s going to have to catch the…

Angel Windell just got some new shoes and she asks her stepbrother Joshua Lewis to help her take pictures of her new shoes for social media. Joshua notices how hot…

Rachel never had a big cock so Nikki decided to bring her down to the local deli where she could try some different meats… Alec Knight was there as usual…

Freya Parker lets herself into her friend’s house. Her friend isn’t home, but Alex Legend is. Freya finds her friend’s dad in the kitchen doing the dishes. She takes the…