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….
Sophia Sterling knows her stepbrother Ricky Spanish has been cheating on his girlfriend. The problem is, he’s sleeping around with trashy girls. Fortunately, Sophia has an idea that will keep…
Addyson James is home alone with her son’s friend Lawson who has been staying over until he gets back on his feet. Addyson has come up with the perfect solution…
A sexy divorcee yearns for love, but is looking in all the wrong places. Her ex has already moved in between the legs of a much younger busty blonde, and…
The sexy Kimber Woods loves gaming, but her snobby wife Desiree Dolce is always on her back about it. To dissuade Kimber from gaming, Desiree has their couch removed, but…
There’s just something about the great outdoors that gets India Summer in the mood for sex. Who else is going to rope in the new studs and teach them how…
If you told Vanessa Cage the wild weekend she had waiting for her at the lake with her boyfriend and best friends, she never would have believed you. It started…
Starring Digital Playground contract superstars Jesse Jane® & Stoya, Kiss Kiss documents very sexy and private encoun-ters taking place in the suburbs of a bustling tourist city. The erotic vignettes…
When Aaron and Katie lost a passport backpacking through Europe and found themselves unable to book a hostel, they veered into hopeless thoughts of despair. But just when they thought…
Bill Bailey wants nothing to do with his stepdaughter, Layla London. So when his new wife demands that Bill spends time getting to know Layla, Bill tells her to politely…
Suspect number three for detective Carter is Miranda Montgomery (Joseline Kelly), a sexy teen socialite who has something of a reputation for flaunting the law. Her tabloid-worthy misdeeds have all…
Emily Mena is horny and wants to fuck all daddy’s employees at the luxury hotel her dad manages. She competes in a public fuck contest to see who can bang…
New Rules My stepdaughter, Aliya Brynn, wants her bestie, Jackie Rogen, to stay over the house this weekend. Of course, I’ll only allow it if Jackie fully understands the house…
Shot entirely on HD, Jack’s Teen America 21 features Digital Playground’s lovely contract star, Lacie Heart in a slam-min’ romp with Scott Nails, Poppy Morgan & Renae Cruz in decadent…
Girls Night Freeuse For All Anna Claire Clouds and Lily Lou are having a chill girls’ night in hopes of helping Anna get over a recent breakup. Anna is still…
Bianca Benett loves Paula Shy, and she wanted to show it with a sensual fuck on their vacation down south. After coming upon Paula relaxing outdoors, Bianca put the moves…
Kimmy Granger is tired of making minimum wage for all the hard work she does, and she’s especially tired of starring in the fantasies of her pervy boss Johnny Castle…
When Jonathan returns from a long stint working overseas, he’s looking forward to seeing his beautiful MILF wife Yukie again…as long as he can keep his desire for teen schoolgirl,…
Gigi Allens is the latest in a long line of blonde beauties that Stevie Shae’s dad has brought home, and she has never gotten along with a single one. As…
In this self-shot sex documentary series from some of the biggest names in the business, Digital Playground gets up close and personal, offering you a behind-the-scenes look at what it’s…
Sexy Alexis Tae is a track and field champion getting ready to try out for the college team. Her private coach, Ricky Johnson, is helping her put in extra practice…
Dana is surprised to find her maid has called out sick- only to be replaced by a hot young substitute. Cleanliness is next to godliness, so Dana makes sure to…
Lola Fae’s perennial struggle with finances reached a breaking point when she found herself penniless. Resorting to theft, she targeted her stepbrothers, hoping to alleviate her financial woes. Suspicion arose…
Bi Girls Share A Big Cock Fuck buddies Kendra and Ivy are about to throw down, but they gotta be quick because Kendra’s boyfriend is coming home from work. Ivy…
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…
Athena Faris and Tyler Nixon check into their room at the Victoria Hotel for a special night, with the two young lovers set to have sex for the very first…
Sexy German teacher Victoria Sin caught one of her students copying at a test again. She called the school’s principal, Mr. Glide, to help her set her student straight. After…
Nichole is always forgetting stuff. This time she can’t remember where she left her homework. Mr. Long knows this bad memory problem is due to a lack of sexual activity….
Where God Doesn’t Look Belle (Penelope Kay) approaches a priest (Tommy Pistol) and confesses that she’s been feeling tempted by sexual desires, even though she knows she should save herself…
Katrina Jade loves a good dick pic. She loves them so much, in fact, that she spent years snapping photos of dudes’ dicks and cataloguing them in a naughty little…
Professor Capri Cavanni finds out that one of her students, Van, only is taking her class because he was told by his friends how hot she was. Capri takes on…
Katrina met the perfect man: thoughtful, giving, who knows what she wants before she does. And tonight he’s giving her to someone else… Uploaded: 2024.02.18 2024.02.17 Show more…
You’ve never had such a good time with any other woman than you have with your girlfriend, Eliza. She is smart, witty and incredibly gorgeous. Life’s never boring with Eliza,…
