Shot entirely on HD, Jack’s Teen America 19 features Jesse Jane and Sophia Santi in intimate and seductive hardcore action! The Jack’s Teen America series arodies beauty pageants and Jack’s…
Nina Diaz likes to play croquet, but she prefers to play with her tits and pussy between strokes. Peeping Jimmy Michaels sneakily turns the sprinklers on, getting Nina’s top all…
Alex Legend and Billy start off with the most innocent of intentions – picking up the keys to a great new place they’re renting. But when they arrive, a fantastic…
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…
Enjoy the lovely Hannah Harper, as you’ve never seen her before, in a mesmerizing and remarkable Digital Playground production. Directed by Celeste and boasting 9 scenes, Hannah Erotique is a…
Callie Klien loves bending over and showing off her tight little butt hole, but her male costar has some news for her. It won’t be tight forever, so see how…
“Jesse Jane: Image” explores the famous and undeniably sexy image of Digital Playground superstar, Jesse Jane®. Her playful fantasies are fulfilled in 4 amazingly provocative scenes. Watch Rick Patrick give…
Trespassing, public indecency: tonight, Riley is breaking all kinds of rules. When this blonde pool hopper attempts a break and enter, even the police want to stop and watch. Uploaded:…
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….
The luscious Desiree Dulce is getting ready for date night with her successful and busy husband. After getting all cleaned up in the shower, she slips on her pantyhose and…
Gallery assistant Whitney Wright has one chance to impress prominent art dealer, Logan Pierce, and she plans to take it! Dressed to the nines in tight, black leather and a…
Madi Collins wants to fuck her Rion King’s dad so he won’t marry Madi’s mom, but she can’t find him. She lets herself into Rion’s house to search high and…
Mouths full, eyes wide open with that begging look that shows they are always ready for more: Gina Valentina and Karlee Grey give it all they’ve got as they race…
She’s waited so patiently, watching all her friends get fucked at the beach, and now it’s finally the blonde babe’s turn! Her pigtails bounce as she rides this dude’s cock,…
Michiko and Shyann Mitchell both star in this clip performing double duty for our black dudes. They seem to think that being there with another girl at the same time…
The bus won’t stop!! We’re out here son! Constantly roaming the streets searching for chicks that’d be down to do anything for some bread. This week we stumbled across this…
The My First Porn series is a comical sex-spectacle of Jack directing his first porn movie. Volume 10 is over 2 hours and features Stoya in a brand-new, amazingly ass-a-liscious…
Kayla Kayden snoops around Luna Star’s bedroom and finds her drawer full of sex toys, deciding to give her wand vibrator a try. Kayla’s clearly enjoying the sensation of having…
Mellany Lapiedra was walking on the street underneath a bridge in super sexy red lingerie and a black fur coat. She dropped the coat to the floor. A jogger ran…
Anya is an innocent young woman looking for a man to satisfy her fantasy of being dominated, and submitting to her Master’s every physical demand. Luckily, Keiran is happy to…
Teen girls are usually experimenting with their sexuality and learning about what turns them on. This blonde teen was doing just that, and what she realized was that she didn’t…
One morning, after Tommy tried his best to convince his side-piece Gabriella it was over, she let herself into his place and set up a giant sex swing in his…
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…
On the surface, Allie seems like a lovely housewife who is loyal to her adoring husband. But underneath her apron, her pussy is dripping wet at the idea of busting…
The sexy Theta sorority girls are about to recruit some fresh meat into their chapter. As the Theta President goes to her room to change for the party, she catches…
Jessy has been recovering well from a viral infection, especially since he’s been visited daily by a homecare nurse named Lena. Lena tends to him from his bed in her…
