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….

Beautiful Nicole Kitt is tending to her lush garden, cleaning the leaves with a spray bottle. Her boyfriend, Will Pounder, comes in to check on her, and he can’t help…

Christmas morning is supposed to be a time for family and holiday cheer, but Lena can’t stop thinking about all sexual escapades she’s witnessed and taken part in at her…

Whitney Conroy knows that the best way to get the day off on the right foot is with a little relaxing solo love. As she slowly slips out of her…

All it took to get Nick all fired up was a quick glance at Timea Bella’s transparent stockings as she lay face down in bed reading. When he saw how…

Experimenting in the bedroom keeps the fire burning between Kira Queen and Timo Hardy. There’s little this couple won’t try, because they keep things fresh in the bedroom and try…

Bill Bailey has come home to find his girlfriend’s sister Dakota Skye packing up half the household items. Turns out Bill is being dumped thanks in no small part to…

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La Sirena69 is a thief! She’s been breaking into sex shops and stealing from gorgeous redheaded crime boss, Molly Stewart. And when Molly’s girls catch her, she decides the best…

Petite princess Vann Bardot usually knows how to juggle with her hook ups, but this time, she fucked it up. She double booked two dick appointments and now both Codey…

Jenny is super excited to finally get Jordi to take notice of her at the local college. She takes advantage of the situation, making Jordi walk her home. However, Jenny…

Brick and his friends were on a road trip when their van ran out of gas and they got stranded on the side of the road! Brick was elected to…

Violet Starr loves to hang out at the house and pass her free time by sketching portraits in her sketch book. Her step brother moved in and he teases her…

Candice Dare acted like she was ready for anything when she showed up, and her costars definitely did all the could to bring her to the breaking point. It wasn’t…

When couples are in need of a helping hand in the bedroom, they call the Rent-A-Pornstar Hotline! Olivia Austin answers the call when Keiran Lee and his wife are experiencing…

After receiving a call to a particular house, I realized it was the brunette slut with the pierced nipples I’ve been sleeping with. Apparently her boyfriend found out about her…

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…

Deeper 4 is a playfully erotic and sinfully fun tribute to Digital Playground’s delightfully fresh Shay Jordan. She is showcased in a multitude of flesh fantasies and she delivers amazingly…

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…

They say we’ve all got an angel and a devil on our shoulders, but what happens when the two are left alone in the bedroom? The sexy devil, Abigail Mac,…

Horny nerds Tyler and Ariana can’t wait to get laid. With grad 1 month away, and top colleges on the horizon, they just have to avoid super bitch Jen and…

James acaba de pasar al mejor noche de su vida al cogerse a Christy Mack pero le cayó de sorpresa cuando Christy comenzó a quejarse diciendo que no cogía tan…

Aiko Nagai is so used to being used by the counselors, that she’s no longer surprised when they take her to the quite room and there’s a mattress with a…

Delilah and Jane are training hard for an upcoming beauty pageant. The girls know they’re attractive, but they have some stiff competition, and if they’re going to win, they need…

Shay: All-American Girl is a heartwarming and sexy tribute to youth growing up in America. Scott presents Shay with a lovely birthday cake, only to have his cock dipped in…

On a Tuesday afternoon, in a high rise building, a conference room is heating up with some tense negotiations. One company wants to buy out the other and everyone wants…

Shuri Maihama is surrounded by horny guys in this full on gang bang. She is blindfolded at first and only feels their hands playing with her clit and pussy to…

We met this cutie Eve Ellwood at a local mini mart where she was quick to show off her perky tits. A little sweet talk later she was in the…

Coming home from a long day of shopping, it was just Goldie’s luck to drop one of her bags in the driveway. But when her neighbor Jax spotted it walking…