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….

Luckiest man on planet earth Johnny Sins can’t keep his hands off his sexy new bride Kissa. Being neglected is not sitting well with Kendra and Peta, so they decide…

It’s Xander Corvus’s birthday and his girlfriend has got gifts! Lame gifts, showering supplies and a cupcake. His two naughty lesbian roomies, Codi Vore and Nolina Nyx have a way…

Sexy Katrina Jade is stranded in the dark when her car breaks down in the middle of the road. Luckily, a man pulls up to assist the damsel in distress….

Natana Brooke puts on her lacy pink lingerie and tells us about how she lost her virginity in the sluttiest way ever! This hot babe now is ready to get…

Check this out! Sandra Romain is such a horny black cock lover that as soon as her boyfriend left the house, she was calling my man Justin to give her…

While exploring her family’s new home Candee Licious discovers a dusty old book and learns of the legend of the Dick Fairy (Chris Diamond). According to ancient lore, all Candee…

Gia Dimarco is a smoking hot personal trainer who gets assigned a new client. Turns out her client is a heavy lifter who needs some tune up work done on…

Starring Digital Playground’s newest sensation, Shay Jordan and an entire cast of young, gorgeous, almond eyed beauties, Jack’s Asian Adventure will please your pallet. Jack uses the tried and true…

Nothing makes Ayumu hornier than getting massaged. Unfortunately her masseuse is a professional and not interested in giving Ayumu any special treatment. She leaves the room so Ayumu can cool…

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Yup, this hot bitch is a tranny. Bet you wish your girlfriend was this fly. Well at least you can watch this hottie suck some cock then take it up…

When Elsa’s friend ropes her into pool hopping at a neighbor’s house, she’s hesitant – she’s not even wearing a swimsuit! And what happens if they get caught? Elsa’s friend…

Laney Grey had problems focusing at college as she wasn’t getting enough sex. So she asked Brad Newman to help her focus by fucking her. It took her at least…

When Ryan and his wife seek help from a sex therapist, Ryan finds that the doctor’s receptionist Jaclyn is best suited to fixing their deep issues.

When Gia Derza arrives at her new boyfriend’s friends’ house for a dinner party, she looks overdressed… or underdressed we should say. The women at the party eye her judgingly…

Holding a gun is something this cute little Asian girl in her soft sweater has never even gotten close to, but it puts a smile to her face. Then she…

There’s no better way to impress a girl who just arrived in the city than by hinting that you’re a big roller in the industry. It worked for Jessy when…

Victoria is nothing but sweet in this sultry exchange between lovers.

We sent a staff member to the locker room to help Emily Thorne. That bastard saw her half naked and couldn’t help but fuck her.

Danny D gets more than he bargained for when he’s shopping for socks. Curvy salesgirl Mila Milan is surprisingly flirty, touching him as she exhibits the wares, then shows him…

Jack’s casting again! This time he’s looking for leg models… sexy, leggy vixens who want to be in fresh, up and coming music videos. In the second volume, Digital Playground’s…