Shot entirely on HD, Jack’s Teen America 18 parodies beauty pageants and Jack’s lovely contestants all compete for the crown. They take off their clothes, they masturbate, they suck, they…
Long-time girlfriends Cherry Kiss and Haley Hill thought their romance lacked spice, but really, all it needed was extra sugar! Enter busty baker Alexa Tomas with the recipe for romantic…
Bill Bailey is watching his sexy stepsister Kylie sunbathe by the pool. She looks so good, but he could never fuck her – that would be wrong. Kylie’s dad asks…
Tana Lea used to work at a University in Texas as a graduate assistant. Office life might be boring for some, but this sexy redhead found a way to spice…
Cathy gets ready for a dreamy night of self-care, prepping a bath with rose petals and pouring oil on herself and into the bath. After a nice long soak, Cathy…
Celeste’s Icon features an amazingly beautiful, all-star cast in some of the hardest scenes they’ve ever shot. Digital Playground’s contract superstar, Teagan Presley leads the way, down a revealing and…
As the 1950s become the 1960s, washed up doo-wop singer Johnny Nathan finds himself without an audience, his musical relevance fading faster than his dignity. As a depressed Johnny contemplates…
Lynn Vega is sick of having her stepson’s girlfriend sneaking out of her house at all hours of the night. It’s the last straw getting woken up by Anya Ivy,…
Eva Murkovski dreams of traveling the world, but she needs to learn geography perfectly for that. Unfortunately, the cutie faces some problems memorizing the positions of the countries on the…
Flexible and fit Emily Blacc shows off her moves for Ryan outside in the yard. With her short shorts and perky tits out she teases his cock before getting on…
Emily Willis is a gorgeous babe. This 20-year old is a Utah native that grew up with Mormon parents. She always knew that she was a dirty whore and she…
Margaret is a beautiful little Asian chick with long straight dark hair that she’s pulled in pigtails for today’s session. She’s pleasuring two men at once, and she loves sitting…
Ashley Alexander eats a hard candy in front of her stepbrother, Jay Romero. She goes on to tell Jay that Halloween is the one night of the year that she…
The sultry Katrina Jade brings out her sexy dark side in her smoke-filled, neon-lit fuck room, waiting for the perfect cock to fill her up. Clad in revealing and alluring…
Sexy brunette Lily Lou teases in a bikini, and she looks scrumptious soaked in oil. The darling girl strips and spreads her holes for the camera, continuously coating her bodacious…
Astrid comes home and finds a video camera set up in the living room. Thinking her husband left it out, she decides to put on a little show. Little does…
Charly Summer first makes a show walking down the stairs in her sexy lingerie. She gives a peek of her perky titties and pussy before getting fucked hard. Her perfectly…
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….
Jack’s at it again! But this time, it’s professional… and even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack’s answer to getting a…
