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…
En un tiempo como este, cuando el mundo está cayéndose a pedazos a su alrededor, Peta Jensen sabe que a veces el único camino para sentirse liberada es ser cogida…
Welcome to the lives of a modern English family: Ian, a father who married a much younger woman, Cathy Heaven, his lesbian daughter Liselle, married Jasmine Jae and they’ve adopted…
Graduate student Abella has a problem: she’s supposed to meet with her doctoral advisor Professor Holmes every week, but she just can’t seem to focus when she’s alone with him….
Kimber has just been accepted to the prestigious Sir Keiran’s School of Anal Training, but she shows up late for her first day, and gets punished by Sir Keiran himself…
Keiran calls in sick to work to stay home and spend the day jerking off. But when his wife comes home unexpectedly, she wants to take him to the doctor!…
Sweet and sexy Skye Blue is concerned for her brother, who’s recently picked up some bad habits from his hot troublemaker of a girlfriend, Lena Paul. When the ladies meet…
What do you get when you mix Adriana Chechik, Megan Rain and Karmen Karma? Three of the twerkiest, bounciest, wettest butts of all time! If you like cuties with booties,…
April O’neil is getting out of her car in a parking lot and the security guard sees her sheer panties when the wind blows up her sundress. He places a…
“Jack’s Playground 31,” the superstar edition, stars the lovely Jana Cova in two delectable scenes, Devon in all her naked splendor and DP’s original contract star, Rocki Roads in brand…
That One Friend of His Lissa just to wants to get some action. But the only action her husband Mike wants is the football game. But when his friend comes…
Imagine Marilyn Monroe was a submissive English slut with a bit of ink… that’s Gigi Patsy — peak fuckable. In Pascal’s shoes, most of us would probably need to shoot…
Alexa Nova shows up for her audition in a beautiful black lace dress. She bends over and presents what’s between her fine legs as she wears her black thong and…
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….
Super hot tranny Khloe Hart gets more than her fill of four thick dicks when she gets gangbanged in the ‘burbs. How will she fit all those cocks, when she’s…
Day 2 in the Project DTF house starts with a late arrival: Mia Moore, and the other girls are ready to welcome her with open legs–we mean arms! Alexis Tae,…
Aubree Valentine is a sweet teen with a tight pussy who’s got a problem. Her dad hates her boyfriend, Lucas Frost. Lucky for Aubree, her hot MILF stepmom Alexis Fawx…
Bridgette B spends her first 4th of July in America, and has a scene during it. When the scene ended, and things were wrapping up, the cops showed up to…
Jack’s Playground 33, features Digital Playground’s one and only insatiable and sexy Devon. She’s eager to make the music video cut and demonstrates her distinct talents on Scott Nails’ throbbing…
Kendra doesn’t want to play Amber’s game, but she can’t help wanting to settle the score, both online, and with Amber’s IRL boyfriend. Part 2. Uploaded: 2024.02.12 2024.02.08 Show more…
Another day, another set of weak business proposals for the investors on the hit Reality TV show "Time to Prove Yourself" to shoot down. But then Madelyn Monroe arrived to…