While her rich husband is being tied to a chair by con artists Tommy (Luna Star) and Max (Damon Dice) and taken for all he’s got, Vanessa Lang (Natasha Nice)…
Five horny teens. 2 sound guys with equipment. 1 contest. 1 winner. Sound familiar? It is. It’s Jack’s Teen America.” Put it in and cast your vote! Jack’s at it…
Dean Sins has had to call a lot of students into his office for plagiarizing over the years, but they’ve never been sexy sluts like Charity Bangs before! It turns…
By day she’s a working professional, and by night she’s Number 4. Get entranced in the morphed world of DP contract star, Eva Lovia, as she conforms into nymph-like submission,…
Katty Soarez has been trying to fuck her roommate for ages without success, so she figures maybe her friend Black Angel will have more luck! She sneaks Angel into Jason…
Ramon is in a miserable marriage with a woman who hates sex. Their therapist suggested spicing up their sex life by visiting a strip club together. Sexy stripper Kagney is…
Sasha Rose’s boyfriend loves teasing her ass before sex. On this occasion, he wants to add an extra element to the foreplay; a camera capturing Sasha’s reactions for his future…
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 volume 3, Digital Playground’s contract…
Layla Price, nervous to present her oral report, can rest assured that her teacher, Bill, is there to put her at ease. Layla is clearly nervous and could use all…
“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…
Esperanza Gomez has a really short temper with her boyfriend’s assistant and starts yelling at him so loud that Chris had to intervene to calm down his dad’s girlfriend. Esperanza…
This horny Asian hottie has never trimmed her massive bush. She lets it grow wherever it goes and she spreads her legs to let a man finger her hole and…
Demure and devious, Rachel Starr is showing off her elegant side in a flowing red dress which tightly hugs every one of her curves. But those dark lips hint at…
Get an extra special glimpse into the bedroom of Lola Myluv and Frida Stark, where every moment is sweet and sensual. In the soft afternoon light these two all-natural beauties,…
Feel the sun warming your skin, and a gentle breeze swishing your hair as it passes. Staci Silverstone loves to be nude, even more when she can be nude outdoors…
Little Humper Jimmy Michaels has a great prank today. He leaves a remote-controlled vibrator in his roommate’s bathroom, and just as he planned, Scarlett Venom thinks the gift is from…
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…
When the mood for hot lesbian sex strikes, Shae doesn’t waste any time grabbing for what she wants. Seizing the moment, Shae wrapped her arms around her lover Charlotte Stokely…
Havana Bleu has a perfectly thick booty and round ripe titties! She has only been in the industry for a month and her sex drive is crazy high! This spicy…
Remy LaCroix gave her brother and her best friend a trip for their engagement, but her friend’s Ex-boyfriend sent her some dick pics. Remy’s brother saw them so Remy stepped…
