Jack’s Playground: Big Ass Show 9 Jack’s busy in his playground casting big-ass babes for leading roles in his “music videos”. This time he gets Alexis Texas and Shyla Stylez…

Jack’s Playground: Big Ass Show 4 Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful butts. They bounce, they roll and they…

Jack’s Playground: Big Ass Show 2 Jack’s busy in his playground casting big-ass babes for leading roles in his yet-to-be-seen music videos. The delicious girls will do anything for stardom….

Teagan Is Back 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…

Teen America: Mission #8 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…

Teen America: Mission #4 Jack’s at it again with Jack’s Teen America Mission #4. This time, it`s even kinkier than before. Jack’s checklist: Backdoor Bonanza, Whip the Pony, Racquetball Rectal,…

Teen America: Mission #3 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…

Teen America: Mission #13 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…

Sophia Santi Belle Sophia Santi: Belle is the new, erotic treat from celebrated director Celeste. Combining gorgeous girls with stellar production values, Celeste creates a stimulating visual experience, which can…

Stoya always gets her man. The series featuring your favorite bone-jumping bounty hunters is back! Stoya is the featured fugitive seeker that’s vowed to always get her man. Mr. Pete…

Shay Jordan: Slippage From the deviant mind of Digital Playground’s director Celeste comes Shay Jordan: Slippage. Full of tight ropes, delicious tease, and wet pussies, Shay Jordan: Slippage stars Digital…

Pirates 2006 AVN Award Winner – Best Video Feature 2006 AVN Award Winner -Best Director – Joone Quick. Batten down the hatches and get ready to set sail on an…

Luxure: My Wife’s Vices These charming wives cannot be satisfied with just one partner. Luckily for them, their husbands are more than willing to share their love. . Anna and…

Gangbang My Face 4 Jake Malone’s movies are marked by a dark perversity, an SM enthusiast’s appreciation for theatricality, and sexually-obsessed, totally gung-ho young bitches who aren’t just in it…

Gabriella Fox Foxxxy Gabriella Fox, Digital Playground’s sultry Latina contract girl, stars in three of six scenes of the must-own Gabriella Fox: Foxxxy. The gorgeous starlet loses all her inhibitions…

Deeper 5 Deeper 5 is a playfully sexual tribute to Digital Playground’s perfect, all natural Goddess, Jana Cova. She captivates the screen in a multitude of scenes including kinky anal…

This woman was scorned. Now she’s about to get screwed. Hell hath no fury like a woman scorned, looking for revenge and screwing over anyone who gets in her way….

Bad Girls Everybody knows that bad girls have more fun, and the Digital Playground girls are the baddest on the block. Digital Playground’s Bad Girls is the latest kinky gonzo…

Bad Girls 2 Everybody knows that bad girls have more fun, and the Digital Playground girls are the baddest on the block. Digital Playground’s Bad Girls 2 is the new,…

The risk is worth the reward. The sleek and seductive Jesse Jane runs a kinky real estate company worth millions of dollars in properties, but it’s all just a deceptive…

Taste Of Stoya, A Stoya, the 2008/2009 Best New Starlet is back and nastier than ever in Digital Playground’s new, tasty showcase A Taste of Stoya. After working herself into…

Mean Bitch The mail is late for the last time. Beautiful Aiden Starr brings her vicous personality and gorgeous tits to the mail room to get to the bottom of…

Insatiable Slut is Tamed with Bondage and Torment Mia James is back for another round, and this time she’s leaving with some marks toremind her of her visit. First, we…

Lesbian Electro Fear Play Young scared electro virgin, Jenna Foxx, loves sex with older women. Hot MILF, Mona Wales, shows teaches her about lesbian electrosex with bondage, the violet wand…

Fetish Hoods & Deepthroat Skills Learn the fetish behind gas masks and hoods, including spandex, leather and latex hoods, and even gas masks. See how to use a variety of…

Yes Queen Betty: Betty Solace Doms Baxxx First time on Divine Bitches Betty Solace takes the soft and sensual approach to domination. But make no mistake she has full command…

2 Grannies for 1 Cock 3 Mature XXX presents a collection of high-end 4K scenes that feature two grannies sharing one hard cock. Prepare yourself for a ton of threesomes,…

Sweet Redhead Naomi S Gets Facialized By Owen R & Joshua C! This nasty and insatiable sweet redhead got a pretty face – she was born for facial porn. Watch…

. Spread Them Cheeks Vol. 1 – Starring:  Mena Carlisle,   SubGirl,   Carissma De Luca,   Bad Bella,   McKenzie Mae,   Kaida Kinks,   Cherry Bomb Bomb,  …

19 yo. First Porn First Older Guy Ona Lash is a long legged cutie with a few kinks and an open mind. She has never been with a much older…

. Kinky Masseuse Rims Her Client’s Ass Then Drains His Balls – Sexy Japanese Babe Rides Stud’s Cock – Cute Japanese Masseuse Satisfies Her Client –.

Estela Silva gets double penetrated hard by a horny couple that picked her up shopping. Estela Silva was just working her shift when a kinky couple started flirting with her….

Little Girls Love Big Dicks 16 Scene 1 -Flip Fucking the School’s Tiniest Nerd A brand new year of school has just begun, and Khloe isn’t really happy about how…

Shay Jordan: Leather and Lace From the imaginative mind of Celeste comes Shay Jordan: Leather and Lace, a modern romance about the fucked up nature of love and sex. The…

MY submissive STEPSIS Tony overhears his stepsister Sophia talkingto her boyfriend. She is saying that she won’t do anything kinky with him, just vanilla stuff for now. But Tony knows…

Perverted Stories 22 Strawcock: The way those corn stalks are moving, there’s more than just wind blowing in the fields. Some say there’s something wicked out in the cornfield. That’s…

Strict Machine Digital Playgrounds’s very own Riley Steele plays the head mistress in this kinky, fetish film. A visual and sexual feast with a super fine cast, legs, stocking and…

Once you’re in, there’s no turning back. Naughty fetishes came to life as gorgeous Riley Steele? explores the kinky side of sexual pleasure. Erik Everhard loves to sniff the sweet…

Old Enough For A Creampie 9 Toys are nice but only dicks come with cream. Kylie Shay loves feeling an older man fill her pussy with cum. Maria Anjel will…

Save the best for last. In the ninth installment of Jack’s Big Tit Show, Jack is on the hunt for big, beautiful boobies, using his trusty music video ploy to…

Jack’s Playground: Big Tit Show 6 Call Jack “The Titty Hunter”. He’s hunting for trophy titties, and will only settle for his favorites; big, beautiful boobies. They bounce, and they…

The One and Only Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful boobies. They bounce, and they shake. There’s more than…

Jack’s Playground: Big Tit Show 4 Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful boobies. They bounce, and they shake. There’s…

Jack’s Playground: Big Tit Show 7 Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful butts. They bounce, they roll and they…

Got D’s? Some More Juice For You To Squeeze. Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful boobies. They bounce, and…

Oops…Jack Did It Again! More D-Cups Are Waiting For You To Unload On! Jack is back and he’s ready to give you more of what you really care about… big…

Jack Says, “Big Tits Are More Nutritious.” Jack’s at it again. In his playground, Jack is busy casting for music videos. The delicious girls will do anything for stardom. Some…

Teen America: Mission #12 Jack is back baby. But this time around, it’s professional… and ten times kinkier than last time! Jack has an eye for the hottest teen sluts…