Featuring Anna Sivona

Her huge 34H-26-34 boobs will indulge your fantasy.

The lovely and sexy 32H Luna Amor!

Checkout a Romanian green eyes model and discover her real breasts that will add to your collection of bustylicious women.

New Busty Model Never Seen Online Before 34J Holly Garner

Happy mid-week, folks!

Suffice to say, all the reaction to our amazing new discovery, the lovely 34J Holly Garner, has been absolutely stellar and with that in mind, she is back for an encore!This marks Holly’s photo set debut and she is looking truly fantastic from top to bottom, so we hope you enjoy this one and please give her some more shout-outs is you like what you see. 🙂

Hottest MILF Monica Mendez

She’s an MILF that you will desire for the rest of your life!

Lana Kendrick Flashing her Big Boobs

Lana Kendrick goes kinky in showing her enormous boobs while in the car.

Girls on Playboy

Home of beautiful models you will see them all naked and naughty. Watch the girls stripping, masturbating, and reaching orgasm you will never experienced for the rest of your life.

Tessa Fowler – Halloween 2016 – 2

Impossible sexy 32GG Tessa Fowler is back, baby! We're here for the pre-Halloween Friday celebration and what better way to celebrate that than with Tessa, are we right? Of course we are... rhetorical question! 😉 Tessa returns with another one of her patented...

Gia Ramey-Gay In Effortlessly Sexy

Cybergirl of the Year Gia Ramey-Gay is effortlessly sexy in this set from photographer Holly Randall. An incredible natural beauty, Gia looks good in just about anything she wears, but she’s damn near irresistible in a dress. “What I wear depends on the occasion,” she...

Brittney Shumaker In Little Red Devil

With help from photographer Jennifer Vaughn, Cybergirl Brittney Shumaker is going to be a very, very bad girl for Halloween, which is a stretch for the blue-eyed beauty. “In my free time, I like to volunteer for my church. I love to help people,” says Brittney, who’s...

Mashup Best Of Costumes Vol. 2

The sky is black, the pumpkins have been carved and the bowls of candy have been filled—it’s Halloween weekend, and our Playboy Plus models are ready to trick-or-treat tonight. First up, blonde-haired Chloe Crawford is a Las Vegas magician’s assistant, and she’s ready...

Brittney Shumaker In Naughty By Nature

A voluptuous, all-natural body is a sight to behold, and when it’s a figure as sexy as Cybergirl Brittney Shumaker’s, it should be downright worshipped. With her buxom chest, piercing blue eyes and delightful derriere, Brittney knows how to work her assets for the...

Unpublished: Before They Were Playmates

You guys asked for it and we listened—thanks to repeated requests, Playboy Plus is opening up the vault and giving you a glimpse at never-ever-before-seen content. Get a whole new look at all of your favorite models with our new series, Unpublished. Kicking off our...

Vera Dimova In Playboy Netherlands

From the streets of Holland to the beaches of Mexico, Dutch beauty Vera Dimova is Playboy Mexico’s Playmate of the Month for June 2013, and it’s not hard to see why that is. The petite blonde is in tune with her body—she knows what her figure wants and what it needs...

Bailey Rayne Is In The Mood

Newcomer Bailey Rayne experienced a flood of emotion during her first Playboy Plus shoot with photographer Holly Randall. The busty beauty wearing red lingerie was very nervous, but so excited to finally call herself a Playboy Plus model after being asked to pose...

Mashup Exotic Beauties Vol. 4

Exotic beauties are our focal point this Mashup Sunday and boy, do we have a diverse collection of sexy models lined up for Playboy Plus fans. First up, Cybergirl Jody Lee is injecting some much-needed Indian spice to our roster with her long black hair and...

Eden Arya In Afternoon Delight

Eden Arya is your Cybergirl of the Month for October 2016, and she’s an afternoon delight in this set from photographer Holly Randall. Clad in a teddy and a slinky robe, Eden’s hanging around in her bedroom. It may be early in the day, but her thoughts are tending...

Tessa Fowler – Wet 5D 1

Hey hey everyone! I am back again in the pool and out of my tiny bikini top, just in time to give you a nice pre-weekend boost here on a Friday... Shooting in the pool is always a favorite of mine, and it's aleways nice when I can take off my top and just let them...

Tessa Fowler – Trekkie Babe 1

Hey everyone and happy October! Tommorrow is the first day of the Halloween month and I have my first Halloween video up today... So if you like Star Trek and big tits, then this should be exactly up your alley. 🙂 Xoxoxo -- Tessa [gallery link="none" columns="1"...

Tessa Fowler – Tiny Mint Top 1

Hey guys and happy Friday! More new HD video is here... are you ready? This tiny top can barely contain my big boobs, so you better watch out! 😉 Xoxoxo -- Tessa [gallery link="none" columns="1" size="large"...

Demmi Blaze – Sexy Shower 2

Starring:Demmi Blaze Supremely busty girl-next-door 32J Demmie Blaze is back with some Friday hot shower action and soapy big boobs play! We're goig to keep it short and sweet yet again this week, because Demmiy really needs no further hype or introduction... Just...

Jana Defi – Jessica Rabbit Blues 1

Starring:Jana Defi It's October! And those of you who have been fans and members with us for a long time or in the past know, that is one of our favorite months, because we get to dress up our fabulously sexy pinup gals here at PinupFiles in a variety of cool, fun and...

September Carrino – Pinup Cami Redux 2

Starring:September Carrino We are back at it on a Friday folks and we have the lovely and soon-to-be retired 32JJ September Carrino to give us one more fabulous look at the many things that make her so fabulous. Sexy September is back at it here at PinupFiles in the...

Dacia Maria In Linger

Newcomer Dacia Maria is a gorgeous natural beauty who always felt her small hometown wasn’t exciting enough. “I was born and raised in a small town that I hated,” laughs the petite former gymnast. “Now, I travel the world for an amazing job that I love.” Calling Las...

Olivia Preston In Free Ride

Olivia Preston has recently become a Cybergirl, and she couldn’t be happier about it. “I want to model for Playboy Plus because they have a long-lasting reputation of representing women in positive way, in a classically sexy manner,” explains the all-natural Canadian...

Marianna Merkulova In Undress Me

Romance is a vital part in any successful relationship, and for International model Marianna Merkulova, it’s the most important aspect. “In the bedroom, I think that love is the main element,” says Marianna as she slips into her black lingerie with sexy cutouts. While...

Jovana Tubic In Playboy Serbia

Say zdravo to Jovana Tubic, a gorgeous Playboy model from Belgrade, Serbia who loves to get creative with her hands. Designing her own jewelry and modeling full-time for Playboy leaves little time for the all-natural Serbian to do much else, especially date—but if...

Gia Ramey-Gay In Good Morning

Cybergirl of the Year Gia Ramey-Gay starts the day so, so right in this set from photographer Holly Randall. In a cute set of pajamas, Gia’s having a cup of coffee in the kitchen. Maybe it’s the caffeine, but she starts to get excited, and before you know it, she’s...

Anita Sikorska In Playboy Poland

Emerging from the beautiful city of Warsaw comes Poland’s Playmate of the Year 2014, Anita Sikorska. The tall, all-natural brunette was an instant fan-favorite amongst Playboy’s Polish audience and now with her photos making their way over to the Western side of the...

Ali Rose In Luscious Lounge

Cybergirl Ali Rose has always been fascinated with astronomy, so when she heard there was going to be a meteor shower, you bet she whipped out her telescope on photographer Damir K’s set. Looking up to the sky to catch a glimpse at the wonders of the universe, the...

Olivia Preston In Amazing View

Newcomer Olivia Preston is making her Playboy Plus debut with the help of photographer Cassandra Keyes—the two teamed up for an adrenaline-pumping set in British Columbia’s scenic Selkirk mountain range, and the results will give your heart a serious workout. The...

Mashup Best Of Brunettes Vol. 5

It’s Mashup Sunday and we’re focusing on International models who rock dark locks. First up, New Zealand’s Lily Rae shows our cameras why a naturally curvy body is always at its sexiest when it’s framed by long, dark hair. Britain’s Ann Denise flaunts her wavy brown...

Lusting Busty Tessa Fowler See-through Lingerie

Hey everyone... Time to brighten your day with some more sexy new photos! I'm back with the see-through lingerie, only there's nothing to see through any more because it's OFF (LOL). Hope you have a great rest of the week! [gallery link="file" columns="1" size="large"...

Bosomy Babe Tessa Fowler In Mint Tiny Bra

Hey everyone! I'm back with more sexy new shots that I just shot (how's that for a double noun-verb usage?) It's a very sexy mint-colored top and it's the perfect shirt for my big boobies. 😉 [gallery link="file" columns="1" size="large"...

Busty Tessa Fowler Wet And Sultry

I'm back with some more fantastic new big boobie bikini video in the pool... Because while the weather may be cooling off, that doesn't mean we can't keep things heated up here in our little corner of the web, does it? 😉 Have a great one and see you next week!...

Irene Hoek In Playboy Netherlands

Playboy Netherlands has been gracious enough to share with us their Playmate of the Year 2010, Irene Hoek. The voluptuous brunette was born and raised in Netherlands, but is a blend of Dutch, Filipino, Chinese and Spanish. Her exotic features and all-natural body were...

Kelsi Shay In Leather Bound

Kelsi Shay is your Cybergirl of the Month for September 2016, and she’s leather-bound in this amazingly hot set from photographer Holly Randall. This awesome gallery sees our CGOM like you’ve never, ever seen her before—her dark hair tied up in a high ponytail,...

Lauren O’Conner In Full Bloom

Wearing her white bodysuit with light-blue roses and jean shorts, Cybergirl Lauren O’Conner came to photographer Holly Randall’s set ready to prove that she’s CGOM material, even though her modeling experience comes from an unusual source. “For the past two years, I...

Ivi Pizzot In Playboy Brazil

Coming to Playboy from the land of curves, plump booties and samba music is international model Ivi Pizzott. The curly-haired Brazilian is a professional dancer on her country’s most-popular variety show, Domingão do Faustão when she isn’t modeling, hitting the gym or...

Kelsi Shay In Summer Lover

Kelsi Shay is your Cybergirl of the Month for September 2016, and she’s a vision in this set from photographer Holly Randall. From the moment she appeared on Playboy Plus, Kelsi earned a rabid following—after all, who wouldn’t drool over this bold, curvy brunette? “I...

Shelly Lee In Weekend Getaway

Cybergirl Shelly Lee thought she had prepared everything she needed for her weekend getaway, but upon arriving to a quaint bed-and-breakfast, she realized she forgot to pack something very important—a change of clothing. “My worst quality is that I’m an over-thinker...

Mashup Confessions Vol. 2

It’s Sunday and our badly-behaved Playboy models are looking to confess their sins on camera for the first time. First up, CGOM Taylor Seinturier shows us that when she’s home alone, keeping her clothes on is nearly impossible, while all-natural Jenna Sativa confesses...

Laura Cattay In Playboy Argentina

Argentinian model Laura Cattay is our hotel cutie in this photoshoot by photographer Luis Sens. Believing that saying ‘good morning’ isn’t enough, the voluptuous brunette shows us how to truly embody the phrase by wearing her absolute favorite black corset with...

Shelly Lee In Bombshelly

Small-town girl Shelly Lee is back at it again with photographer Cassandra Keyes for her latest shoot where the bombshell with the long, black hair and voluptuous figure transforms into her femme fatale alter ego, Bombshelly. Wearing her black, sheer lingerie complete...

Mashup Tropical Treasures Vol. 1

Nothing suggests hot, sexy times like tropical locations, and with that in mind, we’re headed on vacation with four of our favorite models. First up, Australian cutie Jessica Ann is sweltering hot on location in Bali, and blonde-haired babe Alana Wolfe is undoubtedly...

Oxana Voznyuk In Playboy Russia

Russian International model Oxana Voznyuk is a wonder in this set from photographer Sergei Korolkov. Tall and busty, with long, chocolate-brown hair, Oxana comes to us from St. Petersburg, where she’s known as Russia’s Miss June 2012. Blessed with a wealth of...

Angel B & Pamela In Perfect Stroke

International models Angel B and Pamela are good-good—no, great—in this golf-themed set from photographers Fredrik Andersson and Stanislav Vorobyev. Both natural beauties from Kiev, Angel and Pam love to spend time with each other. Today it’s golfing in little tank...

Kailena In Feels Like Heaven

International model Kailena is heaven on earth in this hot, wet set from photographer Stanislav Vorobyev. Last time we saw Kailena, she was shooting on an island in the Mediterranean—and in keeping with that sunny, semi-tropical theme, we whisked her off to Thailand...

Tessa Fowler – Cave Girl

Hey there everyone...Time to head back to the cave of big boobies! 😉 I love to shoot outdoors and this cave location at the beach where I was shooting turned out to be the perfect place. [gallery link="file" columns="1" size="large"...

Leanne Crow – Diary Day Piano Perfect – Set 2

Hey hey gang...Who is ready for some more fab diry shots of a big breasted babe (now who could I possibly be referring to?) playing piano? You would be surprised what you can do when you have a pair of 32K's!  😉 [gallery link="file" columns="1" size="large"...

Lana Kendrick – Comic Beauty – Set 3

I was discovered by the photographers at Pinup Files and decided to give modeling a try. I had gone to those modeling scout outs before but they always wanted me to lose weight. For the first time, the wanted me as-is. 🙂 [gallery link="file" columns="1" size="large"...

Deanna Greene In Show Me Your Room

Cybergirl Deanna Greene is sweet and a little bit spicy in this set from photographer Michael Valentino. We knew we had a good thing on our hands with Deanna, but we didn’t anticipate such a strong outpouring of support—Miss Greene is one of the most popular models...

Lana Rhoades In Lip Service

Newcomer Lana Rhoades pays us a little lip service with this seductive set from photographer Holly Randall. An all-natural brunette from Chicago, Illinois, Lana is the girl next door and the sexy femme fatale, all rolled up in one gorgeous package. “In high school, I...

Sapphira In Exotic Allure

International model Sapphira is back, and she’s a ray of sunshine in this set from photographer Stanislav Vorobyev. With her dark hair and tanned skin, Sapphira stuns in a bright yellow dress. Lifting up her skirt, she gives us all a peek at what’s underneath, and...

Mashup Sexy Showers Vol. 2

Beautiful women taking hot, steamy showers—come on, what’s not to like? First up, all-natural Alissa Arden can’t even wait to undress before jumping in the shower, and Marga Cifuentes and Celeste Sablich get all lathered up together. European sweetheart Anna Tatu gets...

Emily Bloom In Forbidden Fruit

Emily Bloom is your Cybergirl of the Month for June 2016, and she’s anything but forbidding in this juicy set from photographer Holly Randall. For her final set, we wanted to do something fitting for a fairy-tale beauty like Emily—so we lit a few candles, spread out...

Jasmine In After Hours Strip

International model Jasmine is absolutely delicious in this hot set from photographers David Merenyi and Gabor Klinzsky. It’s late, but Jasmine isn’t the least bit tired—in fact, she’s ready to strip down and be your midnight snack. Treating yourself never felt—or...

Sabrina & Brittney In Bedroom Romp

Sabrina Nichole and Brittney Shumaker get naughty with each other in this searing hot set from photographer Jennifer Vaughn. When we first teased this pictorial on social media, the response was overwhelming—Sabrina and Brittney are two of the hottest models on Plus,...

Deanna Greene In Hot Commodity

Newcomer Deanna Greene is not so innocent in this set from photographer Michael Valentino. An all-natural brunette from Virginia Beach, Deanna is a model and Hooters girl who rightfully turns heads w wherever she goes. Talk about a hot commodity—they’ve gotta be...

Clara In Good Morning

International model Clara gets your day off to a sweet start with this set from photographer Robert Haas. In pale pink satin, Clara wakes up and decides it’d be more fun to spend the morning in bed. Slipping out of her pajamas and into the nude, she tangles herself up...

Josée Lanue In Barber’s Chair

Newcomer Josée Lanue is a cut above the rest in this set from photographer Cassandra Keyes. Petite and all natural, with brownish-red hair and blue eyes, Josée comes to us from Montreal, a French-speaking city in Canada. “I think all healthy bodies are beautiful,” she...

Alyssa Bennett In After Hours

Cybergirl Alyssa Bennett stays late in this hot set from photographer Cassandra Keyes. In a set of black lingerie, complete with garter belt and stockings, Alyssa is closing down the bar in the best possible way. “I had so much fun shooting these photos,” she says...

Skylar Leigh In Magnetic Meadows

International model Skylar Leigh goes frolicking in this sexy set from photographer Cassandra Keyes. On her home turf in rural New Zealand, Skylar felt more than comfortable, and didn’t hesitate to take her clothes off and enjoy nature. “New Zealand is a really...

Tahlia Paris In Rich Indulgence

Cybergirl Tahlia Paris is indulgent in this set from photographer Holly Randall. For her first set, Tahlia was the girl next door, so this time around, we gave her the full sex kitten treatment. In a sheer lingerie, full-length gloves and heels, she’s looking every...

Kailena In Secret Lover

Ukrainian International model Kailena is simply delicious in this gorgeous set from photographers Fredrik Andersson and Stanislav Vorobyev. In little more than a bra and panties, Kailena’s hanging out in the garden, and she fits right in with her surroundings. From...

Cindie Louu In Honeysuckle

Newcomer Cindie Louu is sweeter than honey in this set from photographer Jennifer Vaughn. Petite and all natural, Texas-born Cindie has sex appeal to spare, so she decided to try her hand at modeling for Playboy Plus. A cute bra and panties, not to mention a bowl of...

Winter Holiday With The Hotties

This Mash-Up Monday, we’re getting the holidays off to a hot start with eight of our favorite Playboy Plus models. First up, dark-haired beauty Stefanie Knight rings in the New Year in the nude, and Cybergirls Ali Rose and Elizabeth Marxs exchange presents—and a few...

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