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! đ 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 sheâs damn near irresistible in a dress. âWhat I wear depends on the occasion,â 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. âIn my free time, I like to volunteer for my church. I love to help people,â says Brittney, whoâs...
Mashup Best Of Costumes Vol. 2
The sky is black, the pumpkins have been carved and the bowls of candy have been filledâitâs Halloween weekend, and our Playboy Plus models are ready to trick-or-treat tonight. First up, blonde-haired Chloe Crawford is a Las Vegas magicianâs assistant, and sheâs ready...
Brittney Shumaker In Naughty By Nature
A voluptuous, all-natural body is a sight to behold, and when itâs a figure as sexy as Cybergirl Brittney Shumakerâs, 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Unpublished: Before They Were Playmates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 listenedâthanks 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 Get a whole new look at all of your favorite models with our new series, Unpublished.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 Mexicoâs Playmate of the Month for June 2013, and itâs not hard to see why that is. The petite blonde is in tune with her bodyâshe 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 sheâs an afternoon delight in this set from photographer Holly Randall. Clad in a teddy and a slinky robe, Edenâs 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. đ 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! đ 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 wasnât exciting enough. âI was born and raised in a small town that I hated,â laughs the petite former gymnast. âNow, I travel the world for an amazing job that I love.â Calling Las...
Olivia Preston In Free Ride
Olivia Preston has recently become a Cybergirl, and she couldnât be happier about it. âI want to model for Playboy Plus because they have a long-lasting reputation of representing women in positive way, in a classically sexy manner,â 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, itâs the most important aspect. âIn the bedroom, I think that love is the main element,â 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 dateâbut 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, Giaâs having a cup of coffee in the kitchen. Maybe itâs the caffeine, but she starts to get excited, and before you know it, sheâs...
Anita Sikorska In Playboy Poland
Emerging from the beautiful city of Warsaw comes Polandâs Playmate of the Year 2014, Anita Sikorska. The tall, all-natural brunette was an instant fan-favorite amongst Playboyâs 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 Kâs 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 Keyesâthe two teamed up for an adrenaline-pumping set in British Columbiaâs scenic Selkirk mountain range, and the results will give your heart a serious workout. The...
Mashup Best Of Brunettes Vol. 5
Itâs Mashup Sunday and weâre focusing on International models who rock dark locks. First up, New Zealandâs Lily Rae shows our cameras why a naturally curvy body is always at its sexiest when itâs framed by long, dark hair. Britainâs 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. đ [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? đ 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 sheâs leather-bound in this amazingly hot set from photographer Holly Randall. This awesome gallery sees our CGOM like youâve never, ever seen her beforeâher 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 OâConner came to photographer Holly Randallâs set ready to prove that sheâs CGOM material, even though her modeling experience comes from an unusual source. âFor 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 countryâs most-popular variety show, DomingĂŁo do FaustĂŁo when she isnât modeling, hitting the gym or...
Kelsi Shay In Summer Lover
Kelsi Shay is your Cybergirl of the Month for September 2016, and sheâs a vision in this set from photographer Holly Randall. From the moment she appeared on Playboy Plus, Kelsi earned a rabid followingâafter all, who wouldnât drool over this bold, curvy brunette? âI...
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 importantâa change of clothing. âMy worst quality is that Iâm an over-thinker...
Mashup Confessions Vol. 2
Itâs 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 sheâs 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 âgood morningâ isnât 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, weâre 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 sheâs known as Russiaâs Miss June 2012. Blessed with a wealth of...
Angel B & Pamela In Perfect Stroke
International models Angel B and Pamela are good-goodâno, greatâin 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 itâs 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 Mediterraneanâand 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! đ 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! đ [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. đ [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 didnât anticipate such a strong outpouring of supportâMiss 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. âIn high school, I...
Sapphira In Exotic Allure
International model Sapphira is back, and sheâs 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 whatâs underneath, and...
Mashup Sexy Showers Vol. 2
Beautiful women taking hot, steamy showersâcome on, whatâs not to like? First up, all-natural Alissa Arden canât 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 sheâs 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 Emilyâso 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. Itâs late, but Jasmine isnât the least bit tiredâin fact, sheâs ready to strip down and be your midnight snack. Treating yourself never feltâor...
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 overwhelmingâSabrina 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 commodityâtheyâve 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 itâd be more fun to spend the morning in bed. Slipping out of her pajamas and into the nude, she tangles herself up...
JosĂ©e Lanue In Barber’s Chair
Newcomer JosĂ©e 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, JosĂ©e comes to us from Montreal, a French-speaking city in Canada. âI think all healthy bodies are beautiful,â 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. âI had so much fun shooting these photos,â 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 didnât hesitate to take her clothes off and enjoy nature. âNew 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, sheâs 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, Kailenaâs 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, weâre 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 presentsâand a few...
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