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Tiffany Fallon is Playmate of the Year 2005, and we?ve got 60 pictorials and 75 videos of Tiffany to commemorate the occasion.?

Models on This Gallery: Tiffany Fallon

Gallery tags: Emo Glamour Gorgeous

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Playboy Plus is on set with Hayden Hayes to shoot her exclusive pictorial. Get to know more about Hayden Hayes by watching our behind the scenes footage and the complete nude version available exclusively on Playboy?

Models on This Gallery: Shawna Lenee

Gallery tags: Boy Glamour Gorgeous

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Super sexy Krystal Webb on the stripper pole!

Gallery tags: Babe Foot fetish Footjob

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Playboy Plus is on set with Brandie Moses to shoot her exclusive pictorial. Get to know more about Brandie Moses by watching our behind the scenes footage and the complete nude version available exclusively on Playbo?

Gallery tags: Anal Blowjob Boy

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Playmate Exclusives March 2005 - Jillian Grace?

Gallery tags: Glamour Gorgeous Pornstar

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Super hot pornstar haley cummings gets her huge big tits creamed and pussy fucked hard in this big real titty fuck picset

Models on This Gallery: Hailey Page

Gallery tags: Big tits Hardcore Pornstar

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Playmate Xtra - Cara Zavaleta 01?

Gallery tags: Glamour Gorgeous Pornstar

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Two bold, bright, beautiful entrepreneurs show how to succeed in business with out-and-out trying. From August 1984?

Gallery tags: Amateur Beautiful Blowjob

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Busty babe in white undies pose under lavander light

Models on This Gallery: Taylor Vixen

Gallery tags: Amateur Big tits Brunette

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Models on This Gallery: Tera Patrick

Gallery tags: Asian Big tits Glamour

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Brunette Squats In White Boots & Stuffs Her Snatch

Gallery tags: Babe Big tits Boots

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Gorgeous Hungarian babe Cindy with a glass dildo

Models on This Gallery: Silvia Saint

Gallery tags: Ass Babe Dildo

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2 Hot Russian Babes Take A Cock & A Glass Dildo

Models on This Gallery: Silvia Saint

Gallery tags: Ass Babe Dildo

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Krystal Lyne - Real American Girls?

Gallery tags: American Girl Glamour

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"Our sexy Sicilian isn't shy when it comes to appearing nudo here. ""I never close my blinds, so many people have probably already had a sneak peek,"" Jia says. When not buried under her med school books, Jia works on h?"

Models on This Gallery: Yuki Mori

Gallery tags: Anal Blowjob Close-ups

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Hiya everyone! I am nearly back from my holiday and back to the grind, but in the meantime I have another new smashing set of big boob photos for you here. It is part two of my Eater Blue shoot so I hope you like them! xoxoxo -- Rachel

Models on This Gallery: Rachel Aldana

Gallery tags: Big tits Brunette Pornstar

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Models on This Gallery: Abbey Brooks Christie Stevens Danny Mountain

Gallery tags: Amateur Ass Boots

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Karol Lilien Sucks Black Cock & Balls In The Tub

Gallery tags: Black Blowjob Cumshot

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Young Russian Babe Neona Masturbates In The Shower

Gallery tags: Babe Gorgeous Masturbation

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Playboy Plus is on set with Lauren Elise to shoot her exclusive pictorial. Get to know more about Lauren Elise by watching our behind the scenes footage and the complete nude version available exclusively on Playboy?

Gallery tags: Boy Game Glamour

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Playboy Plus is on set with Nancie Le to shoot her exclusive pictorial. Get to know more about Nancie Le by watching our behind the scenes footage and the complete nude version available exclusively on Playboy Plus.?

Gallery tags: Blonde Blowjob Boy

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It's not hard to see why Brandy is one of our most popular models: she has that rare mix of stunning looks, magnetic sex appeal, toned and tan body, succulent lips and heavenly hooters, not to mention she's a pretty fun and funny gal to be around.

Models on This Gallery: Brandy Robbins

Gallery tags: Big tits Blowjob Brunette

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Rosalina Love Rubs a Huge Magic Wand on Her Snatch

Models on This Gallery: Silvia Saint Stacy Silver

Gallery tags: Babe Foot fetish Gorgeous

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Playboy Plus is on set with Trina Marie to shoot her exclusive pictorial. Get to know more about Trina Marie by watching our behind the scenes footage and the complete nude version available exclusively on Playboy Pl?

Gallery tags: Ass Big cock Big tits

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Models on This Gallery: Tera Patrick

Gallery tags: Asian Big tits Pornstar

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The hell fucked out of sexy Bella Baby by Sabby

Gallery tags: Foot fetish Footjob Hardcore

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Playboy.com is on set with Sydney Barlette to shoot her exclusive pictorial. Get to know more about Sydney Barlette by watching our behind the scenes footage and the complete nude version available exclusively on Pla?

Gallery tags: Big tits Boy Brunette

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WINTER WONDERLAND From ski bunny to Playboy bunny, Miss January Karina Marie hits the sauna Photography by Sasha Eisenman Imagine the ultimate ski trip?on the sun-kissed slopes of Chamonix, perhaps. Now imagine?

Gallery tags: Boy Glamour Gorgeous

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Monica Mendez in tangerine gown

Gallery tags: Brunette Busty

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Mancow's nude Playboy photo shoot is udderly outrageous. Mancow Muller, America's most sex-obsessed radio host, stepped out from behind his mike and put his Nikon where his mouth is. Demonstrating his way with th?

Gallery tags: Amateur Blonde Boy

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When this week's Cyber Girl told us she was already in the Cyber Club, we were dumbstruck that we didn't recognize the blue-eyed beauty. As it turns out, Chem Leigh rolled by us so quickly, we hardly had a chance to?

Models on This Gallery: Brooklyn Chase

Gallery tags: Club Girl Glamour

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Playboy Plus is on set with Deanna Brooks to shoot her exclusive pictorial. Get to know more about Deanna Brooks by watching our behind the scenes footage and the complete nude version available exclusively on Playbo?

Models on This Gallery: Deanna Brooks

Gallery tags: Boy Glamour Gorgeous

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Models on This Gallery: Alice Romain Tera Patrick

Gallery tags: Amateur Asian Big tits

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PREMIUM PLAYMATE insurance secretary Lori Winston is a delightful June dividend Because insurance companies evoke images of monolithic statistical tables and multipage rate charts and contracts, we were especial?

Gallery tags: Glamour Gorgeous Pornstar

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Models on This Gallery: Tera Patrick

Gallery tags: Asian Big tits Glamour

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Congratulations to Jennifer Vaughn, our Cybergirl of the Year 2013! Cybergirl Jennifer Vaughn is a little bit of everything. She?s Spanish, Italian, Slovak and Czech, with the blonde hair, blue eyes

Models on This Gallery: Jennifer Vaughn

Gallery tags: Blonde Blowbang Blowjob

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Heya there everyone...I have another fab big boobs photo set to take you into your weekend and, much like the last one i put up, it's got MORE purple! ;-) Have a great weekend and I will chat with you next week! xoxoxo -- Rachel

Models on This Gallery: Chanel Preston Rachel Aldana

Gallery tags: Big tits Brunette Dad

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Gallery tags: Glamour Gorgeous Pornstar

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Very lucky black dude shagging four horny naked hotties

Gallery tags: Amateur Blonde Blowjob

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When Playboy first set eyes on Sylvie during the 25th Anniversary Playmate hunt, the Québécoise was living in Toronto, multitasking as a hostess on TV's The $128,000 Question, a model and seller of men's cloth?

Gallery tags: Amateur Blowjob Boy

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Gallery tags: Amateur Girl Glamour

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Big boob babes massaging each others gorgeous tits

Gallery tags: Ass Babe Gorgeous

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Breast Men's Vision Of Paradise Toying In A Sauna

Models on This Gallery: Silvia Saint

Gallery tags: Big tits Foot fetish Lesbian

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Playmate Xtra - Courtney Rachel Culkin 04?

Gallery tags: Big tits Blonde Blowjob

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Playboy Plus is on set with Stephanie Emma to shoot her exclusive pictorial. Get to know more about Stephanie Emma by watching our behind the scenes footage and the complete nude version available exclusively on Play?

Gallery tags: Amateur Boy Girl

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While we've often featured Playmates with outdoor proclivities, our sportsman's loving cup goes to China Lee, our August Playmate, one of the most athletic young lasses we've ever encountered and also one of the most?

Gallery tags: Ass Big tits Blonde

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Playboy.com is on set with Carly Madison to shoot her exclusive pictorial. Get to know more about Carly Madison by watching our behind the scenes footage and the complete nude version available exclusively on Play?

Gallery tags: Anal Blowjob Boy

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Playboy Plus is on set with Jurgita Valts to shoot her exclusive pictorial. Get to know more about Jurgita Valts by watching our behind the scenes footage and the complete nude version available exclusively on Playbo?

Models on This Gallery: Natalia Starr

Gallery tags: Ass Boy Ffm

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What?s a nice girl to do when her Grammer?s just so bad? In 1993, corn-fed Kansas beauty Tammi Alexander arrived in California from Las Vegas to try her luck as a model when she met her future fiancé, actor Kelsey Gr?

Gallery tags: Girl Glamour Gorgeous

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Busty Rachel in panties showing super huge titties

Gallery tags: Ass Blowjob Brunette

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What do we look for in a girl? Well, start with a free spirit. After that, beauty, brains and a certain athleticism rank high on the list. Mix all that up in one girl and you've got a winner. Take Heather Rene Smith,?

Gallery tags: Big tits Dildo Girl

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A reunion with 11 Centerfold ladies from years past proves that some women, like some wines, get better with age. See the original pictorial from December 1979 plus never-before-seen photos.?

Gallery tags: Glamour Gorgeous Pornstar

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Fascinated by the human brain, Cyber Girl 100 candidate Dayna wants to become a psychologist?she specializes in penetrating the male mind. ?I?m the kind of girl guys love to talk to,? she explains. ?I always know wha?

Models on This Gallery: Ava Vincent

Gallery tags: Anal Blowjob Girl

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Playboy Plus is on set with Kortnie O'Connor to shoot her exclusive pictorial. Get to know more about Kortnie O'Connor by watching our behind the scenes footage and the complete nude version available exclusively on?

Gallery tags: Boy Glamour Gorgeous

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Hi gang! It is Easter Weekend and while you are out hunting for Easter Eggs, how about hunting for some big boobs in a bubbly bubble bath, too!

Models on This Gallery: September Carrino

Gallery tags: Amateur Big tits Brunette

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Hey there everyone! That would be me, my gigantic boobs, lots of awesome big booby closeups, my big succulent nipples and the fantastic sexy outfit to show it all off! It's also an all-nude photo set and I know you'll like that! xoxoxo -- September

Models on This Gallery: Aubrey Adams September Carrino

Gallery tags: Amateur Babe Big tits

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Domme Eve Angel in Latex Spanks Liza del Sierra

Models on This Gallery: Silvia Saint

Gallery tags: Brunette Foot fetish Latex

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In February 1963 we noted that no picture story provided a bigger kick (for our readers and ourself) than the Playmate Holiday House Party in our Eighth Anniversary issue. Following a full dozen of Playboy's pretties?

Gallery tags: Blonde Boy Brunette

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Fuck Haley in her bubble butt and blast a thick load of dick snot into her sky blue eyes,

Gallery tags: Hardcore Pornstar

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Newcomer Amirah stuffs her nice and juicy twat!

Gallery tags: Babe Foot fetish Footjob

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Russian Blonde Babe Spreads Herself Wide in Doggie

Gallery tags: Babe Blonde Gorgeous

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Playboy Plus is on set with Nicole Woodruff to shoot her exclusive pictorial. Get to know more about Nicole Woodruff by watching our behind the scenes footage and the complete nude version available exclusively on Pl?

Gallery tags: Beach Blonde Boy

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Russian Hottie Kristall Rush Sucks On Monster Meat

Gallery tags: Blowjob Cumshot Pornstar

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Models on This Gallery: Tera Patrick

Gallery tags: Asian Big tits Pornstar

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Latina pornstar Emanuelle Diniz gets her ass stuffed

Gallery tags: Amateur Ass Hardcore

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Playboy Plus is on set with Natalie Taylor to shoot her exclusive pictorial. Get to know more about Natalie Taylor by watching our behind the scenes footage and the complete nude version available exclusively on Play?

Gallery tags: Boy Glamour Gorgeous

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Yes, the face is familiar. Two years ago, when Playboy was scouting the West Coast for coeds to put in the Girls of the PAC 10 pictorial, somebody handed us a slip of paper with a name and number: Call this gi?

Gallery tags: Boy College Face

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Playboy.com is on set with Evelyn Garcia to shoot her exclusive pictorial. Get to know more about Evelyn Garcia by watching our behind the scenes footage and the complete nude version available exclusively on Pla?

Gallery tags: Boy Glamour Gorgeous

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We are very excited to announce that 32DD Shay Laren is the latest new hot busty babe to bring her talents to our web pages! Shay is another amazing babe with a fantastic body and big natural breasts topped off by a terrific smile.

Gallery tags: Ass Babe Big tits

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Gallery tags: Amateur Asian Big tits

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The Holidays are upon us, and Erika Knight and Justine Miller are up on each other in this beautiful pictorial. The girls are decorated in black lingerie, draped with a string of lights like a Christmas tree. They?re?

Gallery tags: Beautiful Black Girl

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Tess gives you a sexy pussy and ass show in heels

Models on This Gallery: Silvia Saint

Gallery tags: Ass Babe Foot fetish

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Technician gets his cock and mind blown by 2 babes

Gallery tags: Babe Pornstar

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Playboy Plus is on set with Hillary Fisher to shoot her exclusive pictorial. Get to know more about Hillary Fisher by watching our behind the scenes footage and the complete nude version available exclusively on Play?

Gallery tags: Big cock Boy Girl

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Playmate Xtra - Jami Ferrell 01?

Gallery tags: Dildo Glamour Gorgeous

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Flawles blonde fucking her pussy with a banana

Gallery tags: Babe Blonde Cameltoe

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Farm Girl Sweet Cat Gets Fucked Doggie In The Barn

Models on This Gallery: Silvia Saint

Gallery tags: Foot fetish Girl Hardcore

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Think the Art Deco buildings are what make Miami Beach so easy on the eyes? Could be, but we think Maria Checa's presence there has a little something to do with its beauty, too. And there's nothing like a Playboy Cy?

Gallery tags: Beach Boy Glamour

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Models on This Gallery: Tera Patrick

Gallery tags: Asian Big tits Glamour

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Playboy Plus is on set with Kimberly Phillips to shoot her exclusive pictorial. Get to know more about Kimberly Phillips by watching our behind the scenes footage and the complete nude version available exclusively o?

Models on This Gallery: Kimberly Phillips

Gallery tags: Amateur Boy Girl

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Models on This Gallery: Aarielle Alexis Tera Patrick

Gallery tags: Amateur Asian Ass

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Gorgeous lesbos fucking with a champagne bottle

Models on This Gallery: Silvia Saint

Gallery tags: Babe Foot fetish Gorgeous

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Hot, hot, hot! Watch as we ratchet up the heat with some extremely sexy and steamy uncensored photos in Special Editions Xtreme.?

Gallery tags: Extreme Glamour Gorgeous

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Busty babe Nicole Aniston and Audrey Bitoni have hot threesome with big cock

Models on This Gallery: Nicole Aniston

Gallery tags: Babe Big cock Big tits

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World travelers may recognize this fabulously beautiful woman. Her name is Giuliana Marino, and she is German Playboy's Playmate of the Year for 2006. Hef met her in Munich on a recent trip and found her charm irresi?

Gallery tags: Beautiful Big tits Boy

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Playboy.com is on set with Jessica Workman to shoot her exclusive pictorial. Get to know more about Jessica Workman by watching our behind the scenes footage and the complete nude version available exclusively on Pla?

Gallery tags: Asian Blowjob Boy

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Playboy.com is on set with Sarah Summers to shoot her exclusive pictorial. Get to know more about Sarah Summers by watching our behind the scenes footage and the complete nude version available exclusively on Playboy?

Gallery tags: Amateur Boy Brunette

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Alysa Gap rubs & gapes her pink delicious pussy

Gallery tags: Anal gape Babe Blonde

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Redhead Cutie Denisa Shows Her Puckered Asshole

Gallery tags: Ass Gorgeous Pornstar

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Hairy pussy pie meets a big red shiny dildo

Gallery tags: Dildo Hairy Pornstar

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Models on This Gallery: Tera Patrick

Gallery tags: Amateur Asian Big tits

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Playmate of the Month August 2005 - Tamara Witmer?

Gallery tags: Big tits Glamour Gorgeous

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Playboy.com is on set with Sarah Clayton to shoot her exclusive pictorial. Get to know more about Sarah Clayton by watching our behind the scenes footage and the complete nude version available exclusively on Playbo?

Models on This Gallery: Amelia Talon

Gallery tags: Boy Game Glamour

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We ask all our Cyber Girls a series of questions to get to know them a little better and then we cull the funniest/sexiest snippets to show you that our Cyber Girls' personalities are just as beautiful as their featu?

Gallery tags: Beautiful Girl Glamour

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Playboy Plus is on set with Kellie Acreman to shoot her exclusive pictorial. Get to know more about Kellie Acreman by watching our behind the scenes footage and the complete nude version available exclusively on Play?

Gallery tags: Amateur Blowjob Boy

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Two fairly horny pornstars fucking peeing babes hardcore

Gallery tags: Blonde Blowjob Brunette

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Alison gives her bf a footjob at New Year's Eve!

Models on This Gallery: Cindy Dollar Silvia Saint

Gallery tags: Foot fetish Footjob Lesbian

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Gallery tags: Ass Girl Glamour

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Dominica Phoenix gets fucked hardcore by big cock

Gallery tags: Big cock Hardcore Pornstar

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Jay Dee taken in sandwich during hot shooting

Gallery tags: Foot fetish Footjob Hardcore

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Rachel Aldana and Denise in Bikini

Gallery tags: Blowjob Brunette Busty

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redfrill-set2

Gallery tags: Big tits Brunette Pornstar

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One look at Kelsi and it?s clear she can cure what ails any man. She plans to parlay that aspect of herself into a successful career as a pharmaceutical sales rep. As for what she?ll notice when she takes one look at?

Models on This Gallery: Jada Stevens

Gallery tags: Anal Ass Girl

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Leanne busts out of her denim bra

Models on This Gallery: Audrey Bitoni

Gallery tags: Amateur Boy Brunette

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Playboy.com is on set with Kyara Tyler to shoot her exclusive pictorial. Get to know more about Kyara Tyler by watching our behind the scenes footage and the complete nude version available exclusively on Playboy Pl?

Gallery tags: Amateur Blowjob Boy

16 Total pics

Joanna Bliss Squeezes Her Amazing Romanian Rack

Models on This Gallery: Silvia Saint

Gallery tags: Big tits Foot fetish Lesbian

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Eva Parcker & Lorena toe sucking and foot worship

Gallery tags: Blowjob Cameltoe Foot fetish

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Czech Teen Cutie Nici Plays wih her Pussy Outdoors

Gallery tags: Czech Gorgeous Outdoor

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Models on This Gallery: Adriana Kelly

Gallery tags: Amateur Big tits Brunette

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Hope you all had a good weekend! My new photos are up today so I hope you like them! Behind-the-scenes are always fun. xoxoxo - September

Models on This Gallery: septembercarrino.com

Gallery tags: Big tits Brunette Extreme

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Artist babe Madlin spreads them legs super wide

Models on This Gallery: Silvia Saint

Gallery tags: Babe Foot fetish Gorgeous

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Models on This Gallery: Lexie Marie

Gallery tags: Amateur Asian Big tits

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Playboy Plus is on set with Breann McGregor to shoot her exclusive pictorial. Get to know more about Breann McGregor by watching our behind the scenes footage and the complete nude version available exclusively on Pl?

Models on This Gallery: Breann McGregor

Gallery tags: Boy Glamour Gorgeous

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Playmate Exclusive February 2009 - Jessica Burciaga?

Gallery tags: Czech French Girl

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Delectable Tess makes love to a pink balloon

Models on This Gallery: Silvia Saint

Gallery tags: Babe Foot fetish Gorgeous

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Hey! I'm back again with another sparklingly sexy photo set today. Where I got to dress up as one of my favorite themes: a hot, tight and sexy black long-sleeve top. There's just something so sexy and so hor about a girl who dresses like this one!

Models on This Gallery: September Carrino

Gallery tags: Amateur Ass Big tits

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"She's one of Special Editions' most popular models, but Joy Behrman is still one of the sweetest girls we've met. When we asked her if she'd like to join the family of Cyber Girls, Joy was ecstatic. ""I felt extremely?"

Gallery tags: Extreme Girl Glamour

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Eve Angel Gets A Hot Hungarian Lesbian Massage

Models on This Gallery: Silvia Saint

Gallery tags: Ass Brunette Foot fetish

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Hot pornstar kristen get finger fucked by 2 hot lesbians in this support our troops naked charity event

Models on This Gallery: Christa Moore

Gallery tags: Amateur Girlfriend Hardcore

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Playboy Plus is on set with Julia Marino to shoot her exclusive pictorial. Get to know more about Julia Marino by watching our behind the scenes footage and the complete nude version available exclusively on Playboy?

Gallery tags: Boy Glamour Gorgeous

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