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Sensual blonde Gia spreads her long legs for us!

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Rachel Aldana in black and yellow

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Horny Eve Angel & Lucy Belle Get The Double Plunge

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

Modelleri: Katie Fey

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Sexy September exposes her amazingly large breasts

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"Reeling off Mei-Ling Lam\'s passions is a slam dunk. They begin and end with her beloved Boston Celtics. ""Kevin Garnett is my favorite player, but I also love Paul Pierce and Ray Allen,"" our 27-year-old Miss June says?"

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Hot clothed chicks washing their body outside with drinks

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"""I\'m really good at having fun!"" says 24-year-old Ashley Mattingly. Evidence of her carefree spirit: She revels in traveling on annual ""girls\' trips"" to such locales as Monaco and Greece (""I\'ve been to Santorini, Myk?"

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34HH Lorna Morgan is here and looking as amazing as ever. This is Part 2 of the set where she dons the tiny blue bikini that can barely contain her whopping HH\'s and then gives us a full blown lesson on the best way to suntan oil them up!

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Rachel Aldana in the sun poolside

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Playmate Exclusives November 2002 - Serria Tawan?

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A True Masturbation Virtuoso With A Glass Dildo

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

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Hot And Horny Italian Babe Valentina Nappi Teases

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Costa Rican by birth, Paulina Sanchez has all the qualities we find irresistable in Latin women. There is, of course, the smoldering good looks, the voluptuous figure and then the zest for life and love of music.?

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Leanne busts out of her denim bra

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Sexy Czech babe with a very hairy pussy pie!

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Sexy babe gets fucked by her big cocked client and has loud orgasms.

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Chrissy Titty & Pussy Fucking A Rabbit Pearl Vibe

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

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Big breasted Czech babe Shione strips for us!

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Playmate Exclusive March 2011 - Ashley Mattingly?

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Modelleri: Kiana Dior

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"According to Donna Edmondson -- Miss November and newly licensed real-estate agent -- the difference between a house and a home is simple: ""The home is what everyone dreams of having,"" she says, ""and the house is wha?"

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Sweet Curly-Haired Anna Mary Spreads Her Snatch

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Sara\'s huge breasts and gorgeous girl-next-door beauty have always been a fan favorite (not to mention one of our favorites) and we love seeing her massive boobs busting out of this tight button down top. Sara is a keeper in this one for sure.

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It\'s always refreshing to meet a woman who isn\'t a slave to fashion. After all, the things that make a woman attractive over the long run are those invisible qualities that come from the heart. So permit us to introd?

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Sarah takes a topless dip in a milk bath

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Young Teen Couple\'s Hot & Horny Outdoor Sexcapade

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

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Photos from Monica Mendez\' diary

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Kelly and Monika munchin on tasty toes and twat

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Lucia Love Teases Us In A Gold Transparent Dress

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Hungarian maid Pamela vacuums her beautiful tits

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Serbian star Cherry Kiss in a hot striptease

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These candids of Leanne Crow really showcase just how lovely she is in front of the camera as she slips out of her leopard-print bra for us. xoxoxo -- Leanne

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"We meet Gail Stanton in her hotel room. She is wearing a blue-satin bathrobe and she smells like jasmine. We ask her what folks do these days down in her home town, Memphis, Tennessee. ""Same as usual,"" she deadpans.?"

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Cybergirl of the Month 01 - Jennifer Hurt?

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

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Welcome to the sexiest Playmate of the Year debut ever! You?ll enjoy hot video clips from behind the scenes at Jodi Ann Paterson?s PMOY video and pictorial shoots, witness Jodi Ann shimmy and shake during her super s?

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Katarina & Laura M. Have Big Breast Lesbian Sex

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Elfin-like couple trying to fuck like porn stars

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Sexy big tis in a tiny bikini anyone? There are fewer things that look nicer than a suckable and squeezable pair of big tits bulging out of a bikini top that is way too small to contain them. Hope you like these! xoxoxo -- September

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Alexis Fucks Herself Silly With A Pink Rabbit Vibe

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Sunshine gets a dinner and double penetration

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

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Kassey Krystal guzzles some cock and cream!

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

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Hot Student Vanda Sucks Two Cocks In The Classroom

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Although Horace Greeley\'s famous travel instructions were addressed to young men only, Cleveland-born Christine Koren corrected the editor\'s oversight several years ago, when she swapped secretarial chores in her hom?

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"""Honey, I\'m home!"" shouts Lorenzo Lamas, bursting through the door of his trailer and into the arms of his bride-to-be, Shauna Sand. ""Darling,"" she replies, ""you\'re filthy!"" It\'s true: Lamas has been brawling (or act?"

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Face it, you\'ve fantasized about settling down with a Playmate. What would it be like to wake up next to her five, ten or even 20 years later? Here are 11 answers.?

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

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Vivian LeBrock thinks a woman\'s body is like a work of art and we couldn\'t agree more after gazing at this buxom brunette. And Vivian knows about art. She attends an art and design school where she\'s studying interio?

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Blanche Bradburry & Tracy Delicious In A Hot 69

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Commando babe finds a rogue dick in the bush

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Busty Lesbian Babes Play Titty Games In The Tub

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Klaudia Fucking Herself with a Champagne Bottle

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

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

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Big titty sexy beauties frolicking outdoors

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30K Karla James is a gal we have been wanting to feature here at PinupFiles for quite some time and we could not be more pleased to finally see that day arrive.

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Delicious lesbian threesome

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

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Modelleri: Luci Thai

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

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Pink Vibrator Travels From Her 34DD\'s To Her Pussy

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

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Big tit pornstar Jayden James masturbates

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

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Cybergirl of the Month June 2014

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Anita fingering & fucking her round ass with a toy

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Katarina takes a pizza boy cock in her office

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

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Sexy Brunette Bobbi Starr Fingers Her Hairy Beaver

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Hey gang! For those of you who really love sexy big boobs (I know I do!) And it is especially sexy when those big boobs are all wet from a nice warm shower which this set has plenty of, so I hope this makes your day a bit brighter. xoxo -- September

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September Carrino outside by the Wagon Wheel

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Beautiful Russian teen Aglaya gets her pussy taxed

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Horny Nurses Pump Each Other with a Purple Dildo

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Playmate of the Month August 1999 - Rebecca Scott?

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Naughty Cayenne Klein Masturbates With A Pink Vibe

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"When we asked this week\'s CGOW, Erin Wills, what turns her on, we were turned on by her answer. ""What people call \'it,\'"" Erin told us. ""I guess it\'s confidence and making me feel like I\'m the hottest chick anywhere!""?"

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Cybergirl of the Month July 2014

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Zafira Stuffs Red Geisha Balls In Her Snatch & Ass

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"Jeannette may be down to earth, but she\'s on a mission and knows exactly what she wants from life. ""one day I want to be married and have a family so I can settle down. But now I want to pursue my acting and modeling?"

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Stephanie\'s ambition in life is to obtain a bachelor degree in criminal justicce, which she\'s working on at the University of Cincinnati. Until recently she had no idea that she was making history in Playboy and on t?

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Audrey Bitoni is one lucky clients hot fantasy for the night and they have hot sex in his room.

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Gorgeous Victoria sets our hard dicks ablaze

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Emma Starr has hot sex with big cocked client in her room.

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Miss April 2001

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Wild Newcomer Takes Two Cocks In Her Ass At Once

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When Jesseca Turner told us that her favorite actor was Jack Nicholson and one of her favorite TV shows was the sarcasm-driven Just Shoot Me, we knew we had one sassy girl on our hands. And while her sense of humor w?

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Netherlands babe Chelsey Lanette sucks a hard cock

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Curvy Blanche Bradburry Deepthroats her Masseuse

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Champagne and cock poolside for Gina Devine

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