Jizz

Kailena

Playboy, RevengeOfTheSenate, PlayboyOnReddit, u_waldforest2

Molly Stewart

Playboy, throwaway855836, MollyStewart, u_millertime8202, u_allneilysfault, ozekiNSFW, PlayboyOnReddit, exhibitiontime, westernmax

Kathie Kern

Playboy, PlayboyOnReddit, SensualPhotography, u_Bill8379

Sunshine

Playboy, classysexy, PlayboyOnReddit

Lilii

Playboy, PlayboyOnReddit, Adorable_Girls

Shelby Chesnes

goddesses, u_Cpt_DeadPool_, Playboy, PlayboyOnReddit, u_tinlizdavis, u_ExistingExperience9, playboy_playmates, u_Vagabondart, ShelbyChesnes, bodyperfection

Tahlia Paris - Cybergirl of the Year 2017

Playboy, PlayboyOnReddit, TahliaParis

Mia Valentine

Playboy, PlayboyOnReddit, u_kkhuslen, westernmax

Katie Calloway

Playboy, PlayboyOnReddit

Haley Sorenson

Playboy, PlayboyOnReddit, u_stilllostwithyou, SexyFrex

Cyber girl from Texas, Casey Michelle (bonus pics in comments)

Playboy, PlayboyOnReddit, shavedpussies

Kara Jo

Playboy, PlayboyOnReddit, iluvnakedchicks

Demi Fray down in HD

Playboy, PlayboyOnReddit, nsfw, u_waldforest2

Erica, Nicole & Jaclyn Dahm

Playboy, PlayboyOnReddit

July Playmates of the Decade (AIC)

Playboy_Albums, PlayboyOnReddit

Laura Lynn

Playboy, PlayboyOnReddit, GayWoman, iluvnakedchicks, MyPornGallery

Sophie

Playboy, PlayboyOnReddit, GayWoman, u_HANNIBAL500

Sarah Porchetta

Playboy, PlayboyOnReddit, SensualPhotography, GayWoman

Brittany Barbour

Playboy, PlayboyOnReddit, SensualPhotography, GayWoman

Playmate August 2018: Lorena Medina Collection (AIC)

Playboy_Albums, PlayboyOnReddit, u_Wahio, playboy_playmates, Playboy

Playmate of the Month May 1994 - Shae Marks

Playboy, PlayboyOnReddit, SensualPhotography

Natalia Andreeva | NSFW

Playboy, PlayboyOnReddit, SensualPhotography

Ana Cheri

Playboy, PlayboyOnReddit, SensualPhotography

Casey Connelly

Playboy, PlayboyOnReddit, iluvnakedchicks, u_Vagabondart, CaseyConnelly

Best of Carlotta Champagne (AIC)

Playboy_Albums, PlayboyOnReddit, u_ChiefCountingPills, redlips

Jana Bubu and Kay J in Sunlit Embrace (AIC)

Playboy_Albums, Playboy, PlayboyOnReddit

Elke Jeinsen -- May 1993

Playboy, PlayboyOnReddit, OldSchoolCoolNSFW, u_bob1497999

Malena Fendi

Playboy, PlayboyOnReddit, exhibitiontime

Playmate of the Month February 1990 - Pamela Anderson Collection (AIC)

Playboy_Albums, PlayboyOnReddit, OldSchoolCoolNSFW, playboy_playmates, Playboy, VintageBabes, u_Gooordooo, u_ChiefCountingPills, NSFWtraveler382, NostalgiaFapping, u_princedevittbcog, lexibellefemmeinspo, u_JPeety1

Shallana Marie

Playboy, PlayboyOnReddit, Lovelyboobs

Playmate of the Month June 2004 - Hiromi Oshima

Playboy, PlayboyOnReddit, u_svenmike, exhibitiontime, NSFW_Faves, NostalgiaFapping, NSFW_Japan, ArmsUp

Jenny McCarthy

Playboy, celebnsfw, PlayboyOnReddit

Elsa Galvan

Playboy, PlayboyOnReddit, u_juventus2019, Playboy_Collections

Caitlin McSwain

Playboy, PlayboyOnReddit, CaitlinMcSwain

Nadine Burger, Cyber Girl Germany 2012

Playboy, PlayboyOnReddit, PWsCollection, u_eegm97, u_Flat_Consideration47

Hillary Fisher

Playboy, PlayboyOnReddit, Playboy_Collections

Sultry Molly

MollyStewart, Playboy, PlayboyOnReddit, PWsCollection, pronudes

Katya Clover

Playboy, rearpussy, PlayboyOnReddit

Daily Double - September 2010 (AIC)

Playboy_Albums, PlayboyOnReddit, u_NachosThrowaway, u_ChiefCountingPills, Playboy, PWsCollection2

Charlize Theron

Playboy, PlayboyOnReddit, u_Vagabondart, nudescelebsmagazine

Marina Baker (1987)

Playboy, PlayboyOnReddit

Christine Gischler - Playboy Italia May 2020 (AIC)

Playboy_Albums, PlayboyOnReddit, goddesses

Best of Playmates of 2007 (AIC)

Playboy_Albums, PlayboyOnReddit, PWsCollection2

Playmate of the Month April 2007 - Giuliana Marino

Playboy, PlayboyOnReddit

Ora Young

Playboy, PlayboyOnReddit, PWsCollection2

Topless Cowgirl

MollyStewart, u_PaganBlack1355, PrettyCowgirls, Playboy, PlayboyOnReddit

Emily Willis in Slow Dance (AIC)

Playboy_Albums, PlayboyOnReddit, PWsCollection2

Tiffany Taylor

Playboy, PlayboyOnReddit

Best of Playmates of 2010 (AIC)

Playboy_Albums, NostalgiaFapping, PlayboyOnReddit, Playboy

Marcella Matos in Playboy Brazil - Playboy Brazil's Miss March 2010 (AIC)

Playboy_Albums, PlayboyOnReddit, CelebsBR, playboy_playmates, u_GhigoTrieste

Julia Logacheva is Incognito (AIC)

Playboy_Albums, PlayboyOnReddit, u_DarthArcher, u_onilatan28, classysexy, noomi, SaffronSubmissions, u_travis6370

Lindsey Pelas

Playboy, PlayboyOnReddit, u_boobscomelook, u_rocketansky

Tiffany Taylor showing (unusually) her beautiful ass

Playboy, PlayboyOnReddit

Miss Kenzie Anne in Static Electricity (AIC)

Playboy_Albums, PlayboyOnReddit

Hands On Hips

leannadecker, Playboy, PlayboyOnReddit, u_travis6370

Sarah Domke in Playboy Germany (AIC)

Playboy_Albums, Trim, PlayboyOnReddit, u_DesertFalcon94

Priscilla Taylor

Playboy, PlayboyOnReddit, ghostnipples

Chelsie Aryn

Playboy, PlayboyOnReddit, u_CCSbR

Mary Jane (2006, not the more recent one)

Playboy, PlayboyOnReddit

Jamie Bradford (2010)

Playboy, iluvnakedchicks, PlayboyOnReddit, u_beardedblackdragon