Jizz

Playmate of the Year 1960 (first of all) - Miss december 1959 - Ellen Stratton

VintageBabes

Playmate of the year 2002, Dalene Kurtis, ten years later and naked again

nsfw

Playmate of The Year

SaraJUnderwood

Playmate of the Year

GirlsWithWords

Playmate of the Year 2008, Jayde Nicole

playboy_playmates

Playmate of the Year 2007, Sara Jean Underwood

playboy_playmates

Playmate of the Year 2006, Kara Monaco

playboy_playmates

Playmate of the Year 2007, Sara Jean Underwood

playboy_playmates, nsfw, breastsubever

Miss January 1998 and Playmate of the Year 1999, Heather Kozar

playboy_playmates, nsfw, breastsubever, 90sTits, NostalgiaFapping, blondebush

Playmate of the Year 2003, Christina Santiago

playboy_playmates

Miss April 2000 and Playmate of the Year 2001, Brande Roderick

playboy_playmates

Playmate of the Year 2004, Carmella DeCesare

playboy_playmates

Playamte of the Year 1999, Heather Kozar

playboy_playmates, u_waldforest2

Playmate of the Year 2001, Brande Roderick

playboy_playmates

Karen McDougal- 1997 December Playmate/ 1998 Playmate of the Year

playboy_playmates

Playmate of the Year

sabrinalynnci, u_millertime8202

Kathy Shower Playmate of the Year for 1986

Playboy, playboy_playmates

Playmate of the year

bodyperfection

Playmate of the Month March 1995/Playmate of the Year 1996 - Stacy Sanches (AIC)

Playboy_Albums

Playmate of the Month December 1984/Playmate of the Year 1985 - Karen Velez Collection (AIC)

Playboy_Albums, OldSchoolCoolNSFW, iluvnakedchicks, AltarOfVenus, u_ItsClyde96, Bubbles

Playmate of the Month December 2018/Playmate of the Year 2019 - Jordan Emanuel Collection (AIC)

Playboy_Albums

Playmate of the Month November 1986/Playmate of the Year 1987 - Donna Edmondson Collection (AIC)

Playboy_Albums, u_ChiefCountingPills

Playmate of the Year 1987 - Donna Edmondson

OldSchoolCoolNSFW, iluvnakedchicks, Playboy

Playmate of the Year 1975 - Marilyn Lange

OldSchoolCoolNSFW, u_carc363636

Playmate of the Month January 1998/Playmate of the Year 1999 - Heather Kozar Collection (AIC)

Playboy_Albums

Playmate of the Month November 1978/Playmate of the Year 1979 - Monique St. Pierre Collection (AIC)

Playboy_Albums

Playmate of the Month January 1971/Playmate of the Year 1971 - Liv Lindeland Collection (AIC)

Playboy_Albums, u_greengiant87

Brande Roderick – Playmate of the Year 2001

playboy_playmates

Brande Nicole Roderick - Playmate of the Year 2001

playboy_playmates

Playmate of the Month November 1976/Playmate of the Year 1977 - Patti McGuire Collection (AIC)

Playboy_Albums, PlayboyOnReddit, ClassySexyCool, u_DesertFalcon94

Playmate of the Month August 1975/Playmate of the Year 1976 - Lillian Müller Collection (AIC)

Playboy_Albums, PlayboyOnReddit

Playmate of the Year 1977 - Patti McGuire

OldSchoolCoolNSFW, vgb, iluvnakedchicks

Karen McDougal -- Miss December 1997 and Playmate of the Year of 1998

playboy_playmates, PlayboyOnReddit

Playmate of the Year 1985 - Karen Velez

OldSchoolCoolNSFW

Playmate of the year

ElixirBlack, bigtiddygothgf, palegirls, BIGTITTYGOTHGF

Playmate of the Month October 1965/Playmate of the Year 1966 - Allison Parks

OldSchoolCoolNSFW

Playmate of the Month October 1965/Playmate of the Year 1966 - Allison Parks Collection (AIC)

Playboy_Albums, PlayboyOnReddit

2001 Playmate of the Year Brande Roderick

playboy_playmates

Patrizia Dinkel - German Playmate of the Month October 2017/Playmate of the Year 2018

playboy_playmates, nothingbutheels, Playboy_Albums, PlayboyOnReddit

Playmate of the Year 1980 - Dorothy Stratten

OldSchoolCoolNSFW, nakedgirlsandhorses, u_HANNIBAL500

Patrizia Dinkel - German Playmate of the Month October 2017/Playmate of the Year 2018

playboy_playmates

Playmate of the Month May 1992/Playmate of the Year 1993 - Anna Nicole Smith Collection (AIC)

Playboy_Albums, PlayboyOnReddit, u_ChiefCountingPills, boltedontits

Brande Roderick - Playmate of the Year 2001

playboy_playmates

Playmate of the Month January 1972/Playmate of the Year 1973 - Marilyn Cole Collection (AIC)

Playboy_Albums, OldSchoolCoolNSFW, PlayboyOnReddit

Playmate of the Month September 1977/Playmate of the Year 1978 - Debra Jo Fondren Collection (AIC)

Playboy_Albums, PlayboyOnReddit

Playmate of the Month February 1994/Playmate of the Year 1995 - Julie Lynn Cialini Collection (AIC)

Playboy_Albums, PlayboyOnReddit

Playmate of the Year 1975 Marilyn Lange On/Off

OldSchoolCoolNSFW, u_carc363636

Playmate of the year

Nudes, Onlyfans_Promo

Playmate of the Month January 1968/Playmate of the Year 1969 - Connie Kreski Collection (AIC)

Playboy_Albums, PlayboyOnReddit, pronudes

Playmate of the Year 1976 - Lillian Müller

OldSchoolCoolNSFW, vgb, iluvnakedchicks, blondebush, tidybush

Playmate of the Month May 1985/Playmate of the Year 1986 - Kathy Shower Collection (AIC)

Playboy_Albums, PlayboyOnReddit

Playmate of the Month February 1973/Playmate of the Year 1974 - Cyndi Wood Collection (AIC)

Playboy_Albums, OldSchoolCoolNSFW, PlayboyOnReddit, iluvnakedchicks, NSFWtraveler382, u_ChiefCountingPills, BusinessSocks, oldschoolhot

Playmate of the Year 2007 - Sara Jean Underwood

NostalgiaFapping, u_texashellyea, u_princedevittbcog, CasuallyBlonde, u_jakay25

Playmate of the Month December 1964/Playmate of the Year 1965 - Jo Collins Collection (AIC)

Playboy_Albums, OldSchoolCoolNSFW, PlayboyOnReddit

Anita Sikorska in Playboy Poland - Poland’s Playmate of the Year 2014 (AIC)

Playboy_Albums, PlayboyOnReddit, playboy_playmates, PWsCollection2, Babes

Playmate of the Year 1983 - Marianne Gravatte

OldSchoolCoolNSFW, iluvnakedchicks

Playmate of the Year 1993 - Anna Nicole Smith

NostalgiaFapping, NSFW_Faves, u_DarthArcher, u_mullhy

Playmate of the Month November 1989/Playmate of the Year 1990 - Reneé Tenison Collection (AIC)

Playboy_Albums, OldSchoolCoolNSFW, NostalgiaFapping, BOUS, PlayboyOnReddit