Jizz

Playboy Playmate of the Year [2007]

nsfw

Patti McGuire: 1977 Playboy Playmate of the Year and wife of Jimmy Connors (World-Famous Tennis Champion)

OldenPorn

Playboy: Playmate of the Year (NSFW)

pics

Playboy Playmate of the year 2011 - Claire Sinclair.

BustyPetite

Hope Dworaczyk (Playboy Playmate of the Year; Celebrity Apprentice)

CelebrityPussy, nothingbutheels

Jennifer Vaughn, Playboy's Cyber Girl of the Year

hollyrandall, Playboy

Anastasia Matrenina Playmate of the Year 2013 ( Playboy Ukraine)

easterneuropeangirls

1992 Playboy Playmate of the Year

ginger

Raquel Pomplun: 2013 Playboy Playmate of the year

BeautifulTitsAndAss

Anna Nicole Smith, Playmate of the Year, June 1993

PlayboyBunnies, Playboy, fapfactory

Ida Ljungqvist Playmate of The Year Playboy Magazine June 2009

WomenOfColour

with playboy ending its run next year of the norm. they should go out with a bang. get christina hendricks.

Playboy

Playboy Germany Playmates of the Year 2014

FullBodyNSFW, HighResNSFW, Playboy, GroupOfNudeGirls, lineups, PlayboyBunnies

Allison Parks: Playboy Playmate of the Month, October 1965. Playmate of the Year, 1966

vgb, OldSchoolCoolNSFW, SaffronSubmissions

Playmate of the Year 2001, Brande Roderick

playboy_playmates

Playboy Cyber Girl of the year 2017 Tahlia Paris

bikinis

Olivia Preston (Playboy Cybergirl of the Year) - Xmas Pinup

XMasBabes

Linda Gamble (Playboy's Playmate of the Year 1961)

JustHotWomen, eyecontact, NostalgiaFapping, 20thCenturyFoxes

June Cochran (Playboy's Playmate of the Year 1963)

JustHotWomen

Allison Parks (Playboy's Playmate of the Year 1966)

JustHotWomen, OldSchoolCoolNSFW

Lisa Baker (Playboy's Playmate of the Year 1967)

JustHotWomen, Playboy

Claudia Jennings (Playboy's Playmate of the Year 1970)

JustHotWomen

Marilyn Cole (Playboy's Playmate of the Year 1973)

JustHotWomen

Cyndi Wood (Playboy's Playmate of the Year 1974)

JustHotWomen, RugsOnly, u_reddirt69

Marilyn Lange (Playboy's Playmate of the Year 1975)

JustHotWomen

Lillian Muller (Playboy's Playmate of the Year 1976)

JustHotWomen

Patti Mcguire (Playboy's Playmate of the Year 1977)

JustHotWomen, u_intensereaction

Debra Jo Fondren (Playboy's Playmate of the Year 1978)

JustHotWomen

Monique St. Pierre (Playboy's Playmate of the Year 1979)

JustHotWomen

Shannon Tweed (Playboy's Playmate of the Year 1982)

JustHotWomen

Marianne Gravatte (Playboy's Playmate of the Year 1983)

JustHotWomen

Karen Velez (Playboy's Playmate of the Year 1985)

JustHotWomen

Donna Edmondson (Playboy's Playmate of the Year 1987)

JustHotWomen

India Allen (Playboy's Playmate of the Year 1988)

JustHotWomen

Anna Nicole Smith (Playboy's Playmate of the Year 1993)

JustHotWomen

Jenny Mccarthy (Playboy's Playmate of the Year 1994)

JustHotWomen, u_clarence91

Stacy Sanches (Playboy's Playmate of the Year 1996)

JustHotWomen

Victoria Silvstedt (Playboy's Playmate of the Year 1997)

JustHotWomen

Karen Mcdougal (Playboy's Playmate of the Year 1998)

JustHotWomen, u_555uplander

Heather Kozar (Playboy's Playmate of the Year 1999)

JustHotWomen, UFs_Big_Boob_Faves

Linda Gamble (Playboy's Playmate of the Year 1961)

vgb, vintagepinup, u_barefoot_lover

Erika Michelle Barre (Playboy Cybergirl of the Year 2002)

NostalgiaFapping, boltedontits, Playboy

Kathy Ann Shower Playboy`s Playmate of the Month May 1985 & Playmate of the Year 1986

VintageBabes

Erika Michelle Barre (Playboy Cybergirl of the Year 2002)

Innie, NostalgiaFapping, Playboy, PlayboyOnReddit

Marilyn Lange - Playmate of the Year 1975

VintageBabes, NostalgiaFapping, Playboy, u_stilllostwithyou, iluvnakedchicks, AltarOfVenus

Marianne Gravatte - playmate of the year 1982

Playboy

Dalene Kurtis, Playboy's Miss September 2001 and the first Playmate with a shaved pubic area. She was also Playmate of the Year 2002.

NostalgiaFapping, CuratedByPDXanon

Playmate of the Year 1987 - Donna Edmondson

OldSchoolCoolNSFW, iluvnakedchicks, Playboy

Playmate of the Year 1979 - Monique St. Pierre

OldSchoolCoolNSFW, u_junhoka, iluvnakedchicks, playboy_playmates, vgb

Playmate of the Year 1976 - Lillian Müller

OldSchoolCoolNSFW, blondebush, iluvnakedchicks, playboy_playmates, vgb, oldschoolhot

Heather Kozar, Playboy's Miss January 1998 and Playmate of the Year 1999.

NostalgiaFapping, blondebush

Dalene Kurtis. Playboy's Miss September 2001, Playmate of the Year 2002, and the first Playmate with no pubic hair.

NostalgiaFapping

OK, as promised I uploaded all my collection (5Gb of pictures all the way to the year 2002) to MEGA. The link to the zip file is in the comments, reddit is deleting posts with the link as spam, so check the comments.

Playboy, PlayboyOnReddit

[r/Playboy_Albums] Cyber Girl of the Month August 2004/Cyber Girl of the Year 2005 - Amy Sue Cooper Collection (AIr) | NSFW

PlayboyOnReddit

Top 40 Hottest Gravure Pics of the Year: 38. Yuno Ohara (大原優乃) Weekly Playboy No 43 10.24.2020

pegginghentai, u_BlaBlaBla1913

Victoria Zdrok: Playboy Playmate, Penthouse Pet of the Year, attorney, and licensed sex therapist. (2000s)

NostalgiaFapping, u_Theibo