Jizz

Playboy's Playmate of the Month - Miss August 1999

nsfw

Ellen Stratton - Playboy magazine's Playmate of the Month for December, 1959 (via /r/VGB)

OldSchoolCoolNSFW, vgb

Anne Randall - Playboy Playmate of the Month - May, 1967 [NSFW]

vgb

Myrna Weber, Playboy Playmate of the Month - August, 1958 [NSFW]

vgb

Playboy's Playmate of the Month Susan Bernard at the age of 19, December 1966

LegalTeens, VintageBabes, RetrousseTits, GoBoobs, nsfw, SocialMediachicks

Linda Forsythe Playboy Playmate of the Month for its February 1970 issue

VintageBabes

Nicole, Erica and Jaclyn Dahm (Playboy Playmates of the month - December 1998)

BeautifulTitsAndAss

Playboy magazine's Playmate of the Month, Ester Cordet

fortyyearsago

Virginia Gordon she was Playboy magazine's Playmate of the Month for the January 1959

OldenPorn

Elsa Sørensen / Playboy’s Playmate of the Month, September 1956

VintageBabes

Adrienne Moreau, Playboy Playmate of the Month March 1963

VintageSmut

Arline Hunter, Playboy's Playmate of the Month for August 1954

OldSchoolCoolNSFW

Dorothy Stratten Playboy Playmate of the Month for August 1979

VintageBabes

Lauren Michelle Hill - Playboy Playmate of the Month February 2001

Underbun, TheUnderbun, ShortShorts, ass, booty, butts

Playboy Magazine's Playmate of the Month in May 1955 and February 1956. The first model to show her pubic hair also the first to be shown in a full-frontal nude pose.

OldSchoolCoolNSFW

Diane Webber - Playboy Magazine's Playmate of the Month in May 1955 and February 1956. The first model to show her pubic hair also the first to be shown in a full-frontal nude pose.

OldenPorn

Diane Webber - Playboy Magazine's Playmate of the Month in May 1955 and February 1956. The first model to show her pubic hair also the first to be shown in a full-frontal nude pose.

HairyPussy

Diane Webber - Playboy Magazine's Playmate of the Month in May 1955 and February 1956. The first model to show her pubic hair also the first to be shown in a full-frontal nude pose.

VintageBabes

Diane Webber - Playboy Magazine's Playmate of the Month in May 1955 and February 1956. The first model to show her pubic hair also the first to be shown in a full-frontal nude pose.

VintageSmut

Kayslee Collins, Playboy Playmate of the Month, February 2015

nsfw

Sandra Edwards, Playboy Playmate of the Month March, 1957

vgb

Danielle de Vabre / Playboy’s Playmate of the Month, November 1971 / photographed by Dwight Hooker.

OldSchoolCoolNSFW

Cindy Fuller, Playboy's Playmate of the Month | May 1959

nsfw, vgb, VintageBabes, nsfwtop, JewishGoddesses, JewishBabes, JustTheBest

Dru Hart, Playboy's Playmate of the Month for September 1968

OldSchoolCoolNSFW, nsfwtop

Jean Jani was Playboy magazine’s Playmate of the Month for July 1957, exactly 60 years ago

vgb

Teddi Smith - Playboy Playmate of the Month, July 1960

Puffies

Dolly Read / Playboy’s Playmate of the Month, May 1966 / photo by Pompeo Posar.

VintageBabes

April 1954 Playboy Playmate of the Month Marilyn Waltz

OldSchoolCoolNSFW

May 1954 Playboy Playmate of the Month Joanne Arnold

OldSchoolCoolNSFW

June 1954 Playboy Playmate of the Month Margie Harrison

OldSchoolCoolNSFW

1962 Playboy Playmate of the Month, Miss August Jan Roberts

OldSchoolCoolNSFW

1978 Miss June Playboy Playmate of the Month Gail Stanton

torpedotits, u_omegamastermaiden, u_mesquite06

Karen Witter Vintage Playboy Playmate of The Month

OldSchoolCoolNSFW, iluvnakedchicks, u_mesquite06

Vintage Playboy Playmate of the Month, Miss March 1967 Fran Gerard

AssAndTits, u_goldmoonraker

1978 Miss June Playboy Playmate of the Month Gail Stanton

AssAndTits

Alana Soares, for Playboy; Playmate of the Month, March 1983

AssAndTits

Alana Soares, for Playboy; Playmate of the Month, March 1983

AssAndTits

Rebecca Ramos, Playboy's Miss January 2003. At age 35 she became the oldest woman to become Playmate of the Month in the history of the magazine.

NostalgiaFapping, u_romins1221, u_bigdieseldick1982, u_mesquite06, u_burner4pr0n

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

VintageBabes

Barbara Hillary. Playboy's Playmate of the Month, April 1970

OldSchoolCoolNSFW, iluvnakedchicks

Marilyn Monroe - Playboy centerfold - 1st issue ever 1953 (called Sweetheart of the Month because it wasn't until the next issue that they began calling these women Playmates of the Month)

vgb, NostalgiaFapping, PervertsPlace, u_gushgooly

Miss Britt Linn - Playboy Playmate Of The Month

PornHailstorm

Angela Dorian, Playboy magazine's Playmate of the Month for its September 1967 issue

VintageBabes, OldSchoolCoolNSFW, u_NachosThrowaway

Heather Van Every / Bunny at the Denver Playboy Club and Playboy’s Playmate of the Month, July 1971 / photographed by David Chan.

thebunnyclub

Heather Van Every / Bunny at the Denver Playboy Club and Playboy’s Playmate of the Month, July 1971 / photographed by David Chan.

thebunnyclub

Heather Van Every / Bunny at the Denver Playboy Club and Playboy’s Playmate of the Month, July 1971 / photographed by David Chan

SatinGirls, thebunnyclub

Heather Van Every / Bunny at the Denver Playboy Club and Playboy’s Playmate of the Month, July 1971 / photographed by David Chan.

thebunnyclub

Susan Bernard, Dec 1966 Playboy Playmate of the Month (Gut yontiff to all now let's let's go get-i some spaghetti)

PornMuseum

Cindy Fuller Martino Playboy Playmate Of The Month May 1959

VintageBabes

Victoria Valentino, Playboy Playmate Of The Month September 1963

VintageBabes

Shannon James, Playboy Playmate of the Month for May 2007.

SchoolGirlSkirts

Dolores Donlon, Playboy Playmate Of The Month August 1957

VintageBabes

Pat Lawler Playboy Playmate Of The Month August 1955

vgb

Jim Brown, Playboy Bunny Dolly Read (also Playmate of the Month, May 1966), Clint Walker on the MGM-British Studios lot in Borehamwood, England, during production of Robert Aldrich’s The Dirty Dozen (1967)

thebunnyclub

Avis Miller (born November 4, 1945 in Ohio) is an American model. She was Playboy magazine's Playmate of the Month for the November 1970 issue. Her centerfold was photographed by Dwight Hooker. She was also a Playboy Bunny at the San Francisco club.

thebunnyclub

Elan Carter, Playboy Playmate Of The Month June 1994

WomenOfColor

Francine Parks, Playboy Playmate Of The Month February 1974

ToplessInJeans

Francine Parks Playboy Playmate Of The Month February 1974

VintageBabes