Jizz

Jennifer Liano, Miss May 1970

nsfw

Any [f]ans of Miss May I here in gonewild?

gonewild

Miss May, Dani Mathers

nsfw

Dolly Read - English pinup model, actress, and Playboy's Miss May 1966 (NSFW)

vgb, OldSchoolCoolNSFW

Miss May 2012, Nikki Leigh

playboy_playmates

Miss May 2008, AJ Alexander

playboy_playmates, u_RichieRahl82

Miss May 2003, Laurie Jo Fetter

playboy_playmates

Miss May 2006, Alison Waite

playboy_playmates

Miss May 2008, AJ Alexander

playboy_playmates

Miss May 2007, Shannon James

playboy_playmates

Miss May 2001, Crista Nicole

playboy_playmates

Miss May 2008, AJ Alexander

playboy_playmates, u_RichieRahl82

Miss May 2006, Alison Waite

playboy_playmates

Miss May 2004, Nicole Whitehead

playboy_playmates

Miss May 2004, Nicole Whitehead

playboy_playmates

Miss May 2008, AJ Alexander

playboy_playmates, u_RichieRahl82

Miss May 2003, Laurie Jo Fetter

playboy_playmates

Deanna Baker - Miss May 1972

VintageBabes, Playboy, PlayboyBunnies

Miss May 2008, AJ Alexander

playboy_playmates

Playboy, Miss May 1955, Marguerite Empey

VintageBabes

Anne Randall, Miss May 1967

vgb

Deanna Baker, Miss May 1972

vgb

Deanna Baker, Miss May 1972

vgb

Marilyn Lange (Miss May 1974)

JustHotWomen

Marilyn Lange (Playboy's Miss May 1974)

JustHotWomen, OldSchoolCoolNSFW, thefullbush, Skryker

Playmates are back: Miss May 2017 Lada Kravchenko out now

Playboy, PlayboyBunnies, Elizabeth_Marxs, SexyWomanOfTheDay

Tishara Lee Cousino (Playboy's Miss May 1999)

JustHotWomen, Playboy

Crista Nicole (Playboy's Miss May 2001)

JustHotWomen, u_omegamastermaiden, Playboy, nsfw, u_zulden

Dolly Reed, Miss May 1966, Also Star of Beyond The Valley of the Dolls

OldSchoolCoolNSFW, u_Valloittaja, iluvnakedchicks

Sucky attempt at posing [f]or you [Miss May]

PM_me_ur_swimsuit

Learn from my mistakes - read the rules :P [f] [Miss May]

PM_me_ur_swimsuit, PLASTT, u_pricardolopes

Anne Randall, Miss May 1967

saudelobaes, OldSchoolCoolNSFW, RetrousseTits, vgb, Blonde

The Carpet Matches the Drapes. Miss May 1973 Anulka Dziubinska

NostalgiaFapping

Maria McBane (Miss May, 1965)

OldSchoolCoolNSFW, bigboobs, u_ItsClyde96, bigareolas, worldpolitics

Dolly Read (Miss May, 1966)

OldSchoolCoolNSFW

Marilyn Lange, Miss May 1974

playboy_playmates, u_Vagabondart

Please, Miss, May I Have Another?

NSFWLW

Tishara Lee Cousino, Miss May 1999

playboy_playmates

Shae Marks, Miss May 1994

playboy_playmates

Shauna Sand, Miss May 1996

playboy_playmates

Crista Nicole, Miss May 2001

playboy_playmates, u_Maxstatss

Shae Marks, Playboy's Miss May 1994.

NostalgiaFapping

Marilyn Lange, Miss May 1974 and pmoy 1975

vgb, Playboy, PlayboyOnReddit, OldSchoolCoolNSFW, NostalgiaFapping, justthejewels, BacklitBeauty, Busty_Girls, SensualPhotography

Sasha Bonilova · Miss May 2011

Playboy, PlayboyOnReddit, u_Ioriindustrial, u_RichieRahl82

UHQ | Sasha Bonilova (Miss May 2011)

Playboy, PlayboyOnReddit

Kym Malin - Miss May 1982

Playboy, PlayboyOnReddit

Susie Scott, Miss May 1983

playboy_playmates, OldSchoolCoolNSFW

Sheila Mullen, Miss May 1977

playboy_playmates

Bridgett Rollins, Miss May 1975

playboy_playmates

Anne Randall - Miss May 1967

VintageBabes, playboy_playmates, nsfw, Playboy, PlayboyOnReddit

Kym Malin - Miss May 1982

Playboy, PlayboyOnReddit, iluvnakedchicks

Terri Kimball, Miss May 1964

playboy_playmates

Katerina Giannoglou - Miss May 2018 for Playboy Germany Collection (AIC)

Playboy_Albums, PlayboyOnReddit, PWsCollection2

Shae Marks - Miss May 1994

Playboy, PlayboyOnReddit