Jizz

Elaine Reynolds: Miss October 1959

Stacked, PerkyChubby

Paris Hilton Best of Instagram October 2014 (NSFW)

Celebs

Ester Cordet | Miss October 1974

vgb

[F]estive socks because I'm a little too excited for October. Can't wait to be fucked in a slutty costume.

gonewild

It's officially October, basics. And guess what?

muacirclejerk

Allison Parks - Miss October 1965

vgb

Janet Pilgrim (Playmate of the Month - October, 1956) has your martini ready.

vgb

1 Halloween Look a Day for October - Plastic Surgery Gone Wrong

MakeupAddiction

A Japanese soldier poses before battle at the German port of Tsingtao during Siege of Tsingtao. (c. October 18th, 1914)

hentiny

DONT MESS WITH US OCTOBER BABIES, MF'ERS!!!

THE_PACK

Patreon content for October, With Liara Roux and Astraia from SG!

virtualgeisha

Majken Haugedal Miss October 1968

vgb

Valerie Lane, Miss October 1973

vgb, WtSSTaDaMiT

I found out today that October is sheer thong month at the strip club I work at and I’m getting really nervous about it ??? [f,19]

gonewild, TinyTits

Spooky October tits reveal! (f) Request ? (Sadly it's just photoshop but I hope you like it)

gonewild, u_zonenhof

Red October

lingerie

Pic of the day for October 16, 2018

hentaibondage

goth traps are perfect for October

traps

Pamela Horton, Miss October 2012

Playboy, PlayboyBunnies, RevengeOfTheSenate, westernmax, PlayboyOnReddit, GoodTasteErotica

Ultima - Blue October

suicidegirls

Pamela Horton - Playmate Miss October 2012

Playboy, u_stilllostwithyou

Playmate October 2019: Hilda Dias Pimentel

Playboy, iluvnakedchicks, u_bmontgomery17

Fantasy Fest | Key West, FL | October 2014

FestivalSluts

Playboy Calendar 1964, October

OldSchoolCoolNSFW, Thingsthatgetmeoff

Martha Hunt by David Bellemere | Lui Magazine October 2015

NSFWfashion, awsmwmn

Cleaning up my phone and found this gem from October that I didn't get around to posting, hope you enjoy!

gonewildcurvy

F/31/5'3" [149lbs>138lbs=11lbs] End of October 2019 to January 2020. Shedding the fall fluff inch by inch! Working on a bit more fat loss and building more muscle.

progresspics

Playmate of the Month October 1989 - Karen Foster

OldSchoolCoolNSFW, iluvnakedchicks

Shannon Long - October 1988

OldSchoolCoolNSFW, Lovelyboobs

Shannon Long - October 1988

OldSchoolCoolNSFW, u_PaganBlack1355

Playmate of the Month October 1975 - Jill de Vries

vgb, u_gushgooly, AltarOfVenus

Playmate of the Month October 2013 - Carly Lauren

Playboy, PlayboyOnReddit

It's October 1962 and Laura Young has The Look

VintageBabes, OldSchoolCoolNSFW, u_lupus44

Playmate of the Month October 1997 - Layla Harvest Roberts (AIC)

Playboy_Albums, PlayboyOnReddit, NotSafeForWater

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

Playboy_Albums, PlayboyOnReddit

Jayden Lee - October 21, 2012 (Throwback Thursday)

faptothatbutthole, AsianHotties, buttspokes

Happy October!!

ericacampbell, u_RichieRahl82

MackzJones October 13th Spanking Video + New Photos (Link in comments)

TikTokNude, WorldPacks, MackzJonesLinks, tiktoknsfw

Playmate of the Month October 2012 - Pamela Horton

playboy_playmates

Playmate of the Month October 1977 - Kristine Winder

vgb

Playmate of the Month October 1975 - Jill de Vries

vgb

Marcy Hanson - Playmate of the Month October 1978

OldSchoolCoolNSFW

Cindy Crawford | Playboy October 1998 | Costa Careyes, Mexico | ph. Herb Ritts

OldSchoolCoolNSFW, NSFWfashion

Playmate of the Month October 1972 - Sharon Johansen (AIC)

Playboy_Albums, PlayboyOnReddit, vgb

Jenny McCarthy, PMOM October 1993

playboy_playmates, PWsCollection2, u_NachosThrowaway

Nadine Chanz, Miss October 1996

playboy_playmates

Playmate of the Month October 1986 - Katherine Hushaw (AIC)

Playboy_Albums, PlayboyOnReddit

Playmate of the Month October 2013 - Carly Lauren

playboy_playmates

Playmate of the Month October 2014 - Roxanna June

playboy_playmates

Playmate of the Month October 1967 - Reagan Wilson (AIC)

Playboy_Albums, RoughnReadyPlayGround, PlayboyOnReddit

Playmate of the Month October 1967 - Reagan Wilson

vgb