Jizz

First date tonight since the end of a 3-year relationship last October. Wish me luck, my lovelies.

ladybonersgw

Ana Cheri, Miss October 2015

boltedontits

Miss October

hugeboobs, Stacked, hugenaturals

17-year-old Japanese ultranationalist Otoya Yamaguchi assassinates socialist politician Inejiro Asanuma in the midst of a political debate, Tokyo, Japan, October 12, 1960 [1280x1063]

HistoryPorn

The impact impression of Kapitanleutnant Heinrich Mathy's body when he jumped out of the burning Zeppelin L31, October 1916. [604x800]

HistoryPorn

Pet Of The Month October 2016

MiaMalkova

Golden october

gaynsfw

Mia Malkova - Pet Of The Month October 2016 (album in comments)

MiaMalkova

Patreon - October work III [F] (Hioshiru)

yiff

Ready for October

EricaFett

Pic of the day for October 01, 2018

hentaibondage

It's October! Submit your sultry vampires, naughty succubi, wicked demons, and other spooky sexy ladies!

FantasyGirls

Happy October Everyone! <3

altgonewild, JizzedToThis

Pic of the day for October 09, 2018

hentaibondage

Every October for the past 4 years, I've emailed my shirt idea to WWE Shop. For some strange reason, I have yet to receive a reply from them...

Wrasslin

Pic of the day for October 23, 2018

hentaibondage

Just Being Cute - October Vote Winner [F] (Zummeng)

yiff, scalieporn, FurrySoftcore

Sacheen Littlefeather (October 1973, Playboy Magazine)

OldSchoolCoolNSFW

Kelly Ann Tough, Miss October, 1981

OldSchoolCoolNSFW, OldSchoolNSFW, Playboy, throwaway855836

Kathy Douglas | Playboy October 1960

OldSchoolCoolNSFW, nsfw

Playmate Shannon Long (Miss October 1988)

VintageBabes

Happy October

ShinMegamiHentai

Claire Sinclair, Miss October 2010

playboy_playmates

Happy October

Artistic_Hentai, hentai

Brittany York, October 1990

OldSchoolCoolNSFW, VintageBabes

Kristine Winder by Mario Casilli for Playboy, October 1977

saudelobaes

Birth of Venus, here is 20-y-o Sara Jean's first appearance in PLAYBOY October 2005 over pages 140 & 141 as one of the Girls of the PAC 10 {Oregon State Beaver - of course} Hef's impressed. So much so Sara becomes issue cover model in body paint as OS

SaraUnderwood, SaraJUnderwood

Amanda Rachelle Cerny October 2011

playboy_playmates, PlayboyOnReddit

Playmate of the Month October 2006 - Jordan Monroe

playboy_playmates, PlayboyOnReddit, u_Hellyeslikedat, Playboy, u_HANNIBAL500, ghostnipples

Granny Gangut (October Revolution) three years after the end of the war on Europe. Out of her four sisters, only Sevastopol survived the war besides her.

AzureLane

Playmate of the Month October 2014 - Roxanna June

Playboy, PlayboyOnReddit

Miranda Jordan, college girl of the week October 6th 2011

Playboy, PlayboyOnReddit

Playmate of the Month October 1962 - Laura Young

OldSchoolCoolNSFW

Roasting with the Cold [HM] (October_Flixard)

Hyiff

Elaine Reynolds, October 1959

VintageBabes, AltarOfVenus, OldSchoolCoolNSFW, torpedotits, u_waldforest2, BusinessSocks, u_el_vato_safado

Claire Rambeau October 1971

OldSchoolCoolNSFW, VintageBabes, Graphis

Playmate of the Month October 2006 - Jordan Monroe

playboy_playmates, Playboy, PlayboyOnReddit

Happy October! (f) [42]

40plusGoneWild

[f] [oc] Happy October ? shifting into spooky porn ?

gonewildmetal, BloodyWomen, Titties, altgonewild, gothsluts, bigtiddygothgf, PunkGirls

?Starting October with a Drop

TittyDrop, boobbounce, gonewild, boobs, u_Mitchaaa

Samples for October Tier 7 set: Scarlet Salor Girl

ChonoBlackofficial

JESSIKA'S CURSE: Diary #15 - October Development Update

lewdgames, NSFWgaming

Playmate of the Month October 1990 - Brittany York

OldSchoolCoolNSFW

Jenny McCarthy - October 1993

OldSchoolCoolNSFW, HairyPussy, NSFWtraveler382

The chill of October's got the girls hard af.

SeattleGW

Playmate of the Month October 1977 - Kristine Winder

playboy_playmates, u_carc363636

Playmate of the Month October 1988 - Shannon Long

Playboy, PlayboyOnReddit, playboy_playmates, VintageBabes, u_LordMoorcroft, VintageSmut, Lovelyboobs, Bustys, bustymom

Playmate of the Month October 1991 - Cheryl Bachman

OldSchoolCoolNSFW

Hilda Dias Pimentel, Miss October 2019

playboy_playmates, PWsCollection, u_nuker56, u_anonymousannus

Playmate of the Month October 1974 - Ester Cordet

vgb

Linda Moon - October 1966 : 4336x8056

OldSchoolCoolNSFW, VintageBabes

Laura Cover, Miss October 1998

playboy_playmates

Playmate of the Month October 2008 - Kelly Carrington

playboy_playmates

Shannon Long, Miss October 1988

playboy_playmates

Jean Cannon, Playboy Playmate Of The Month October 1961

VintageBabes, u_DesertFalcon94

All natural Denise Cotte | Playboy Germany October 2014

Playboy, PlayboyOnReddit

Marcy Hanson PLAYBOY'S MISS OCTOBER 1978 [AIC]

VintageBabes

? My tattoo is finished till October, than I'm gonna add more trees all around my ankle ?

u_LeylaLowe, RealGirls, Nudes, Nude_Selfie

Playmate of the Month October 1976 - Hope Olson

vgb

Playmate of the Month October 2011 - Amanda Cerny

playboy_playmates, DigitalPornCollection, u_theelusivej5695