Jizz

Elaine Reynolds: Playboy's Miss October 1959

hugeboobs

Blue hair from back in October. :)

GirlswithNeonHair

January/October

birdswithhumanpenises, NotTimAndEric

Colleen Farrington (October, 1957)

vgb

Colleen Farrington (October, 1957)

OldSchoolCoolNSFW

Eve Babitz and Marcel Duchamp playing chess at the Pasadena Art Museum, October 18, 1963. Photo by Julian Wasser.

OldSchoolCoolNSFW

Miss October

Stacked, Playboy

Sasha Grey Playboy Magazine October 2010

Sashagrey

Miss October

AnaCheri

Jean Bell, Miss October, 1969

VintageBabes

Morning nudes 41 yrs old come October

40plusGoneWild, wifesharing, GoneMild, realmoms, WouldYouFuckMyWife

Kathy Douglas, October 1960

OldSchoolCoolNSFW

[OC] How has this place been hidden from me?! I LOVE being creepy-sexy in October! Enjoy my Ice Queen costume (mild)

NSFWCostumes

Linda Moon - October, 1966

vgb, NostalgiaFapping

150 upvotes and I’ll stay locked all of October.

gaychastity, GayKink, chastity, keyholdercaptions

[Emily Willis, 19] Is October’s Starlet of the Month and the 11th Starlet of the Year Nominee!!!

PornStarletHQ

Pic of the day for October 02, 2018

hentaibondage

It is October so time for themed yiff ;) (SigmaX)

gfur

Pic of the day for October 17, 2018

hentaibondage

Perky peekers wanna press into your heater, feel your squeeze and warm demeanor on this chill October day. ?

onmww

Rhonda Shear USA Up All Night October 1993 Playboy photo

OldSchoolCoolNSFW

Pic of the day for October 26, 2018

hentaibondage

Janet Brown, Club International, October, 1974

OldSchoolCoolNSFW

Happy October!

ass, nsfw, u_ggyyuuee, u_Hausluvfeet, HolidaysNSFW

Emblem October is Out Now!

EmilyBloom

[ON/OFF] 2B is here for October! I love her so fucking much. Links below ♡

Kerocchi, OnOff, cosplayonoff

I’ll be with FreshieJuice and SugarBooty the last week of October! Email me if you’d like to commission a custom g/g or g/g/g clip!

AllysonBettie, u_JuneAndCash

Come meet me at Exxxotica NJ Saturday October 26th

AllysonBettie

Join me at the beach? It’s not THAT cold here in the UK in October, honest ??

Gumdrops

Susanne Saxon PH October 1976

OldSchoolCoolNSFW, VintageBabes, AltarOfVenus

Cynthia Brimhall October 1985

OldSchoolCoolNSFW, VintageBabes, handinpanties

Patron Monthly Pinup October [MTF/TGTF; Teacher Milf Age Progression/Milfication] by Grumpy-TG

transformation, gendertransformation, tgtfbot

Playboy Calendar 1968, October

OldSchoolCoolNSFW

Stacy Moran, Penthouse Pet October 1993 and an icon of 1990s nude magazines.

NostalgiaFapping

Bristol [2020] October food society

NakedUniCalendar

Leah de Wavrin | Hussein Chalayan Spring-Summer 2007 show | Paris, October/4/2006

fashionextramile, NSFWfashion, With_Or_Without

Karen Foster, Miss October 1989

playboy_playmates

Playmate of the Month October 2014 - Roxanna June

Playboy, PlayboyOnReddit

Ellie Gonsalves | Treats! October 2016 | ph. Daniella Midenge

SexyButNotPorn

Cyber Girl of the Month October 2004 - Danielle Gamba Collection (AIC)

Playboy_Albums, PlayboyOnReddit, u_Trinni2thaBone, u_nyjahritchelsdick

Playmate of the Month October 2008 - Kelly Carrington

playboy_playmates, u_Maxstatss

Julia Prokopy is waiting in the Shower | Playboy Germany 2018 October

Playboy, PlayboyOnReddit, u_waldforest2, iluvnakedchicks

Playmate of the Month October 1987 - Brandi Brandt

playboy_playmates, u_Vagabondart, NotSafeForWater

Reagan Wilson, Playboy Playmate of the Month for its October 1967 issue

VintageBabes, OldSchoolCoolNSFW

Lucifer CEO of Hell is here to RULE this October! Bow before her and don't complain

Kerocchi

Hope Olsen, October 1976

OldSchoolCoolNSFW, VintageBabes, NostalgiaFapping

Mackenzie Jones Rear pussy: october onlyfans leaks 2020

TiktokNaked

Playmate of the Month October 1990 - Brittany York (AIC)

Playboy_Albums, PlayboyOnReddit

Medic's PSA of October (and also, everytime)

TF2Pyro

Rosemarie Hillcrest, Playboy Playmate for October 1964

OldSchoolCoolNSFW, oldschoolhot, goddesses, Playboy, VintageBabes, playboy_playmates, PlayboyOnReddit

Miss October 2005, Amanda Paige

Playboy, PlayboyOnReddit, GoodTasteErotica

Quarantine can work wonders on the female body. @nataldee from March to October 2020.

ProgressiveGrowth

Mardi Jacquet, October 1980

OldSchoolCoolNSFW, VintageBabes, NostalgiaFapping, u_peacock4u

Cynthia Brimhall, Miss October 1985

playboy_playmates

Elena Krawzow (Paralympic swimmer) | Playboy Germany October 2020 | ph. Sacha Tassilo Höchstetter

celebnsfw

Playmate of the Month October 2006 - Jordan Monroe

playboy_playmates

Playmate of teh Month October 2060 - Jordan Monroe

Playboy, PlayboyOnReddit

Emily Agnes - Playboy Portugal October 2019

Playboy, PlayboyOnReddit

Playmate of the Month October 1996 - Nadine Chanz

playboy_playmates

Erika Michelle Barré - Cyber Girl of the Month - October 2001

Playboy, PlayboyOnReddit