Jizz

Christmas in October!

curvy

Playboy's Miss October, 1959 – Elaine Reynolds

curvy

Young Marines waiting to be shaved at the Marine Corps Recruit Depot Parris Island, October 1971 [980×663]

HistoryPorn

Ramallah, October, 2000: Palestinians holding the internal organs of 2 reserve soldiers who made a wrong turn into their neighborhood. They were butchered and their body parts paraded by children and adults.

The_Donald

Linda Durst - A Chicago Playboy Bunny appearing in a Photoshoot in October 1974

vgb, mistyfront, BustyPetite, Stacked, nsfw_rising, LegalCollegeGirls, JustTheTop, bodyperfection, JizzedToThis, goddesses, LaBeauteFeminine, skirtnoshirt

Sharon Johansen PMotM October 1972

OldSchoolCoolNSFW

Kicking off October schoolgirl style

B_Cups, scrolller_com

I LOVEEE OCTOBER!!! (AND HOT GIRLS)

THE_PACK

Ms. October

AnaCheri, scrolller_com

Lindy Edwards, PB Girls of the Pac 10, October 1978

OldSchoolCoolNSFW

Spooky October special!

BreadStapledToTrees

Miss October

AnaCheri

Marcy Hanson, October 1978 Playmate of the Month

OldSchoolCoolNSFW, peachfuzz

Amanda Cerny (Playmate October 2011)

JustHotWomen, AmandaCerny, scrolller_com, Playboy, PlayboyBunnies, LegendaryLegs

Y'all...it's not October yet, but at least my Preds are back at it with some pre-season hockey tomorrow!!

predsgirl92

Happy October ? here are the sales I'm running all month!

u_xoxokayla

Natasha Eklove by Christopher von Steinbach for Playboy US (September / October)

NSFWfashion, WindowBeauty

Pic of the day for October 04, 2018

hentaibondage

[F50] These are far more mild than our October weathrrrrr

GoneMild, u_BrooklynSpringvalley

daddy's kitty ?[October Contest]

JustClits, u_karbofos33, GodPussy, u_bigd2230

Hope you like pink ??! [October Contest]

JustBooty, gonewildcolor

Pic of the day for October 11, 2018

hentaibondage

Still October somewhere!

hentai, u_8-----------------8

Miss October, 1960

OldSchoolCoolNSFW, u_Steelyd7

Collinson Twins, Playboy Playmates, October 1970. Also stars of Hammer Horror's Twins of Evil.

OldSchoolCoolNSFW, TwinGirls, underthemattress

Looks like Hitomi will play a succubus in an upcoming release. My guess would be it'll be out around October.

Hitomi_Tanaka

The October Issue of Emblem Mag Will Have a Desert Vibe

EmilyBloom, fortyfivefiftyfive

Subtitles for PPPD-788 commissioned, release on 6 October!

Hitomi_Tanaka, hugeboobs

For October: PPPD-796

Hitomi_Tanaka

Regina Deutinger | Playboy Germany October 2006 | Oktoberfest

Playboy

Valerie Lane October 1973

OldSchoolCoolNSFW, VintageBabes, NostalgiaFapping, iluvnakedchicks, tanlines

Tips Celebrating an Extended October ~ (gats)

PizzaThot, lewdares

Kristine Winder October 1977

OldSchoolCoolNSFW, VintageBabes, exquisitenudes

Who says ghosts are only for October? [f]

ghostnipples, u_sush58

Mardi Jacquet October 1980

OldSchoolCoolNSFW, VintageBabes, tanlines, iluvnakedchicks, AltarOfVenus

Valerie Williams | Mayfair magazine October 1987 | ph. Jean Pierre Bourgeois

OldSchoolCoolNSFW, topless, RetrousseTits, BeachNymphs, BarelyTied, SexyFrex, SexyButNotPorn, u_greengiant87

Playmate of the Month October 1988 - Shannon Long

OldSchoolCoolNSFW, iluvnakedchicks, u_555uplander

Playmate of the Month October 1975 - Jill de Vries

OldSchoolCoolNSFW, u_Stithmeister, iluvnakedchicks, vgb, tanlines, PervertsPlace, AltarOfVenus

Playmates of the Month October 1970 - Madeleine and Mary Collinson

OldSchoolCoolNSFW, u_Stithmeister, iluvnakedchicks, vgb, u_gushgooly

Celine Huber - German Playmate of the Month for October 1989

OldSchoolCoolNSFW, iluvnakedchicks

Playmate of the Month October 1977 - Kristine Winder

OldSchoolCoolNSFW, Playboy_Albums

Playmate of the Month October 1978 - Marcy Hanson

OldSchoolCoolNSFW, u_Stithmeister, iluvnakedchicks, u_gushgooly

Playmate of the Month October 1971 - Claire Rambeau

OldSchoolCoolNSFW, u_Bootzsingh007, u_Stithmeister, PervertsPlace, u_grasscutlow, vgb, u_gushgooly

Elaine Reynolds - October 1959

OldSchoolCoolNSFW, Stacked

Celine Huber - German Playmate of the Month for October 1989

OldSchoolCoolNSFW, AltarOfVenus

Two Years of Randalin. First image is from mid 2018, 2nd from October 2019, then December 2019, and finally April 2020. Check out the waist-to-thigh ratio

ProgressiveGrowth

Playmate of the Month October 1977 - Kristine Winder

OldSchoolCoolNSFW, iluvnakedchicks, VintageBabes, NostalgiaFapping, BusinessSocks, u_anonymousannus, BiCuriousGuysChat

Playmate of the Month October 1965/Playmate of the Year 1966 - Allison Parks

OldSchoolCoolNSFW

Valerie Lane Miss October 1973

OldSchoolCoolNSFW, BusinessSocks

Miss October; Miss Tanith by TheMaestroNoob

Warhammer_Smut

Miss October; Miss Tanith [final] by TheMaestroNoob

Warhammer_Smut

Natasha Hoffmann serving pretzels at the Oktoberfest | Playboy Germany October 2020

Playboy, PlayboyOnReddit, DirndlNSFW

Tammy Hill - Pet of the Month - October 1979

OldSchoolCoolNSFW, iluvnakedchicks

Playmate of the Month October 2006 - Jordan Monroe

Playboy, PlayboyOnReddit, u_NachosThrowaway, Playboy_Collections

Playmate of the Month October 1984 - Debi Johnson

OldSchoolCoolNSFW

I know it's not October, but can we appreciate how well done this is?

campbuddy

Kristine Winder - Playmate of the Month October 1977

OldSchoolCoolNSFW

An October sky and an old yellow chair

NakedAdventures, BestPornCompile

Cyber Girl of the Week - October 2003: Gianna DiMarco (AIC)

Playboy_Albums, PlayboyOnReddit, Playboy

Celine Huber (German Playmate October 1989)

OldSchoolCoolNSFW