Jizz

I've often wondered what happens to playboy models when they get older. Here's a milfy example.

milf

a friend of mine made it all the way to Playboy.. here she is getting body paint..

Boobies, HotgirlsinBodyPainted

She wants to be a playboy bunny

AsianHotties

A local Belgian politician promised to pose nude for playboy if she got 1000 votes. This is her campaign poster. [slightly NSFW]

pics

[f]THIRD POST - just turned 18 - redhead w/big tits & tattoos - on all fours on playboy logo - more to come

gonewild

I was asked to cross post this from R/GirlswithBodypaint. Eugenia Diordyichuk in Animal Instincts After Dark Body Paint Playboy

NSFWCostumes, GirlswithBodypaint

I didn't marry her because of the Playboy offer she turned down years ago (but it is fun to brag). x-post from r/cleavage

burstingout

I didn't marry her because of the Playboy offer she turned down years ago (but it is fun to brag). x-post from r/cleavage

mycleavage, burstingout

I didn't marry her because of the Playboy offer she turned down years ago (but it is fun to brag).

cleavage

Wow! When I was 12 I stole my dad's playboy. This is the page that I used to "explore myself" for the first time... I must say; I had good taste!

nsfw

My friend went to the Playboy mansion Halloween party last weekend. This was the line at the bar.

pics

An invitation to Hugh Hefner's "Playboy Pajama Party" Dec 31, 1979 - model Caren Stevens

OldSchoolCoolNSFW

Emma Watson Nude. Click here to see her new Playboy pictorial.

circlejerk

Nancy Cameron, January 1974 Playboy 26 pics (the Jan ’74 issue was the 1st to feature a double-sided centerfold)

OldSchoolCoolNSFW, oldschoolhot, OldSchoolDrool

Naughty tennis player Ashley Harkleroad decided to pose for Playboy

nsfwsports

1973 Playboy directions on public sex and how to "Keep it clean". Possibly NSFW

pics

No more of this on playboy but you can sure count on me to keep them posted (f)

gonewild

[F] She dreamed of being on the cover of Playboy - but she knew this was the closest she'd ever come to that.

IntenseBDSM

Leanna Decker- Playboy A to Z special (May 2014) scans

leannadecker

Karen Morton (reportedly Playboy's smallest breasted Playmate of all time) has reason to be envious of Rosanne Katon

BreastEnvy

Added some brand-new images to my Kaplan twins album (from Playboy Netherlands 7/17). Album link in comments.

TwinGirls

Sermine Shahrivar, born in Germany, parents are Iranian is the first Persian celebrity to appear in Playboy Magazine. She is a former Miss Germany and Miss Europe

exotic_oasis

The first woman I ever crushed on in my life was Karen McDougal, from one of the first Playboy magazines I managed to get my hands on in the 90's. I was so disappointed recently after learning a few months ago she became Donald Trump's lover. So yeah, FUC

FuckYouKaren

Not really that into her now, but back when Kim Kardashian posed for Playboy I pretty much fapped exclusively to her for about a month straight

NostalgiaFapping

Echoing Playboy's very first centerfold (which even predates me ?) to celebrate 1,000 subscribers - thank you all! ??

Bloom_Butt_Blossoms, 50plusGW

I have to remember this one!!! Love these old Playboys!!!

HotwifeXXXCaptions, u_MeMeEmEm7

I wanted to sling so much cum at cute playboy girl Brooke Berry back in the day

NostalgiaFapping

Kelly Monaco was a mega-babe. Easily one of the most beautiful women to ever pose for Playboy.

NostalgiaFapping

Lisa Matthews was one of the cutest things ever to grace the Playboy page

NostalgiaFapping

Shari Belafonte @46 y.o., 2000 Playboy photoshoot (link to album in comments)

celebnsfw

Janet Lupo, Playboy's Miss November 1975. Her 38DDD boobs are believed to be the largest of any Playmate is the history of the magazine.

NostalgiaFapping

You might want to keep your eyes on the road, playboy [f]

altgonewild

One of the hottest women to ever pose for Playboy: Kelly Monaco.

NostalgiaFapping, iluvnakedchicks, u_Sayon121

Sherlyn Chopra, the first Bollywood actress to do a Playboy shoot [AIC]

Celebhub

Nyannyan Visconti (Did You Know That a Playboy Can Change His Job to a Sage?) [SilverTsuki]

bakunyuu

Profile from Playboy.com - apparently she loves to get naked and has a lot of sex

elizabethostrander

Linn Thomas, the first woman to be both a Playboy Playmate and a Penthouse Pet.

NostalgiaFapping

Megan Samperi, Lorena Medina & Emily Shriner 'Road to Palm Springs' by Christopher von Steinbach for Playboy US

nakedcamping

Get closer to me and get 7 days free on Playboy Plus

AbigailMac

Following me for nudes is like jerking to old Playboys. It works, but could be so much better ?

NaughtyWives

Following me for nudes is like jerking to old Playboys. It works, but could be so much better ?

Nipples

Following me for nudes is like jerking to old Playboys. It works, but could be so much better ?

HugeHangers

Following me for nudes is like jerking to old Playboys. It works, but could be so much better ?

burstingout

Following me for nudes is like jerking to old Playboys. It works, but could be so much better ?

mycleavage

Pamela Anderson as the Labatt Blue Zone Girl, 1989. When Hugh Hefner saw this pic he invited Pam to pose for Playboy. The rest is history.

NostalgiaFapping

One of the best couples to fuck in the LS, they were on Playboy swing too!

Swingersgw

Yet another outtake of one of the booty poses from her Playboy shoot Julia Fox by Greg Manis 2015. I'm looking for a partner, follow the instructions on momentgirl.com to contact me!

juliafoxsub

The four playboy playmates who went to the Moon on the Apollo 12 mission, 1969

OldSchoolCool

Payton Marie: Playboy girl goes to the ankles once again [aic]

anklepanties, u_texashellyea

Susan Bernard, Dec 1966 Playboy Playmate of the Month (Gut yontiff to all now let's let's go get-i some spaghetti)

PornMuseum

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onlyfansgirls101

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RedditOnlyFans, DirtySocialMedia

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naughtychicks