Jizz

Hugh Hefner's new fiancee

ass

Would Consider Having Sex with Hugh Hefner

randomsexiness

All natural, all beautiful, Barbi Benton (1970's Playboy cover girl & girlfriend of Hugh Hefner)

VintageBabes

Barbi Benton (Playboy model & former girlfriend of Hugh Hefner)

OldSchoolCoolNSFW

[X-Post from r/tilgonewild] | Playboy's original name was Stag Party, and instead of a rabbit, its mascot was a buck. Hugh Hefner changed the name to Playboy at a friend's suggestion after the name Stag Party was challenged in a trademark infringement cas

feet, TILgonewild

Really wish I was Hugh Hefner

Playboy

Hugh hefner spotted with victory electronic cigarettes

electronic_cigarette

Pamela Anderson topless for Hugh Hefner

nsfwcelebs

In my Hugh Hefner Robe, maybe you can provide the pipe? ;)

GoneWildPlus

From the very first issue (December 1953): PLAYBOY's Mission Statement, written by Hugh Hefner

Playboy

Hugh Hefner getting a blowjob from Miss December 1971

nsfw, pics, Celebs, HistoryPorn

Hugh Hefner’s longtime girlfriend, Barbi Benton, topless on the beach in 1970 [NSFW]

vgb, OldSchoolCoolNSFW

To think that at one time they gave Hugh Hefner a hard time. nsfw

NSFWFunny

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

OldSchoolCoolNSFW

Linda Lovelace, nee Linda Boreman, with Hugh Hefner, 1973.

OldSchoolCoolNSFW

Hugh Hefner threw a Playmate reunion at the Playboy Mansion in Sept 1979 and here are the pics, NSFW for the site

pics

NSFW Hugh Hefner's "Library" at the Playboy Mansion featuring a bare-breasted bust of Barbi Benton [OC](mid-1980s)

mildlyinteresting

Lily Cade > Hugh Hefner

cfnf

Hugh Hefner's sister-in-law Caya Hefner

AsianBeauty, AsianHotties

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

OldSchoolCoolNSFW

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

OldSchoolCoolNSFW

Pamela Anderson giving Hugh Hefner a cake for his birthday on Girls Next Door

bimbofetish, BimboOrNot

American Playboy The Hugh Hefner Story s01e06-09 (2017)

nsfw

Hugh Hefner and the bunnies, circa late 1950's (fro m /r/oldschoolcool)

NekoIRL

Hugh Hefner, Iconic founder of Playboy has died at 91.

Playboy

RIP Hugh Hefner. You were an icon for the industry and an inspiration to many. Thank you for being amazing.

Ellie_Silk

RIP to Hugh Hefner, who fought a lifelong battle against the birth rate.

ImGoingToHellForThis

Torrie Wilson when she was in Playboy.R.I.P. Hugh Hefner!

WrestleWithThePlot, Playboy, PlayboyBunnies, NSFWWhatever

RIP Hugh Hefner

virtualgeisha, ass, HungryButts

In Honor of Hugh Hefner [OC]

Gonewilds_Secret, NakedCurvyGirls

If Hugh Hefner ever posted in this sub.

ImGoingToHellForThis

R.I.P. Hugh Hefner

NekoIRL

Hugh Hefner & friends

nsfw, NSFW_AwesomePornPics, OldSchoolCool, better_nsfw, JustTheTop

Claire Rambeau, Miss October 1971 for Playboy. One of the hottest playmates ever. (album in comments) RIP Hugh Hefner, you legend!

nsfw, NSFW_AwesomePornPics, Playboy, PlayboyBunnies

R.I.P Hugh Hefner, my adolescence thanks and will never forget those centerfolds

Playboy

In honor of Hugh Hefner, here's the first woman I ever jizzed to

JizzedToThis

Hugh Hefner with Stacy Sanches, Tiffany Fallon, Irina Voronina, Holly Madison, and Cara Zavaleta

playboy_playmates

Pouring one out for Hugh Hefner

ImGoingToHellForThis

Hugh Hefner with Angel Boris, Deanna Brooks, Jessica Lee, and Suzanne Stokes

playboy_playmates

Honoring Hugh Hefner

DesiBoners, indiangirls

We can't all be Hugh Hefner. Wait, actually we can!

WTF

Hugh Hefner not even dead one month and SJWs are taking over Playboy

The_Donald

Stacy with Hugh Hefner

StacyValentine

Alexandra Johnston – American Playboy The Hugh Hefner Story (2017) s1e1

celebnsfw

Chelsie Preston Crayford, in American Playboy: The Hugh Hefner Story

CelebrityPussy

Just because Trump fucked a Playmate doesn't make him Hugh Hefner either.

ImGoingToHellForThis

Alexandra Light in American Playboy: The Hugh Hefner Story 2017

WatchItForThePlot, u_akhinsfw

Rest in Peace Hugh Hefner.

ImGoingToHellForThis

Playboy's Playmate House Party 1977 - Hugh Hefner, Patti McGuire, Sheila Mullen, Laura Lyons, Susan Lynn Kiger, Sondra Theodore, Hope Olson, Denise Michele, Lisa Sohm.

Playboy, iluvnakedchicks, NostalgiaFapping, GroupOfNudeGirls

* OLA RAY * - the Stunning Beauty discovered by Hugh Hefner for his "PLAYBOY" magazine before being discovered by Michael Jackson for his "THRILLER" music video!

hairyvintage

Irina Voronina with Hugh Hefner, Stacy Sanches, Tiffany Fallon, Holly Madison, and Cara Zavaleta

IrinaVoronina

The Hugh Hefner of the Viera [Straight] [BLEACHED] [HUMAN'D] [Raceplay] [Viera] [Non Human] [Maledom] [Instant Loss] [Impregnation Fetish] [Convoluted Narrative] [Part Two]

hentaicaptions

Bound Playboy Bunny (Hugh Hefner Tribute) [My Art]

bdsm

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

[3] Hugh Hefners

PickOne

Young Hugh Hefner

thebunnyclub

Young Hugh Hefner 2

thebunnyclub

Young Hugh Hefner 3

thebunnyclub

Pamela Anderson and Hugh Hefner

thebunnyclub

Do you want to be my Hugh Hefner?

InnocentlyNaughty