Jizz

playboy girl Tiffany Ryan (link to gallery is in comments)

Bikini, Sexy_Facebook_Girls

[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

I present to you my former English teacher, the playboy model Elaine Morton

nsfw

A few of you like my "Playboy Spread" post on GW.....but I don't want to leave you ass lovers hanging [F]

asstastic, gonewild

playboy sure know how to lingerie pictures

BonerMaterial, lingerie

To kick things off here is an old Playboy picture of Sherilyn fenn

VintageStars

had to redo my pink playboy panties pic, (f)or whoever wants to see.

gonewild

In ON HER MAJESTY'S SECRET SERVICE (1969), James Bond waits for a safe to open and looks through a "Playboy" (in a nod to the novel appearing in the May '63 issue). Although the film series never purposefully features nudity, there is an unused reverse an

movies

This girl I went to high school with has always been trashy, even into pregnancy! The Playboy logo she wears all the time is really a nice touch. (Xpost /r/trashy. More in comments)

trashyboners, NSFWPregnancy

Customize these Pink Lace PlayBoy panties worn for u up to 5 days if you like, add extras to customize your panty [SELLING] [usedpanties] [Ladyebony] $49 free shipping

wetpantiesbyladyebony

Diane Webber - Playboy Magazine's Playmate of the Month in May 1955 and February 1956. The first model to show her pubic hair also the first to be shown in a full-frontal nude pose.

OldenPorn

Diane Webber - Playboy Magazine's Playmate of the Month in May 1955 and February 1956. The first model to show her pubic hair also the first to be shown in a full-frontal nude pose.

HairyPussy

Diane Webber - Playboy Magazine's Playmate of the Month in May 1955 and February 1956. The first model to show her pubic hair also the first to be shown in a full-frontal nude pose.

VintageBabes

Diane Webber - Playboy Magazine's Playmate of the Month in May 1955 and February 1956. The first model to show her pubic hair also the first to be shown in a full-frontal nude pose.

VintageSmut

Playboy shoot imgur rehost (put /zip at the end to download full album)

presshearttocontinue

Playboy g string needs to be torn off

MenGW

Watching Battlestar Galactica always makes me want to jerk my penis to Tricia Helfer's Playboy shoot.

JizzedToThis

Anyone have a name. She's definitely busty, looks to be petite. Image has that "playboy" look. Would love to find more of her - her smile is priceless. As are her tits

LegalCollegeGirls, NSFW_Gonewild_TEEN

Playboy decided to bring nudity back. Let's worship Elizabeth Elam's ass.

ass, BootyPics

Margaret Scott aka Marilyn Waltz who was the first of only two women to be a three-time Playboy centerfold, 1954

OldSchoolCoolNSFW, nsfw_rising

Playboy How to Kiss

girlskissing

Documenting my life on [snp]. From showers to cupcakes to stretching and strip teases, I'm like hgtv meets playboy.

Sexsells, ghostnipples

I used to always sneak out of bed to watch 'Wild on E' with Brooke Burke. You could imagine my excitement when I found out a couple years later that she posed nude for Playboy

NostalgiaFapping

Sila Sahin - First Turkish model to appear on PlayBoy cover

RepressedGoneWild, MiddleEasternHotties, TurkishWomen

Posting here kinda makes me (f)eel a bit like a playboy model. Curious about how many of you will click to get a better look, and how many guys that I will never meet IRL will use my body to power their fantasies for who knows how long into the future. I

gonewild

Posting here kinda makes me (f)eel a bit like a playboy model. I wonder how many of you will click to get a better look, and how many guys that I will never meet IRL will use my body to power fantasies for who knows how long into the future. I am honored

TributeMe, gonewild

I wanted to say thank you I will be posing for playboy next year and I have to give credit to y’all for always being awesome ?24 [f]

PetiteGoneWild, GoneWildHairy

Did You Know That a Playboy Can Change His Job to a Sage?

OppaiLove

Rebecca Ramos, Playboy's Miss January 2003. At age 35 she became the oldest woman to become Playmate of the Month in the history of the magazine.

NostalgiaFapping, u_romins1221, u_bigdieseldick1982, u_mesquite06, u_burner4pr0n

Sherlyn's playboy shoot. All credits to Playboy and affiliates

SherlynChopra

More from playboy shoot. All credits to Playboy and affiliates.

SherlynChopra

10 Years ago, I submitted this picture to Playboy in an attempt to pose for them, I was never contacted.

normalnudes, Normalnudesgonewild

Janet Lupo, Playboy's Miss November 1975. With a bust size of 38DDD, many believe her to be the largest-breasted Playmate in the magazine's history.

NostalgiaFapping, u_tpc671, Lovelyboobs, Titties, uniboobs, u_soloassisland, u_macattak33

I tend to be more Playboy, but sometimes I get Penthouse...

u_RosiBlossom, pussy, 40plusGoneWild, RealGirls, u_hammerhemi87

Shanna Moakler, the first woman to be both Miss USA (1995) and a Playboy Playmate (December 2001)

NostalgiaFapping

On the left: Carol Eden, Playboy's Miss December 1960. On the right: Simone Eden, Playboy's Miss February 1989 and the first Playmate to be the daughter of a previous Playmate.

NostalgiaFapping

Playboy days. I'm looking for a partner, follow the instructions on momentgirl.com to contact me!

Sabrina_Nichole

Playboy Swedish Blonde Alexandra Andersson My Teen Crush. I'm looking for a partner, follow the instructions on makefastdate.com to contact me!

blondehairblueeyes

Ever bust a load to this pic? Gemma Hiles (Playboy)

NostalgiaFapping, u_texashellyea, BlondeBombshells

Playboy shoot NSFW. I'm looking for a partner, follow the instructions on momentgirl.com to contact me! Tiktok julypussy

HotLohan

Playboy hottie. I'm looking for a partner, follow the instructions on momentgirl.com to contact me! Tiktok julypussy

MollyStewart

Playboy Swedish Blonde Alexandra Andersson My Teen Crush. I'm looking for a partner, follow the instructions on momentgirl.com to contact me! Tiktok julypussy

Elsas

Dru Hart (Playboy 1968) - come listen to the Beatles with me

OldSchoolCoolNSFW