Jizz

The image I saw in 1999 that made me a fan of latex.

ShinyPorn

I picked up this wall scroll in 1999 & have never encountered its source image online. Have any of you? (Possibly NSFW)

evangelion

Psyching myself up for impending doom on 1999...

Bioshock

The Beauty of Bioshock Infinite - 1999 mode, No UI - SPOILERS

Bioshock

Sarah Chalke - Y2K 1999 - See through top, pokies and downblouse

Celebs

Charlize Theron - Playboy, May 1999

CelebrityNipples

Brooke Burke had those 1999 Plots in Wild On [E!]

WatchItForThePlot

Valls, Dino - Criptodidimo, 1999 [669x798]

ArtPorn

Kimberly Spicer, 1999

Playboy, PlayboyBunnies, WaterBoobs

Mena Suvari 1999

sexygirlsinjeans

Caroline Ducey, Romance (1999)

SheLikesItRough, StrugglePorn, StruggleFucking, CelebsGW, celebnsfw, Clothes_On

One of the models in Erwin Olaf's "Mature" gallery (1999)

gilf

Globeleza 1999

ComplexionExcellence

Shannon Elizabeth (1999)

areolapeaks

Do-yeon Jeon - Happy End, KR-1999

NSFW_Korea

Totally Terry - internet amateur 1999-2000 AIC

Saggy

James (Jaime) King, GQ Spain, 1999

NostalgiaFapping

Heather Kozar (Playboy's Playmate of the Year 1999)

JustHotWomen, UFs_Big_Boob_Faves

Cara Wakelin, Miss November 1999

playboy_playmates, u_Hellyeslikedat

Heather Kozar, PMOY 1999

Playboy

Jaime Bergman, the 45th Anniversary Playmate (January 1999) and star of "Son of the Beach."

NostalgiaFapping

Playmate of the Month May 1999 - Tishara Lee Cousino

Playboy, retrofucking, OldSchoolCoolNSFW, classysexy, iluvnakedchicks, u_intensereaction

Jennifer Rovero, Miss July 1999

playboy_playmates

Playmate of the Year 1999 - Heather Kozar (Album)

Bubbles, u_husnuzeybek

Jaime Bergman (January 1999)

Playboy, NostalgiaFapping, blondebush

Playmate of the Month June 1999 - Kimberly Spicer

playboy_playmates

Natalia Sokolova 1999

Playboy, PlayboyOnReddit

Mary Jane At Work [The Amazing Spider-Man (1999) #1]

ComicPlot

Natalia Sokolova, Miss April 1999

playboy_playmates, PlayboyOnReddit

Shannen Doherty (1999)

NostalgiaFapping

Miss May 1999 Tishara Lee Cousino (some more pics inside)

Playboy, PlayboyOnReddit, u_waldforest2

Rebecca Scott, Miss August 1999 (right) with Anna Nicole Smith

playboy_playmates

Nicole Kidman, 1999

NostalgiaFapping, ginger

Miss Oct 1999 Jodi Ann Paterson. She was also voted PMOY 2000

Playboy_Albums, PlayboyOnReddit

Cara Wakelin, Miss November 1999

playboy_playmates

First ever piccie of myself dressed girly back in 1999. Huzzah!

NonBinary

Thora Birch - 'American Beauty' (1999)

celebnsfw

Mary Helen from sexy girls next door (1999)

Playboy, PlayboyOnReddit, SensualPhotography

Kristi Cline, Miss September 1999

playboy_playmates, u_bluewaterfree

Donna Ewin (aka Nina Downe) 1999

Playboy, PlayboyOnReddit

Brooke Richards, Playboy centerfold for December 1999 where only one nipple is in focus

playboy_playmates

Playmate Of The Month May 1999 - Tishara Lee Cousino

TurboNSFW, OldSchoolCoolNSFW

Heather Kozar (January 1998 Playmate of the Month and 1999 Playmate of the Year)

NostalgiaFapping

Shannon Tweed in the 1999 film "Scandalous Behavior" Let the debate begin - Real sex? Simulated sex?

celebnsfw

zdenka podkapova - 1999

NostalgiaFapping

Marketa Janska, 1999

ClassicInternetPorn

Red Sky in the Morning, Shepherd's Warning! - This is me circa 2002, my boobs are at only 50% of their full potential ? Little did I know they'd balloon to epic Milf proportions a decade later. - Watch all my Vintage / Retro videos (1999 forward) over at

u_chicktrainer

Jenna Jameson - Dream Quest BTS 1999

OldSchoolCoolNSFW, legs, PornStarPlanet, YourDadsOldPorn, tanlines

Melissa Joan Hart (1999)

NostalgiaFapping