Jizz

Thong hiked up like it's 1999...

GoneMild

Katy Perry faked by Madd Hatter (1999×2850)

CelebFakes

Cameron Diaz (1999)

Celebs

Caroline Ducey. Romance (1999)

CelebrityPussy

Kids Choice awards, 1999

sweatermeat

[Album] 44 Photographs from the two Liberian Civil Wars (1989-1997, 1999-2003)

CombatFootage

I was going through an old backup from 1999 and ran across this. [NSFW]

WTF

Salma Hayek - Dogma (1999)

OnStageGW

Naomi Campbell, Playboy, December 1, 1999

celebnsfw

Heidi Klum wearing nothing but body paint in the 1999 Sports Illustrated Swimsuit Issue

NostalgiaFapping, u_balibaloux, SISwimsuitGirls, celebnsfw, u_goldmoonraker

Shannon Elizabeth (2017 / 1999)

OnOffCelebs

[Topless] Heidi Klum for 'Fit for Fun Magazine' (1999)(25y.o.)

CelebNudeDebut, u_BobsUrUncle6

Tishara Lee Cousino (Playboy's Miss May 1999)

JustHotWomen, Playboy

My 52 year old wife - another from that 1999 set.

maturemilf

Playmate of the Month June 1999 - Kimberly Spicer

Bubbles, NostalgiaFapping

Playmate of the Month January 1998/Playmate of the Year 1999 - Heather Kozar Collection (AIC)

Playboy_Albums

Heather Kozar PMOY 1999

Playboy

Siesta en Estufador by Alberto García Alix, 1999

saudelobaes

Stacy Marie Fuson, Miss February 1999

playboy_playmates, u_Maxstatss, u_Hellyeslikedat

Nudist no. 8 by Torbjørn Rødland, 1999

saudelobaes

Adriana Lima | Marie Claire Italia May 1999 | ph. Darren Keith

fashionextramile

Playmate of the Month May 1999 - Tishara Lee Cousino

playboy_playmates, u_Hellyeslikedat, OldSchoolCoolNSFW, iluvnakedchicks

Sharon Stone - The Muse - 1999

celebnsfw

Playmate of the Month May 1999 - Tishara Lee Cousino

Playboy, PlayboyOnReddit

Девушки Playboy 1999 год [альбом в комментариях]

Pikabu

Playmate of the Month November 1999 - Cara Wakelin

playboy_playmates

Tishara Lee Cousino, Miss May 1999

playboy_playmates

Britney Spears, 1999

NostalgiaFapping

Playmate Of The Month May 1999 - Tishara Lee Cousino

OldSchoolCoolNSFW

Cara Wakelin, November 1999

OldSchoolCoolNSFW

The whipped cream bikini in Not Another Teen Movie(2001) was not actually whipped cream, but shaving cream, as real whipped cream would melt under the set lights, which they learned in Varsity Blues(1999).

MovieDetails

Sandra Lindquist & Josie Whittlesey - Cradle Will Rock (1999)

celebnsfw

Natalia Sokolova 1999

Playboy, PlayboyOnReddit

Playmate of the Month September 1999 - Kristi Cline

OldSchoolCoolNSFW

Playmate of the Month September 1999 - Kristi Cline

playboy_playmates

Jennifer Rovero - Playmate of the Month July 1999

OldSchoolCoolNSFW

Shannon Elizabeth (1999)

Playboy_Albums, PlayboyOnReddit

Alexandria "Lexie" Karlsen, Miss March 1999

playboy_playmates

Untitled by Antoine D'Agata, 1999

saudelobaes, Indierotica

Kelly Monaco (Idle Hands, 1999)

NostalgiaFapping

Corrin is a perfect bride (w (1999 kyu)) [Fire Emblem Fates]

CuteTraps, rule34, Hentai4Everyone, traphentai, DeliciousTraps, FemboyHentai, Hentaiaddict, SissyHentai

Brought to you by RJ - Subverting expectations since 1999 (top panel was taken from r/PrequelMemes)

saltierthancrait

Gretchen Mol in Forever Mine, 1999

celebnsfw, CelebrityNipples

Shannon Stewart 1999

Playboy_Gifs, OldSchoolCoolNSFW

Stephanie Dahl by Earl Miller 1999 - 35mm Transparency Slide From Personal Collection

NostalgiaFapping

Britney Spears in 1999 (Aged 18)

NostalgiaFapping, JerkOffToCelebs

Jenna Jameson's amazing body & tits (Dream Quest BTS, 1999)

OldSchoolCoolNSFW

Catherine Oxenberg in the 1999 film "Time Served" 1 of 2

celebnsfw

Catherine Oxenberg in the 1999 film "Time Served" 2 of 2

celebnsfw, 20thCenturyFoxes, u_zipzzzz

Natalia Sokolova - Miss April 1999

Playboy, PlayboyOnReddit

Lorri Bagley in the 1999 film "Trick"

celebnsfw, CelebrityNipples

Nicole "Coco" Austin (1999)

NostalgiaFapping, CocoAustin, 90sTits, Celebsnudess, OldSchoolCoolNSFW, Celebswithbigtits, celebnsfw, NudeCelebsOnly, CelebrityNipples, CelebrityPussy, u_neel090992, u_DuckOrdinary, u_boobscomelook

Terinee Beier, 1999

AltarOfVenus, iluvnakedchicks

German Playmates (1999)

Playboy, GroupOfNudeGirls, u_Easy_Eggplant_5103, boobs, PlayboyOnReddit