Jizz

Angeline Jolie - Foxfire (1999) 1080p (Vid in comment)

nsfw

Eyes Wide Shut, 1999 (NSFW)

CinemaPorn

Throwback Thursday! Let's Party Like it's 1999 (yes I was legal to look at :D) (F)

GoneWildPlus

Naomi Campbell, December 1999

PlayboyBunnies, Playboy

Thora Birch-American Beauty(1999)

nsfw

Gisele Bundchen by Steven Meisel for Vogue US, November 1999

GiseleBundchen, BrazilianBabes, JuicyBrazilians

Miss January 1998 and Playmate of the Year 1999, Heather Kozar

playboy_playmates, nsfw, breastsubever, 90sTits, NostalgiaFapping, blondebush

Miss November 1999, Cara Wakelin

playboy_playmates

Miss July 1999, Jennifer Rovero

playboy_playmates

Miss October 1999, Jodi Ann Paterson

playboy_playmates

Miss July 1999, Jennifer Rovero

playboy_playmates

Miss October 1999, Jodi Ann Paterson

playboy_playmates

Miss February 1999, Stacy Marie Fuson

playboy_playmates

Miss October 1999, Jodi Ann Paterson

playboy_playmates

Miss February 1999, Stacy Marie Fuson

playboy_playmates

Miss February 1999, Stacy Marie Fuson

playboy_playmates

Miss October 1999, Jodi Ann Paterson

playboy_playmates

Miss February 1999, Stacy Marie Fuson

playboy_playmates

Miss December 1999, Brooke Richards

playboy_playmates, 90sTits

Miss July 1999, Jennifer Rovero

playboy_playmates

Miss December 1999, Brooke Richards

playboy_playmates

Miss July 1999, Jennifer Rovero

playboy_playmates

Miss December 1999, Brooke Richards

playboy_playmates

Miss December 1999, Brooke Richards

playboy_playmates

Miss October 1999, Jodi Ann Paterson

playboy_playmates

Miss October 1999, Jodi Ann Paterson

playboy_playmates

Miss October 1999, Jodi Ann Paterson

playboy_playmates

Miss December 1999, Brooke Richards

playboy_playmates

Miss October 1999, Jodi Ann Paterson

playboy_playmates

Miss December 1999, Brooke Richards

playboy_playmates

Miss July 1999, Jennifer Rovero

playboy_playmates

Miss December 1999, Brooke Richards

playboy_playmates

Miss October 1999, Jodi Ann Paterson

playboy_playmates

Britney Spears, 18 years old, 1999

sexygirlsinjeans, LegalTeens, Gonewilds_Secret, legalxxx

Charlize Theron circa 1999

Celebs, Playboy, PlayboyBunnies

Laetitia Casta (1999)

nsfw, NSFW_AwesomePornPics

Jessica Alba - Idle Hands (1999)

HorrorMovieNudes

Veronica definitely knew how to party in 1999

cumonherfacedotcom

Taime Hannum (Lowrider Magazine September 1999)

NostalgiaFapping

Fantastic Breasts - Nostalgia Edition, Heather Kozar PMOY 1999

FantasticBreasts, NostalgiaFapping

Ayane Anno's Abs [Gold Digger (1999) #53]

ComicPlot

Sofia Moon (1999 - 2020)

mortalporn, HighResNSFW, nsfw2, nsfw

Veronica's Friend, Sandra (1999)

cumonherfacedotcom

Voodoo Trying on Clothes [Wildcats (1999) #15]

ComicPlot

My hot blonde mom in 1999: big, juicy DSLs and a big, juicy, tan ass. WWYD and where would you cum?

jerkofftomymom, amateur_milfs

Jezebelle's Dress [Undertaker (1999) #9]

ComicPlot

Lorri Bagley in Trick (1999)

BattyForNudity_PICS

Catherine Deneuve photographed by Ellen Von Unwerth (1999)

found_femdom