Jizz

Peeter Allik - Melanhoolia/Melancholy (1999) [r/museum]

Heavymind

That denim handbag is so 1999!

CandidFashionPolice

[NSFW] The Columbine Shooters, April 20, 1999 [1773x986]

HistoryPorn

Cara Wakelin, Miss November 1999

Playboy, PlayboyBunnies

Eyes Wide Shut [1999]

CineShots

Cameron Diaz wet titties, 1999

Celebs, SexyButNotPorn

correva l'anno 1999 quando Rocco Siffredi faceva pubblicità per un gioco Dreamcast

italy

Winona Ryder In Girl, Interrupted (1999)

bois

Karin Taylor, Jami Ferrell, and Rachel Jean Marteen are on safari (1999)

Playboy, PlayboyBunnies, Bottomless_Vixens, LoveToWatchYouLeave, Boots, GroupOfNudeGirls, TrueFMK

Gisele Bündchen by Irving Penn for Vogue US, July 1999.

BrazilianBabes

Carrie-Anne Moss - The Matrix - 1999

CelebrityButts

I feel like it's 1999 again. Thanks for the memories and for the new adventures to come, Nintendo-sama... ???

u_Trish_Collins

Throwback Thursday. My all time favorite porn star. Krystal Steal and her epic ass. Circa 1999.

nsfw

Miss Kitty Armageddon 1999

WrestleWithThePlot

Tishara Lee Cousino (Playmate May 1999)

JustHotWomen

Tishara Lee Cousino (Playmate May 1999)

JustHotWomen

Tishara Lee Cousino (Playmate May 1999)

JustHotWomen

Tishara Lee Cousino (Playboy's Miss May 1999)

JustHotWomen, OldSchoolCoolNSFW

This was all the plot I needed from The Lost World circa 1999

NostalgiaFapping

Melissa Joan Hart - Bikini Magazine (1999)

NostalgiaFapping

My 52 year old wife. Let's move the clock up from yesterday's 1999. This is from a set we took in 2006 while at Disney for the first time with the kids. She's 40 here.

maturemilf

Sex Couture by Thierry Mugler for Playboy, 1999

saudelobaes, NSFWfashion

Jaime Bergman, Miss January 1999

playboy_playmates, u_Hellyeslikedat, u_mesquite06

Tishara Lee Cousino (Miss May 1999)

JustHotWomen, nsfw2

From 1999, This One is Fucking Hot!

tickling

A Classic From 1999 (Sagemonn)

Femnautica

Kate Winslet, 23 y.o. (Holy Smoke, 1999)

fullfrontalcelebs

Lolo Ferrari - you probably remember her if you had the 1999 Guinness Book of World Records

90sTits, 1000ccplus

Andrea Thompson, 39 y.o. (A Gun, a Car, a Blonde, 1999)

fullfrontalcelebs

Jacinta Stapleton (1999)

NostalgiaFapping

Britney Spears (1999)

NostalgiaFapping, sexygirlsinjeans

[4k BluRay] Rachel Weisz in The Mummy (1999) - [See comments]

CelebrityArmpits

Christina Steffer (1999)

Playboy, PlayboyOnReddit, SensualPhotography

Playmate of the Month August 1999 - Rebecca Scott (AIC)

Playboy_Albums, PlayboyOnReddit

Jennifer Lopez in 1999

NostalgiaFapping

Jodi Ann Paterson, October 1999

OldSchoolCoolNSFW, VintageBabes, NostalgiaFapping, Bottomless

UHQ | Tishara Lee Cousino (Miss May 1999)

Playboy, PlayboyOnReddit

Anita Blonde 1999

YourDadsOldPorn, OldSchoolCoolNSFW

Jaime Bergman - Miss January 1999

Playboy, PlayboyOnReddit

The rare, full-on Lita / Amy Dumas butt shot (circa 1999 ECW)

WrestleFap

Tishara Cousino - Miss May 1999

Playboy, PlayboyOnReddit

Hero Training [Birds of Prey (1999) #100]

ComicPlot

Keisha - Cumback Pussy 25 (1999)

ClassicXXX

Kira Kener - The Window (1999)

YourDadsOldPorn

NEW! "Wineglass" (Video, 3:18) - Hop into that DeLorean with me, set the dial to 1999, and stuff some banana peel into the flux capacitor. Let's watch cute little 'Blond Britney' drink her first cum load from a glass. ??? Some pretty acrobatic pussy fucki

u_chicktrainer