Jizz

Marilyn Manson being interviewed in 1999 by an FX reporter in a see-thru blouse

pics

Shannon Elizabeth - American Pie [1999]

celebnsfw, WatchItForThePlot

Catherine Zeta-Jones in 'Entrapment' (1999)

WatchItForThePlot

Shannon Elizabeth- American Pie (1999)

celebnsfw, CelebsExposed

Marion Cotillard in Furia [1999]

WatchItForThePlot

Idle Hands (1999) Kelly Monaco as Tiffany

celebnsfw, CelebsExposed

Naomi Campbell. Playboy Magazine December 1999.

celebnsfw, Playboy, WomenOfColor, NSFWfashion, PlayboyBunnies

you loved the brolly so much here is the open 1999 ATi brolly. behind is NSFW.

Amd

[img] Hanna Hays from FTVgirls (born 1999)

FauxBait, adorableporn, LabiaGW

Ann Beate, Playboy 1999

OldSchoolCoolNSFW

Charlize Theron for Playboy [1999]

celebnsfw, differentstr0kes, YeOldeNudes

Shannon Elizabeth Playboy 1999

NostalgiaFapping

Gisele Bundchen by Irving Penn for Vogue 1999 (outtake)

NSFWfashion, Celebs, u_BenOpen6

Cara Wakelin - PMOM, Nov. 1999

Playboy, pigtails, PlayboyBunnies, Isa_2, u_karbofos33

Denise Luna - Sweetheart of the Rodeo - Sept 1999

OldSchoolCoolNSFW

The way a broke chick with a 1 megapixel Kodak camera gave Christmas presents in 1999

HairyPussy, FuzzyPeeks

Albanian family finding out their father and husband was killed by Serbian forces, Kosovo 1999

MorbidReality, kosovo

My 52 year old wife. Taken in 1999, about 4 months after delivering child #2 (she was 33). This set was taken on film, and we're pretty sure someone somewhere (besides us) kept a copy of the negatives.

maturemilf, OldSchoolCoolNSFW, EraserNipples, GoBoobs

Melissa Joan Hart (1999)

celebnsfw

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

celebnsfw, NSFWfashion, dragonraptor64

Mena Suvari in American Beauty (1999)

celebnsfw, Celebritywild

Thora Birch in American Beauty (1999)

celebnsfw

Kimberly Spicer June 1999

OldSchoolCoolNSFW, VintageBabes, NostalgiaFapping

Miss January 1999 Jamie Bergman

OldSchoolCoolNSFW, u_alextwotg

Gisele Bündchen | Valentino prêt-à-porter Spring-Summer 1999

NSFWfashion

Jessica Alba - Idle Hands - 1999

celebnsfw, u_sneily420

"Son of the Beach" star and January 1999 Playmate of the Month Jaime Bergman.

NostalgiaFapping, BOUS

Heather Kozar, Playboy's Miss January 1998 and Playmate of the Year 1999.

NostalgiaFapping, blondebush

Britney Spears, 1999

NostalgiaFapping

Playmate of the Month September 1999 - Kristi Cline (AIC)

Playboy_Albums, PlayboyOnReddit, u_NachosThrowaway

Jaime Bergman - Miss January 1999

Playboy, PlayboyOnReddit, NostalgiaFapping

Playmate of the Month April 1999 - Natalia Sokolova (AIC)

Playboy_Albums, PlayboyOnReddit

Stacy Marie Fuson, May 1999

OldSchoolCoolNSFW

Playmate of the Month January 1999 - Jaime Bergman Collection (AIC)

Playboy_Albums, PlayboyOnReddit, u_T_Rayleigh

Monica Sweetheart [Pornstar from 1999-2006]

NostalgiaFapping

Reese Witherspoon in Cruel Intentions, 1999

CelebrityButts

The Girls of Hawaiian Tropic (1999) (AIC)

Playboy_Albums, PlayboyOnReddit

Kimberly Spicer (Playboy, 1999)

NostalgiaFapping

Stacy Marie Fuson, 1999!

Playboy, PlayboyOnReddit

Cara Wakelin, 1999! (Anotha one!)

Playboy, PlayboyOnReddit

Playmate of the Month June 1999 - Kimberly Spicer

Playboy, PlayboyOnReddit, SeriousSapphic, MyPornGallery

Rena Mero (Sable) 1999

NostalgiaFapping

Playmate of the Month February 1999 - Stacy Marie Fuson (AIC)

Playboy_Albums, PlayboyOnReddit, Elsas

Playmate of the Month February 1999 - Stacy Marie Fuson

playboy_playmates

Monica Bellucci | Max calendar 1999 | ph. Fabrizio Ferri

OldSchoolCoolNSFW, celebnsfw, NSFWfashion, myerotism

Playmate of the Month December 1999 - Brooke Richards Collection (AIC)

Playboy_Albums, PlayboyOnReddit

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

OldSchoolCoolNSFW

Sunset (@RoseTime_1999)

yaoi

Jennifer Love Hewitt - Maxim November 1999

NostalgiaFapping

Melissa Joan Hart (1999)

celebnsfw, NostalgiaFapping

This is what it looks like when a 50-year-old amateur pornstar decides to come out of retirement and go head-to-head with a billion skinny 19-year-olds on TikTok and OF. Times have changed so much since 1999, gotta keep up with the times... ??

u_chicktrainer, u_TommCat48

Heather Graham - Austin Powers: The Spy Who Shagged Me (1999)

WatchItForThePlot