8 XXX : x 1999

Famous shot from the movie Entrapment [gif] (Catherine Zeta Jones in 1999)

imgur.com category @PursuitOfHirsute

Anna Friel - A Midsummer Night's Dream (1999)

imgur.com category @[deleted]

Jennifer Aniston - topless Paparazzi pics taken in 1999. More explanation in comments.

imgur.com category @wileecoyote1969

Sarah Michelle Gellar & Selma Blair in "Cruel Intentions" (1999)

gfycat.com category @pretty-ladies

Caroline Ducey. Romance (1999)

imgur.com category @[deleted]

Mia St. John, I.B.A. Featherweight Champion - November 1999 [xpost /r/Playboy]

imgur.com category @OfficialCardinalSins

Kids Choice awards, 1999

imgur.com category @AllGoodInTheHood

Katy Perry faked by Madd Hatter (1999×2850)

imgur.com category @hvy_wpns_guy

[REQUEST] Young Sarah Michelle Gellar, like in the movie Cruel Intentions (1999)

imgur.com category @shibaizutsu

Mena Suvari 1999

imgur.com category @Chris_DK

Charlize Theron - Playboy, May 1999

imgur.com category @atticus138

More of Ms Cavalotti - fingering onstage in "Guardami" (1999)

gfycat.com category @DS_Lite

Elisabetta Cavallotti's Blowjob scene from "Guardami" (1999)

gfycat.com category @DS_Lite

Caroline Ducey handling Rocco in "Romance" (1999)

gfycat.com category @DS_Lite

Yekaterina Golubeva and Guillaume Depardieu getting it on in "Pola X" (1999)

gfycat.com category @DS_Lite

Loredana Cannata fingers herself in "La Donna Lupo" (1999)

gfycat.com category @DS_Lite

Severine Caneele rubs her pussy in "L'Humanité" (1999)

gfycat.com category @DS_Lite

Déjà Vu's Showgirl of the Year contest, 1999

imgur.com category @OfficialCardinalSins

Horst P. Horst (photographer, 1906–1999) Odalisque III, New York , 1943

imgur.com category @[deleted]

Charlize Theron nude in Playboy, May 1999

imgur.com category @kellyepulido

Tania Russof, 'Tatiana' 1999

gfycat.com category @Whitestripe71

1999

tumblr.com category @Mad4Reddit

Kelly The Coed 4 (1999, Vivi Anne, Anne Howe, Naughtia Childs, Regan Starr, Allysin Chaynes, Nancy Vee) - 000540.45.532x399

imgur.com category @porngifbot

EXTENDED: Danielle Rogers doing anal in Chamber Of Whores 2: Porn World (1999)

gfycat.com category @goofball_jones

Danielle Rodgers and Herschel Savage from Chamber Of Whores 2: Porn World (1999)

gfycat.com category @goofball_jones

Danielle Rogers doing anal in Chamber Of Whores 2: Porn World (1999)

imgur.com category @goofball_jones

Hole performing Celebrity Skin at Big Day Out festival in Sydney, Australia 1999 (Courtney Love rocks out with her tits out)

youtu.be category @reddit-equals-idiots

Shannon Elizabeth - American Pie (1999)

imgur.com category @CopYesOrNo

Caroline Ducey, Romance (1999)

imgur.com category @2shake

Caroline Ducey, Romance (1999)

imgur.com category @2shake

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

imgur.com category @CJ105

Complete works of Cara Wakelin - Miss November 1999 [X-post /r/playboy_albums]

imgur.com category @Kalrin

Naomi Campbell - Playboy December 1999

imgur.com category @CJ105

Naomi Campbell – Playboy December 1999

imgur.com category @CJ105

Ann-Beate Lund Norwegian Playmate April 1999

imgur.com category @Neidegaia3

Christina Aguilera, 1999

imgur.com category @pepsi_next

Shannon Elizabeth - American Pie (1999)

gfycat.com category @CopYesOrNo

Caroline Ducey, Romance (1999)

imgur.com category @2shake

My Wife - An album from a set we took in 1999. She was 33 for these, and was about 4 months past delivering our second child

imgur.com category @NudesNudesNudes

Elisabetta Cavalotti shlicking in Guardami (1999)

gfycat.com category @DS_Lite

Pyramides 1999

imgur.com category @OfficialCardinalSins

Elisabetta Cavallotti from “Guardami” (1999)

imgur.com category @NSCC

VESTIDO ETERNO, MÉXICO, 1999.

tumblr.com category @ceally

Shannon Elizabeth - American Pie (1999)

gfycat.com category @CopYesOrNo

Tara Reid topless in Body Shots (1999) [MIC]

gfycat.com category @[deleted]

Cara Wakelin, Miss November 1999

imgur.com category @DoctorJSmith

Caroline Ducey, Romance (1999)

imgur.com category @2shake

Cara Wakelin - Miss November 1999

imgur.com category @Kalrin

Salma Hayek - Dogma (1999)

gfycat.com category @frecklefactor

1999 bachelor party pic

imgur.com category @vipstrippers