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Julia Ann and Nikki Fritz nude in Veronica 1999

kate winlet in Holy Smoke 1999 (4)

Aspen Brock, Barett Moore, and Jewel De'Nyle with Peter North in North Pole 8 (1999)

Kari Wuhrer in Vivid 1999

Shu Qi In Iron Sister (1999)

Elia Galera - La mujer más fea del mundo (The Ugliest Woman in the World)(1999) 2 (1)

Kate Winslet in 'Holy Smoke (1999)'

/r/celebrityplotarchive - Jessica Alba in Idle Hands (1999) - Cropped

/r/celebrityplotarchive - Jessica Alba in Idle Hands (1999)

Sigourney Weaver in 'Galaxy Quest (1999)'

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

Dita Von Teese - The most explicit thing she has done on camera in 'Pin Ups 2' [1999]

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

Elisabeth Shue's DAYAMN booty in "Molly" (1999)

Dita Von Teese in 'Pin Ups 2' (1999)

Kate Winslet PUSSY plot in Holy Smoke (1999)

Helen Mirren plot in The Passion of Ayn Rand (1999)

Nanette Bianchi in The Killer Eye (1999)

Caroline Ducey's condom philosophy in Romance (1999)

Rosanna Arquette - One of Hollywood's All-Time Best Bodies in Sugar Town (1999)

Nikki Fritz, Julia Kruis - Sinful Obsession (1999) --- full clip in comments

Stacy Valentine can't believe size of big dick fucking her in Sex Commandos (1999)

Elia Galera - The Ugliest Woman in the World (1999)

Amateur has her furry pussy exposed in a crowded night club (1999/2000s)

Caroline Ducey in Romance (1999)

Kobe Tai in "Awakening" (1999). She was one of my favorite 90s porn stars; I loved her tight little body and enthusiastic performances.

Lucy Liu delivered her most plot ever in Flypaper (1999) and as a bonus it's also kinda weird [Edited]

Loredana Cannata masturbating in La Donna Lupo (1999)

Tera Patrick in Payback (1999)

Julia Lemmertz's slim plot in 'Fit of Rage' (1999)

Nicole Kidman getting her plot groped in "Eyes Wide Shut(1999)" (60 FPS Enhanced & Reverbed)

Janine Lindemulder in Amnesiac. 1999

Gesine Cukrowski in "Der letzte Zeuge" S02E06 (1999)

Born in 1999, Am I to old for you?

Busty German Tennis Player Lydia P. gets double teamed by two big dicks in Ferkel 1 (1999)

[Topless] Sarah Lancaster in Lovers Lane (1999)

Patricia Velasquez [as Anck-su-namun] in The Mummy (1999)

Robin Tunney in End Of Days 1999

Brandy Davis in The Pleasure Zone (1999) - Part 2

Brandy Davis in The Pleasure Zone (1999) - Part 1

Stephanie Swift & Jessica Jewel in Sex Safari (1999)

Bree Turner in Deuce Bigalow: Male Gigolo (1999)

Hijiri Kojima in ‘The Perfect Education’ (1999)

Kirsty Smith in The Diary 2 (1999)

Tess Broussard in The Pleasure Zone (1999) - Scene 3 - part 2

Tess Broussard in The Pleasure Zone (1999) Scene 3 - part 1

Tess Broussard in The Pleasure Zone (1999) Scene 2 - part 2

Tess Broussard in The Pleasure Zone (1999) Scene 2 - part 1

Tess Broussard in The Pleasure Zone (1999)

Nikki Fritz in The Pleasure Zone (1999) - part 2

Nikki Fritz in The Pleasure Zone (1999) - part 1

Fabiola in The Pleasure Zone (1999)

Samantha Phillips in Scandal: On the Other Side (1999)

Regina Russell in The Pleasure Zone (1999)

Raquel Devine in Nightcap (1999)- part 2

Raquel Devine in Nightcap (1999)- part 1

Peggy Trentini in Nightcap (1999) - part 2

Peggy Trentini in Nightcap (1999) - part 1

Ashlyn Gere in Stripper Wives (1999) - part 3

Ashlyn Gere in Stripper Wives (1999) - part 2