Jizz

The Penthouse Pet from 1996 has become decidedly milf-y.

milf

Alicia Machado, Miss Universe 1996

Boobies, nsfw

Rachel Weisz, Liv Tyler - Stealing Beauty 1996

celebnsfw

Jennifer Aniston - Rolling Stone, March 1996

Celebs, JenniferAniston

Jennifer Aniston - Rolling Stone, March 1996

Celebs, MagazineCollection

Jennifer Connelly in 1996

nsfw, CelebrityJOMaterial

Karin Taylor, Playmate of the Month June 1996. Kingston, Jamaica

WomenOfColour

Mia Sara – Undertow (1996)

WatchItForThePlot, celebnsfw, CelebsExposed

Brazilian Actress Paloma Duarte (1996)(album in comments)

RugsOnly

Indira Varma - Kama Sutra (1996)

celebnsfw

Angel Boris, Miss July 1996.

NostalgiaFapping

South Beach Academy 1996

WatchItForThePlot

Jessica Lee, Miss August 1996

OldSchoolCoolNSFW, iluvnakedchicks

Pandora Peaks ('Striptease' - 1996)

90sTits, u_phan1985

Minka - Orient Sexpress (1996)

90sTits, 1000ccplus

Playmate of the Month March 1995/Playmate of the Year 1996 - Stacy Sanches (AIC)

Playboy_Albums

Playmate of the Month May 1996 - Shauna Sand

TheHangingBoobs

Angelina Jolie taking her shirt off in Foxfire (1996). A masterpiece of mammaries.

NostalgiaFapping

Tatjana Simic -- Pl@boy Netherlands Nov 1996

Playboy, wet, celebnsfw

Kathy Ireland, who appeared in every SI Swimsuit Issue from 1984 to 1996.

NostalgiaFapping

Playmate of the Month June 1996 - Karin Taylor Collection (AIC)

Playboy_Albums, playboy_playmates, Playboy, PlayboyOnReddit

Playmate of the Month June 1996 - Karin Taylor

Playboy, iluvnakedchicks, playboy_playmates, NostalgiaFapping

Sammi Walker - Glamour Girls 1996

OldSchoolCoolNSFW, thefullbush, AltarOfVenus

Gina Gershon and Jennifer Tilly [Bound, 1996]

NostalgiaFapping

Девушки Playboy 1996 год [альбом в комментариях]

Pikabu

Streaker at a soccer match in 1996

OldSchoolCoolNSFW

Jessica Lee, Miss August 1996

playboy_playmates

Salma Hayek in From Dusk till Dawn (1996)

NostalgiaFapping

Shauna Sand, Miss May 1996

playboy_playmates

Playmate of the Month July 1996 - Angel Boris Collection (AIC)

Playboy_Albums, PlayboyOnReddit, OldSchoolCoolNSFW, iluvnakedchicks

Holly Witt with Leslie Nielsen -- feb 1996

Playboy, PlayboyOnReddit, SensualPhotography

Playmate of the Month April 1996 - Gillian Bonner (AIC)

Playboy_Albums, PlayboyOnReddit

Playmate of the Month January 1996 - Victoria Alynette Fuller (AIC)

Playboy_Albums, PlayboyOnReddit

Jennifer Allan, August 1996

OldSchoolCoolNSFW, VintageBabes, NostalgiaFapping

Melissa Alonzo -- college girls (1996)

Playboy, PlayboyOnReddit

Name: Shane Kramer in Mary Jane's Not a Virgin Anymore (1996) Known For: Actor.

CelebrityPenis

Julie Bourque (1996)

Playboy, PlayboyOnReddit

Mari Alexandre, 1996

Playboy, PlayboyOnReddit

Kate Winslet in Jude, 1996

CelebrityNipples

Catherine Bell in Showtime's series Hotline, The Brunch Club episode, 1996

OldSchoolCoolNSFW

Eline by Andres Serrano, 1996

OldSchoolCoolNSFW

Playmate of the Month February 1996 - Kona Carmack (AIC)

Playboy_Albums, PlayboyOnReddit, u_ChiefCountingPills, playboy_playmates

Playmate of the Month October 1996 - Nadine Chanz

OldSchoolCoolNSFW

Meg Tilly and Gina Gershon “Bound” 1996

JerkOffToCelebs

Nadine Chanz, Miss October 1996

playboy_playmates

OTD in 1996, a spark started above the DJ booth at the Ozone Disco in Quezon City, Philippines. The fire spread after smoke was seen near the booth. 162 people died as a result, most were students celebrating graduation or end-of-school-year celebrations.

CatastrophicFailure

Please rate an italian 1996 pussy!

Ratemypussy

Angelina Jolie in Foxfire, 1996

CelebrityNipples, angelinajolie

Angelina Jolie in Foxfire (1996)

NostalgiaFapping

Amy Locane in the 1996 film "Carried Away" 1 of 2

celebnsfw

Amy Locane in the 1996 film "Carried Away" 2 of 2

celebnsfw, CelebrityNipples

Elisabeth Shue, 1996

NostalgiaFapping, ElisabethShue_

Pamela Anderson (1996)

NostalgiaFapping

Alyssa Milano, 1996

NostalgiaFapping

Best of Playmates of 1996 (AIC)

Playboy_Albums, u_thiswasntmyusername, PlayboyOnReddit, RoughnReadyPlayGround

Playmate of the Month October 1996 - Nadine Chanz

playboy_playmates