8 XXX : x-1999

Michelle Costa 1999

imgur.com category @mister_checkers

Kimberly Spicer 1999

imgur.com category @mister_checkers

Julie Du Page in 'Les Steenfort, maitres de l'orge' (1999)

gfycat.com category @BoDudely

Catherine Oxenberg - 'Time Served' (1999)

gfycat.com category @BoDudely

Raining Down Cum (Private XXX 01 (1999))

gfycat.com category @keiranleeworship

Leslie Stefanson - The General's Daughter (1999)

gfycat.com category @sensualattack

Kate Winslet - Holy Smoke! (1999)

gfycat.com category @WatsonHV10

Kristy Swanson Groped in Supreme Sanction (1999)

gfycat.com category @2RsPeople

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.

imgur.com category @mywife1986nudes

My 52 year old wife - another from that 1999 set.

imgur.com category @mywife1986nudes

Messy DP Friendly Fire (Private XXX 01 (1999)

gfycat.com category @keiranleeworship

Michelle Costa, PB Brazil 1999

imgur.com category @xoneek

Catherine Oxenberg - 'Time Served' (1999)

gfycat.com category @BoDudely

Julie Du Page in 'Les Steenfort, maitres de l'orge' (1999)

gfycat.com category @BoDudely

Charlie and Jonathan Simms on a pool table in Philmore Butts Porn Valley (1999)

gfycat.com category @raincoater

Playboy's Miss November 1999 Cara Wakelin

imgur.com category @spheresnsfw

Repost: Briana Banks and Brandon Iron in University Coeds 18 (1999) Brandon recently passed away. Rest in Peace.

gfycat.com category @raincoater

Charlie and Jonathan Simms on a pool table in Philmore Butts Porn Valley (1999)(now w/sound)

gfycat.com category @raincoater

Charlie and Jonathan Simms on a pool table in Philmore Butts Porn Valley (1999)

gfycat.com category @raincoater

"But I know you came here to see me get naked. I'm not going to disappoint you!" - The Kat, WWF Armageddon 1999 [gif]

gfycat.com category @DasWucj

Playmate of the Month January 1998/Playmate of the Year 1999 - Heather Kozar Collection (AIC)

imgur.com category @ratsono

Playmate of the Month May 1999 - Tishara Lee Cousino

imgur.com category @ratsono

Playmate of the Month June 1999 - Kimberly Spicer

imgur.com category @ratsono

Joana Prado - Feiticeira (Playboy Brazil, December 1999)

imgur.com category @mdrdownloads

Rose Forrest aka Thorn [Birds of Prey (1999) #79]

imgur.com category @lordhater1

Julie Du Page in 'Les Steenfort, maitres de l'orge' (1999)

gfycat.com category @untilIneedglasses