One of the earliest internet MILFs, Rachel Aziani, who started her own website clear back in 1999. zNSFW

https://i.imgur.com/kjj5P4Q.jpg

User: ChivalrousPervert

Categories: NostalgiaFapping

Her pics were all over kazaa in the early 2000's

Fundamental teenage viewing

Tiffany Taylor's Playboy shoot did it for me EVERY time...

Alley Baggett

Melissa Joan Hart

OG ass queen Vida Guerra

Marilyn Lange

Demi Moore Early 80's

Marina Sirtis

Susan Smith (September 1981)

WWE Diva Torrie Wilson. The first pair of tits I ever saw.

Kelly Monaco

Anna Nicole Smith

Alyssa Milano

Tara O'Connor

Adele Stephens

Patricia Ford was legend of men's magazines and Usenet in the 90s.

National Lampoon 1983- Beverly D'Angelo

Gorgeous

Leelee Sobieski

Cassandra Peterson (before she was Elvira)

Vida Guerra

Nikki Cox in 2001 (she turns 42 today)

Joy Behrman 1998

Emily Scott (2006)

Liv Tyler

Hanna Hilton

Cori Nadine

Brande Nicole - 2001

Molly Ringwald