8 XXX : oldschoolboners

Gloria Walker, June 1956 Playboy Playmate and the woman hailing a cab on the front page of OldSchoolCool right now.

imgur.com category @notbob1959

Danielle de Vabre / Playboy’s Playmate of the Month, November 1971 / photographed by Dwight Hooker.

imgur.com category @[deleted]

Ellen Stratton - Playboy magazine's Playmate of the Month for December, 1959 (via /r/VGB)

imgur.com category @[deleted]

Alyssa Arce, Playboy Playmate of the Month for July 2013

imgur.com category @[deleted]

Katie Vernola Playboy Miss June 2010

imgur.com category @[deleted]

Marina Emanuela in Playboy Italy [X-Post from r/Playboy_Albums]

imgur.com category @bravo205

Playboy's Miss December 2014 Elizabeth Ostrander Leaving the Bedroom [HTML5]

gfycat.com category @resaysay

Playboy Greece playmate Vaso Villegas

imgur.com category @[deleted]

Two Big Asses at The Beach, Spicy J & Miss Raquel

gfycat.com category @PM_ME_YOUR_ASIAN

Alana Soares, Playboy's Miss March 1983

imgur.com category @eelover08

Playmate of the Month October 2011 [xpost r/NSFW_GIF]

gfycat.com category @mnwththxcptnldck

Karolina Witkowska - German Playmate of the Month for October 2013

imgur.com category @SyazaRaqman