Gramps had a large stack of both TRUE and ESQUIRE magazines and only a few PLAYBOYs from the '50s and '60s that I inherited, skimmed and later disposed of. One risqué cartoon stands out: A couple on their wedding night are in bed, unclad, and um, ready, but the bride is rigid with fear. Her body is literally stiff as a board with her weight
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Pay site, but a good jumping off point.
This site has cartoons archived NSFW
http://www.ebaumsworld.com/search/Playboy%20cartoons/
https://www.ha.com/c/search-results.zx?N=0+790+231&Nty=1&Ntk=SI_Titles-Desc&Ntt=from+the+playboy+collection&type=https://www.google.com/
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