1750s Japan
These two images by Suzuki Harunobu are shunga – japanese erotic and pornographic wood block prints from the 18th, 19th and early 20th century. Shunga had a wide and popular audience, and depict a (very) wide selection of sexual practices.
1920s USA
This is from a 1920s tijuana bible : under-the-counter bootleg pornographic comics that often appropriated mainstream cartoon characters in their stories.
Fritzi Ritz was a popular flapper character from a long running strip in the New York Evening World newspaper.
You can see the whole of the (very rude) story by clicking on the image on the right…