Nothing Funny About Getting Boob-Dangled, Bob!
It’s not explicitly shown but the inference here is that our unfortunate heroine has been hung up in the dungeon by her boobs. Her dungeon companion may think this is funny as may we, the readers — but she clearly does not!
Per the signature and legend, this bondage cartoon is by Earl Engleman and must have appeared in an issue of the long-forgotten sexed-up tabloid newspaper National Informer. But the cartoon came to me from the art on the front of this rare QSL postcard. (If you are not old enough or radio-nerdy enough, you may not know what QSL postcards even were. Ham radio operators and CB radio enthusiasts often self-published these — or at least past up their own collage of art and messages to be printed by a service — to send in confirmation of radio contacts. The cards were avidly collected among radio hobbyists and served to memorialize distant, difficult, or interesting radio connections. My impression is that they were not normally risque.)
Elsewhere on Bondage Blog: