After Japan’s defeat in World War Two, the United States occupied Japan and called it a ‘workshop of democracy’. Although the occupation ended in 1952, US forces claiming to protect Japan have remained because of the Security Treaty (1951), with Japan providing military bases and fiscal support for seventy-plus years. The arrival of American troops prompted the phenomenon of streetwalkers, or ‘Pan-Pan Girls’, who provided sexual services to American GIs. Previous scholarship painted Pan-Pan Girls as symbols of Japan’s defeat and subjugation, a sexual parallel to the new post-war relationship between Japan and the United States. This article, however, contends that Japanese often saw Pan-Pan Girls as symbols of resistance to both the Japanese and American governments, as demonstrated by images appearing in popular culture formats such as manga and magazine illustrations. For Japanese, drawing Pan-Pan Girls was a political act, because the very existence of Pan-Pan Girls in the ‘workshop of democracy’ contradicted US claims about democratising Japan and Japan’s claim to being a democratised country. That view of Pan-Pan Girls can also be seen in post-war manga, especially amid the anti-Security Treaty and anti-Vietnam movements of the 1960s and 1970s and in more recent debates over the revision of Article 9 of the constitution, which would allow them to rebuild the Japanese military to better assist US forces. This article argues that Pan-Pan Girls in graphic arts represent Japanese voices of contestation aimed at transforming the US–Japan Security Treaty system – a post-war bilateral form of imperialism in Asia.