Natalie Mei (1900–1975) was the only woman in the Estonian art field who dealt with and displayed the theme of prostitution in her oeuvre in the 1920s. Through feminist reading and applying Juri Lotman’s theorisations concerning the negotiation of borders between cultural and ‘non-cultural’ spheres, this article examines the ways in which Mei, in a few drawings, deviated from and challenged the dominance of the traditional patriarchal canon of the prostitution image.