The notion of the boundary was a key aspect in Lotman’s model of semiosphere and a heuristic concept to make sense of dynamicity and change in socio-cultural systems, working as bilingual filters of translation. This paper seeks to shed light on the idea of crossing cultural boundaries by drawing a parallel between the mythological figure of the trickster and that of the alien or the outcast (izgoj), as discussed by Juri Lotman and Boris Uspenskij. The present study proposes a reading of F. Douglass’ Narrative from the standpoint of the semiotics of culture, by an interpretation of Douglass as a boundary figure and as a cultural translator between two worlds.