Diane Arbus took a series of photographs of transvestites which began with her meeting Vicki, the subject of this portrait, in 1966. At their first photo session, after spending the night in jail for prostitution, Vicki told Arbus that she was really a man. Of the revelation, Diane said that she 'was very calm but... really sort of pleased' (Diane Arbus, Aperture, 1972). This encounter was the beginning of multiple sessions that would lead to a series of portraits that would make Vicki one of Arbus' most photographed sitters in this genre of her work.