In this chapter, Faderman reviews the historic and literary perception of women cross-dressing as men during the 16-18th centuries. She notes that women passing as men [or transgender men, although this framing was not typically used at the time the book was published] were considered a more serious issue than lesbian sex, as long as that sex was between “feminine” women. One difference was that sexual encounters could be framed as a transient amusement whereas passing women were engaged in a long-term transgression.