This chapter is probably the one of most interest in the book, cataloging and discussing cases of female cross-dressers. The text alternates between detailed case studies and general discussion.
In 1912, in Portland Oregon, Harry Allen (alias Harry Livingstone) was arrested and eventually charged with violating the Mann Act (transporting a woman across state lines for immoral purposes) due to having written to her partner (who presented herself as his wife) Isabelle Maxwell in Seattle, asking her to come to Portland, where she then engaged in prostitution to support them both.