We laughed in Pleasure by Lou Sullivan, goes through his diaries and experience as a gay trans man. Its heartbreaking, funny, enraging and inspiring all at once.

Trans Liberation: Beyond Pink or Blue by Leslie Feinberg, basically an exploration from multiple angles and a questioning of rigid takes on gender and sexuality. Some of the terminology in hir book is a bit outdated but the ideas and structure are still solid today as when it was written. Good as intro to the area as well.