This chapter explores the histories of transgender expression, identities, communities, and activism globally in both premodern and modern eras. Histories of settler colonialism, slavery, war, and imperialism have transformed the terms and conditions by which people of transgender expression and experience understood themselves and were perceived by others. While an abundance of archival records chart widespread practices of “transing” gender globally, a complex web of factors influenced how a given community or individual defined, understood, and judged such efforts. Race, religion, region, culture and class are some of the key contextual forces that gave meaning to trans and gender variant sexualities throughout history. A wide range of concepts have been used to describe and make meaning of gender variant people throughout history, from two-spirit, hijra, and third gender to the more recent transgender, nonbinary, gender expansive. Many other terms that have been used throughout history were deemed derogatory by those individuals and/or communities to which they refer at the time or have since been determined to be derogatory by later generations looking back. This creates a fundamental tension for everyone writing these histories between the importance of recognizing the past on its own terms and the importance of not further perpetuating harm against a long-stigmatized group.