Traditional discourses on gender and sexuality, even as they helped shape the processes of urbanization, commercialization and state-building in the ancient world, were themselves profoundly affected by the growth of political, economic, and religious networks across Eurasia and northern Africa. This chapter examines literary representations of masculinity and femininity in 'world-encompassing' genres like epic and romance, showing how imaginative models of male and female behavior increased in variety and complexity in conjunction with the evolution of trans-regional political and economic network. The first millennium CE witnessed a transformation of ideal masculinity and femininity in Chinese literature as well. Women, indeed, wrote, and their writing on gender relations and sexuality can be found in a variety of the genres that emerged in the context of states, empires, and networks. Trans-regional networks connected human beings across communities and cultures, and thereby created trans-regional relations of gender and sexuality.