Chapter 1 begins with a quote from El Libro de Buen Amor, a fourteenth-century work of Spanish literature which praises the complex role of the medieval alcahueta, a kind of professional sexual matchmaker, often an older woman. The word alcahueta is loosely translated as a “bawd.” The chapter focuses on the legal history of sex work in Spain. First it discusses the role of the bawd in Spanish law codes, especially the thirteenth-century siete partidas, which influenced the viceregal judicial system. Along with bawds, Spaniards also participated in sex work by visiting or working at legal brothels, which had royal and municipal approval until 1623. Lastly, men, commonly known as “ruffians” also procured their wives, although all legal codes and courts penalized this moneymaking scheme. The second half of the chapter presents several case studies from Mexico City, which illustrate how the Spanish legal traditions mentioned earlier in the chapter changed and adapted according to New World situations and conditions.