As we saw in the Introduction, didactic literature defined the prostitute in contrast to an idealized ‘honest’ woman, utilizing invective that classified dissolute and sexually devious women as a homogenous category. However, literary texts and historical evidence suggest that women's involvement in the flesh trade took a wide variety of forms. Most of late medieval Europe institutionalized prostitution through municipal brothels until the late sixteenth century when reformist movements such as the Jesuits ignited protests culminating in the prohibition of prostitution across Catholic Europe; yet, within this broad unity of approach, the prostibulary milieu varied widely from one locale to another. In this chapter, I give an overview of the history of prostitution in the early modern Spanish Mediterranean, focusing on how the language used to describe carnal commerce functions not solely as descriptors but rather as a rhetorical strategy to regulate and constrain female sexuality. I examine the characteristics of the Roman sex trade during the era of elite courtesans that briefly emerged in the early sixteenth century and that is fictionalized in La Lozana andaluza to demonstrate how the resultant stratification of the sex trade and some of the courtesan's defining characteristics, such as imitation of elite mannerisms as an economic strategy, persist in later picaresque fiction. Finally, I explore the debates over prostitution stemming from Catholic reform movements that led to its eventual prohibition as well as the rise of custodial institutions designed to house and enclose the former prostitute. Throughout the chapter, I examine in detail the place of prostitution in the early modern Spanish Mediterranean, setting the stage for later chapters that will investigate specific spaces and their use in the practice of literary prostitution. I argue that the early modern sex trade was hierarchically structured and fluid as women engaged in a range of strategies, analysed in subsequent chapters, to renegotiate their erotic capital: the price they can command through the sale of their body. I demonstrate that architectural space plays a key role in this struggle to retain financial security, a point I develop throughout later chapters. In these later chapters, I argue that the stratification of the sex trade allows male authors to present pícaras as sexual predators who manipulate male clients through their manipulation of space.