Burglary and pickpocketing were the two most prevalent forms of male and female offending, respectively, in the flourishing colonial capital of Melbourne during the late nineteenth and early twentieth century. Using court records and newspaper accounts, this article compares the prosecution patterns and public perceptions of male burglars and female pickpockets. Both offences were associated in the Anglophone world with membership of the criminal classes and in the colonial context with concerns about a remnant convict populace. Moreover, both male burglary and female pickpocketing occurred in intimate contexts that threatened the possibility of sexual violence or uncontrolled female sexuality. Yet although both crimes were the subjects of community concerns, the conviction rates for burglary and pickpocketing differed dramatically. This article examines the ways in which the gendered contexts of burglary and pickpocketing—in relation to constructions of victims as much as defendants—exacerbated the usual differences found in trial outcomes for men and women, as well as other factors that served to place men at far greater risk of conviction. It is suggested that a close reading of the victimization narratives of these two offences complicates traditional perspectives on the policing of male and female sexualities in the criminal justice system.