By the onset of the Depression, the birth control industry had grown swiftly despite bans from the American Medical Association, obscenity legislation, and mini-Comstock laws that prohibited the sale of birth control. Contraceptive manufacturers and sellers—reliant upon a variety of print advertisement forms—were successful in their attempts to encourage women to purchase commercial devices through a ‘bootleg trade’ where products were promoted as euphemistic mediums of “female hygiene,” creating a rhetorical safety net that made it practically impossible for authorities to charge retailers with violations of anti-contraceptive laws. Analyzing the linguistic and visual elements of such ads, this thesis will explain how the modern contraceptive market emerged through initial—albeit partially illicit—economic configurations dependent on sexualized themes of empowerment and liberation, revealing a world in which gender, commerce, and reproduction were inconspicuously interwoven.