Based on an extended case study of a large‐scale tomato farm in northern Limpopo province, the paper examines how the restructuring of agriculture transforms the sexual economy through shifts in the composition of labour and management practices on farms in this area. The employment of Zimbabwean migrants, rather than relatively permanent Venda families, suggests a potentially greater variety of people participating in the sexual economy. While families as units of employment have declined, black supervisors increasingly serve as a primary locus of coercion on the farm and in the sexual economy. The monetization of erstwhile paternalistic services places pressure on women to earn income however they can, including transactional sex. Contested interpretations over the causes of infant deaths on the farm, in the form of hygiene, blood‐mixing and infanticide, provide an ethnographic framework for a deeper analysis of the sexual economy and its social effects. While the sexual economy presents opportunities for women to increase their income, it also exposes them to the risks of HIV/AIDS and unwanted pregnancies, resulting in contradictory implications for the status of women on farms.