The "blesser and blessee" phenomenon has been prominent in South African media since the year 2016. This is a form of transactional sex in which older rich men ("blessers") tend to entice young women ("blessees") with money and expensive gifts in exchange for sexual favors. In most cases, these older men are married men who secretly engage in extramarital affairs with these young women. In this light, there have been many debates on whether transactional sex should be equated to prostitution or sex work. However, many researchers argue that both practices at the end of the day are proven to be equally high-risk sexual behaviors for HIV infection in sub-Saharan Africa. In this regard, the purpose of this study was to explore and describe perceptions and experiences of young women regarding factors that influence their susceptibility to transactional sex and the risk of HIV infection in rural South Africa. Twelve young women aged 18 to 30 years participated in two focus group discussions and 12 individual in-depth interviews. The findings of the study revealed that there are sociobehavioral, sociocultural, and socioeconomic factors that influence the susceptibility of young women to transactional sex and HIV risk. The study concluded that it was imperative for researchers to explore the context and motivation for transactional sex among young women in sub-Saharan Africa to be able to develop and implement appropriate and relevant HIV prevention interventions for this vulnerable population.