Recent media reports on the phenomenon of the ‘blessers’ or ‘sponsors’ point to a new trajectory in transactional sex relationships in which younger women in most cases are opting to get sexually involved with older, married and presumably rich men, for purposes of acquiring consumer goods and related luxuries. The idea of the ‘blesser’ is associated with social media practices in which young women notoriously post pictures of themselves amid what appear to be ostentatious lifestyles, with the claim that they have been ‘blessed’ (Makholwa 2017). The link to social media is important in making an argument for the increased visibility of this type of woman who unapologetically flaunts her body while also claiming that she is using her beauty to acquire expensive goods from her admirers. Unlike prostitution, where sex for money is the main object, transactional sex relationships are also about intangible attachments such as love, and loyalty. They are contradictory in nature, and often, women identified as ‘blessees’ are easily dismissed as leeches, gold-diggers and sluts, among other derogatory terminologies. Young women who refer to themselves as ‘blessed’ counter expectations of what they are supposed to be. This chapter engages with the layered gendered readings of transactional sex relationships in the context of consumerism. As Leclerc-Madlala (2004) points out, these relationships are formed ‘in pursuit of modernity’. Similarly, Cole (2010) and Mojola (2014) urge for a different approach to reading young women and their relationship to consumerist goods in the context of transactional relationships. According to Cole, whose investigation of the lives of young women’s transition into adulthood, to make moralistic assumptions about this process is to ignore a variety of influences both past and present, that that influence the lives of these young women. Cole stresses the point that these young women make particular choices as they navigate the life they find themselves in. Mojola whose research takes place in Kisumu, Kenya, also argues that in most cases, women make choices regarding why they get into transactional relationships. One interesting finding for instance, is that against the common notion that young women get into relationships because of poverty, it is those women with the highest chances of negotiating their positions in sexual relationships are also the most likely to fall victim of HIV/Aids. In other words, it is the women most bent on acquiring certain consumer goods, who are also mostly at risk. Such intricacies point to ideas of negotiation and freedom (Fabian 1998). The research above tells us that it is useful to look at the subject positioning of young women in narratives about transactional sex relationships. What are read as aggressive, if somewhat defiant positions are also where one locates elements of freedom. In a context such as Kenya, how might such freedoms be interpreted through gendered discourses of punishment and public shaming?