The English novelist, Doris Lessing elucidates the rigidity of a society, which is based upon patriarchy, in her novels, The Fifth Child and Ben in the World. This essay illustrates the causes and the effects of a patriarchal system in the light of feminist ideology supported by Freud’s theories about the acquisition of gender roles. The analysis in this essay of patriarchy and masculinity shows that the novels’ societies as a whole, as well as their criminal subcultures are upheld by people who hold prejudice against others, who do not fit in society’s normal structures, believe in authoritarian social systems and prefer rational solutions to decisions for reasons of conscience. Lessing depicts the complexity of the social relations between characters of different social classes and their relations to society’s institutions. Her unprejudiced penetration into the minds of society’s marginalized people and into the minds of those who represent the oppressive established society illuminates different sides of patriarchy. Lessing gives us to understand that it is extremely difficult, from a moral point of view, to distinguish the established society from its criminal subcultures or society’s oppressors from its victims. Society’s accepted gender roles in the patriarchal system are often ironically described in these novels, certainly with the aim of making us question normative manners, habits and attitudes.