This study addresses, from a sociological and sociohistorical point of view, the transitions to adulthood of two generations of Russian women by focusing on their entry into sexuality, into conjugality and into motherhood. Interviews were held in Moscow and in Saint Petersburg with women (N=32) and men (N=12). A majority of respondents are highly educated and reached adulthood before and after Perestroika (between the 1970s and the 2010s). Atypical life course experiences are overrepresented among them (having a late first child, not having children, homo- and bisexual life courses). In addition, two series of press articles were analyzed (articles and features devoted to readers’ letters from both a Soviet popular medical magazine, and a post-Soviet teenage magazine).From one generation to the next, the transition from State Socialism to capitalism has brought new opportunities and constraints, while developments in the way contraception and abortion have been managed by the authorities since the 1970s have led to the emergence of new models of self-government, regarding fertility control. The average age at entry into motherhood has risen and the norms (in particular those related to gender and age) that prevail in early stages of sexual and love trajectories have been largely reshaped. The unprecedented diffusion of technological contraceptive methods (especially condoms and, to a lesser extent, the pill) has played a key role in those developments.An analysis of gendered socialization with respect to sexuality and birth control (for instance in the family, at school, among peers or via the media) is conducted for each of these two generations. The generation of women who had a first child while being students in higher education, or very quickly afterwards, was followed, in the large cities of post-Soviet Russia, by a generation who experienced an unprecedented “sexual youth”. This term is understood as a life stage that is legitimately devoted to ideally protected (hetero)sexual relationships, within one or several successive relationship(s), cohabiting or not, possibly with no prospect of marriage or childbearing. However, the increasing importance of this ideal of fertility control in early sexual life does not necessarily signify that the first birth is experienced as a concerted and carefully planned conjugal project. Young women advancing through their twenties are increasingly exhorted to take their conjugal life seriously, and once they are in a stable heterosexual couple, injunctions to early motherhood may conflict all the more strongly with the ideal of avoiding pregnancy. As a consequence, it tends to be common – or even valued – to tacitly shift from a sexuality involving contraception to a potentially fertile sexuality, and to experience the first birth as one’s inevitable maternal destiny and as a form of self-sacrifice.