Risky sexual behaviour such as early sexual initiation, inconsistent condom use and sexual intercourse with multiple partners are relatively prevalent among youths in sub-Saharan Africa. Sexual intercourse is an important event in one’s life trajectory and the contributory factors are: proximate and distal environments. The proximate environment includes micro systemic influences such as one's attitudes and beliefs, and extends to one's family. The distal environment includes one's community and culture. However, there are core forces which influence personal choices and behaviours like the self, family and community, and networks and cultural influences. While there are a variety of factors that contribute to early sexual initiation, proper parenting behaviour has been identified as a key strategy for reducing adolescents’ risky sexual behaviours. Even though early sexual initiation process is subject to a number of barriers, there is still less focus on parenting behaviour and its relationship with early sexual initiation among adolescents. Therefore, this study applied social survey to assess sexual initiation age and its related risk-taking behaviors among the adolescents in urban secondary schools in Nairobi County. The study found the common period in which adolescents initiate sex and even befriend strangers as age (15-16years). The findings have shown that children are capable of initiating drug use at any given period. This suggests the need for parent to undertake close monitoring of their children at all ages to curb drug abuse and encourage health talk with them on the effects of drug use.