Studies have suggested the persistence of risky sexual practices among adolescents in Kenya but relatively less is known about the perceptions, norms and gender relations that govern the sexual behaviour of adolescent females and males, or the strategies they use to deal with the twin risks of unwanted pregnancy and STI/HIV infection. This study was, therefore, conducted to explore these issues through data drawn from 16 FGDs among 184 rural male and female adolescents aged 15-19 years in Makueni District of Eastern Kenya. Findings suggest that adolescents are quite aware of risky behaviours and the protective role of abstinence, faithfulness to one uninfected partner and condom use. However, adolescents face a number of obstacles in translating this knowledge into safer sex practices. Misinformation concerning ways to protect themselves abound. Both females and males report reticence in communicating about sexual matters and contraception with their partners. At the same time, they are reluctant to seek condoms in public places for fear of disclosure and reproach. Females face difficulties in negotiating safe sex, in reconciling the desire for condom use with norms demanding submissiveness and lack of assertiveness in contraceptive decision-making.