A basic ecological and epidemiological question is why some women enter into commercial sex work while other women in the same socio-economic environment never do. To address this question respondent driven sampling principles were adopted to recruit and collect data for 161 female sex workers and 159 same aged women who never engaged in commercial sex in Kibera, a large informal settlement in Nairobi, Kenya. Univariate analysis indicated that basic kinship measures, including number of family members seen during adolescence and at present, not having a male guardian while growing up, and earlier times of ending relationships with both male and female guardians were associated with commercial sex work in Kibera. Multivariate analysis via logistic regression modeling showed that not having a male guardian during childhood, low education attainment and a small number of family members seen at adolescence were all significant predictors of entering sex work. By far the most important predictor of entering sex work was not having any male guardian, e.g., father, uncle, older brother, etc. during childhood. Results are interpreted in light of the historic pattern of sub-Saharan African child fostering and their relevance for young women in Kibera today.