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Research into the sexual behavior of children remains in its infancy despite growing awareness that, under certain circumstances, it can at times be harmful to those involved. Of the research undertaken thus far, much has focused on descriptive data (Who did what to whom? What is the age difference between the children involved? How many times did they do it?). Little or no research or theorizing has been directed to the questions of “why it occurred” and “what it means” to the children involved. This article examines the cases of 2 boys whose sexual behaviors with other children were found to be problematic by child protection authorities. By considering the transference-countertransference relationship in the treatment setting with each of these boys, it is argued that an examination of the conscious and unconscious procedures, motives and meanings of such children, expands professional horizons of understanding about the phenomenon of pre-pubescent problem sexual behavior. This arrticle concludes that research, particularly through the lens of contemporary psychoanalysis, has much to offer clinicians who assess and provide treatment to children whose sexual behaviors fall outside the normal range.