Male pseudohermaphroditism (MPH), which causes ambiguous genitalia, rarely presents during adolescence. Herein we report two siblings diagnosed with MPH at the ages of 16 and 12 years and raised unambiguously as girls. Individuals with MPH provide caregivers the opportunity to observe the complex interaction between the biologic and psychosocial forces which shape gender identity. Factors which contribute to gender identity and the management of sex assignment may differ between cultures with regard to dominating sociocultural attitudes towards masculinity and femininity in a given society. The decision to perform feminizing surgery on both patients was made in consideration of these issues.