Despite the declining rate of teen pregnancies in the United States, academic and public health experts have expressed concern over the still relatively high rate of rapid repeat pregnancies among adolescents, particularly among minority youth. Using a sample of over 300 African American female adolescents, the current study used insights from the prototype/willingness model of adolescent risk behavior to explore this risk. More specifically, it assessed the relationship between entry into unwed motherhood during mid-to-late adolescence and changes in prototypes of unmarried pregnant teens. Further, it explored the extent to which these changing prototypes accounted for young mothers' later contraceptive expectations. We tested the possibility that social images were affected not only by personal experience (the birth of a child) but also by the family and community context in which this experience took place. The findings show that the early entrance into teen motherhood was associated with a shift toward more favorable prototypes of unwed pregnant teens, but that this was only the case for young mothers in disadvantaged contexts. Given this, prototype changes helped to explain the link between teen motherhood and contraceptive expectations only for those in disadvantaged contexts. We discuss these findings in terms of their practical and theoretical implications.