There are limited contextual data regarding first sexual experiences of younger adolescent men. Yet these data that are needed to inform sexually-transmitted-infection and early-fatherhood-prevention efforts, particularly in lower-income communities. Using qualitative methods, 14 adolescent men (ages 14-16, all low-income, most African American) from a mid-sized US city were asked about relationships and sexual experiences in a one-hour face-to-face semi-structured interview, with two follow-up interviews at six- to nine-month intervals. Story-telling was encouraged. Descriptions of first sex were identified and then analysed for narrative structure and shared concepts. The dominant narrative of first sex proceeded through three steps: (1) preparation, which involved identification of a sexualised space, mentoring and pre-planning, (2) the event, which involved looking for cues indicating sexual interest and consent from a female partner, feelings of fear/nervousness and first sex itself and (3) afterwards, which involved a return to prior activities, minimal verbal exchange and a general positive feeling, sometimes accompanied by later disappointment. Mentorship, initiation by the female and idealising sex as a romantic experience, played important roles in constructing the context of first sex. These factors should be incorporated in harm-reduction interventions for young men in similar contexts.