Although various biopsychosocial factors have been associated with dyspareunia, research to date has focused on retrospective reports of adult women, and lack of consensus regarding etiology remains. By targeting girls at the beginning of their reproductive life, this study aimed to examine the biomedical, behavioral, and psychosocial correlates of chronic painful intercourse in sexually active adolescents compared to pain-free girls. With written informed consent, data were obtained from 1425 girls (12-19 year olds) from seven metropolitan high schools using self-report questionnaires pertaining to gynaecologic/biomedical history, physical/psychological/sexual abuse, anxiety, depression, attitudes towards sexuality, and social support. While the chronic painful intercourse (n = 51) and pain-free comparison group (n = 167) did not differ significantly on biomedical variables, painful intercourse was associated with significantly more pain during tampon insertion, and avoidance of tampons was linked to a fourfold risk of experiencing pain during sex. Cases also reported engaging in significantly more detrimental vulvar hygiene habits than pain-free girls, whereas no significant group differences were observed for self-treatment using over-the-counter antifungal preparations. Sexual abuse, fear of physical abuse, and trait anxiety were identified as significant psychosocial correlates of chronic painful intercourse. A logistic regression further identified pain during first tampon insertion and trait anxiety as statistical predictors of adolescent pain during intercourse. In addition to a possible intrinsic dysfunction in central pain processing, findings suggest that psychological variables, such as anxiety, play a significant role in painful intercourse's very first manifestations in adolescent girls.