Purpose: The context in which first sexual intercourse takes place has lasting implications for subsequent sexual behavior. This study examines how adolescent disability associates with boys' age of sexual debut, relationship at first sexual intercourse, degree of discussion about birth control before first sexual intercourse, and contraceptive use at first sexual intercourse. Methods: Data were used from the National Longitudinal Survey of Youth 1997, a nationally representative survey collected annually in the United States. Multinomial logistic regression of a base sample of 2,737 boys examines the likelihood of (1) sexual debut at ages 12-14, 15-17, or >= 18 years; (2) first intercourse with a stranger, casual acquaintance, dating partner, in a committed relationship, or in an undefined relationship; (3) level of discussion about birth control; (4) contraception; and (5) condom use among those who contracept. Results: Compared to boys without disability, those with learning or emotional conditions are more likely-and those with sensory conditions are less likely-to report very early sexual debut. Boys with chronic illness are both more likely to have sex in a committed relationship and in an undefined relationship and also more likely to contracept at first intercourse. Boys with learning or emotional conditions are more likely to discuss birth control but less likely to use condoms if they do contracept. Conclusions: Boys with and without disabilities-and boys with different types of disabilities-vary significantly in multiple aspects of their first sexual experiences. It is pertinent that sexual health interventions are tailored to address this diversity. (C) 2016 Society for Adolescent Health and Medicine. All rights reserved.