Using data taken from the 1995 National Survey of Family Growth, this study investigates the relationship between childhood living arrangements and the risk of first premarital intercourse. Both statuses and transitions associated with the parent histories of children are considered. Black and White women are examined separately, as well as two broad birth cohorts (from 1950 to 1959 and from 1960 to 1969). The findings show that experiencing more transitions and being born out of wedlock increase the risk of first premarital intercourse, and they are consistent with two theoretical perspectives: (a) socialization, and (b) instability and change.