Using Hofstede’s cultural dimension of masculinity/femininity, this quantitative content analysis investigated the coverage of virginity loss (i.e., occurrence, tone, and association with negative consequences) and pregnancy (i.e., occurrence, tone, and negative consequence of sex) in 2,496 feature stories from all issues of three U.S. and three Dutch teen girl magazines from 2006 to 2008. Stories about virginity loss and pregnancy occurred equally often in the U.S. and Dutch magazines. Pregnancy was attached with a negative tone in both the United States and Dutch coverage. Virginity loss, however, was portrayed with a positive tone more often in the Dutch coverage than in the U.S. coverage. In addition, pregnancy was depicted as a negative consequence of sex more often in the U.S. coverage than in the Dutch coverage. Implications are discussed in terms of differences in adolescent sexual socialization in the United States and the Netherlands.