Research about masturbation tends to be limited to the assessment of masturbation incidence and frequency. Consequently, little is known about what people experience connected to masturbation. This might be one reason why theoretical approaches that specifically address the persistent gender gap in masturbation frequency are lacking. The aim of the current study was to explore several aspects of masturbation in young men and women, and to examine possible associations with their social backgrounds and sexual histories. Data from 1,566 women and 1,452 men (ages 18 to 22) from 52 Swedish senior high schools were analyzed. Comparisons between men and women were made regarding incidence of and age at first masturbation, the use of objects (e.g., sex toys), fantasies, and sexual functioning during masturbation, as well as about their attitudes toward masturbation and sexual fantasies. Cluster analysis was carried out to identify similarities between and differences within the gender groups. While overall more men than women reported experience with several of the investigated aspects, cluster analyses revealed that a large proportion of men and women reported similar experiences and that fewer experiences are not necessarily associated with negative attitudes toward masturbation. Implications of these findings are discussed in consideration of particular social backgrounds.