Most quantitative research about lesbian, gay, bisexual, and queer (LGBQ) people’s sexual subcultures and sexual practices has used non-probability samples due to data limitations. This paper used the Generations study, a national probability sample of LGBQ Americans in three age cohorts, 18–25 (n = 510), 34–41 (n = 294), and 52–59 (n = 425), who also identified as Black, white, or Latina/o. This paper analyzed men (n = 590) and women (n = 639) to answer the following sets of research questions: (1) What is the prevalence of subcultural identification as bear, leather/kink, twink, and jock among men, and how does it differ by cohort, race/ethnicity, and sexual identity? (2) What is the prevalence of men who describe themselves as a top, versatile top, versatile, versatile bottom, and bottom? What is the relationship between penetration practices and masculinity? (3) What is the prevalence of gender labels among women as femme, androgynous, and butch? How does the prevalence differ by cohort, race/ethnicity, and sexual identity? (4) What is the relationship between women’s gender labels and masculinity? Penetration practices were fairly evenly distributed among men, and there were few differences in masculinity based on penetration practices after controlling for demographics and subcultural identification. Most women did not use gender labels, but butch identities were more common among lesbians and femme labels were more common among Black women and Latinas.