This chapter brings together personal essay and literature review to examine how the cultural constructions of vaginal and clitoral orgasm reinforce patriarchal notions of gendered sexuality in the United States. The author looks to popular culture, Victorian-era texts on hysteria, Freudian psychoanalysis of the 20th century, and the second wave feminist movement in order to understand the Western history of vaginal and clitoral “female” orgasm she was born into in the 1980s. The author identifies women’s glossy fashion magazines as the primary resources available to her as a teenager trying to understand her own body and sexuality. Using existing research on the impact of such magazines on women’s self-concept, along with her own personal history, the author outlines the ways in which these magazines taught young women that sexual empowerment and fulfillment could only be obtained by reaching orgasm during penetrative sex with cisgender men. The author explores how the external and internalized pressure to focus on her own orgasm as the goal of sex has impacted her understanding of orgasm, intimate partner communication, and her own sexuality. Finally, she suggests some paths forward for social workers to impel curriculum and clinical norms that encourage communicating sexual desire and challenge remaining patriarchal understandings of “female” orgasm.