The “orgasm gap” refers to the finding that cisgender men, on average, have more orgasms than cisgender women during heterosexual partnered sex. In the current research, we replicated evidence for several orgasm discrepancies across sexual contexts and assessed men’s and women’s perceptions of the orgasm gap. Our sample consisted of 276 heterosexual, cisgender, sexually active undergraduate students (56.52% women; M age = 18.84). We assessed participants’ self-reported orgasm frequencies with a familiar partner, with a new partner, and during masturbation, as well as participants’ perceptions of their partners’ orgasm frequencies. We found evidence for orgasm discrepancies between young men and women within contexts and for women across contexts. Additionally, men perceived the size of the orgasm gap to be smaller than women perceived it to be. We used qualitative analyses to assess participants’ perceptions of driving forces behind the orgasm gap and their responses could be grouped into five overarching themes: Sociocultural Influence, Women’s Orgasm Difficulty, Biology, Men’s Fault, and Interpersonal Communication. This qualitative data can inform education and advocacy efforts focused on improving orgasm outcomes for young women, particularly by disproving prominent biological justifications for orgasm difference and addressing relevant sociocultural concerns. Additional online materials for this article are available on PWQ’s website at http://journals.sagepub.com/doi/suppl/10.1177/03616843221076410 .