Simulation-based training has been increasingly used to fill gaps in knowledge and skills in medical education. This observational study investigated the impact of a newly implemented simulation curriculum on medical student confidence in conducting gender-sensitive exams (breast, gynecological, and male urological). We found that standardized patient encounters with gynecological teaching assistants (GTA) and male urological teaching assistants (MUTA) improved self-reported student confidence in sensitive examinations and that this increase in self-reported confidence was comparable to that observed following other simulation cases in our curriculum. Notably, both male and female students reported equal improvements in confidence when examining patients of their own and opposite gender identities. Qualitative surveys and focus groups of students, faculty, and standardized patients revealed common factors—including limited prior exposure to sensitive examinations, skill-based feedback, and a learning environment supporting self-reflection—yielding improvements in performance of male and female sensitive examinations, regardless of the gender identity of the learner. This study expands upon prior literature on the effectiveness of simulation in enhancing learner confidence in sensitive procedures and suggests that integrating such curricula could address gender-related confidence gaps in patient care across multiple clinical settings.