This study aimed to investigate gay men’s gender experiences, their ways of coping, and what strategies they arm themselves with to fight sexual prejudices at the Taiwan Police Academy. This qualitative study used narrative inquiry, based on feminist perspectives, for data analysis. Four gay men who were currently attending the Taiwan Police Academy or had graduated within three years participated in semi-structured interviews. The analysis of their stories revealed the following: (1) The cultural environment of the Taiwan Police Academy is (a) a bureaucracy that is not conducive to promoting the visibility of gender equality issues, (b) traditional closures that cannot keep up with the evolution of the times, and (c) de-gendered collective life management and training. (2) Gender-related cultures are (a) threatened men’s right and anti-feminism, (b) heterosexual hegemony of lecture arrangement, and (c) masculinity of femininity-rejection. (3) Participants reported experiencing homophobia and discrimination from faculty and peers, as well as the intersectionality of multiple oppression. Homophobia and discrimination can be divided into three categories based on the following three topics: (a) Non-heterosexual sexual orientation, (b) atypical gender expression, and (c) gender difference. The first topic of discrimination can be divided into three subcategories: implicit discrimination, personally experienced discrimination, and common ubiquitous discrimination in everyday life. Discrimination against atypical gender expression was targeted toward men who spoke more feminine. The third type of discrimination against gender differences occurs in gender stereotypes and the misogyny or objectification of women. (4) With respect to impact, there are two phenomena from the finding: (a) Feeling alone was the shared experience of the participants in the homophobic and oppressive environment. They all consistently mentioned that they had few gay friends in police academies. (b) The participants experienced different degrees of internalized homophobia; some said that an unfriendly environment made them less self-accepting because of their gay status, whereas others said they would never want to be gay again in life. Additionally, regarding coping strategies, the participants developed different strategies to deal with the discrimination, isolation, and microaggressions they encountered in schools. These strategies included three types: (1) direct responses (self-deprecating, counterattack, and education in an opportune time); (2) indirect self-regulation (pretending to be heterosexual, intentionally ignoring unfriendly comments, assuming that it can divert attention if viewed from a different respective, and choosing an identity with advantageous attributes); and (3) seeking support from friendly peers, professors, and faculty of student corps (especially Captain, Associate Captain, and Lieutenant); furthermore, some participants availed themselves for counseling and guidance resources. Surrounded by a patriarchal, bureaucratic, and heteronormative system with restrictive structures, gay men at the Taiwan Police Academy had indeed experienced real discrimination and homophobia. Although they had developed different coping strategies to survive in the environment, they still needed to protect their educational status and safety by hiding their sexual minority identity. Implications and recommendations for faculty and counselors to reduce oppression or discrimination against LGBTQIA and students studying at the Taiwan Police Academy were provided based on the findings of this study. In future studies, researchers can explore other sexual minorities in police academies, such as lesbians, bisexuals, and transgenders. Suggestions for Police Academy teaching and team management can be summarized as follows: (1) School leaders take the lead in promoting gender equity education; (2) Implementing gender-related regulations and laws in traditional closures; (3) Create a gender-equal and friendly life management and training space; (4) Create a learning environment free from gender bias and discrimination. Additionally, practical advice to the Counseling Center in the police academy includes how to reduce the stigma associated with counseling and how to explicitly take a gender-friendly stance. This is the first study to investigate the educational experience of sexual minority students, especially gender experiences, at the Taiwan Police Academy. More research on sexual orientation and gender identity experiences at the Taiwan Police Academy is needed to promote an understanding of gender equity in masculine-dominant educational systems.