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The international literature on workplace experiences of lesbian and gay (LG) people evidences how these workers are affected by heteronormative pressures and segregation policies. It also establishes that many experience discrimination and microaggressions in the workplace as having an impact on psychological health and job and life satisfaction. To investigate the workplace experiences of LG individuals, a total of 24 in-depth interviews were conducted with 6 Italian cisgender lesbian women and 6 Italian cisgender gay men, based on the principles of the Free Association Narrative Interview Method. Through the analysis of the interview accounts, four major themes were identified: (a) double discrimination, particularly the prejudice related to the intersection of homophobia and sexism for lesbian women; (b) outness and sexual orientation disclosure having a beneficial effect on job satisfaction and satisfaction in personal relationships, alongside an awareness and/or expectation of experiences of discrimination; (c) the negative role of heterosexism, stigma, together with the presence of microaggressions; and (d) horizontal relationships as protective factors from the effects of stigma on well-being and job and life satisfaction. The study findings further evidence aspects of the international research literature in further supporting a need to implement interventions aimed at addressing the effects of stigma, discrimination, and heterosexism on LG workers and promoting well-being at work. The study findings also highlight the role of government and companies in implementing and perfectioning workplace antidiscrimination, diversity, equity, and inclusion policies, practices, and legislation.