Same-sex sexual practices among men in Mexico City are stigmatized. This article analyzes sexual practices and experiences of gay men in Mexico City and its implications on emotional and sexual health. The concept of sexual practices is used from a public health perspective, and the concept of sexual experiences from a psychological one, intending to understand both physical and emotional discomfort and pleasure in sexual contexts. The aim of this article is to analyze sexual practices and experiences of gay men in Mexico City and its implications on health, particularly emotions that can lead to depression, anxiety, substance abuse, and unsafe sex. Fifteen in-depth interviews were carried out with gay men of three generations who live in Mexico City. The data were analyzed using techniques from grounded theory to identify categories, and critical discourse analysis as an analytical approach to understand how social discourses affect subjectivity, emotions, and practices. Sexual practices and experiences are the result of homoerotic desire, which gender and heteronormative culture encourage to be kept hidden and clandestine. This leads men into risk contexts where practices are hardly negotiated, thus exposing themselves to sexually transmitted infections and abuse. These practices also produce a series of emotions such as guilt, shame, fear, and sadness that may develop into mental health issues such as depression and anxiety. Interventions at all levels must consider homophobic discrimination as part of gay men's daily lives and should be oriented toward decreasing it, to diminish discomforting emotions and reduce the probability of unsafe sex practices.