Abstract: Sexting, herein defined as the sending of self-made sexually explicit images has mostly been studied within the context of heterosexual relationships and among adolescent and young adult populations. This exploratory mixed-method study aims to investigate the prevalence, context and perceptions of sexting among non-heterosexual men of various generations. The study used two datasets. A quantitative survey was conducted among 684 non-heterosexual men between 18 and 77 years old (M = 34.29 years old; SD = 13.41), and qualitative interviews were conducted with 80 non-heterosexual men (M = 37.41 years old; SD = 15.93). Overall, 66.4% of the non-heterosexual men had sent a sexting image, and 84.7% of those who sexted indicated that they were unrecognizable in their images. The qualitative interviews showed that sexting is perceived as a risky but unproblematic practice by non-heterosexual men of all generations. Few generational differences were observed. Sexting takes place within the context of online dating and is perceived as a normative behavior within dating apps. The participants were aware of the potential risks associated with sexting and they protected themselves by sending images in which they were unrecognizable, thereby ensuring their safety and anonymity in online spaces.