The present study contributes to recent scholarship on homosexism and side sexualities by providing empirical evidence that supports stigmatizing societal responses to non-penetrative sexual practices among men who have sex with men as well as to those engaging in such practices. The study provides a close reading of two scenes of the series Cucumber (2015) which depict marginalizing attitudes toward a man who prefers non-penetrative to penetrative anal sex with other men as well as findings from interviews with men who identify as sides on a permanent or occasional basis. The findings confirm that the lived experiences of men who identify as sides are not different to the Henry’s in Cucumber (2015), and participants of this study challenge the absence of positive representations of men who identify as sides in popular culture.