Sex is central to the internet. It exists everywhere online and yet is everywhere constrained, sanitized, normalized, and invisibilized. This panel will investigate the ways in which sex seeps, spills, and oozes across boundaries, both online and off, despite efforts to control and limit its impact beyond consumer capitalism. Author 1 examines online ‘gooning’ communities, oriented around prolonged masturbation sessions to multiple streams of pornography. Gooners build community around the fetishization and roleplaying of porn addiction, but simultaneously produce a problematic queerness that reifies some elements of heteronormativity. Author 2 examines the ways that Generative AI imagines queerness, probing AI systems by asking them to imagine the figure of the ‘twink’. The end result is “glitchcraft,” which refers to creative practices of engagement that underscore the excitatory enchantments of generative AI, their frustrating constraints, and the accidents–exploited or serendipitous–that might result. Authors 3, 4, and 5 examine alternative social media aimed specifically at enabling users to engage in sexual expression. They document both the affordances of these platforms for creating sex-positive and kink-friendly online spaces, and their constraints, as they introduce new norms, and thus new forms of exclusion and marginalization. Author 6 examines anal sex practices as mediated by gay hook-up apps like Grindr and shows how these apps increasingly mediate larger portions of gay men’s everyday lives. Grindr inflects the way they imagine, propose, seek out, and react to a diverse spectrum of anal activities (such as fisting, spanking, caressing, and rimming).