Drawing inspiration from Clegg's [2008. "Femininities/masculinities and a Sense Self-Thinking Gendered Academic Identities and the Intellectual Self." "Gender and Education" 20 (3): 209-221, 241] statement that "less traditional universities and areas of course provision and research might be important sites to investigate in relation to academic identity," I undertake a single strategic case study of an expert, older, male critical educator, employed as an instructor in two "less traditional", for-profit settings: one online university and one brick and mortar university. The article departs from a theoretical consideration of "future directions" of three subfields: masculinities and higher education (HE) from critical and feminist perspectives, masculinities (and other identities) online (through the Internet research subfield of gender and technology), and masculinities and aging from critical and feminist gerontological perspectives. It employs the methodological strategy of "sketches," arguing that these settings, which appear to position critical and feminist pedagogues in the proverbial "belly of the beast", are important spaces in which to explore how a critical pedagogue navigates "less traditional" HE settings.