Riley—an educator, scholar and leatherman—serves as coordinator of the Great Lakes Bootblack contest, a title he himself won in 2007. A history geek at heart, Riley, 30 (but 29 when he was nominated), also serves as a coordinator of the Leather Archives and Museum Roadshow, the traveling team which presents the LA&M’s exhibits of leather and fetish history around the world.

Riley is also a co-founder of Trans Gynecology Access Program (TGAP; qphc.org), which provides transmen, butches and genderqueers with the option of having a transman health educator in with them for any part of their exams to help them feel more at ease and to share expertise. As a part of this program, Riley is writing a comprehensive safer-sex guide that includes self-defense techniques and tips on disclosure, harm reduction and negotiation.

Did you know? When not working or volunteering, Riley enjoys manhandling, whip-throwing and a well-stocked humidor.