Caelan gets into the history of medieval trans woman (and nun-f*cker) Eleanor Rykener. Anthony (47:33) gets into the amazing and surprising history of Michael Dillon’s transition.
Caelan had some weird audio glitch, so skip to Anthony’s part at 47:33 if you can’t deal with it.
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Sources: Eleanor Rykener: One, Two / Michael Dillon: One, Two, Three