I am also a guy who often plays with a female character/avatar.
I feel it has less to do with sexuality/orientation than it has to do with one's approach to role playing and whether or not they want to identify personally with the character or experience new points of view. In terms of role...
Currently wearing my Mephistos, about $250 for some of the most comfortable dress/walking shoes available. Ridiculously expensive but they come with a lifetime warranty, they get damaged in any way and I can send them back to the factory for free repair.
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