He also has a male account but he uses the female one more. I found 14 men on there and he seems to enjoy talking to them about happy ending massages. I am kind of turned on though. The chats are pretty sexual.
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Its pretty rare, but there is a type of man out there that is both bi-sexual and transgendered (the two are not necessarily linked; the occurence is merely incidental), that would do exactly this kind of behavior.
See if he is interested in roleplaying as a woman in the bedroom with you or something to confirm the latter. I think initiating with the men online is probably proof enough of the former.1