Give it a try and see what happens.You said he's seen you crossdress many times.Why would he do that if he's straight?I think he's at least bi-curious.
I like tgirls and I bottom for them sometimes but I never crossdressed or liked guys.If this dude likes to see you crossdress countelss times as you said and is ok with your sexual preferences maybe he's not as straight as you think he is.
As far as that friendship issue goes,if he's a real friend of yours he won't mind if you express your feelings.It could be a shock but real friends are supportive I guess.
Who knows,maybe he wants to suck your cock and let you fuck him but he feels shy.Give it a go!
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