well considering we got nene playing a guy in power of regret i dont think its impossible or out of reach idea but i doubt it would be for a big and important performance that the event focuses on. maybe for a practice or some sort of study :o although id really like for this to happen plsplsplsplsplsplspls ive been dreaming about tsukasa playing a female role for almost three years now.
i dont think a role of the opposite gender would bother tsukasa as we can see from the recent 4koma! it reminds me of the holy night event where he was a little taken aback "are you going to have me playing a little girl!?" but i think tsukasa has grown since and has come to terms with the fact he wont always be playing prince charming ^_^ so i dont think he would be against it, on the contrary i think it would be motivating for him to try something new!