Yeah, I don't know his exact story either, obviously. But as I understand it, it's established that Ai and Eri doesn't know about his crossdressing, and I don't like them being tricked.
And that part of the Dearly Station broadcast where it was revealed, it would not have been good even as a parody to me. Still, it's probably the only big disappointment I've ever had with iM@S, so I'll get by anyway. ^^