Preparing a Bro-Lita

I have recently met a cross-dresser in college that has a very vested interest in lolita, but he has never worn it in public before. This is a fairly small and fairly conservative small town, so I can understand his initial reservations. I gave him his first few pointers and a basic introduction to the fashion, directing him to here, Hellolace, and Sew_loli, but I couldn't find anything in the Memories about reactions concerning first time bro-litas. I'm scared he might end up being put off by the reactions he might get. He seems like such a sweet boy, and I don't want him to get hurt, so I want to prepare him and warn him properly.

I understand a boy would probably get more of a reaction wearing lolita than a girl, but would it be any different than regular cross-dressing for him? Will the reactions be more severe because he is a boy? I've been called whore out the windows of passing cars in this town while wearing head-to-toe classic, so I wouldn't put it past these people in this small town to get really nasty.