I think getting an actual wig is better as it is easier to style and would look better in photos. I love Tomoko and WataMote is one of my top favourite animes, but I don't think her as male would have facial hair, especially since it's not permitted in school like you said. I picture him to look the same as Tomoko, still being masculine, but having some feminine and youthful features. Also, I know this is kinda off-topic, but when you are done with your cosplaying, please post pictures. I would love to see how your cosplay came out and I also run a Tomoko Kuroki page on FB that's fairly popular called Tomoko "Ms. Popular" Kuroki. With your permission I would love to share it on there.