Ugh! I just can't get my head around this fetish that Japanese dudes have for wanting to crossdress. If I were to believe what I see in manga, 90% of Japanese guys willingly crossdress when asked (or not even asked to do so) and there are 2 or 3 horny dudes on every street corner ready to drag women down the alley and rape them.
This was an odder one, had a creepier bent to it. Though, I don't like crossdressing, maybe that... Now, naw. Forcing your brother to wear clothes your crush would wear is definitely weird even for crossdressers.