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It's kinda funny what happens to him, really.
He has this kid-crush on this girls' older sister, but the girl's a total bitch and is all GTFO. So the other sister, the dumb one, helps him crossdress and fit in. This works until boy realizes he's actually out window-shopping for women's clothing.
This continues to spiral until he's found a pile of abandon fetishwear on the riverside. Next ep is him in a maid outfit with little frilly socks and everything. It's awesome.
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Oh, just like real life.
Edit: The lack of realism in anything is what makes me avoid most anime.