On the boobie squishing issue, I'd like to say from my own crossplaying experience: it can be done, no problem. It's *painful*, but it's not too tricky. Duct tape does the trick real well, just hurts a lot. However, there are rather ingenious binders by T-Kingdom, which not only bind you relatively painlessly, they give your chest nice manly shape. *hearts~*
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PS. I'm D-cup, for the sake of comparison.