I've known boys who wore girls underwear and girls who wore boys underwear and didn't really mean anything by it. I think the thing is that... well, other people may think you are gay or weird sexually. Not that there is anything wrong with being gay or having you know, tranvestite things going on...but you may have to accept the idea that your family and friends are going to be freaked out if they find out. What about boxer briefs?
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