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I'm 14 and I actually hate boxers, but I like the look, so I actually wear those shorts with the double band that make it look like my boxers are peeping over the top, but I'm actually wearing briefs underneath.
Yes, I wear briefs under all board shorts, normal shorts (even the ones the liner in, as I don't like the feel of it). I usually wear briefs under my swimming trunks too, as the trunks are kinda loose around the legs, and I don't want to anyone to see my junk (Well, actually, it's more of a 'they might not want to see my junk' rather than me not wanting them to see it).
I don't see a problem with it personally - I can't even tell I'm wearing them half the time, so why go without?