Clothing Answers

How can you tell if a boy wears boxers or briefs?

If they are showing you can, obviously, quite easily tell. Although both briefs and boxer-briefs look fairly similar poking out of someone trousers - often, boxer-briefs have stitching on the butt which might help you tell the two apart. As for boxers, just look for lots of baggy fabric.

If they are wearing translucent/tight bottoms then you can, most often, see what they're wearing through their trousers. If the trousers/shorts are translucent, most colours will show up fairly well but the darker the colour the better you'll be able to see. And if the trousers are tight you can usually see the seam lines/outline of the underwear - if there's a line on the legs they're wearing boxers, if there's a line on the butt legs they're in briefs and if there's both lines, chances are they're sporting boxer-briefs.

Your best bet, however, is to just ask him. Assuming he's comfortable with it, he'll be your best source.
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