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1.
Wearing so few clothes you might as well be wearing only underwear.
Girl: that girl's clothes are so skimpy, she is such a slut
Dude: yeah, love it when girls go around underwearing.
Other dude: yes, girls that underwear as so sexy.
by ChouChou March 26, 2014
 
2.
when someone is underneath you, so insignificant that they're on your butt.
Oh my gosh, you're so underwearing me.
by The Cotton Ball March 07, 2011