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ever gone commando and wish you hadn't?

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No. Never had any unfortunate accidents or anything. It's never been a thrill, either, though.
Sometimes in college. Not a good idea sitting in class in shorts and no underwear, especially in class at the University of Georgia which has a well established and well earned reputation of being loaded with hot girls...thousands of hot girls.
I don't normally like commando. The feel of jeans and zippers does not appeal to me against my unsupported private parts. It can get rather uncomfortable. But I DO go commando when working out (lifting, not cardio.... I like support when doing that) though. I am often just wearing sweat pants.
I went commando, forgetting I had a waxing appointment at lunch. Slightly awkward, but pornos start that way...