Nice dare. I did something like this in the walk home from a night out.
I took my underwear off (by removing my pants and shoes) stuff my boxxers into my pocket and left the flies (Zipper) undone, with my dick flopping out. I was walking along a main road, but because it was 3 am there were few cars. When there was one, i'd quickly put it away.
I should try this in the daytime though :P!
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