We're in high school, Grade 12 or our OAC year (final year in Canada back in the 90s). We would all hang out in a hallway. Somebody chimes up and says I would pay money to see a guy walk around the school in their underwear. Everybody laughs, somebody else says I would too. Then a third person offers to.

I look at my buddy and figure fuck it, let's do it, I jokingly said I'll do it and my buddy says, I'm in. It was more calling their bluffs. Another guy comes and asks us if he can join. We got the money up to $50. The three of us head to the bathroom to get undressed, we are now down to our gitch and working up the nerve to do this. It was scary because we knew we were getting in trouble,

As we are in this bathroom, in underwear and back then it wasn't boxer briefs, I think my brand was Hercules then and it was pretty small. This is also my Mom just buying me underwear back then so it wasn't to look sexy.

As we are building up the nerve a teacher walks in and asks "What are you guys doing?". Three guys, shirts off in their gitch. Our heads drop, nobody speaks, then I chime in. "We were dared to walk around the school like this and we were going to get paid." I say this very awkwardly and quietly. His reply "Put your clothes back on and get to class. You guys are stupid."

I didn't get paid and everyone had a good laugh,