While at uni, I once bet nudes of my then GF with a dude I didn't particularly get along with. He was kind of a loudmouth, had rich parents, but he was also friends with a good friend of mine, so our paths crossed from time to time AND he had an incredibly cute girlfriend I went to high school with.
He was an ardent fan of a rival soccer team that was much better than my team at the time, so when my team lost against his (he was part of the group I watched the game with), he bragged quite a bit about it. I got annoyed, so he suggested we should bet on the next game our teams play against each. I agreed, but forgot about it quickly.
The evening of the next time our teams played each other, I got a text from him out of the blue, asking if I'm still up for the bet. I said yes, of course, but he then suggested such a ridiculous sum of money (something like $500 which was just way too much money for me, a poor student, at the time), so I declined. He then accused me of being a pussy, which kinda got to me, but I openly admitted that this was just way too much money for me.
He then texted that betting is only fun if there are some real stakes involved, which I completely agreed with, which is why he quickly offered me the other wager, to which, according to my own arguments, I basically couldn't say no to. And the chance of getting to see his GF naked was just too good.
We agreed on the terms (i think it was: no face, spread, both holes visible, some way of identifying that it's actually her, but no contacting her about it) – what a weird text convo that was, lol – and the bet was on.
Unfortunately, it was pretty obvious from the start that my team would be losing this game. I still remember how, after conceding two goals in the first half, he wrote me how much he's looking forward to checking his mailbox (this was in the age of digital cameras and right before smartphones) right after the game.
So, after the game ended, I did what I had to do and sent him a mail with a photo attached. He sometimes teased me when our teams played against each other again and asked me if I wanna bet again, but my team was getting weaker and weaker, so I declined.
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