Not exactly a bet; but here it goes...
I had a friend in college who I used to "sext" with. Everything was quite tame (I would even say it couldn't be called sexting, but rather online-teasing), as the sexiest photos she sent me were while wearing a bra. I asked her time after time to show me her nips, but she refused the same number of times.
One of those days, she organized her birthday party; but I couldn't make it because I had a lot of things to do (and school was first). A day before the party, we were "sexting" and when I asked her to show me her boobs, she told me that she would it if I attended her party.
I didn't think it twice and I didn't sleep the whole night finishing my projects.
I had an amazing time in her party; and I honestly thought that she was not going to show me her boobs and it was all a trick to make me attend. But when people started leaving, she asked me to stay a little longer. A few minutes after, she told me to go with her to her room to pick some things. Of course I was suspicious but I couldn't get my hopes up, maybe she really wanted us to pick some things.
But when we were alone in her room; she told me that she owe me; and lifted her blouse and her bra to let me see her brown nipples. She flashed me for like ten seconds, and it was amazing.
Few years later, we ended up fucking (another story); but that first time that I saw her nips is engraved in my memory.
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