2 times
1. A close female friend had spilled whipped cream on her chest. I said I'd get it and went in to lick it off, to my surprise she put her shoulders back, to let me, so I went ahead and did it. I told her, jokingly we should check and see if any got on her nipple. To my surprise she pulled her shirt down and exposed her nipple. So I put a little whipped cream on it, and said "you want me to get it?" She said sure, so I sucked her nipple. When I finished, she said "there's a little more you missed." I said "Did I actually miss some or did it just feel good?" She said "Maybe a little bit of both" so I sucked some more. She took out her other boob and I sucked that too. And like a fool, I stopped there. She totally wanted me to keep going, I never had sex with her and that may have been my only shot. I was young and foolish lol.
2. A very pretty girl was quite infatuated with me and my then-girlfriend. Both her and my gf got naked, we were partying just the 3 of us, but she was getting plastered drunk. She was drinking a lot, I believe in an effort to excuse her actions later. She was flirty all night, but by the time she got around to hinting (all but outright saying I want a threesome) I was waayyy too uncomfortable with how drunk she was to go through with it, and I told her as much. I said that we shouldn't do any penetration because she was too drunk and I'd feel like I was taking advantage. She called me a pussy and left. Call it the noble thing to do, but a missed opportunity, it certainly was. I to this day have never had a 3some... there was my chance.
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