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I approached things well initially, but it quickly escalated, and her perception was that I was almost yelling at her. Mine is she was very uncooperative, expected since I did wake her up, but it bothered me that she was uncooperative because that was one of the issues.
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If this guy though is satisfying to you in the oral department, and can rock your world without a larger penis, then I don't think that you should be worrying about it, and focus more so on what an amazing guy and boyfriend he is to you. If though, you aren't satisfied at all from your sex, then you could easily look up different positions that you guys can try or you could wait a couple months (and a few more wild nights) to see if things get better, or if you could get used to it.
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IMHO, I think she might be a bit too young to have any sense to test him on his confidence or his abilities as a mate. She's just a child and I find it hard to believe that she has had enough experience to set him up like this. If anything, I'd said that her comment, "it probably would never happen" is a sign of her insecurity as a young female. I think she's trying to get the inside scoop on your buddy and is fishing for information regarding his feelings towards her.