For me personally, “many partners” is not a positive - the best men I’ve encountered in bed are those who have been in long term relationships and really genuinely care about my enjoyment (there aren’t many of them).
These two things means learning over time what it is to be a good sexual partner to one person, and also that they understand that your idea of a good partner isn’t the same as someone else’s so they have to listen to you, work with you and figure it out. They won’t feel offended if you make suggestions, ask for something specific, ask them to stop if something isn’t working, etc.
No man is a good sexual partner to huge numbers of women after a few encounters - the sad fact is that so many women have a very low bar for what makes a man good in bed.
A couple of things:
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Just because you like him, you don’t have to like or even try the things he’s done in the past if you don’t want to. Don’t feel any pressure in that regard, just as he shouldn’t feel pressure to try anything you like and he doesn’t.
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Do you feel confident in what you like and your own sexuality? Do you feel comfortable expressing these things? When I was younger I thought I knew what I liked, but I realised most of that was learned accidentally from what partners did to me and I just went along with whatever they wanted as I didn’t feel confident in speaking up or completely letting go. Things like the book Come As You Are and OMGYes (google it) completely changed the way I felt about my sexuality. I wish I’d had access to both years ago (and I definitely wish my partners had too!)
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I’m sorry it was painful. I have endometriosis and sex was painful every time I had it until I was with my DH. He’s the only person who’s ever spent serious amounts of time before sex to make sure I’m satisfied and that it won’t be painful. This may be because he’s well endowed and used to this problem.
Also using lubricant, which I never used before as I didn’t think I needed it, but it makes so much difference. Even after a few years of no sex, it’s not painful (okay, some positions are as we have a size discrepancy! But I just say so, and we do something else).
So it definitely doesn’t need to be painful if he’s doing it right, and he should be making sure that it’s not and stopping if it is.
I suspect he may not be the super-lover he’s built himself up to be - I mean, who says that about themselves anyway?!