Partner has trouble remaining hard because of past issues–what to do?

I’ve been seeing someone for three weeks, and it’s going really well, I like him a lot. We have great chemistry, and I think that he’s attracted to me (he told me so many times ‘you’re so hot’, ‘love your body’) so I don’t think attraction is the issue.

But he has troubles staying hard because

1) He had issues in the past with his foreskin hurting during sex, and he got a surgery a few months ago. He can masturbate freely, but it’s always touchy with a partner, he fears the pain and gets in his head because of the pain

2) since he gets hard, then unhard, then hard again, it’s hard for me to stay fully aroused. Previously I’ve had this ‘crescendo dance of hornyness’ where you make-out aggressively, touch each other, get hard/wet, do foreplay, do penetration…I mean not all steps are mandatory but when we get close to he ‘he’s touching me, I touch him’ he gets soft, and then I lose a bit of my enthusiasm.

3) three weeks isn’t a lot, and I guess that he needs to feel more comfy with me

So I guess my questions are : what can I do to make it better? I’ve been trying a lot of stuff with my hand, ask him constantly what feels good, but the fact that he fears the pain and gets in his hand is hard to handle. I’m not frustrated or whatever but I would LOVE to make him cum and it sounds really hard to do, which debilitates my confidence. I also can’t come with a partner (only with toys) so…. sex is hard, I guess.

I’m sure many men have went through this and I’d love their feedback on what their gf did to make it feel better, and also as a woman : how do you not let your confidence get destroyed?

Thank you 🙂