A two-part query about butt sex

Hey, gay bros. I have been in a very happy and fulfilling relationship for over 3 years now, but we've never done anal sex, due to many reasons - some explained below. But lately, I have been wanting to try it. But before talking to my partner, wanted to throw it get some perspectives of you good folks.

Part I

Is it okay to have anal sex when you have hemorrhoids? Not active pain-in-the-butt hemorrhoids, but inactive ones that just are there as dead skin. I have read conflicting information on the internet, so anyone with real-world experience? Any tips on how to make it better, or even deal with the problem permanently at home? I can't get them operated/checked for the foreseeable future, at least.

Part II - This one's more conflicting

My boyfriend isn't into anal sex. In his previous relationship, he had a terrible experience where his ex didn't stop when asked and that left him pretty scarred. Led to a tonne of long-term health issues as well (hemorrhoids + UTI). This was right after we met each other so he was pretty sure he doesn't want anything to do with it ever again.

But I have vocalized my intentions that I'd probably be into it in the future. He seems to always say something to the tune of that we'll cross the bridge when we reach it, so I guess he is not totally averse to the idea.

Now, the thing is I imagine both of us being versatile, if and when, we start doing it. But I don't want to be the guy who forced him to do something he doesn't like/against his will. So even if he somehow is onboard to be the top, I am not sure if I should even openly suggest him bottoming, especially if he doesn't like it. I don't want to force him into doing it, but also want to experience this with him. Any suggestions on how to proceed? Guys who have been in similar situations, what has helped to have this conversation and how did things turn out?

Thoughts?

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Thanks, everyone in advance!