Hi there and welcome!
I honestly wouldn't support the idea that condomless intercourse is a milestone that we should be waiting for in any sexual relatonship, simply because they pretty much always offer a barrier to the transmission of STIs. From a health point of view they're almost always a good thing.
I would suggest talking to the person you're thinking of having sex with about sexual health and what both of your thoughts are surrounding intercourse without a condom... Is it something you both think about in the same way? Do you feel like either of you know all you need to know to feel confident about making sexual health decisions?
I'd also suggest looking into how and where you can access STI testing. If everyone involved in a sexual scenario hasn't had sex with anyone else for around half a year and has had negative STI screening results through that time many STIs would have shown up on a (full) screening or shown some sort of symptoms in that time so the overall risk does go down, which would definitely be a better place to be in when thinking about going condomless.
"In between two tall mountains there's a place they call lonesome.
Don't see why they call it lonesome.
I'm never lonesome when I go there." Connie Converse - Talkin' Like You