Trying to cope in a healthy relationship after a toxic one

So, I am in a bit of a predicament. I have a problem of letting my insecurities get in the way of my relationship. Let me elaborate, I have been cheated on in literally every relationship I have been in, except for this one. And I tend to overthink about if I am enough. If I can make him happy.

Before I continue, I feel it must be said that I don’t get jealous of his girlfriends. Never have. I trust him 100%...i just can’t help these thoughts from getting in the way of how I feel. I am not scared of him cheating on me, because I truly feel he isn’t the type to do such a thing. I am more afraid of him leaving me for another girl who is seemingly better. Someone who has more to offer.

He has never given any indication of doing so, but I cannot shake these feelings. The two of us have discussed them in the past, but recently I have kept them to myself. Simply because I do not want to annoy him with my questions of “am I enough” and things like that.

I guess my question(s) for all of you ladies is:

1. Do I approach him with my feelings about this?

2. If I do, how exactly do I do it without sending the wrong message or annoying him?

3. Whether I do or don’t, what can I do to make these insecurities fade?

Thank you for taking time to read and/or respond to my post ❤️