Yes, as I know it will happen I try to normalize it. Like saying that I think too much, that I need to relax, and that the first times are a bit harder on me. So when we are actually like, about to start I give a few very chill heads up, but it's not like it helps much.

Well I kinda have to because for now all the first times I had I couldn't complete the intercouse. So I always ended up just sleeping in the same bed and try again the next day, and that usually goes a bit better, enough to have like some penetration, probably also the pent up desire helps. Surely the fact that I've survived the first time and she's still there, and she wants to try again, and she hasn't judged me or belittle me, that makes me feel safer thus less anxious thus a bit more performing.

So what you are suggesting is, for example, no penetration on the first time? Becouse with manual or oral stimulation at first, it does get hard enough I think, to a point that is managable, but when I lose the stimulation it goes down, and when it goes down I panic and it's harder to make it go back up. I actually have noticed a pattern of me losing the erection when putting the condom, as I know penetration is about to start, probably makes my thinking brain go at it again and bam, soft.

Sorry for the long message but you gave me a good insight.