Backstory, ignore if you will

Hello folks, here is my question with some graphic description.

Im 20 right now, and I got my first head at 16, it was good I came. Then after that I didn't have sex and stayed away from girls, then had sex again, but never came. I guess it was either because the partner was ugly as fuck (Im not exaggarating), or because it happened very late (4am) and I was tired. All these times I didn't really feel the sex, its like I was being bothered by the things happening. One time I had sex with a hot girl and I felt something but still, I couldn't ejaculate.

Well, nowadays my life is much better, Im making gains in a lot of areas. I stopped watching porn and now masturbating with a soft grip (I used a hard one, now using a few fingers to grip it). I can't stop fapping, because I will turn into a mindless zombie then.

I feel more confident in myself and much less insecure compared to my older self, I also have the good "selfishness" attitude towards sex, if you know what I mean.

The problem

I will have sex, but still. If I can't cum again what could be the problem? Also how to handle if I can't cum? Just idgaf?