The trick to soldering is you're not trying to put solder on things from the the iron. You heat up the joint with the iron, and then feed solder into the joint.
You put a bit of solder on the tip, but that's just to help apply heat to the joint.
Yeah, I've once watched a short clip of someone properly applying solder and realized I've been doing it wrong the whole time. I keep meaning to watch some educational material on the matter, but for now I've conceded that it's just some kind of higher magic.
Solder flows like water, it "wants" to stick to absorbent material via capillary action. The only difference is the material needs to be clean and free from oxidization so it has a direct metal contact (that's why solder has a flux core), and it needs to be hot. If you take care of that, the solder will pretty much do what you want it to.
