was I being a pushover?

Only if you let randos decide for you.

That said, I personally would never see someone like that again.

There were ways he could have voiced his confusion without being pushy, like "ah, want to be doubly-protected, eh?" and then proceed to put it on.

IMO it's good practice to, at the very least, START any physical relation with barriers. If you want to move away from them over time, that's something all parties need to give enthusiastic consent for.