Does it get easier?

I'm tempted to answer: "Only if you do it wrong". If you go weight-lifting it's hard. If weight-lifting isn't hard you don't put on enough weights. You do get better with practice but that doesn't necessarily mean it's easier.

You will likely both experience easy and harder mediations as you go forward.

My hardest mediation was one last year. It was the first meditation at a 5 day seminar, when I already had years of meditation experience. Nausea raised up in me and there were moment where I was calculated the escape route in case I have to throw up.