I've been playing 25 years and my fingers always hurt when I return to the steel string.
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Try changing your technique. See how little pressure you can apply and still get a good clean note out.
When you return to steel string??
are you normally playing a classical, then occasionally pick up a steel string?
I think you might have to build your callouses to different level (I.E. spend a few weeks playing steel string consistently).
I wrapped a newspaper ’round my head
So I looked like I was deep
My answer to your question is, "No," it should not hurt to play after as much time as you've put in. The first guitar I owned hurt my fingers and nothing changed that; it just wasn't a good enough guitar with respect to action. Good enough action does not need to mean expensive. Anyway, think about going down to the music store and playing a few guitars--see if it makes a difference. Another thing you could do is have the luthier at your favorite store take a look at it.