The official (but not fully authoritative) word from the Catholic Church is "no". That link cites Isaiah 66:22 "Before she was in labor she gave birth; before her pain came upon her she was delivered of a son. Who has heard such a thing? Who has seen such things?" OK, that could be a reference--or maybe not. It doesn't cite Revelation 12:2, which is cited in other contexts to refer to Mary as Queen of Heaven, and which refers to pain in childbirth. Further, arguments like "Many Fathers of the Church and theologians down through the centuries deemed it fitting that Mary alone would be exempt from such pains as a sign of her unique holiness. Thus, Mary’s freedom from the pains of labor is one of many reasons for belief in her Immaculate Conception." are a bit circular.
I don't know. I'm not obligated to believe in the Immaculate Conception, though I will cheerfully concede that her relationship to her son was not going to be ordinary. But stipulate the doctrine for the sake of the discussion. (FWIW, the Orthodox reject the doctrine, since they don't have the doctrine of Original Sin, which, as Chesterton noticed "is the only part of Christian theology which can really be proved." But they believe in a painless birth.)
What would Mary have answered if God had asked her "Would you rather have a painless childbirth, as a reminder of what Eden was supposed to be and as a promise of what will be, or would you rather share the pain your sisters do?" She wasn't going to be pain-free later (Luke 2:35). Her Son came and shared our pain.
And her pain was great at the end of her son's life as well.
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