I would think that with proper positioning that the damage to the nipples would have a chance to heal and the pain that occurs from this sort of positioning would decrease. However, as for the inner type nipple pain this mom describes, it is possible that the sensitivity will not go away until after birth. I tandem nursed throughout my last pregnancy, and experienced nipple pain/sensitivity from the 3rd month on that was severe enough that I had to limit nursings. To my amazement and joy, this pain disappeared immediately after I gave birth. Ione