These sound like a version of intususcepted nipples -- usually the nipple
telescopes into the areola.  Pumping pulls out a normal-looking nipple.  If
you palpate the areola you can feel the whole nipple lying inside.  Your mom
sounds as if she is in horrible pain so perhaps a "bandaid" approach would be
appropriate.  How about a M___ nipple shield which (depending on anatomy)
would either prevent the nipple pulling out and exposing the raw flesh or
allow it to pull out but give the mom a barrier between the nipple and the
baby.
Joanna Koch IBCLC