Pumping. Does it get easier?

So my boobs were leaky yesterday and i stopped and thought that maybe if i pumped i could save it and therefore not have it wasted by flooding my shirt. I'm 36 + 4 and baby has been trying to come since week 28 but my cervix is completely closed. So i figured even if it caused a bit of dilation I'm close enough to 37 weeks that it may be ok. Anyway i used my breast pump and just OMG. It was so painful! I literally started crying.

Does it get easier after the baby gets here and you breast feed? I really don't want to be the only one making night feedings like i was with my other 2 children which is why i bought the pump but I'm not sure if i can handle that pain if it never eases up.