Does breastfeeding or hand expressing hurt if you have very small breasts (AA or A)?

I’ve always been flat-chested and my breast tissue and nipples have always been very sensitive to the point that I really don’t like anyone doing anything to my nipples (as a foreplay thing).

Everyone and everything says breastfeeding, pumping, hand expressing—all of it—“shouldn’t” hurt if “you’re doing it right.” But...if you have very small boobs (usually they are more sensitive than larger breasts), is it possible you can do everything correctly and it still hurts or is uncomfortable?