I had very flat nipples with one slightly inverted. Breastfeeding dd took some getting used to because of the way she had to stretch my nipple out. After the first five weeks or so I was breastfeeding in all different situations and positions. It takes perseverance and time. I haven't stopped breastfeeding since then, although dd weaned at 2.5. At 2 ds is feeding lots still and was easy to feed from day one. Good luck.