Scowgirl - I have similar shaped/size breasts. It has always been a challenge to breastfeed. I got the breast pillow that the poster above suggested - the one that fits under the breast for a better position. I tried it out and I think it's going to work really well. I actually got a size larger. Even though the measurement said I needed medium, because my breasts are more longish - I got a large. It seems to fit well. It's the utterly yours breast pillow.