Dee,
I feel your pain. Well, I did feel the pain when my lo was the same age. I had a nightmare lactation consultant at the hospital (I was in for a week with c-section) who not only was a witch, but she told me that my lo was not latching on properly and made me unlatch and relatch numerous times at every feed when she was there. I am convinced this is what made my nipples so bad. In the end, once I got home, I solved the problem myself. Firstly, I slathered on lansinoh ointment after every feed. This helped a LOT with the healing. Second, I didn't use shields, I had a few toe-curling days where I was literally sobbing through feeds because of the pain, but I stuck with it because I was committed to continuing to bf.
Finally, I ended up resorting to turning Tyson's lips out for him (bottom lip mainly) as well as physically pushing his jaw open further once he was on the nipple to widen his jaw and improve the latch.
By week 3 ish, he had worked out his suckling style and the nipples had stopped bleeding. But I continued using lansinoh religiously for at least a few months. Helped a lot.