Pain using nipple shields, thinking of stopping breastfeeding

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I'd be grateful for any ideas. DS is five months old and has been bf using nipple shields from one month (syringe, cup and bottle prior to that). Despite concerted efforts to wean from the shields (and advice from a bf counsellor) I've not been able to get him to latch. it hadn't really mattered until recently when it suddenly became very painful to feed. DS is really clamping down hard on the end of my nipples. I think he might be teething and he is also very hungry. It's so painful and I don't think I can carry on like this for much longer. I'm guessing it will get worse as teeth come through?
If anyone can suggest anything to help me continue breast feeding, I would really appreciate it as I would love to.

I haven't got any advice regarding the BF as such, but when I lost all hope of breast feeding I decided to exclusively express. Was much happier after that.

Thank you, I think it might have to come to that, though would rather not!

Hi, I breastfed all three of my children for a year, but for my first and third it was a nightmare in the beginning. With the first I thought it was just my inexperience but after feeding my second with blissful ease, I was surprised to have problems again with my third - bleeding nipples and pain so intense I'd start crying the same time as baby when the feed was due. Because my DH has multiple allergies I was committed to feeding - as you are with all you have tried. So firstly - if you can't - it sounds like you have done a brilliant job so far so be kind to yourself if it doesn't work out. If you do want to continue I understand your tenacity. In my quest I saw several midwives, health visitors, GP's and La Leche groups. Finally I called the local maternity hospital and managed to convince a midwife - who trained other midwives in breastfeeding techniques to come and sit with me for several successive feeds over a week. She helped me to develop a technique that worked for baby and me. In my case it was being meticulous in making sure that baby was latched very tightly with so much breast in her mouth that my nipple passed the hard part of her palate and was half way down her throat (which from all the diagrams I saw is quite normal for babies!) I needed to be rigorous in watching her all the way through the feed and using my little (washed and clean) finger to gently detach her as soon as my breast slipped even slightly out of her mouth. This repeated detaching and reattaching to keep my nipple very far back in the soft part of her throat did the trick. I also used Lansinoh cream on my nipples after every feed as it protected the poor things and is edible for baby so didn't need wiping off. My bleeding nipples healed and I could start to enjoy feeding my lovely daughter. At the time I was told that painful feeding can be caused by a high palate and small mouth. She is now 8 and the dentist comments every time he sees her that she has a very small mouth and she has a lovely singing voice which apparently comes with a high palate! So do persevere if you are able and don't be shy in calling and asking different health professionals to come and watch you feed and help you find the way that works for you and your baby. In an article in women's hour this week an expert was saying we have very low breastfeeding rates in the UK, so you have every right to keep asking and getting help from all you can until you find the answer that works for you. Do let us know how you get on. :)