Thank you for your advice and encouragement!

I like the suggestion of slowly offering the sore breast and building up - I currently aim to feed twice a day football hold on the sore side but it is a struggle and sometimes it hurts too much and I have to take him off and give him the "good" breast (and express the sore one) as he just doesn't latch on painlessly- I usually try this at the mid morning and afternoon feed when I am relaxed and sometimes I can feed well this way but when I try it again to make it three feeds - it's over - it gets so sore I have to have him off the sore side for 24hrs.

I think my nipples do point outwards a bit and I think u are right about trying to "trick" him into feeding off the right hand side using the football hold (again, this way is not painfree for me yet) . I am worried as I am imagining myself being out and about and struggling to b/feed in public bse he will only latch on properly with the football hold I can't do this without props - pillow etc. Will I ever be able to feed him "madonna" style if he learns "football" style?

As I said the frustration is that sometimes I can get him onto the breast (like this morning he fed well "madonna style" without hurting me - a miraculous fluke as I was in a shopping centre parents room!), but mostly it doesn't happen. I am desperately hoping this will settle down in a few more weeks (months?). I feel like an idiot not being able to get him to latch on after all this time and afterall, it is my second time round

PS I tried baby-led attachment - it was hit n miss, he got on beautifully one day - but chomp-arama the next!