i'm sorry things aren't working out as you are hoping.
if you are still wanting to breastfeed and using your expressed milk, is it possible to try out a different pump, perhaps from the maternity team?
would you also consider using a supplementer for his top-up milk (though I think again you may need to access your maternity team to get hold of one) or even encouraging to sip from a cup or syringe instead of bottles? bottles are a lot easier to get milk out of, even the slow-flow teats.
there are also bottles available which claim to be breast-like. whilst i personally don't see any bottle as being a breast equivalent, i have met a couple of women who used them in difficult early situations and felt that the way the bottle squashes round the face more like a breast was a help in switching their babies over to the breast in the longer term.
i really hope you get to work things out and that your breasts heal quickly for you. by the way, it is normal for nipples and breasts to be different on each side.