Hey hun,
You are doing all the right things so far - keep pumping and keep offering him the boob.
Something you may find useful is pumping on your left side until your milk lets down, then offer it to LO. At that point, you'll probably have the most luck as your milk will be flowing more and your nipple will be more protuding.
Nipple shields are fantastic as a last resort - Scarlett used them for the first 5 weeks, and then all of a sudden latched, so it can be done! However, some people find it hard to wean their LOs off, and it can effect your supply if you use them too often. Maybe use a nipe shield on the left breast until your nipple has come out a bit more, then take it off and try offering the boob?
I had horrible latch issues at first - Scarlett just didn't want/know how to latch. It came with time, though, and now she is 9 months old and we're still going strong! There is almost always a way, so don't give up
Hope this helps - I'm a bit tired, so I apologise if I've rambled!
I've tried offering my left boob once it's let down and he still can't latch - that boob almost always leaks too so I try getting him to latch by showing him there's milk there but still no luck. I tried nipple shields too but they make my nipple soo sore and it squashes into a funny shape? I'm really struggling with my right boob now too because I'm only feeding him from that side all the time and not giving him the expressed milk because he screams when I try to cup feed him and I'm scared to give him a bottle incase he gets confused between breast and bottle. Last night was so stressful, I hate that I dread feeding him
Lover - have you tried different positions? i had to rugby ball hold Owen on one side for a while.
Yes I've tried cradle hold, cross cradle, rugby and laying down - none of them will get him to latch on to the left side though and we can only feed in the cross cradle and rugby holds from my right side.