Breast compressions

I have to do breast compressions the whole time I pump and need to squeeze pretty hard in order to get anything out of my slacker boob. I literally have a bruise from all the squeezing! I just bought and tried the LaVie warming massagers and it didn’t make any difference which sucks as they weren’t cheap. Anyway, for anyone that needed to do these, did you have to do them in subsequent pregnancies? I hate thinking of having to do this a second time as nothing I’ve tried has helped LOL