I've had similar issues with earplugs, including waking up in the middle of the night because they were so painful-- I've definitely found some that were a lot less painful than others (maybe smaller? fancier? unsure) and if you make sure to put them in correctly (lift your ear upwards? i think the plugs usually have instructions) I think it can help. there's also silicone earplugs, which aren't nearly as good at blocking out sound but are different enough that they might not have the pain problem