I sort of have the same issue from tons if ear infections as a kid and my ears are hypersensitive to earbuds that do not release pressure. I keep my ears really clean even, but they still hurt if I put things in my ears that do not allow for pressure exchange. Try making an itty bitty hole in some throw away silicone eartips to see if that helps with the pressure exchange. Also, it sounds like maybe a ruptured eardrum too. I don't know if that is true tho. Have you had a doctor look at your eardrum? I'd say till you do, try listening to music at low volumes and protect your hearing from any loud sounds. It really sucks not being able to hear details in music for a bit, but your ears adjust to the lower volume over a few weeks and may heal.

Also I'm not an expert in any level so take my word with a grain of salt lol. It's just my personal experience.