I love playing on headphones, just because of the surrounding effect... it helps with immersion, and with fighting sometimes. (Although the Supermutants' "gore bags" sound is extra disgusting on phones :yuck: )
That said, though, any time your ears are telling you something is too loud, they are telling you that you're doing damage. It's a nice natural way our ears have of protecting themselves.
Whether it's at a rock show or on your phones, if you feel like it's hurting, you are right: it is hurting.
The svck thing about hearing damage is that you never really get back what you lost... once it's gone, it's pretty much gone.
...And yet, there's no way to really illustrate that so anyone can get a true understanding of how it feels, so everyone is kind of on their own to experience it--- and then it's too late to get it back #%@#!!!
The best you get is to take everyone's word for it: don't subject your ears to hits that make them flinch, or pretty soon you'll be sitting across a tiny table from your friend in a restaurant and you won't be able to hear what they're saying.
Man does that get old. "What?" "Wait, say that again?" "What?"
Now I have to wear earplugs at shows, and when I practice, and I've given up seeing really loud bands I used to love, and I f---ing hate it when they overdrive speakers at movies. Ouch.