Yeah I think it does hurt the ear. I did that for about 2 months cause I didn't feel like buying new headphones now I'm half deaf in my right ear.
No trollin', dead serious. I'm thinking of going to a hearing specialist.
EDIT: I started getting consistent aching when listening to music even moderately loud to the point where it had to be very, very quiet for the aching to go away.
I'm not sure why, must be some imbalance in the brain that's overloading one side of your brain or something. Either way once the numbness started happening more often I stopped. The pain is still prevalent and I have a distinct muffling in my right ear because of it..