[renji1337]

I have a pair of ultrasone pro 550's and HE-400's and whenever I listen to music, I can hear well, but my right ear feels like its "free" and my left ear feels more confined and it feels like theres pressure in it, what could this be from?
 
 
Everything still sounds good, soundstage etc. its just my left ear sounds maybe off? Ive taken audio tests online and stuff and i can hear fine out of both ears. its just the left doesnt feel as free, it has some annoying pressure

 

[squallkiercosa]

Do you wear glasses? 

 

[renji1337]

nope

 

[fluidz]

I have the same issue with He-500's which can distract me from concentrating on the music because i'm constantly thinking about the Pressure above my ears.  I wear glasses and I've gone as far as putting foam under them to dampen the weight, yet it only adds more pressure to the clamp.  If you do wear glasses, try using thinner frames.  
 
Edit : Op doesn't wear glasses, oh well. Lol.

 

[fluidz]

Have you tried swapping the headphones around?, from L - R to R - L instead.
 
Edit : scratch that, op has the issue with both headphones. 

 

[renji1337]

Maybe flushing my ears with water will help

 

[squallkiercosa]

Unfortunately there is nothing you can but to get used to.