[TwistedKestrel]

Reserructing my old Head-Fi account to ask some knowledgeable people a question. I did a quick search and didn't turn up anything, but I'll still accept a flogging if this gets asked a lot.
 
Future Shop recently had a decent web sale on the Sennhesier HD558 ($139.99 CDN) and I was thinking about an upgrade from my old (but reliable) Sony set. So I bit the bullet, even got a "fancy" Grado 1/4 to 1/8 cable so the otherwise enormous adapter that the headphones come with wouldn't break off any headphone jacks on my stuff. So far I like the sound, BUT - using them for extended periods results in increasing discomfort, like somebody's slowly screwing a C-clamp on my head. Eventually I get frustrated and take them off. I took my old Sony's to work today and realized how much more comfortable they were. What gives? Am I wearing them "wrong" or something? I don't have a massive or tiny head (I wear a Shoei medium motorcycle helmet, if that means anything to anyone, dunno my hat size). Do they break in and get more comfortable? I'm considering returning them or selling them.

 

[MegaMushroom]

I'd say to go ahead and sell them.  I haven't really noticed a change in comfort in mine, granted I find them extremely comfortable.  Appears that the 5x8 series of Sennheisers aren't for everyone.  

 

[juantendo8]

Interesting. I think most would agree that comfort is the HD55x/59x strong suit. If they are not comfy immediately, they probably will never be for you as they don't have much of a "break-in" period.

 

[GigaFi]

The 558s are a little bit tight. The 598s are alot more comfortable.

 

[prayer86]

I own a pair of HD558s and yes, they can be a bit tight. I've demoed a well used pair of 598s at a local shop and they were much looser. In saying that however, I don't find the 558s so overbearingly uncomfortable that I'd want to get rid of them, and I'll gladly sacrifice the little discomfort I experience for the sound. =)

 

[fabio-fi]

You dont need to sell them. Stretch them a bit before using them, the clamping force will go away. 
 
This way i dealt with my HD-25's which have a strong clamp force. 

 

[Hailin]

I have been storing my HD598's over the arm of my couch to help stretch them a bit. I found them uncomfortable at first, because the oval pads rest right on my temples.
I would also try loosening the headband a few more notches so that the top of your ears are almost touching the upper part of the pad. That helped me a TON.