[Seijun]

I am not a very big person. Rather, a short female. I owned the original PX100's and loved them. After they broke, I bought the new PX100-II. They hurt my ears a lot. My ears would be numb after about 10 minutes. I stretched them out over a box for a month to see if I could get them to loosen up, but It didn't seem to affect them in anyway. I gave them to a roommate who has been using them about a year. I try them on occasionally to see if anything has changed, but they are still just as tight and horrible as ever.
 
Now I own a Koss Portapro and a Sennheiser HD 239. Both are very comfortable. I am not too thrilled with the bass on the Portapros, though, and have been looking for an alternative that has less bass and that have a more compact fold. I see the PX100-II's recommended over and over again, and everyone raves about how comfortable they are. Do you think my first pair were just lemons? Should I give them another chance? Alternatively I guess I could just buy a pair of used PX100's..

 

[KG Jag]

Headphone comfort is a very individual thing.  Sizing, shapes and sensitivities are unique to each person.  We can point you to headphones that are generally considered to be comfortable and mention others that have garnered complaints for being uncomfortable (like the Portapro that you like--but which many including me--find to be a thinly disguised torture device with its bare metal headband and paper thin ear cushions).  However, the only way to know for sure is to wear them yourself for a time equivalent to your longest listening session.