i’ve had the same issues with ear infections from cramming earbuds in my ear. the ear canal has very little “give.” i have a teeny-tiny little bit of scar tissue in mine from a past little scrape – probably from an abrasive earplug – and in certain weather conditions it still flares up. feels like an angry frog is sitting in my ear.
anyhoo. i would go with the sennheisers mentioned, or the sonys here:
http://www.musiciansfriend.com/rec/navigation?N=100001+308865
you might try melodee music as a close-by alternative to best buy, and/or guitar center.
good luck widdit,
mkg