Same Issue, But i found the best solution yet
Tried earbuds - never found any that worked
Used a Chatterbox bluetooth setup - drained the battery on my phone in the mtns / impossible to use / too much work just to listen to music / music would stop if someone called - and the music would never come back on / just a big pita / but they sounded great when they worked
Switched to the cheapo helmet speakers and velcro'd the tiny ipod to the side - they sounded horrible / couldn't hear anything at highway speeds / not worth it
Then I decided to invest in a high end pair of earphones under the circumstances that they were noise canceling, didn't protrude out of the ear, and used an ear-foam tip.
For $100 I got the Shure 215's of amazon.
http://www.amazon.com/Shure-SE215-K-...ds=shure+se215
Here is a picture of them in my ear
http://3.bp.blogspot.com/--pKPRT7pdP...right%2529.jpg
They are flat. Noise Suppressing. Have a metal flexible wire that runs around the ear to keep them in place. They sound amazing.
I've put well over 1000 miles on them now and couldn't be happier. I keep them at an extremely low volume and can hear the music, my exhaust, and traffic perfectly. The tip is "foam" so I mash it up, then insert it into my ear, and it expands to keep it in place. Since the actually body of it lays flat against my ear I do not get any pressure from the helmet. I only put my helmet on carefully and they have only came out once or twice. When I take off my helmet they loose their seal and I have to re seal them back into the earhole before I put my helmet back on. But if I need to stop and talk to someone I just turn off the music, and as long as they speak in a normal voice, I can hear the conversation just fine. They are definitely high quality and have tons of good reviews (there are also brand whores who think that Dre is the only good earphone) and a lot of other motorcyclists have came to the same conclusion as myself. For $100 these are perfect for what I need them for.