I just accepted that they would not stay seated and the seal wasn't perfect. some tunes is better than none. however these new soundmagic e30's sit flush in my ear and should work great inside my helmet. my helmet is the Shark RSR 2 and it has no special spots for earbuds.
there was some discomfort in wearing mine, but it was very very minor. only bothered me after about 4 hours of continuous wear.