[GTRagnarok]

Recently got the Westone 4R for this purpose. But while they're comfortable normally, they still put a sharp pressure on my outer ear when I lay my head sideways on my pillow. Seems I just need a smaller IEM. Right now, I'm looking at the ATH-CK10. They're extremely small and there's almost nothing hanging out when inserted deeply as seen in this review:
 
http://www.head-fi.org/t/441422/my-review-of-audio-technica-ath-ck9-and-ath-ck10
 
The problem is that they seem to be very hard to come by these days. Any ideas?

 

[StyleElements]

I can lie down comfortably with my IE80s in. I didn't use to be able to, but I recently acquired foam tips and with a soft pillow, I now don't have any problems. Perhaps look into them? I should mention that if you love the W4R's sound, you might not like the bass-heavy IE80.
 
I agree that smaller IEMs would work for you. I had a look at the CK10 and it looks tiny indeed! Maybe try to acquire some, I've read that it sounds awesome. Good luck!