Phones like the CX300s are good for laying on my side and nodding off. I normally remove the phones and set them on the nightstand prior to falling asleep though.
I have UM2's and they hardly stick out at all, i've almost fallen asleep with them in a couple of times.. But i won't be doing that until i get the 3's as a replacement
ER6i's with short/small foamies or bi-flanges would insert well into the ear canal. I don't use the Etys for falling asleep, though -- I use Creative EP630s (and take them out before falling asleep) or Sennheiser PX100's. I tried the Future Sonics Atrio M5's once for this, and not only is the form not ideal for sleeping, but the sound is so good I resisted sleeping!
Among IEMs, the Westone UM1 and UM2 would provide an excellent fit for lying on your side.
I sleep with my UM2 pretty often. They're pretty much invisible after a while. The cable helps. The E500 fits pretty flush too, but the cable is much more obtrusive.
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