I was experimenting a bit and I found there are a few possibilities for positioning where they don't hurt. Rule one, don't jam them into the ear so hard like I usually do. Rule two, allow them to lie 'flat' in the ear, not sticking outwards. Both are doable and fortunately the sound is completely independent on the earphone positioning. However the fit isn't so good then so they tend to move around and the memory wire does more damage then good for sticking out. So still not a win-win.
Well, triple tips kinda help the issue, but I'm not a fan of those. 2-flange tips might help, but I don't have any with this diameter. Future sonics are insanely expensive. I might try foam tips. So the question now is: which are a better fit for these, Shure Olives or Comply T100? I have some olive-like foams but they don't fit and are too small. Also, not a fan of bass really, the sound of R50 is perfect as it is.