Update: I just sucked it up and used the tiniest tip. It was never particularly comfortable but I got used to it. Used them for a couple years for running. They broke (accidentally snapped a bud in half removing it from the charger) and now I use a pair of over ear headphones and I love them. I use the Kinivo 240 (https://www.amazon.com/Kinivo-BTH240-Bluetooth-Stereo-Headphone/dp/B00AWIPITS), if I wanted to spend a little more I'd get the 66 Audio BTS (https://www.amazon.com/66-Audio-592-91466-AUDIO-Headphones/dp/B01M8M4R7K)
I must have tiny ears (or tiny earholes?) so whenever I try to use a pair of "in-ear" (here) headphones, it is a painful experience. The silicon tips feel too big for my ear, even when using the smallest type in a set. When I do manage to cram it in my ear, the way that they close off my ear canal is disconcerting, similar to how your head feels stuffed up when you fly on an airplane.
I recently received a very nice pair of in ear headphones (powerbeats 2 wireless - like these) so I am wondering is there anything I can do to make wearing them more comfortable? The best solution would be one that makes them wear more like earbuds.