Wanted to share my experience here. I too was disappointed when I got these as they hurt my ears. My issue was the main cartilage area of my ears, where the larger body of the AirPods sit...
This sounds very similar to my experience - the tips felt fine, it was the, hmm, lower back curve of my ear that hurt after wearing them for a bit. And it wasn't like APP are super hot, or pointy, just a matter of them
touching my ears for a while caused surprising pain. I was concerned that I might have to take them back. I thought about exchanging them for non-Pro AirPods (I've never had either before now). Initial attempts to settle them a bit further into my ears, in hopes of transferring the weight/contact away from the outer edge, were fruitless (all this with the original medium tips).
I ended up trying the larger tips, and just gently pushing the APP a little "forward" in my ear (hmm, rotating them along the same axis as if you held your arms out at your side and then brought your hands together in front - essentially leaving the ear tip in the same place and pushing the end of the stalk a little closer to my face, rotating the body a bit away from the cartilage)... and some combination of the different tips, the repositioning, or just my ears getting used to them... and now they're completely fine! I went from worried that I'd have to give them up, to really happy with them (the noise cancellation was always great, the sound is quite good, and the convenience is amazing). My one remaining annoyance is that the large tips are a little "floppy", and occasionally when I remove them one of the tips will invert (like an umbrella in too much wind). This is very easily remedied, but it means (in those cases) it's more than just one simple motion to put them away.
My previous good earphones (which I haven't been able to use in quite some time) were a pair of Etymotics IEMs with custom earmolds, which fit amazingly, were crazy comfortable and secure, and sounded fantastic. Unfortunately, after many years of service, the cable got munched, and, well, I'm much less interested in using wired headphones with a Lightning adapter.
I've been saying for a long time that Apple should make a variant of the AirPods with "spare" room in the case and some sort of grooved fitting replacing the AirPod's smooth exterior, to give custom earmolds something to attach to (with the "spare" room allowing them to remain attached while in the case) - the convenience of AirPods with the noise isolation and comfort, and secure fit, of my beloved custom Etymotics. As usual, Apple has arrived at a good solution by following an entirely different path than I had expected/urged - sealing out the sound in a partly physical, partly electronic manner, obviating the need for the earmolds. The comfort... seems to be getting there. I'm cautiously optimistic, and no longer considering returning them.
As a bonus, the substantially shorter stalks remove most of my feelings of them looking weird - I'd previously thought a darker color would mitigate the way they stood out... again, they fixed that a different way than I expected (I asked for a faster horse, they gave me a car). If the comfort keeps up, I'll be very happy with these.
(I still wish there was a way to change the volume without asking Siri. Sometimes I have my phone in my hand and it's quite convenient to use the side-mounted volume buttons. Other times the phone is in my pocket and it's considerably less convenient to change the volume - noise cancellation lessens the need to "ride the gain" though. But I kind of miss the small pod of physical buttons hanging reliably just below one ear.)
