I have the same problem - headphones are uncomfortable for me. I can tolerate the HD800S reasonably well, but every other headphone is a no-go comfort wise.
I recommend trying a decent set of IEMs. They have come a long way in terms of sound quality, rivaling headphones. I currently listen primarily to the Nightjar Singularity IEM, which has phenomenal sound quality that’s close to the HD800S in terms of enjoyment. MusicTeck and Bloom Audio sell a wide array of IEMs, including ultra-high end ones. Headphones dot com also sells a wide range of IEMs and allows you to return them for a full refund. Thie Audio and Elysian Acoustics are two well-regarded IEM manufacturers that you might want to read about and consider.