Have you tried IEMs? I have ears where regular earbuds don't fit well too, Apple's are incredibly uncomfortable for me. But IEMs like the Shure SE215 fit really

Have you tried IEMs? I have ears where regular earbuds don't fit well too, Apple's are incredibly uncomfortable for me. But IEMs like the Shure SE215 fit really well and I barely notice them. The Meelectronics X6 works great for a pair of cheap Bluetooth gym headphones too.