As a scuba diver pressure on ears is something I've experienced so to add my 2 cents....
I used to have trouble when descending into deeper water where I couldn't 'clear' my ears using the Valsalva technique, pinching the nose and exhaling against the obstruction. With the large pressure differences experienced in the water, failure to clear the ears on descent will result in eardrum rupture (not before lots of pain etc!)
I was told by my instructor that I was not clearing often enough, allowing too much pressure to build between clears and causing myself problems. Now on descent I clear with almost every other breath, not allowing the feeling of pressure to build. On the way up, with pressure reducing, the ears normally clear themselves.
So, I would suggest perhaps clearing the ears quite frequently throughout the descent, starting as soon as the descent begins. It doesn't need to be a violent process, just breath in, pinch your nose and gently try to breath out of your nose, gradually increasing the force. You should feel a kind of 'click' maybe a 'squeak' as the pressure difference is equalised, and you may notice your hearing will suddenly improve too. Obviously pain is natures' way of saying something is wrong, so if it hurts while you're doing this, you may be blowing too hard, or too much and pushing the eardrums out too far. Olbas pastilles can be useful for helping to temporarily clear out your tubes as it were (if you can stomach them!)
Hope the above helps.