Hi! Yes, I've experienced a lot of ear pain in the past -on my first dives for certification and every time I've been on an airplane. I had a lot of ear infections as a child and always wondered if it was a physical problem. However, my last 4 "refresher" dives proved that it can be done! I took a look at this website:
http://faculty.washington.edu/ekay/MEbaro.html
Practiced a few of the techniques that I felt comfortable with a few days before going diving. The day of the dives I took a 12 hour decongestant 2 hours before the first dive of the day, and started equalizing more and more the closer to the dive I got. At first I could only get one ear, but eventually I got the other ear to pop as well -then came the moment of truth...
Now, the more relaxed you are the easier it is to clear, or at least that seems to be the case for me. I got in the habit of equalizing about every other breath on the way down and actually found that the normal technique of pinching the nose and trying to blow out of it would pop my right ear, and then a hard swallow would pop the left. Weird, but whatever works, right?
The keys, I think, are practice and relaxation. Even right now I can pop my left ear by swallowing. The right one takes the pinched nose technique and a lot of pressure to pop, but it will pop.
There's also a video presentation (fairly long) about ear clearing complete with an "ear-o-scope" to show exactly what happens when you "pop" your ears. I'm kindof a biology geek, so I found it very interesting:
http://www.uwtv.org/programs/displayevent.asp?rid=789
Last thing: The biggest change in technique from when I started out to now is that before I'd go down until I felt pain, then try to clear. That doesn't work -there's already too much pressure. You have to clear BEFORE you feel the pressure -hence my "every other breath" technique and all of the suggestions of "clear early and often". They're right on the mark. You can't clear it too often (unless you get light-headed)