My son has a problem swallowing pills too. He is 11 now. I actually had the same problem when I was younger. I couldn't swallow them until I was about 12 or 13 but I don't know what happened to make it easier. For DS, he had a broken leg and was in the hospital for a while. He didn't like getting the pain meds injected after they removed the IV and he had to take stool softeners which came in liquid but the taste was nasty and hot. He suffered through quite a few shots and I had him try pudding. Put the pill in a spoonful of pudding and since it is thick it seems to do the trick. He hasn't mastered it but when he "needs" to take a pill we still use the pudding. Good luck. It is very frustrating not to be able to swallow a pill. Lots of meds come in liquid form but not all so it is important to be able to swallow a pill.
One day, for what ever reason, I just did it. Now I can swallow a mouthful and not give it a second thought. I heard some one say once that a spoonful of sugar helps the medicine go down, but I can't remember who 
What I do now is put the pill in my mouth, then fill my mouth with water or whatever and then swallow. Seems to work for me!

