Sounds more like you are having trouble equalizing your ear canal."Ear Block" as they call it. Probably need a decongestant/Antihistamine, many of which are Not OK to fly after taking. Flying more is probably only making matters worse. Take some time off from flying and see a Doctor.
Here are some info to read:
"Stretching the eardrum can lead to pain. The tube that drains the middle ear can become plugged, leading to pressure changes in the ear that can painfully stretch the eardrum. A common time for this to happen is when flying in an airplane (during the final descent). The elevation change causes the ear tubes to close off. We feel as if our ears need to “pop”. In some people, especially young children, this really hurts. When we yawn or swallow, the motion opens the ear tubes, relieving the pressure and pain.
These ear tubes can be plugged by things that cause swelling around them. Second-hand cigarette smoke, hay fever and colds are common reasons that ear tubes become blocked. These earaches do not require antibiotics if there is no infection. "
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"Ear Block.
1. As the aircraft cabin pressure decreases during ascent, the expanding air in the middle ear pushes the eustachian tube open, and by escaping down it to the nasal passages, equalizes in pressure with the cabin pressure. But during descent, the pilot must periodically open the eustachian tube to equalize pressure. This can be accomplished by swallowing, yawning, tensing muscles in the throat, or if these do not work, by a combination of closing the mouth, pinching the nose closed, and attempting to blow through the nostrils (Valsalva maneuver).
2. Either an upper respiratory infection, such as a cold or sore throat, or a nasal allergic condition can produce enough congestion around the eustachian tube to make equalization difficult. Consequently, the difference in pressure between the middle ear and aircraft cabin can build up to a level that will hold the eustachian tube closed, making equalization difficult if not impossible. The problem is commonly referred to as an "ear block."
3. An ear block produces severe ear pain and loss of hearing that can last from several hours to several days. Rupture of the ear drum can occur in flight or after landing. Fluid can accumulate in the middle ear and become infected.
4. An ear block is prevented by not flying with an upper respiratory infection or nasal allergic condition. Adequate protection is usually not provided by decongestant sprays or drops to reduce congestion around the eustachian tubes. Oral decongestants have side effects that can significantly impair pilot performance.
5. If an ear block does not clear shortly after landing, a physician should be consulted."
. Is there something else I can try? If it doesnt go away, is it something that could disqualify me from renewing my medical? Any info is much welcome.