I've had several chronic issues with my ears--some similar, but none precisely like yours, however. So here's my basic schtick:
Go see a doctor, preferably an ENT (Ear, nose, throat). Seriously. "Pressure" can indicate a wide variety of middle-ear issues, many of which can result in serious hearing loss or vertigo or balance issues, not to mention severe pain. Get some qualified medical help to figure out what's wrong in order to deal with it as best you can. You will not--unless extremely lucky--find this sort of help here, despite the fact that most of us have had trouble with our ears at some point in our lives.
Having said that, I get feelings of "pressure" quite often. Some are related to (observable) scarring on my eardrums; some to eustachian tube blockage, which can be temporary. Some have to do with a condition called benign postural vertigo, which features salts collecting within certain minute structures in the middle ear. Some are the result of wearing earplugs. Some have never been diagnosed. And some seem to be subjective manifestations of objective hearing loss due to wind and other noise while riding.
Hope that's helpful.