It sounds like a number of things could be going on with your feet. Your symptoms could simply be from a minor bruise of the heel in which rest would improve your symptoms. However, seeing how it might be a chronic condition, you could have developed some tendonitis or plantar fasciitis (a inflammatory and degenerative disease of the bones/tendons of the soles of your feet caused by repetitive stress). Both these conditions can be helped with rest and ibuprofen. In severe cases, corticosteroids can be directly injected to lessen the inflammation. Finally, another cause of heel pain could be achilles tendonitis which is caused by increased and repeated stress on your achilles tendon; it is treated by avoiding walking up stairs and ibuprofen.
Try conservative measures such as staying off your feet when possible, wearing more sensible shoes (no high heels), investing in some insoles with heel pads and arch support. If the pain worsens or does not improve and/or affects your daily routine, then you might try visiting an orthopedits or podiatrists.