Hey bud, glad to be of help. Yes, retracting that foreskin will help some with desensitizing the head of your penis. I'd suspect that your issues with pain and some discomfort are related to the fact that your head is so very sensitive as a result of having been covered so much for so long. On the stretching, be patient and persistent, you'll notice changes really soon. I'd say that you should continue to masturbate as you have, but add some stimulation to the head of your penis, the more it is exposed to such stimulation, the less sensitive and more pleasureable it will become. Keep in touch for other questions!
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Masturbation Question? 
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