Ok, here's my situation.

First of all, I'm 20 years old. I also have fairly severe phimosis. As in, I can't retract it half-way when it's flaccid. I haven't been able to get any betamethasone cream because I don't have health insurance. Or, rather, my health insurance is of the variety that refuses to cover anything that won't affect me paying them. So I'm trying manual stretching, and it went from not being able to move it at all to a third of the way down when flaccid. So, phimosis is problem 1.

Problem 2 is occasionally, (and this only started when I started doing the stretches), I get sharp pains down the left side of the penis (head and shaft), but no ball pain. It's as if someone put something in there while I was sleeping, and I can't get it out because of the phimosis. It's like a funny joke where I'm the only one not laughing. It's only on the left side, too, and it especially hurts when the skin around the painful area moves over the actual gland (which is why I think something got stuck under there). This is a recent development, and it makes all sexual activity that involves my penis extremely painful to the point where a raging hard on turns into a frightened turtle in seconds.

Problem 3 (that might be related to problems 2 and 1) is that when I try to do stretching exercises, the left side of the foreskin doesn't budge, unless I specifically pull down on it. However, given problem 2, I can't quite do that without wishing death upon myself and those around me.

Any suggestions from the enlightened ones?

I have been there and lots of other guys too, so don't worry you aren't alone.

The pain you describe sounds like something beneath the foreskin rubbing on your glands and seeing as you probably have never exposed your glands properly due to phimosis, the sensitivty will indeed be unpleasant, e.g. it may hurt. Another guess is that, there might be an accumulation of smegma underneath there that also maybe rubbing on the glands. Either way, the only solution to prevent this is to see what's going on beneath the foreskin.

The only real solution to your problem, is to go see your doc, he/she might be able to prescribe you some cream to help with the stretching. If all else fails you can go down the surgery route of having: circumcision or a dorsal slit. I recommend the circumcision - but that's my opinion.

If you have any more questions about these, just ask in your next reply - I'm sure some others would find this helpful.

If the left won't retract, but the right side seems more willing, you might have an adhesion on the left side. Try gently pulling on it, after applying baby oil.
If that doesn't work, you may have to see a doctor. Nothing to worry about, they give you a local anaesthetic, do a quick slice of the adhesion, and tell you to apply vaseline, to keep the sides of the wound from adhering again.