Originally Posted by Shelly L

Why won't the head of my uncircumcised penis come out?

This is one of those classic problems associated with uncircumcised penises. There are lots of reasons (such as stenosis, or narrowing) why you may have difficulty pulling back your foreskin.
Basically, the only treatment at this point may be to have a circumcision. That doesn't mean this is a serious condition, but if you keep traumatizing the area, the stenosis can worsen. It can become very uncomfortable and painful, and you may experience a kind of tearing or ripping in the area.

Another common problem is an irritation of the skin on the head of the penis and foreskin, which is usually caused by poor hygiene. It takes a little extra effort to keep this area clean. Note that there have been no reported cases of penile cancer in a circumcised male.

These are all reasons some advocates say that getting circumcised is a healthier choice. Obviously, this is a personal decision that you have to make, but the fact that you're experiencing pain means you should have it checked out by a doctor, preferably a urologist, and consider having a circumcision.