Ok, first I'll give some information I think is relevant. I'm 17, I am not sexually active, I masturbate once a week, I am cirumsized. I have completely stopped masturbating, because I thought that might be the problem.

Now the problem. The head of my penis is painfully sensitive. When I put on a pair of boxers and the cloth brushes me, it hurts! The pain is at the tip of the head.

One more thing, thank God for the internet b/c I do not want to go to the doctor unless necessary.

Sounds like you may need to have it looked at by a doctor. I know you don't want to do that but, dude it is your equipment and you are 17 think about it. How long has it been this way? Did you change your laundry detergent. Go swiming in a pool? Is there any blistering. Have you been nude sunbathing? If no is the answer and no person but you has touched it then you may have to look at your hygenic habits. Washing hands after the bathroom. Showering every day. That kind of stuff. I had a yeast infection (jock itch) once so bad I thought I was going to die.

One more time it is your equipment...you want it to work for some time to come so do the right thing. I would be more afraid of what it is than who is going to see it.

Try switching to briefs - there will be less clothing movement against your penis. Also, try putting a little bit of Vaseline on the tip of your penis where it hurts each day after coming out of the shower.