My husband is not circumcised, and had this problem as a youth.  In addition to the infection issue, them AND their partners--UNcircumcised men are more likely to pass an STD to a partner-- there is cleanliness, and a sensitivity issue.  If the foreskin does not retract fully, the glans may become super sensitive--even to the rubbing of underwear.  The good news, is that unless there is scarring or some underlying problem, skin stretches.  Every time your son goes to the bathroom, and after his bath, he should pull the skin down off the glans, and as far down the shaft as possible, till it bunches at the base like a loose sock. KEEP DOING THIS, till the skin loosens, and then KEEP IT RETRACTED.  The glans will toughen, he will be able to keep clean, and he WON'T need a circumcision!  If the skin will NOT loosen, then he should see a urologist.  Good Luck.  

Still can't see replies, or even some of the original posts.  Getting fed up.  My sister went to CafeMom.  I'm considering.