Hi K,

Many men have the same issue as you; where the foreskin simply does not stretch over the penis entirely. This is likely not a problem unless it is hurting before you pleasure yourself. It may only be hurting because you are forcing it. Every foreskin comes in a different size and thickness just like the penis, some fit over the penis and some do not.

If you regularly masturbate then perhaps try to do it with some lube and gently work your way around the area, rather than being vigorous with it, which may be making it painful. Try to avoid forcing your skin into places it doesn’t naturally want to go, as this could do you more damage than just soreness.

If it is hurting even before you masturbate- then I would pay a visit to your doctor. They can discuss your options with you as there are other possibilities for you if this problem persists.