I have a friend I worked with who's sone had a medically required circ, but that was from an infection point of view. The poor little guys was on and off antibiotics for about 9-12m with UTI's and in so much pain.
He was about 4 when it was done I think, and was just susceptible to them.

On a side issue - my XH used to have a really tight foreskin when we first started together (he was about 21 at the time) and it was painful for him to have sex the first few times. It loosened up with time, but I guess because of the nature of his beast his mother never really took the time to show him how to keep it clean. He used to smell....... alot. So I guess it will loosen up with time, but its important to ensure he knows about the hygiene side of it throughout his teenage years otherwise he might get a cranky wife one day who decides shes not that attracted to his smell beneath the sheets