First, for all you moms out there, anytime your son starts a season, have him wear it daily. A couple of hours a day for at least a week before his season begins. This will get him use to it, and not distract him during his first practice or game.
Next, when possible, get him use to wearing a jockstrap. Right now, he may not need the support, but he needs to get any stigma, out of his mind about wearing one. The worst thing ever, is having your son, wearing any sliders, compression shorts, or briefs with a built in cup pocket. A jock, though not perfect, does a better job of holding things that dangle. This is very true, everytime he will squat or bend at the knees. Sliders stretch and things do dangle. So if you see your son always complaining or adjusting his cup, this is a major reason.
Also, when your son hits the twelve to thirteen y/o age, make sure his cup is a good one. He will, and trust me you to will, want a cup that has a lot of ventilation holes while still being durable. For this reason, I rated this product poorly. The groin produces a lot of sweat and heat. Which, can lead to fungus problems.