This is a popular piercing because there's something about dimples that symbolizes childhood. When a person smiles and has natural dimples, there's an element of innocence that remains even when the person is older. These adorable cheek piercings can give anyone that youthful look.
Your cheeks are a pretty thick area of flesh to pierce through, and there's a lot of blood vessels inside the mouth, so it's not a real pleasant piercing, especially since you have to get two. But it does usually heal relatively well, as long as you follow good aftercare, which is a combination of facial piercing and oral piercing care. Women have to be careful when using makeup and hairspray - men need to take care when shaving, especially during the initial healing stages. Smoking is definitely a no-no!
Standard jewelry for dimple piercings is a 16 to 12 gauge labret stud. The flat disc inside your mouth doesn't pose as much danger to your teeth and/or gums as a lip piercing, but if you have an oral fixation and can't resist the urge to rub the discs against your teeth, then you're definitely at risk for a problem. If you notice your gums flattening out, bleeding, or having any other signs of trouble, you probably need to remove the piercings. Your oral health is much more important than keeping a pretty piercing.
With a healthy immune system and proper aftercare, your dimples should heal up in approximately 8-12 weeks. At that time, it's important that you change to a shorter labret bar to avoid excessive contact with the teeth and gums.