Even when properly done with appropriate jewelry, cheek piercings are notorious for being very problematic. It isn’t to say people can’t heal cheek piercings, but clients should understand certain things when it comes to them.
1) Be prepared for the investment. Beyond the initial cost of having them pierced and the initial jewelry, you have several downsizes ahead of you. So you will need to pay for more jewelry later on as the swelling slowly goes down. Expect a minimum of 2-3 downsizes later on.
2) They tend to take a long time to heal. In some cases, even after a year or more they can still flare up and become irritated.
3) Your initial jewelry is going to look long. Really long. This is because cheeks can swell quite a bit. More than you’d expect from other piercings you may have had.
4) Not all reputable piercers will offer to do this piercing. This doesn’t mean the piercer isn’t experienced enough, and it doesn’t mean it’s a non-viable piercing. Some piercers simply choose not to offer this service because of how problematic they *can* be.
So having said all that; if you decide to have them pierced, seek out a reputable piercer with a lot of experience doing cheek piercings. Ask to see healed photos of ones they have done in the past. I don’t want to give the impression that cheek piercings never heal, as lots of people have successfully healed them and kept them for years and years.
It’s just a matter of preparing yourself for possible hurdles along the way to healing.
You can also read more about oral piercing risks you should be aware of here.