Marniemcc, even if you are comfortable in 5 or 6 inches high heels, your feet and spine won't. Just because you are used to not eating it doesn't mean your body doesn't starve, and just because cutting yourself doesn't hurt anymore, it doesn't mean your skin is not suffering.
What I want to say with this is that, even if you get comfortable in really high heels (which really depends on the person and how they tolerate the pain), you shouldn't wear them on a daily basis. Once in a while is more than fine, but not everyday, especially if you commute on foot/walk a lot.
Personally, I can't handle +2 inches daily, and I will do 3 inches on special occasions, but I'm really bad with heels and my feet are cushionless so it doesn't help.