It takes practice. First you need to begin to get flexible ankles. A exercise you can practice is sitting on the floor with your back straight and bend your toes to the ground as far as possible. When you point your toes while standing up keep your knees straight and hips square. reach your leg in front and keep it straight ( no bent knees point your toe by bending your ankle.
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You can start pointe when your dance teacher thinks your feet are strong enough ;)
Pre-pointe is basically the strengthening of the calves, toes, feet, and overall body in preparation for pointe work.
in the beginning, yes, your feet will hurt, but once you have broken in your pointe shoes they will start feeling like a second skin, and you will be able to practice and do pointe exercises more fluently and more easily.
At first, yes pointe does hurt. But the more you do it, the more you get used to it and the less it hurts.
If worn and used properly then they shouldn't. When you do pointe for the first times you might get blisters and your feet will hurt, but there shouldn't be any permanant damage.