A problem I see with asking for permission for one piercing then moving onto another is he may think you're beginning to go down the slippery slope to pincushionhood. I'd suggest you ask for the eyebrow piercing first if it's the one you really want. It might turn out to be the case that the room's only big enough to allow you to get that one foot in the door.
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You can't give a Dementor the old one-two!
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