I think for most dancers, until they find their own "sweet spot" and balance point, it hurts. Try to work into it by leaning most of the way back, then crossing over and going the rest of the way…like you're going into a wrist sit. It'll cut down on the skin twisting.
Also, are you engaging your thighs, rolling them inward, and clenching your butt muscles? I refer to it as "IRS audit ass" and it creates a little triangular bed of muscle that helps make the CKR and CAR more secure and less painful, at least in my experience.
It's like with any new pole trick–it hurts at first but then one day you've got it, no more pain! 🙂