If it hurts at all, you are not doing it right. It shouldn't hurt. Use lots of lube, and go very slow to allow things to stretch naturally.
The anus will stretch if you do it slowly. If you're really interested, you can get a '3 Prong Anal Speculum' on E-Bay. Some of them have an adjustable screw that controls how much it is open. You can insert it and then open it a little bit at a time to gently stretch your anus. If you do it yourself you can control it so it gently stretches without hurting. Just practice until you get to 'the right size', then go for it!
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