Despite increasing pop culture coverage, anal sex is still heavily stigmatized.
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I've done it with a few guys and it's always been a mutual desire. Anal sex feels great when you're with someone who lets YOU be in control of the speed and force, if that makes sense. I don't think you have to get waxed. I really like silicone lubes, like Pjur or Uberlube.
For me, it's something that only lasts five minutes. I don't have to start as slowly anymore, usually, unless it has been a very long time. There are times, however, when a larger penis may cause cramping.