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What to Know for Your First Time. For the insertive partner, the tightness around the penis can be pleasing as well. Anal sex can be very pleasurable or very painful depending on how it is performed. Anal sex can be an extremely pleasurable experience or a very painful one. The way they do that is by never going further than what feels good. They are muscles, though, and as long as they are properly stretched, there is no harm in exercising them.
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Woman D: I think doggy style is most conducive. I usually use a vibrator on my clitoris along with anal penetration, but not always. Once I was comfortable, however, I was begging him to speed up and go harder. Anal sex feels great when you're with someone who lets YOU be in control of the speed and force, if that makes sense. The truth: Lots of people are. When it happens, it's because I've conceded.
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