You should try practicing this technique four to six times before going for full penetration. The truth: Yes, I have actually heard this in my office more than once. The truth: Just like the myth that the vagina gets irreparably stretched out from childbirth, this is also a misconception. If you stimulate your clitoris at the same time, it can encourage the pleasure-over-pain response. The truth: Well, not quite.
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Many women find it incredibly pleasurable, and some even report having orgasms with it. Some even more so, because the lining of the anus is much thinner and can be broken more easily if too much dry friction occurs again, please refer to the importance of lube use. If you stimulate your clitoris at the same time, it can encourage the pleasure-over-pain response. Regular, healthy use of anal sex will not lead to this outcome.