I think it has to do with how forceful they are being, and the level of anxiety the person getting penetrated feels... look at all the couples that practice anal sex all the time with no problems and all pleasure... then you hear stories of people anally raped and ending up ripped and torn and can't sit for weeks etc... its something when done wrong can go very very terribly and be a painful if not worse experience..
I think if you are terrified you are going to be even more tight there, tense, making it much more painful than if you were relaxed so more than lube, relaxation is necessary for it to take place without much pain also patience on the mans end to not force his way but to work it slowly, over time if necessary, and not be in a hurry to plant that flag... to give it a few sessions to get past your anxiety and get comfortable relaxing.




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