It makes a difference. They often find that the rest of their sex lives improve, too. Even slower than that. And when those emotions are linked to past experiences of painful sex or sexual trauma, they can be held even more tightly. The best way to keep that from happening is to go super slow and invite their ass to relax. And even folks who have plenty of experience with anal play can sometimes not be into it because they had a rough day.
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One of the many ways in which porn is terrible sex ed is that the performers almost always just dive right in, without any warm-up or lube. It helps if you know lots of different ways to do that, and you might be surprised to discover just how many options you have. Arousal makes things feel better, and doing something that you know you like makes it feel safer. Third, there are two distinct sensations that can affect how someone enjoys anal play. That creates more relaxation and expands their capacity to feel good. The best way to keep that from happening is to go super slow and invite their ass to relax.