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You might have heard that too much lube takes away the friction that makes it feel good for the dude. Drew Pinsky. A good way to remedy that is using lots of lube and smarting with smaller objects, rather than big ones.
The best way to become skilled at anything, especially a new sex act, is to try it out yourself first. If you have ever pooped before which I know everyone reading this has then you already know how to relax this muscle.
Before embarking on the full monte of penetrative, anal sex, you can—and should! Listen, they don't make those wild-looking, three-pronged sex toys for nothing. If you hate it, you hate it, and that is fine.