There are beginner, intermediate, and advanced levels of any activity, and anal play is no exception. If you're just starting to scratch the surface, the best butt plugs for beginners is a solid place to start. As with all things new and unfamiliar, consulting an expert never hurts.
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Training and stretching your ass for anal sex takes practice and patience. But if you want a more exact idea of what size you should begin with, play with your fingers. Lube them up, see how many you can fit in your butt, then measure their circumference.
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