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Training and stretching your ass for anal sex takes practice and patience. Lube them up, see how many you can fit in your butt, then measure their circumference. Divide your measurement by pi and choose a plug with a diameter as close to this as possible. This should give you a challenging, yet fun and doable stretch. If you try a smaller increment, you may find it too easy and too similar to your previous toy. I think the easiest way to prepare yourself for a thicker toy is to wear your current largest plug long-term. I have another article that focuses on long-term plugging tips.