Training and stretching your ass takes practice and patience. Whether you want to have anal sex, use bigger dildos, or you simply enjoy feeling stretched, the same principles apply. 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. Divide your measurement by pi and choose a plug with a diameter as close to this as possible.
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