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People frequently ask me how long it took me to be able to handle the large toys I play with, and how they can accomplish the same thing. Well, I can remember playing with my butt as far back as I can remember, but I didn't have access to toys like dildos and vibrators until I was an adult. And I really only started playing with truly huge toys in my 40's. I usually play with some kind of toy about every other day; sometimes more frequently, sometimes less.
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October 13, January 7, 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. 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 bigger toy is to wear your current largest plug long-term.
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