Well, tampons are round too, and they stay in. The vagina is rather stretchy and muscular, and it's the muscles that hold it in. I'm not sure about upside-downiness myself, but then I physcially can't go in upside-down rides anyway, so that's a moot point. Anything else, I figure if I can do it with a tampon, I can do it with this. And probably more.
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From:
Re: TMI Warning!