The first time you use them, I guess you generally buy the smallest size just to learn how to put it in, but medium might work just as well. You don't "pound" it in, many tampons have an applicator that makes it easier to insert. It takes some practice, though. The different sizes are for different types of flow, not for different sizes of vaginas, naturally. :-P
It depends on the heaviness of the flow. But for the first time, smaller is better. I tried to use one that was too big my first few times. I went though an entire box without getting it to work. Then I switched to a smaller size, and it didn't hurt.
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