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I can feel if it hits my cervix. It’s sometimes painful, but even when it isn’t, it’s definitely noticeable to me. Then again, I’ve sometimes hit my cervix with my finger (it feels kind of like a closed flower bud in shape), so I know what that feeling means.
In general, I’d say don’t worry too much about hitting your cervix. It’s not going to cause any harm, it just might trigger cramping sometimes. If you have menstrual cramps, irritating the cervix causes similar cramps but way less intense.
As for pregnancy, if it’s safe to have sex, it’s also safe to dilate. So unless your OB-gyn says otherwise, it’s fine. In fact, I’d recommend keeping up with the dilation since vaginismus can make you more likely to tear during labor, according to some studies I’ve read. I am also trying to conceive, and I’m planning to keep dilating during pregnancy to make the labor easier.