If you watch girls masturbate, even in porn, you'll see that each has her own way she prefers to touch herself. Each woman is different; has a higher or lower concentration of nerve endings, has a larger or smaller clitoris, and has a tighter or looser clitoral hood.
Due to my own structure, I have to be pretty careful with my clitoris, and it helps that I've been with the same man for 12 years. I can't imagine somebody new and unfamiliar going to town down there. The very thought makes me cringe. Touched the wrong way, the clitoris can be a source of pain. When I describe it to my husband, I liken it to the sensation of having the raw bed of your fingernail exposed. If the clitoral hood slips back and I get jabbed, I'll yelp and shoot through the roof. Ow!
Another thing to consider is that women become more receptive to pleasure and less receptive to discomfort as their level of sexual arousal increases. Those endorphins are powerful. What might hurt at any other time could feel wonderful in a highly aroused state.
Have I confused you even more, DE? 
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