Orgasm Help

I’ve never had an orgasm despite being pleasures by my boyfriend and trying on my own. The closest I come to reaching one is when I grind on top of him. For some reason, fingers don’t do the trick. When he touches my clit (same goes for myself), it’s sometimes more painful than pleasurable. Is there anything I can do to change that? Like I moan and shake but it doesn’t feel the same pleasure as when I grind on top.

Is it odd that sometimes I feel more pleasure from finger penetration than clitoral stimulation? I know logically I shouldn’t, but perhaps I’m getting off on him getting pleasure from that? I’m confused. Please help!