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depends on the woman. most women Ive been with liked a little assplay during vaginal penetration but I wouldnt say a full finger all the way in, mostly just light brushing or stroking on the outside with slight pressure seems to get the best response. Same applies if your going down on her, Thumb in her pussy, mouth on her clit, and index finger tickling her ass, or even light tickling with your tongue should be acceptable, but again, depends on the woman. Push her boundaries and see where she draws back, and dont push further, thats the only advice I would give.
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