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I discussed with one lady recently a guy she knew that was too thick for her before she had children but she doubted that he would be a problem now. It is most likely that an average to larger guy in both length and thickness that has his stroking action well tuned stands a better chance of taking a lady over the top. A lot of the stimulation comes with motion and longer stokes have the potential to cause more stimulation.
It is often said that it is how you use it that counts. Position has more to do with G spot contact than length but pointing up vs. Thicker is good because it stretches the pussy out and it is only reasonable to believe that a pussy that is streched out to its comfortable potential maximum is more sensitive than one that is penetrated by a pencil dick. Too long can also be problematic if the guy hits bottom because hitting the cervix takes enough of the edge off so the lady will never get over the top and indeed she may even get sore. It is a lot easier if it is a long one to do frantic fast stroking without the risk of pulling back too far and having it fall out.
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On the lady front there does not seem to be a reliable relationship between overal body size of the lady and her capacity to take on a big one. that can take on some mighty big guys in positions where maximum penetration occurs with comfort.
Alternativly some taller ladies can wince when penetration is too deep.