Forgive me for sounding crude, and anyone with great knowledge please correct me, but I do believe it is impossible to penetrate a woman completely for the first time without breaking her hymen. My first girlfriend was heavy into martial arts, so hers was already broken (her story anyway) but I do believe that's the way of it.
Your right to build up to it though, there is nothing worse than placing a feeling of urgency behind it. She may have to get to the point where she is willing to take the pain with the pleasure. Having only been with two women in my life i'm no expert, but my first girlfriend did complain about my size, and she was more comfortable "spooning", or "cowgirl", so that may help.
Best of luck.




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