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Had this a while back and tfp where very supporting and useful back then. Went through various types of lube and different techniques, in the end though the thought of her crying in pain every time we made love stopped me wanting to try. We broke up, not over this, but I'm glad in a way that we did.
In our case she had hang-ups over sex anyway which exaserbated the issue.
If you're looking for a silver lining I'd say the one thing that help was having her cum first. Do whatever you need to do, be it fingering her, or using toys, just let her come once before you enter her. She'll already be relax from having cum and tired too. Sounds wierd but her whole body will just accept you more, especially if you assisited in her getting into that state.
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