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Description:As for how deeply your boyfriend's penis can or should be inside your vagina? Your body is the best guide for what feels good versus what is too much. That's up to you and about what feels comfortable and good for you. Was he in the wrong hole before? This opening is very, very tiny, so it likely isn't the opening you're talking about. I don't think these questions are silly or foolish. There are other reasons besides having genitals not fit together in a way that is comfy for your body for intercourse to be uncomfortable, painful, or not pleasurable.