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Damn, that was a lot of words and detail. Part of your problem is clearly you getting stuck in your head. Some of us just aren’t strong finishers. It’s far better than the opposite problem. Sex is mostly a visual/mental experience for me as opposed to physical sensation. See a doctor to get checked out physically and a therapist for mentally. And put a couple of drops of lube inside the condom before putting it on.
Just to be clear: Do you think it's reasonable for guys not to take this literally given our experience and that other commands like “deeper” aren't literal? Do you know see why guys make this misinterpretation? Would you tell a women to communicate that this is supposed to be taken literally? Or just tell her that her bf is dumb and stupid and that his misunderstanding is baseless? You've restated that this command is supposed to be taken literally. And I understand that. I hope it's clear that I've never disagreed with that, I've only explained why it's misunderstood.