Does sex hurt for you for the first few strokes?

It always does to me, sometimes it's such a sharp pain that it feels like I'm losing my virginity all over again. When I lost my virginity the pain was horrible, he couldn't even move at all without having me saying "aw that hurts" 😂 I am always wet, like dripping wet lol but it still hurts. Even if I just go down on him for a few minutes then go back to the proper job it hurts a bit. And he's not huge, he's average but always says that I'm just tight as and my vagina sometimes hurts his dick lol

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