How many times do u need to have sex for it to not be painful and hard to put it?

I've tried having sex a few times .... we put it halfway and it hurt too much so we stopped and then another time we put it in all the way but I had to pee so we stopped and a for a few days I had light bleeding and then this time I put it all the way in and we did stuff but it hurt in some positions ... kinda hurts in missionary but when I'm on top it doesn't hurt THAT much and it's way easier to put it in lol but we decided to try this other position where I have my legs up and I'm at the end of the bed and he is standing up and omg my legs were shaking and it hurt and it felt like i had to pee and idk then I bled a little. But yeah so my question is how many times until it just goes it and doesn't hurt??