First time

I’m a virgin and I’ve recently started to feel like I’m ready to take that big step and lose it to my long term boyfriend of 1 year. I’m 16 he’s 16. He’s way more experienced than I I am. He’s had sex before and probably other stuff too. I haven’t done anything except got fingered before and it kinda hurt. But does the first time really hurt as bad as people exaggerate it to be? Also when I got fingered a third time I was spotting afterwards. Does that mean he was doing it to hard or did he “pop the cherry” or what. It didn’t hurt as bad the third time as it did the first and second time so I don’t think the bleeding was because he was doing it to hard.