almost sex

So I tried having sex with my so, but its my first time. I thought i was ready so we tried, but everytime i feel the pain, i stop.. we tried a few times but good thing he's very understanding about it.. i feel like I don't what im doing and my self confidence was attacked.. we even tried with both condom and no condom but it still hurts everytime, so i stop as well and it's just prevented..