1st and 2nd time sex

So ladies.. I had sex for the 1st time on the 24th December and it honestly wasn't as sore as everyone kept warning me it would be. Although I really felt pain when my boyfriend went in and when he came out n when he did slow thrusts. He came and I didn't maybe because I was nervous. Anyway yesterday 29th December we tried again and this time with a condom and it was soo painful I couldn't handle him fit inside like last time and he tried to calm me down and turn me on again but I think I just wasn't as excited as before and we were not at his place so I might have also been uncomfortable. Now after a lot of trying.. He gave up n asked me what's wrong n I told him it's sore and he said it is sore when he comes in and thrusts for the first few times and I told him no this time it's not like that and after a few minutes I felt my vaginal opening burning like just when you have an open wound and it burns because water or something liquid gets on the wound. So I told him to look if he sees anything and he said nothing that shouldn't be there.

So my question is how come I felt a different pain this time and is it really true that it's going to be sore every time he comes in.

I feel like I am failing him and myself because he really turns me on but when he puts it in.. I stop him because of how painful it is and I really want to enjoy it but with no pain.

He really does stop when I say stop n when he can see that I'm dry or not okay and he'll make sure to arouse me again and reassure me that he is being gentle and he doesn't want me to be unhappy or sad or cry because of him.

Does it get better and are there any ways that you've seen that lessen the pain even though the articles I read say it's not supposed to be painful after the 1st time. His argument is even older woman feel the same pain I do n I'm still going to feel it and If I continue at this rate, he might never hit.