How long will it hurt for?

So I had sex for the first time in a year the other day and I guess I’ll say that I TRIED. I was ready to push myself farther than last time but it just hurts so damn much because I’m so tight... and my man took a break for a second after trying for about 10 minutes and I told him we can try again if he wants and he just looked at me and shook his head no. He didn’t want to hurt me anymore but it just sucks. I wanted to do it for him but he wouldn’t even let me because he knew I couldn’t. So I’m just asking how many times will my experiences be like this? How long until we can both actually enjoy sex?