Unimaginable pain..

So my bf and I have tried anal before and it has always gone well. I don’t like it all that much but he enjoys it so we do it sometimes. He always uses a lubricated condom and it goes fine. But last time he didnt use a condom he just used lube and it was the worst thing Ever! He barely put the tip in before I was in so much pain I had to get off and lay down. I just curled up and couldn’t move for a while because I hurt so much. Has this happened to anyone else?? I don’t know why not using a condom would have changed anything but it was so awful 😭😂