Pain during sex

A little background, I am 22 and still a virgin. My boyfriend and I have tried having sex maybe five times, but I can’t seem to handle it. I don’t have the highest pain tolerance, but I don’t think it’s that low! Every time he attempts to insert, he only gets so far before I make him stop because of the pain. We make sure to have plenty of foreplay, we use lube (and I still get pretty wet on my own), we’ve tried different positions. It’s making me really insecure and frustrated that I can’t do it (my boyfriend is wonderful about it, though). Has anyone else experienced this? Could there be something wrong with me that is making sex hurt?