Penetration pain

So ladies, here it goes, I’m currently engaged, and I love to have sex, except everytime he’s about to go in, it hurts so bad it’s not a searing pain but really uncomfortable, I’ve tried lube and more foreplay, the issue isn’t that I’m not “ wet enough” because it’s a river down there. I can’t figure out what to do to make it better, could it be a size logistics or maybe positions ? we have tried all kinds of positions too. Is this a medical condition ?

As well as after we are done my vag gets swollen and sore.