Pain during intercourse?

Bianca • hard shell, hard soul, soft heart 🌚
So I've been having sex with my SO for a year and a bit, it's been great (he's my first) and I have such a high sex drive. Recently, in the last month I've been quite dry during foreplay: he goes above and beyond to ensure that I'm wet but it just doesn't happen. We do use a lot of lube during penetration but even if he's super careful, I end up feeling little rips and it makes it uncomfortable. I do use the pill and I know that dryness can be a side effect, but why would it manifest itself almost a year after starting it? (And the issue is not me not being around enough: we had penetrative sex just after I had come from clitoral stimulation, so I should have been "good to go").
This is making me feel down and hopeless, whilst my SO thinks I'm not attracted to him. 
Is the dryness that is caused by me anticipating the pain? Or is the pain caused by the dryness even if we use lube? I'm at total loss for an explanation for this