Painful sex

So I lost my virginity nearly two years ago, I didn't have sex again at all until about a month ago. Losing my virginity was quite painful, and so terrible that I didn't want to do it again with my now ex boyfriend. I expected it to be painful, as we were both virgins. My current boyfriend is more experienced, though I still expected pain for the first couple times. But my boyfriend and I have had sex nearly everyday I've been here, so roughly 20 or so times, and it's still painful. Sometimes the whole time, other times it's just when we start then it starts to feel okay, not painful or good, it's just neutral, but it always ends up being painful and we usually have to stop. My boyfriend usually comments on how wet I am while doing it, so I don't really think that's the problem. we also don't use condoms as I have the implannon and don't see the need for them . I'm 19, any suggestions?