Having Difficulty having sex

So it's been a bumpy ride in the sex category. Technically, I don't even think what we have done can be considered sex. There was the hymen issue but I think that's handled. The real issue is this: he can make it in but I immediately get a sore/ tight feeling when he goes halfway in. We both think I'm just tense but even when I'm loose as can be (that sounds gross XP) it's still painful. I'm so tired of wasting condoms. He tries to tell me that it's ok but I know it upsets him. I really love him. Soon-to-be eloped but can't have sex. Makes me feel pathetic. Does anyone know what might be happening? Am I just too tight?