Tightness..

I love it when he tells me this because we are always in the middle of intercourse &he like whispers it &its such a huge turn on hearing him say that &&also because he loves it. 

What bugs me kinda is that he always tells me I'm tight.. ALWAYS. When we see eachother we sometimes have sex about 3 or 4 times but it always hurts when he goes in &even when he fingers me he could feel the tight ness &he loves that its tight but I don't. It hurts really bad. We've been active for almost 4 months. Shouldn't I be a little loose or something? Or is it normal?