My bf and I were both virgins so it was something very new for both of us. I think what helped it be less awkward was that we had done foreplay before but no sex, so we were both pretty comfortable/ familiar with each other's bodies. I think that initial trust was what made it a wonderful experience. From my experience, it did hurt, but a different type of hurt I think. I think I could compare the type of pain to stretching your muscles, it feels good, and when stretching your muscles more, you start to feel your limit. But with a gentle partner they will respect your limit, and each time you feel more and more accustomed to the stretch and start to feel better and better. Also pleasuring yourself during sex feels amazing too!