It is not unusual for the first few times to hurt. My first time, which was many many moons ago, We couldn't get it in. It took quite a few attempts. I believe this is normal.

Be patient, relax, make sure he is the right one for you, use lots of foreplay and lubricant.

It sounds like he is sensative enough not to want to 'tear' straight into you. That is a good thing.

Sex takes a while to master and start to enjoy.

Good Luck.

tt