I agree with the last post. The first time will be painful, and how painful varies from women to women.
Hopefully the guy is one that loves you. Why go thru such a first time painful experience with just any old guy?
Some guys will be ruff just because they can, and will not care about your wishes once they get started. Please be very sure you are ready to do this, and to do it with this person you've mentions.
It would be wise to start out with a guy with a small penis.