Circle dot X's and O's mark the spot?

My boyfriend and I have been sexually active for a month now. I am not on birth control and he is not using condoms. The first time he climaxed and finished inside he was really freaked out. I talked to his mom about it and she sat down with him one on one and calmed him down and he seemed to be alot less stressed when I asked him about it again. That was about 7 days after I had finished my period. The second time he finished was yesterday and my period is due on the 9th. He expressed he was a little scared the second time and I told am not at this point. If I am pregnant then I will have the baby. He smiled and kissed me. Does this mean he is okay with me being pregnant? Is there a big possibility I am pregnant?