you could be pregnant
yes he could go to jail
its the 20th today, you could go buy the morning after pill to reduce your chances of being pregnant
but hopefully you aren't pregnant, so why not stop worrying about it for the next month and hopefully you get your period again like normal
if...
he sounds...a little bit weird
i guess everyone has unusual points, but umm. i guess you would really have to think about it. maybe tell him you aren't entirely comfortable with it and see what he says and just go from there