Well my opinion is that you definitely shouldn't have sex right away with a stranger. First, you don't know him, and if I am not mistaken, you didn't said how old he is, and age does matter. You just have to consider that some people do crazy stuff, what if he is 18 and overpowers you during sex and hurts you (I know that it sounds crazy, but he is a stranger and you are 16...) Second, I know that in nowadays that is somewhat changed, but sex is all about trust, expressing your love, and yes, experiencing pleasure too, but that is a stranger and you have to consider is you are really go out and let him take away your virginity. My overall opinion is not to directly have sex with a stranger, three--four dates are much better period of time taking our age into a consideration, as I just turned 17.
However, what's even more bothering me about those dates and online starting relationships is that you don't know what type of person you are dealing with. Last year I was at the same situation as you and I had found one other guy. He had sent me tons of pictures and videos, but luckily I didn't get to meet him in person, but he was anything but the boy from the pictures and the description on the dating site... So, you better get a more well-build friend of yours with you tomorrow, who will help/defend you if things don't go as planned.
I hope I didn't scare you or something, but it is for your best to be a bit too careful, than to to be in trouble. Anyway what you decide, I wish you all the best and have a nice time