Should I take the oppurtunity to get my first kiss?

Okay, so theres this guy who is one of my best friends (jacob) and i’ve known him since fifth grade. We have “dated” before but they were just middle school dumb little things. But over the years he’s become my best friend, and I can talk to him about anything.
We are both freshmen in the high school play and he has been attempting to kiss me many times and when I lean away he makes a joke out of it. Finally, since he does it so many times, after play practice I texted him and asked him if he was really going to kiss me. He said he would if I wanted but “let’s make it last” and he also told me we wouldn’t be a couple after that either.

The thing is, I don’t mind not being with him if we kiss because I don’t like him. But I’ve never had my first kiss, and I kind of want to get it over with. Also, if I mess up, I would like it to be with him and not anyone else… I’m just not sure if I should do it or not. Please help! Thanks (=