Guy advice, please help!

Ashley
So I've been talking with this guy for a while now, and he's incredibly sweet. He does adorable things like rub my back when I don't feel well and tells me I'm beautiful when I don't feel very confident some days. He also knows that I'm a very high stress person but he doesn't seem to mind it at all. If anything, he always makes sure I'm happy and offers to do anything to help. I think I'm falling for him. The only thing is, Im not sure he's ever had a girlfriend and i know for sure that he's never kissed anyone before. I want to kiss him, but I'm not sure when or how to take that step. I've never kissed anyone before that hadn't already had their first kiss. Have you ever been someone's first kiss, and was it awkward? How do I let him know that I want to?