Guy friend keeps on asking for nudes?

I've been really close friends with this guy for about 12 years. He's my next door neighbours' son so he's a family friend. He's one year older (18)
Anyway, I've recently split up from my boyfriend and suddenly, he's started talking to me a lot on Facebook. We mainly joke about stuff and talk about normal things But my family and his family keep on telling me he likes me. When we all meet up, he's also really shy in person which is weird! But I see him more as a best friend. Anyway, he tried to flirt with me but because we joke about everything, I just kind of joke back instead of flirt with him and hope he didn't mean it! But now suddenly he's started asking for nudes. I've already told him he's in the friendzone and he made a big fuss out of that, but with the asking for nudes thing, he won't stop!
I've told him over and over again that I did not want to send him any nude photos of myself because I know how people can use them against others! It's horrible! When I was with my ex, I sent him photos (just of myself in my underwear, I didn't go all nude) but it's still a very silly thing to and I would never send anything like that again. He hasn't shown anybody but I do regret it.
Anyway, it got to the point where I had to tell my friend the reason why i never want to send them again and he seemed to understand and we changed the subject. But then the day after, he started asking for them again but in a jokey way?
I have thought about maybe hanging out with him more and maybe even going on a date, but the way he's suddenly acting makes me think he's looking for one thing.
He has never had a girlfriend and he's continued to flirt with me on and off for years. His mum also believes he's 'in love' with me? But, no guy, if they really loved a girl would ask for nudes right!
I'm worried that our friendship could be in trouble, if he liked me, why can't he just be more serious about it than saying things like 'you're hot send nudes' ? Does he like me?
Guy friend keeps on asking for nudes?
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