This dude is playing you. You need to take ownership of your own sex life. If you just want to hook up with him, hook up with him. If you want something more and he isn't okay with that, move on to somebody else. Don't allow his choices to dictate your actions. Get the information you need from him and make your own informed, confident decision.

This guy sounds like a complete douche, by the way. He's your typical "big fish in a small pond": really proud of being super popular in middle school and high school. As if that matters. And it sounds like you're buying into it.

It has been a while since I was your age (I'm 30) but here's a tip that I learned over the last decade or so: the world is bigger than your hometown. It's bigger than grade school. It's bigger than college. This dude doesn't matter. Him being popular with girls in grade school doesn't matter. Ask yourself why you like him. Is he presenting you with anything that demonstrates his value as a person? Or do you like him because he's handsome and other girls like him?

Find out what you actually want, and pursue it.