I know that you want to try to avoid being awkward with him but the best way to go by this is to tell him up straight and just deal with the awkwardness. It's kinda sad that we live in a world where talking about sex and the like is considered awkward when really it shouldn't be. Sex is natural and almost everyone does it at some point in their life so it's not like it's a big secret or anything.
Anyway, back to the point. I say that you should just talk to him because he can't read your mind. He doesn't know what you're going through and he doesn't know how you feel. That's why it is your job to be able to express what you want so then he doesn't unintentionally do something that you don't like.
I understand that you're worried about being awkward. Some of it may stem from the fact that you aren't used to talking about stuff like this. Some of it may stem from being afraid that he'll judge you because he has more experience or whatever. I've been in very similar situations before so trust me, I get it. But it's not going to do you any good if you keep quiet and it's not going to get any better if you try to subtly give hints that he may or may not get. So if you're feeling awkward because of the first reason, then that's just something you'll have to march right through. You're not going to get used to talking about sex and sexual activities unless you start talking about it. I'm not saying that you have to be promiscuous and talk about sex all the time or anything like that, but you just need to change your mindset about sex as something that people do and isn't something extremely taboo. If your reasons for awkwardness is the second one, then let me tell you that it's nothing to be too worried about. So what if he has more experience than you do? He's been in your shoes before where he had little experience too and should be able to understand why you don't want to get super sexual yet and that you aren't ready. He shouldn't judge you based on the fact that he has more experience than you and therefore you should do whatever he wants. And if he does, then that just shows that he isn't as good of a person as you thought he was because he doesn't care about how you're feeling.
Some of the biggest mistakes made in relationships - whether it's dating, friendships, or in your case kinda a friends with benefits sort of relationship - is the lack of communication. Unless you're okay with doing whatever he wants all the time, you need to speak out your wants and needs. So if you want things to work out between the two of you, you need to discuss this with him and make sure that both of you know what each other wants. If things end up going sour, then the current relationship you have with your friend was never meant to be because if something so simple can ruin it, then it wouldn't have gotten any better anyway even if you guys didn't talk about this. Anyway, I wish you luck!
