New at Hickeys, Help?

tiredtheatre
TLDR: The questions I have are at the end of the post, relating to hickeys and awkwardness associated 

My boyfriend and I have been dating for a little under a month. Before we went back to school, we spent the entire day together, and a good portion of it was spent making out. Neither of us have a lot of experience in that department (or any sexual one for that matter - he was my first kiss), so we were experimenting with stuff for a little while. He wanted to give me a hickey, so we tried a couple times and eventually I ended up with two on my neck.
From my side of it, it felt amazing. Apparently I moaned at some point? I was REALLY, REALLY into it.
From his side of it, he said the actual act of giving a hickey was awkward/difficult for him. It wasn't that he didn't enjoy it (I think he did), it sounds like it was just that it was a new and weird action to embark in.

I am here in search of advice:
1. Is it always awkward to give hickeys? Any tips? I wanted to try giving him one next time we see eachother, but I don't want to let awkwardness get in the way of whatever's going on.
2. How might I help him feel more comfortable with giving hickeys? Whether it be physically, verbally, or emotionally? He said he wants to give me them, but I don't want him to feel psyched out by it.
New at Hickeys, Help?
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