First time outside your comfort zone always is awkward, even if you actually know what you are doing. :P Next time, betting it will just be fun for both of you, no awkwardness at all.

And hey! Least now you got to try it both ways! More experience is always a good thing, when it comes to sex! ^-^

Yeah man! we've known eachother for a while so that helps too. No stress of meeting someone completely new :)
And hell yeah! I should make badges to grade my level lol

That's totally true when you try something new out of your comfort zone. It's good you experienced the other side, because the more you know of that, the better you get in your own thing. A lot of tops did start as bottoms (not all of course), but they have a better understanding how flick some switches in a bottom or know when something starts to feel uncomfortable.

Also, pain is usually never a good thing, unless it's your thing. Try more foreplay, or prepare before you even fool around at a later date and take it slow. As soon it's just painless you can do whatever you want and you will notice, how much more you gonna enjoy it.

Lol, i'm like the inverse. Looks like i'm a bottom that started top. And it's true. If I get to understand both point of views I can easily turn on the other guy and vice-versa.
But yeah.. for pain... It was my first time so it's obviously going be a little bit painful. Nothing gut wrenching of course but it was also enjoyable ^^

Haha, yeah. But usually first time tends to come up as a surprise. In the chance that one would knew beforehand, then you could like prepare for it, in the sense of using a toy or your fingers every day until it happens so your body isn't like shocked. XD
But anyway, it's good when it's a pleasant experience. Maybe you're a switch and not just fixed to one thing, who knows.

That'd i'd be the most efficient sex machine? SPECTACULAR!~
But yeah. it was also an extremely different kind of pain from what I excepected. And we used some fingers before too but they dont go that deep.
He decided that after two strokes he wanted all in. So that's a thing xD