ClueChick: real clues from a real chick

I just got my first email from down under, if I read things right! This fellow is newly single after a long time:

So now I am exploring the world of casual loving and am loving going on dates, meeting new people and all the excitement. I've had some great experiences, have come across a problem I've never faced before at the age of 33 - first kisses. Just about all my relationships/shags involved me be seduced rather than the other way around as is usual. Now I have to start making the first move! ... I can sometimes tell when the right time is when the girl is giving me all the well-known body language signs, lots of eye contact and we are generally having a good time. No problem there.

But there are other times, I think when the girl is more reserved that I'm not sure...

So what are some amusing/fun/disarming ways a bloke can go in for the first kiss?

I love this question, and not just because I was fantasizing about kissing on my drive home tonight. Kissing is really great, and it gets short shrift in the world of casual sex; people are often rushing ahead to the main event, missing a lot of great scenery along the way.

I think I'd like to address this question in the course of multiple posts, because there are so many great ways to make a move, and I'd love to hear from readers on both sides of the first kiss (kisser and kissee, if it went down with someone initiating, or kissers both, if it was entirely mutual). What are first kisses that have gone well? What are moves you wouldn't make again if someone paid you? What's a trick that didn't go smoothly but worked out anyway?

But first, let me tell you a first kiss story that has come up several times recently, and that is a very fond memory:

There's this boy. He's super cute, and at the time this story takes place, I'd known him socially for a handful of years, but only peripherally. Around this time, I was getting to know him and his wife better, and we all ended up at a sex party together, where he and I spent some time chatting about a variety of things, including how weird it can be to be at a sex party where it's kind of unclear what your role as an observer is... but that's neither here nor there.

So we're chatting, and partway through the conversation, I was struck absolutely stupid by the desire to kiss him. He was still talking and, apparently, I was, too, though I really don't know what either of us said, because all I could think about was kissing him, and here we were surrounded by people in various states of undress and somehow, I was not in the middle of kissing him, and that was causing me all kinds of consternation.

But, a real problem here is that I'm shy. Oh, sure, I flirt like nobody's business, but when it comes to making a move, I'm about as smooth as a thirteen year old boy. So, of course, I went with the classic route of hoping he'd kiss me. But it wasn't working and thus, we still weren't kissing.

Well, this went on for an embarrassingly long time, until his wife came collect him for bed for the evening. Seeing my moment escaping from me, I decided to leap, and before I tell you what I did, I want to say that in retrospect, I think this is a classy approach that I would recommend to anyone:

We were wrapping up the conversation (I still don't know what we were talking about at that point) and I looked him in the eye and said, "Would you mind if I kissed you?"

He made an eyebrows-raised surprised face and then said, "No, I'd like that!" So we did, and it was awesome. Contrarily, I'm still shy to initiate with him (though, actually, that might add a little bit of fun to our flirtation), but I've had a hell of a lot of fun kissing him from time to time, and I look forward to doing it more in the future.

(Full disclosure: After I told this story to his wife, recently, she then passed it on to him, and he came back to me and said, "But hadn't we kissed the year before at that other party?" And, I'm embarrassed to say he's entirely right, so this isn't actually a first kiss story, but it acts like one, so I'm just adding this addendum onto it, even though it makes me look silly for forgetting the first first time I'd kissed him!)