I find that with kissing, if you are supremely confident and comfortable in your movements and actions as you are doing it (or at least appear to be), then you can actually initiate the kiss in a surprisingly wide range of situations. Nervous guys are always telling themselves 'she won't want to kiss me', and this hesitation and uncertainty shines like a beacon to her, and puts her right off.
The thing is, and this applied most specially if she is at all drunk, most people who are being kissed don't automatically push the person away. what i mean is, if a woman was to kiss you, you'd just go right along with it unless you realised you shouldn't be.
So be assured in your actions, and smoothly transition into it, you'd be surprised just how receptive most women are.
P.S. As an extra point, although not completely related to your question I didn't think this deserved its own thread. No this may not apply to you, but from your 'drought spell of more years than you'd want to know' part, i think it could. I think most of us guys have, at some point, felt that our relationship history was inadequate. You could be talking to a really hot girl who talks about her past boyfriends etc and you realise that you've experienced little in comparison. Now here you can either lie and make up some stuff when she asks you, or just say this, that you don't like talking about all your past relationships too much because it makes them feel less special to you, it degrades the value you had for them.
Now this does two things, firstly it serves as a handy barrier to further questioning from her, at least until a time where you are comfortable enough with her to tell her more, but also demonstrates how much you value your relationships. a lot of guys are left bitter by bad breakups, so for her to find a guy who still respects the time he spent with someone would attract her greatly.
As ever, if you don't agree with me on this, i'd love to hear your thoughts.