Lampshade it. Next time you're out talking to a HB and things are going well, bring up the topic. Something along the lines of:
YOU: 'I bet you'd never guess that I was a bit of a doofus a few years ago, right?'
HER: 'No, really?'
YOU: True bill babydoll. (Allude at this point to exactly how you were such a chump/ nerd/ whetever - perhaps even throw in a few true stories or show exactly how you would have behaved).
Because you've told her a bit about your past, it'll be more difficult for her to reconcile the idea of you as a chump vs. you the really amazingly cool guy talking to her now. Then, whenever one of these stories does get back to her, she'll be like, 'I already know that.'
But can I ask - are you sure that's the reason you're getting blown off? The reason I ask is because I'm from a relatively small city as well and when I went out, I had the illusion that lots of people knew about my 'background' and what I was like, only to find out that while some people knew who I was (and only in a pretty vague sense) most didn't know me at all. The point being that its easy to convince ourselves that we have some sort of negative rep or black mark against our name when we go out, when in fact thats generally not the case.
Either way, I'd reckon it says more about these ladies who spurn your second day advances. If she's going to listen to a few comments from someone else about you, rather than go by her own pleasurable experience.... well... I'd be pressing the 'release the hounds' button myself on that particular girl.
'Course, could be you've just got a really solid rep as a bad boy!
