One simple fix.
Sean,
You are right in thinking that people might be unpleasantly surprised by the operation of your menu. But it is not hard to fix.
Instead of having a new line of menus appear following a click (when people click on a link they expect to get to the page they are looking for not another list of links), just use a drop down menu so that when someone hovers over the links those that require additional choices will have those in the drop down menu and they will click on that.
If you will permit the suggestion, instead of describing your site as "Possibly the world's most pointless website..." why not say "Possibly the world's most important website, because it's about me." Actually you could come up with something better, but what I am suggesting is that you get what you expect from yourself and others. It is always better to plant expectations of something positive than something negative.
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