I have a couple of non-specific recommendations:
First, I'd say start by smoking Robustos and Churchills. They are the vitolas that set flavor standards, in my book. They're a great way to see how some smokes are one-dimensional and others complex...they are big enough, especially the Churchill, to develop flavors. Make the time to enjoy longer cigars. Smaller cigars are good, too, but sometimes are a bit harsher or more intense flavor-wise. Cool, leisurely smoke and smoking is pretty much the essence of cigars in my book. Churchills are perfect for that.
Second, smoke a premium cigar very soon. Something like a Padron Anniversaire 1964 or 1926 or an Opus X. I say this because it helps develop your taste to know what a 'really good cigar' tastes like. One of my very first cigars was a Cuban Romeo y Julieta, and I thought 'ah, that's what it is supposed to taste like.' Helped me develop my taste a lot.
Buy up five-packs. It has been said many times here, and it is always true: if you don't like 'em, trade 'em. Someone out there probably likes the smokes that don't do it for you.
Best of luck. I remember getting started with cigars and developing my preferences. Great time and very fun.
John