Is this Robert Smith?? Kidding.
I have not the foggiest idea, as eyeliner falls into the category of "scary makeup" to me. By that I don't mean I think it looks scary, but that I am scared to even attempt to apply it. I love how it looks when other people apply it for me!
That being said, it definitely takes a brave soul and a steady hand. My advice to you is to go to a MAC or Sephora, or other place where a professional can demonstrate the proper application for you. It sounds as if you definitely want an edgier look, so MAC would definitely be good. I would not recommend the Clinique or Estee Lauder counter, as they will probably give you a more traditional look, i.e., "ladyish".