Two tricks with this:
Smudging just enough
Where to place the eyeliner
The problem that many women, T or not, face is that they may not have those big, doe eyes that we see on a lot of the models. However, they still follow the same makeup advice and that is not always a good thing. If you use eye liner over and under the entire eye, it can give you a very racoon look and make your eyes look a lot smaller.
With this in mind, practise just applying eyeliner from different areas and seeing how it impacts your everyday look. Once you find a comfortable spot move on to the next step.
Smudge the line just a touch. I do this with a finger (bad habit due to oils) or the corner of a makeup sponge.
Apply a dark eyeshadow using your eyeshadow brush and smudge it across the area you just applied the eyeliner. How far out, up, and down is completely up to you. Want to make it shine a bit? Try applying vaseline across your eyelids or adding just a touch of glitter makeup (I picked up a Calgon spray with very small pieces of glitter, adds just enough without making you look like some Rave kid looking for your next tab of X).
The smoky look can take some work before you find what works best for you.
