I recently was asked for some advice by a male friend of mine concerning eyeliner and I thought I'd include what I recommended to him:
You can pick up eyeliner at any drugstore, CVS or Walgreen's. A nice basic black eyeliner I recommend is L'Oreal Pencil Perfect self-sharpening eyeliner in Ebony.
It is black on the outside with gold writing and a gold cap. Definitely get the self-sharpening one, the way it works is that you just twist it up once you've worn it down. This way you don't have to worry about buying an eyeliner sharpener or possibly scratching your eye when the liner gets too low and the tips of wood are sticking up.
Now for application: Key is to start out with a little cause you can always add more but it is hard to remove once it's on. (Actually you might as well pick up some eye make-up remover at the store too, cause eyeliner can take days to come off-and just basic soap and water won't work that well and may irritate your eye) So back to the application, rim your bottom lash line with the liner using a light touch, you could even just dot it on then take a Q-tip or cotton swab and swab over the area you applied. At that point step back from the mirror and see if you like the effect or if you want to make it heavier. If you want it heavier just repeat the step above until you get to the look you desire.
I don't suggest you line the top lid to begin with, especially for guys I think that just eyeliner on the bottom is the most effective. However upon application you are now a make-up artist and as an artist you call the shots. So experiment with it. There really aren't any rules - you can even get some eyeliners in different colors - start out perhaps with browns or grays and go from there.
As for removal take the eye make-up remover and put some on a Q-tip and swab off, depending on how much liner you put on will determine how easily if comes off. You'll probably want to wash your whole face after wards because most make-up removers feel pretty greasy.
Well let me know if you have any other questions.
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Personally I think eyeliner looks great on guys, gives an edgy rock-star pirate look. I noticed just last Halloween that anyone dressed up like a pirate had the smoky eyes a la Johnny Depp - I don't think anyone will be able to dress up like a pirate in the future without it and we can all thank the brilliant artists who worked on the Pirates movies.