I have fair skin, too, and I love wearing dark lipstick! Whenever I use it, I first exfoliate my lips by gently brushing them with my toothbrush; this removes any dead skin that might make the color uneven. I then use DuWop Reverse Lip Liner.
I love this lip liner because it's colorless so you don't get the tacky lip liner line around your mouth but it also really prevents the color from moving off of your lips.
I finally use my finger to apply the lipstick. I dab my finger onto the lipstick and then dab my finger onto my lips. For some reason it always looks better when I apply the lipstick with my finger rather than directly with the lipstick.
After applying the lipstick, you may want to dab it slightly with a piece of tissue to make sure there isn't too much color on your lips. Also, to prevent the lipstick from getting onto your teeth, don't forget to put a finger in your mouth, close your lips securely around it, and pull your finger out with your lips still around it. This way, all the color that was in the position to transfer itself to your teeth gets on your finger!