This was SO me, but I have just sort of pushed myself into it. It took a lot of just wearing it regardless of how stupid I felt, but I am finally comfortable wearing just about any lipcolor.
It also helps if you go to Sephora or something and tell tehm you are looking for a good red lipstick to complement your skintone. They can match you with one that has the right undertones for your skin, so
Also, one trick I did when I was easing myself into red lipstick was wearing a pink and just adding a leeeetle bit of a red. Eventually I weaned myself from the pink and went ALL-RED
I used to feel the same, I only wore it for the stage. You need to get one with blue undertones, because you're quite pale. Barry M do some amazing lip pencils that are really easy to put on