I have not found an real trick to lipstick. It all depends on what you are trying to do and for how long.
There are very expensive ones you apply and they'll look amazing for a week, but do you want to wear it for a week straight? There's also the basic drug store stick type that last a couple hours.
I use basic stick lipstick. I first use a good lip balm, then once it's absorbed, I use a lip pencil to outline the shape on my lips, I'm going for. Then go over that with a stick lip stick. I buy my lipstick and pencils at an good Drug Store. They work fine. The style and shade depends on the color and fashion I'm wearing that night.
Yes, the lipstick will have to be reapplied after a couple hours, but that's nothing new. Why do you think women carry a purse and lipstick in those purses ? They need to reapply it as well.

Hope that helps.

Thanks for your gracious reply and invaluable tips. Been having a lot of fun experimenting and feeling very fem in make up and lingerie. From demure to slut.

XXX Carla

Thanks for your gracious reply and invaluable tips. Been having a lot of fun experimenting and feeling very fem in make up and lingerie. From demure to slut.

XXX Carla