I would definitely suggest lipstains for you, because all lipsticks are intended to sit on top of your skin, and so they will transfer onto anything your mouth touches, even if they’re “longwear”. Most longwear lipsticks are simply fade-resistant and feather-resistant… but if you’re going to be eating, drinking (and kissing!) your lipstick will need a reapplication.
Lipstains, on the other hand, settle into your skin and lock in the pigment for much longer. Since they don’t sit on top, they won’t come off nearly as quickly!
My favorite lip stains are Revlon Just Bitten, because the colors are really vibrant and they don’t dry up your lips! One side is the stain, and on the other end is a glossy lip balm for added pizazz.
I’ve also recently gotten into ELF’s Essential Lip Stains, which came out in the spring. For only $2 they’re excellent - really pigmented, quite long lasting and fade resistant.
I’m really more of a lipstick girl these days, but if I know I’m going to be out and about for most of the day, I’ll first layer on a lip stain, and then go over top with a similarly colored lip stick. That way I’ll know that my lips will stay colorful for hours, even if I have a meal or two!
The nice things about lip stains, also, is that you can easily layer a lip balm over top of them without ruining the color. Most are quite drying, but that usually indicates longer lasting color.