If you want a really long wearing lipgloss then look no further than MAC's Pro Longwear Lipglass. This new ( ish) gloss wears like glue. I got several hours of wear including drinking out of mine. That's unusual for a gloss.
It is more tacky than most glosses but not drying. It has moisture and it sticks.
Shown are shades Driven by Love (red) and Ready or Not ( nude).