I always read and hear about lipsticks that don't last, fade quickly or transfers on coffee cups, etc.

Any lipstick, especially a creamy one, will transfer onto the rim of your cup/glass when you are drinking. That is just a fact and there is really nothing you can do about it.
Why not rather try a matte lipstick, lip crayon or eve just a lip pencil?
Any product that is matte and waxy will stay on your lips for much longer. Well,  your lips will feel a bit tight  and dry .
Keep in mind that ANY product that you apply prior to your lip colour, like a lip conditioner will be the result of your lip colour not lasting or transferring.
Anything that you apply over the lip colour, like a gloss, will make the colour last longer, but you will still get a transfer on your cup.
Tricky, isn't it!
So, Keep layering you lip colour and you will have a stain left by the end of the day.
What I mean:-
Colour in your lips with a lip pencil or crayon.
Over this, you can apply your favourite lips stick if you want to, but not necessary.
Finish with  a LITTLE gloss, for shine (If shine is what you are looking for, but just a LITTLE)
The gloss will transfer or eventually disappear, but you will be left with stain on your lips.

OH, and remember, don't eat or lick your lips. Your colour will come off.