Use lip balm at night, if your lips are chapped, cracked or peeling.
Use a sharp matching lip pencil first, which defines lips, and discourages colour bleed. You can use it to enhance the "bow" at the top, or make lips look fuller or slimmer. Balance your smile if it is lopsided, or if one lip is bigger than the other, by drawing just outside the natural line on the smaller side. You can plump up your pretty pout by drawing inside the line at the corners, and one sharp pencil width outside at top and bottom.
You can overwork here. A lip brush is for experts. Don't bother. If you do like to use one, make it top quality. Go the whole hog and use a wax oil anti-colour bleed just around the lips, then a lip plumping product, lip stain (Warning: lasts for days), mouth watering gloss, and finish with a lip sealer to stop any coming off.
Separate lip gloss is not required. If you do use it, Revlon ColorStay Liquid Lip does stay on. The same can be achieved with glossy lipstick (though matte lasts longer), or a touch of Vaseline on the centre of the lower lip for the perfectionist. In this photo, gold glossy lippy has been used inside a cerise matte shade for maximum pouty sexiness!