According to the Urban Dictionary, Cherry Chapstick is a term that refers to when a person, usually a female, wears red lipstick. It is used as a playful and flirtatious way to describe a woman’s appearance. The phrase is derived from the brand name Chapstick, which is a lip balm and the cherry color that is often associated with red lipstick. It can also be used in a more vulgar way referring to the red lipstick left on someone’s genitals after oral sex. Please note that this phrase is vulgar and not appropriate in most settings and I would advise you to use it carefully.