An action taken on by a member of the male gender in which the male inserts his penis into the vagina of a virgin girl. Since Christopher Columbus sailed the seas and was the first to discover America it is only proper to name a sex act after him.
Garrett is a sexually frustrated boy who wants to have sex with Kristina; Kristina knows this. However, Garrett thinks he is being slick and sly and hiding his fantasies very well.
Olivia: What is Garrett's deal? he seems really weird around you...
Kristina: Yea, I know... He wants to Christopher Columbus my Vagina.
Olivia: HOLY SH*T, I will not let him be your first!... I'll knock him out for you.