Take the virginity of a Trekie (usually a female).
The phrase is of unknown origin but it seems that it comes from the "franchise" of
Star Trek porn parodies such as "Sex Trek: the
next penetration" and "Where no man has cum before".
Fred:
Hey, you know what? I slept with Janice last night!
Bob: No! Janice the Trekie?
Fred: Yeah..
Bob: That's what I call "To boldly go where no man has gone before"!