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"!
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A description of sex with a lesbian.
I shall now beam down,
To boldly Go where no man has gone before