Captain Kirk Award
A very rare award that will only be given out once in human history, to a single person, and never again. This person will permanently hold the title for all of eternity, and be remembered as a hero to mankind.

This great honor shall be bestowed upon the very first human being to have sex with a sentient alien life form.

Convincing another human to fuck you is hard enough, but to be able to overcome a cultural and language barrier of an entirely different species and STILL convince one of them to fuck you is the pinnacle of finesse and game.

(Captain Kirk is the protagonist of the famed Star Trek series, and is known for gallivanting across the galaxy and gettin' the honeys.)
In the year 2199, Commander Larry Shepard of the United Earth Space Navy made first contact with the first known sentient species of extraterrestrials in the galaxy: the Shag-Shag.

This feat pales in comparison to Shepard's next accomplishment: earning the Captain Kirk Award by seducing the royal princess, thus becoming the first human being to have sex with an alien.

The war that followed was brutal, and brought our two races to the brink of extinction. It turns out that in Shag-Shag culture, a girl's parents must be present during intercourse. Not doing so is a major taboo in their culture. However, despite this chaos, you cannot deny that Commander Shepard has some fuckin' game.