By going to an actual prostitute, that's how. It becomes a rite of passage, like getting your driver's license or flaying your first sabre cat.
Consequently, brothels have a long and squelchy history as a portal into manhood, spanning the globe from Gilead (a fictional place) to the Netherlands (allegedly a real place). Napoleon lost his virginity to a prostitute he found near the Louvre. Mussolini lost his by hiring "an elderly woman who spilled out lard from all parts of her body." Charlie Sheen and JFK might be famous walking sex dispensers, but both paid for their first times. Bryan Cranston's first woman was a Dutch professional; Roger Ebert's was South African. Oliver Stone's dad booked his son's first woman, leading him to say, "My father was a generous man, and I love him to this day for it." This also explains a significant portion of the family relationships in Oliver Stone's movies.
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"She just kept asking for me to move back and to the left. I guess it just sort of stuck."
According to Marcos, in El Salvador, it's generally the Oliver Stone experience -- a father takes his son out to a prostitute for his first time, most often when he's 15. That means ...