Riverboat Drink Server
For a few years in college I was a drink server on a riverboat. If it was already a windy day, women would dress usually accordingly. But if it was sunny and there was no wind when people stepped outside their houses, women would have a tendency to wear lighter skirts that are prone to the wind-aided upskirts.
Being on the river alone will have natural gusts of wind to it that are stronger than when you just step outside your house. And the riverboat is also cruising 15-20 miles per hour itself. But from my experience it was the random gusts of wind that would usually catch women in skirts off-guard.
In my three years working as a riverboat drink server, I saw so my wind-aided upskirts that I lost count. Usually just a little buttcheek or panty flash. A full "Marilyn Monroe" never happened that I saw. But many girl's butts in their underwear. The best was when it would happen to an older mature woman, but those sightings were rare. Girls in their 20s though it happened often.
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