It did not take much Googling to find out that Annapolis "drag" has nothing to do with crossdressing.
According to an article in the November 29, 1948 issue of Time, "drag" was the Naval cadet nickname for a date, i.e., the girls the cadets dated were called "drags."
I guess if a cadet dated a crossdresser, his date would be a "drag in drag."
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