www.alphadictionary.com

Drag is a four-letter word that has multiple uses and meanings depending on context. The context I am thinking about is in regards to streets and vehicles which are tightly coupled.

Here is what I was musing about "The Johnson boy was caught drag racing down the main drag of town in his new dragster. Oh my, it will all end in tears."

Drag has been used as a description for sleds, carts, and wagons. The first motorized car or drag was invented in the late 1700s. The street is called a drag, main that is, was coined in the 1850s. Drag racing was coin probably earlier than later since even boys in horse draw carts race. I think there is a 1600s Greek or Latin root to this, but the reference alludes me now.

I know there is a wonderful coherent story to be told about all of these things that relate to one another. The slang dictionaries have lots of confusing notions about "drag" but what are "just the facts."

Is dressing in drag related. Naturally, when your doll is all decked out you want to take her for a promenade down the main drag. So are cloths referred to as drags? Rags? Thus, men dressing in drag.

Here's the link to etymonline's page on this one. It's pretty convoluted, with the noun section referring back to the verb, though the noun predates the verb by nearly a century.

Drag racing it dates specifically to 1947, though.

A meaning I associate with "drag" is to attend an event with a date, as in "stag (without) or drag (with)". In particular, I associate it with the U.S. Naval Academy in the 1950s, when one's date was referred to as a "drag". It almost certainly predates that, but that's when I was in a position to be in touch with that environment.

This seems a possible precursor to the current meaning, of a man dressed in women's.clothes. Some chronological exploration would be necessary to validate that conjecture.

My guess is that the navy boys using it was in the sense of a put down, as in "annoying, boring person or thing". They must maintain the macho image, after all.

The transvestism sense is mentioned in the linked page. Either from theater days, or Yiddish.