To tell you the truth, Jack, I worked so many Halloweens I can't think of anything I personally did. Between the ages of 18 and about 32 I worked either as a bartender or cocktail waitress. I'd like to say it's because I did my best work at night, but in all honesty, this was chiefly due to my ex-husband's schedule - working day shift in the Marine Corps - and having two young children. (err.. well, no kids until my mid 20's).
But, I can think of one particular instance of Halloween get-upping that I still think of to this day and laugh about.
It was Halloween circa 1993, I was living in Eastern NC in a Marine Corps base town. The bar I worked at was having the usual shindig. I was walking around out on the floor, doing the routine crap amongst the crowd when I spied a guy I knew who had dressed in drag.
This guy, really more a kid at 21, was not very tall - maybe 5'7" - blond, with little or no body hair. His costume consisted of black patent-leather type boots to his knees, pantyhose, mini skirt, white blouse tucked in, blond wig and a truly amazing make-up job. However, the pièce de résistance was his breasts. Yes, breasts.
With incomparable skill, he'd stuffed a bra with absolute precision and glued pencil erasers on each as nipples. The effect was utter genius. Those sweet little nips perfectly grazed the blouse with their oh-so-seductive perkiness.
All throughout the evening I watched as one tanked jarhead after another hit on the dear boy. Towards the end of the night I went to him and inquired how many propositions he'd acquired. Laughing it off, he replied no less than 20, with many pinchings of his butt and attempted gropes at those bodacious ta-tas.
True, this was just a memorable costume, but I suspect that if any of those drunken Marines had known he possessed a penis and balls under that attire, there would have been some serious gagging.