Halloween in a small town like Wakefield was prime time for the kids. There was complete safety and freedom of movement throughout town. Real acts of vandalism were rarely seen, although Halloween certainly pushed these limits. There were no pimps or pushers or wrong sides of town. Alcohol was the drug of choice and was fully legal at age 18. Other drug usage seemingly did not occur, even though marijuana grew wild along the creek banks. The folks in Wakefield would not recognize a marijuana plant in a lineup. They would probably not recognize a lineup. It was a fine little town for raising kids until Halloween arrived. Everyone knew this was the time for testing the limits.
At school, the closest thing to testing limits was the Halloween Costume Ball. As was always the case, some would refuse to participate, while others got into the activity with enthusiasm. There were numerous awards for the costumes which included things like most novel, most elaborate, and best overall. Following the costume portion of the evening, everyone would get undressed and the dancing would start.
Student behavior at school dances was a strange, if not hypnotic scene. Most of the girls sat in one section of the auditorium, and most of the boys sat in another, a considerable distance removed from each other. This strange behavior seemed to parallel certain school classes. For instance, in my four years, I never knew a girl to take shop, nor a boy to take home economics. It would have been more fun, but gender roles in small towns were firmly fixed and were rarely questioned. The boys were supposed to ask the girls to dance. In performing this task, he was supposed to remove himself from his comfortable group of guys, walk across that uncomfortable space between the groups, select out one of dozens of willing girls, ask her if she would like to dance in front of all the other girls, and then wait for the answer, which could be “no”. The entire scene was repugnant to most males, who found it far more comfortable to sit and watch. There was a lot of sitting and watching.
Anticipating this scene, it made a lot of sense to go to the ball as a woman. I could sit with the girls, listen to the girls, be one of the girls, and sit on the other side of the dance floor. This was a whole new ballgame with a limitless set of untested possibilities.
Initially I considered my fitness for the task. At the time I had no more facial hair than most of the girls, and my legs passed muster nicely. Breasts were an essential add-on, preferably large enough to act as a distraction. A wig and hat would be needed to hide any personally identifying qualities. A dead giveaway was voice recognition. For this reason I decided to engage only in sign language. As I knew no sign language, this meant I would have to meander among the students in silence.
My mother, Gertrude, had a large assortment of costumes, most of which she wore to school every day. They were brightly colored dresses straight off the rack in Mexico with bows and lace, with and without sleeves. To wear any of these would be a giveaway for the girls in the school. Then we uncovered a number of black dresses which belonged to Aunt Edna. She frequently dressed in witch-like fashion and wore black, wide-brim hats. One of the dresses was perfect with long sleeves, a neckline high enough to cover the enhancements, and long enough to reveal a seductive amount of leg. Black flats, a black wig, and a wide brim hat finished the outfit in style. A little bit of makeup and a touch of perfume finished a complete make over. The only disguise needed was a simple black mask over my eyes and nose like that worn by the Lone Ranger. It worked perfectly. I was stunning, and did not recognize myself in the mirror. The lady in black was ready for the ball.
Getting to the ball presented several complications. I could carry the costume in a box and change at school. Changing in the boys or girls locker rooms or bathrooms was a titillating idea, but I could not figure out how to undress in one and redress in the other. There were no private bathrooms in the school. While the classrooms were usually unlocked, the chance of discovery while changing was simply too great. Had there been a telephone booth at school, I could enter as Clark Kent, and depart as Super woman. The only reasonable choice was to change at home, a short block from the school. That way I could call upon Gertrude to be sure every detail was perfect, and then be careful not to be seen while leaving the house.
At the witching hour, I sneaked out of the house and across the block to the school without incident. I entered the gymnasium where the students were assembled and mingling. My entry was an eye-opener. As I could not talk, I mostly listened. I heard a lot.
The lady in black became a focus of attention from the outset. There were cat calls and hoots and whistles from all the guys. The girls did what girls do automatically, they checked me out in every detail from head to toe. Fortunately all the details had been covered. Then they all began referring to me as the lady in black, and at that moment I knew I had won. The breasts received special attention, probably because they had never been seen in Wakefield before. The boys all wondered if they were real, and the girls were all worried they might be. I could see myself sitting with the girls at the dance already.
It was quite easy to avoid conversation. In response to direct questions I would nod yes or no or make any one of a dozen hand signals. The signals were challenging, and became quite comfortable as the evening wore on. I survived the mingling without discovery for what seemed like an eternity. There was not a hint that I could be other than I appeared. This spark of overconfidence led me to step momentarily out of character.
I could still be in costume today had I not pinched Betty Carpenter. She blew the whistle on my one indiscretion. Then she confided with several friends, put my two and her two together, and concluded that nice girls just don’t do that sort of thing. As all the other guys had been identified, my body was the only one remaining which could be lurking behind that beautiful pair. It was still exhilarating, but the deception was over.
For me the dance which followed took on a whole new dimension. My street clothes were still at home. It made some sense to leave them there and continue the charade as though nothing had happened. I sat with the girls at the ball waiting for some guy to ask me to dance. He never did, and I learned exactly what it was like to sit wistfully and wait. Had I been asked I would have said no, depending, of course, on the guy!
Then I discovered that girls will do what boys would not consider. They readily dance with each other. What’s more, they had no problem dancing with me. It made sense to take full advantage of this startling opportunity. The rest of the ball was history, dancing the night away with the school’s bevy of beauties.
The judges, in their inimitable wisdom, awarded me a consolation prize as Wakefield’s First Cross-Dresser, a category in which I was the only entry. Such an award in no way detracted from the high I experienced dancing with all the girls.