This is the next in a series of posts where I am trying to sort out where it all began and how badly it all went wrong before it got right again. For chronology and context, see Where did it all begin? and Why Didn’t I Buy Nike?
By the time I was in high school, I had developed a perception problem. By “perception problem,” I mean that I was always overly worried about the way other people perceived me. It wasn’t that I wanted to stand out or be popular. Just the opposite! I wanted to blend in, to fade away. The worst thing I could do is stand out. If I could be perceived as normal, then people wouldn’t take notice of me. I was already tall, overweight, and socially awkward, so I really couldn’t do anything else that would brand me as “weird”.
Between marching band, art class, and a small gaming group, I was able to get together a social circle for myself of people who weren’t so judgmental, who weren’t so quick to label. They weren’t perfect groups (marching band, in particular, had its share of almost-bullies), but they kept me safe enough. Outside of those circles I just ducked my head, stooped my shoulders, and tried to be invisible.
It was during these high school years that I first put on a dress. I don’t remember my first time, exactly. It was probably sometime during my junior year, because that’s when the opportunity would have first presented itself. By opportunity, I mean times when I was at home alone with access to my mom’s and sister’s closets. I would often come straight home from school, while both my parents were out working and my sisters were occupied by extracurricular activities. I wasn’t so fat back then, and so I could occasionally slip into one of my older sisters’ things. And my mother was shorter than I was, but also overweight, so there were plenty of her things that I could wear. In particular, I remember a blue dress that she would wear occasionally to weddings and such, that fit me just well enough that it became my favorite one to try on. I usually had about an hour between when I got home from school and when other people would start to get home. I know that I didn’t do it every day, but I also know that by the later half of my senior year I was doing it often.
I didn’t know what to think about myself at the time. I didn’t think it was natural and I knew I needed to hide it, but neither of those thoughts stopped me from doing it. That was when my cycles of shame spiraling began — the highs of dressing, followed by the lows of realizing what I was doing.
By fall of my senior year, I was deep enough into these feelings that, when my one and only opportunity to legitimately go out of the house “en femme” presented itself, I siezed it. My high school held a school Spirit Week leading up to the Homecoming Game, as high schools sometimes do. As part of it, they declared each day a different “dress-up” day. Participationin the dress-up days was a way to show support for the upcoming game. Go football team! Rah rah! I didn’t give a damn about school spirit — heck, some of those meatheads were bullies who had picked on me in the past — but I did give a damn that the first day of Spirit Week was “cross-dressing day.”
I don’t remember where I drew the courage from, but wherever it came from, I did it. I dressed up for cross-dressing day. I wore a blue knit sweater of my mom’s, with small balloons taped underneath it for “boobs,” and a white skirt that I think was made of a cotton jersey material (I don’t remember for sure; I sucked at fabrics back then). I also borrowed a pair of her pantyhose, whcih I didn’t tell her about and which I slipped on in my car when I got to school. I didn’t have women’s shoes in my size (men’s 12s back then), so I wore my regular sneakers with socks folded down “girl style”.
I remember being very happy that day. I walked into the school and into the little corner where “my people” (the band members) usually socialized. The guys — none of them participating — laughed, while the girls were delighted and attacked me with makeup. As the day went on I played along with crowd; I laughed with the guys about how absurd I looked; I joked with a girl I was sweet on in art class about how I looked better than her. At lunchtime, the vice principal came over and talked to me, almost like she was suspicious of something, but I invoked my school spirit and she walked away satisfied. It was a good day. No, it was a great day.
To hide my true intent, I participated in the rest of the spirit days, too: pajama day, little kid day, backwards day, school colors day. I remember somebody saying to me that week, “Wow! I didn’t know you had so much school spirit!” Inside I was thinking, No I fucking don’t, if you only knew. Still, the comment was socially validating. It meant the people saw me as normal. It meant that no one suspected anything. I did get some funny looks from a few teachers that first day, but I was insulated by the cause. Screw you, econ teacher! I have school spirit! Rah rah!
My memories of that day of high school are more vivid than just about any other single day in four years there. It’s like my mind was recording everything I expereinced that day as a keepsake. Without a doubt, it is my favorite memory from that time in my life, and one of the few memories I have of crossdressing that isn’t attached to a moment of shame.