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Prom Night(mare)

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PROM TUXEDO
Arthur Tilley via Getty Images

Most guys don their first tux at age 17 as a ritual that goes hand-in-hand with attending The Junior Prom. In my case, however, God didn't get the memo, and I found myself at Priscilla's of Boston with my mom, grandmother and older sister trying on creepy dresses in various shades of pastel.

I'm guessing most teenage girls would've relished this moment, but being transgender, I was in no way like most teenage girls. Chewing glass would have given me more pleasure. I didn't even wanna go to the stupid Prom but felt that not going would make me more of an outcast than donning a pink tea-length dress. So I played the part and went with my friend, Nick, who asked with very respectable lead-time. He was the kid who hit puberty in like 6th grade - "the big one" who towered over all the other boys. He was good-natured, funny, and got along with everyone, including our limo-mates: "Schu" and her date, who lived on my street and Marianne and her date, who'd recently suffered some type of mental breakdown. I was having my own breakdown after coming home from the salon and taking a good look at what had been done to my hair. I didn't know it was capable of achieving that level of poofdom and asked my sister to try to fix it as well as to apply the minimal amount of makeup necessary to pull off this whole ensemble. She kept telling me how pretty I looked and didn't understand why I was so upset. If you only knew, I thought.

But with years of practice under my belt, I'd become a good actor. And while I wasn't dying for the role of female prom date (or any role that began with "female"), I did my best to play the part-wearing the wrist corsage (at least for the first hour), posing for cheesy photos, partaking in a few obligatory slow dances...Looking back, how I made it through that event stone cold sober is truly beyond me. Thanks to an incident the year before, the principal made it very clear there would be no tolerance for anyone drinking or found drunk on the premises. Now, I know what you're thinking, and the answer is yes. The same policy was later adopted in 1993 at West Beverly High, although in the end, Donna Martin was allowed to graduate.

Back then I envied all the guys in their tuxes, some with bow ties and cummerbunds to match the color of their dates' dresses. Ten years later, I was putting one on for the very first time in preparation for an event at the Harvard Club that my dad had asked me to attend. The tux was a classic shawl collar model with flat front pants and had been given to me by one of the partners at the ad agency where I was working. It was his first tux and since he'd just bought himself a new one and noticed we were roughly the same size, he brought it into work one day and sheepishly asked me if I'd like to have it, figuring I most likely didn't already own one and with some alterations it would probably fit me pretty well. I was stunned by his kind gesture and extremely grateful. And he was right. Once my tailor worked his magic, you'd think that tux was made for me.

I bought a classic wing collar tuxedo shirt, black onyx cufflinks and studs and a black silk bow tie and cummerbund from Saks. I completed the outfit with a pair of patent leather tuxedo shoes and checked my look in the full-length mirror. Holy shit! Who let James Bond in here? On a scale of 1 to 10, I was definitely a 007.

One can't help but feel hyper-masculine in a tux and at age 26 when I strode into the Harvard Club, just one of a sea of penguins, I finally felt like I belonged to a different club -- the one I'd been denied entry to since birth.