Skip to the article, or search this site

Home: The Toast


When I was in seventh grade I got cast as a chorus nun in our middle school production of The Sound of Music. In the cast with me was an eighth grade boy, Wayne, playing Franz, the Von Trapp’s butler. He was in a bowtie and I was in a habit, but backstage, out of costume in rehearsals, we were talking about different roles for the future: we were going to go to prom in drag.

I think in seventh grade I’d decided I was a lesbian. I bounced around a lot in terms of labels in those tween years, though the term ‘tween’ had not been scientifically created yet. At some point amidst seeing Annie Lennox in the Sweet Dreams video at age seven and seeing softcore porn for the first time around age eleven I’d realized that I thought girls were sexy and I also thought suits might be nice to wear. Wayne was already ragingly gay at age thirteen. We hit it off great and he taught the girl playing Elsa Schmidt how to walk in heels.

These days I like to define my gender and sexual orientation as CONFUSER. I wear a lot of baseball shirts and boxer briefs, and also red lipstick and pearl earrings. These days Wayne is named Sara, and is a professional drag performer and entertainer. Everyone meets their own dreams in their own ways.

A note on pronouns, since that is a very pertinent subject: I asked Sara her preference for how I tell this story, and the direct quote from her was “I have no problem being referred to as ‘he’ back when I was a he. LoL.” It’s a tricky, sticky subject, but when it comes to drag and gender performance, sometimes hes are hes, hes are shes, shes are hes, and Wayne was a boy in a dress.

I was in seventh grade, and Wayne was in eighth grade. Wayne had spent a lot of time getting bumped around in the foster system, and so it wasn’t clear where he’d be in the next year, when he’d be going in to high school. We made an oath, though, that come the last years of high school, we’d both be in drag on prom night, no matter what.

Wayne moved away from Nashville after middle school, but we stayed in touch. We wrote letters to each other. Yes! Actual, physical, pen and paper letters to each other. In the mail, with stamps! It was the nineties. Things were hard back then. We wrote each other about plans to write fantasy novels together, he sent me drawings of elven characters we’d made up, and there wasn’t much of any talk about gender at all.

At some point Wayne read the Last Herald Mage trilogy by Mercedes Lackey, that wonderful stupid book series about tragic beautiful gay wizards with magic soul ponies, and decided his new name was going to be Vanyel Sean Fairchild. And at the same time, he was starting to do drag in earnest, and took the name Butterfly for his queen persona. Me? Christ, I was confused.

I mean, think about 1996. Jeffrey had come out in 1995, and while there was a transgender character in that movie, it was a joke that she was a woman in a man’s body who was also a lesbian. By high school I’d figured out that liking girls didn’t mean I couldn’t also like boys, but I also figured that liking boys meant I obviously couldn’t want to be a boy. My whole conception that you could even start out a girl and become a boy later was vague at best; mostly I just wanted to be Annie Lennox. Hell, I mostly still just want to be Annie Lennox.

Here’s how I learned that gender identity and sexual identity were not connected: I found a precious mid-90s Nine Inch Nails fansite of someone deeply in love with Trent Reznor. Said person was a transman (although I did not know this term at the time) and wrote in detail about his erotic fantasies along the downward spiral. I remember reading this site, red text on a black background, and having my little confused teen mind blown. You could be a girl who wanted to be a boy and also like boys? Holy shit. I include this story because I find it a hilarious way to realize the axis of gender and sexuality.

So, I started wearing the suit my brother had worn to all his friends bar mitzvahs when he was thirteen. I’d shaved my head at the end of eighth grade, so my hair was short. I put an Ace bandage around my boobs, got my suit and tie on, and was the most dapper little gent that the Sbarro in the mall had ever seen. I told my best friend I thought I might want to be called Lucas. I still wrote letters to Vanyel.

Somewhere in there, we lost touch, though. I called myself variously a girl or a boy, straight or bi. I went to my junior prom as a totally sexy goth girl with my best friend Stephen as my date, as my boyfriend had dumped me three weeks previous. Wayne or Vanyel — I can’t remember which he preferred at the time — he went as the date of another friend of mine, in a tux, but he and I danced dramatically all night to hot late 90s hits. I remember for one song we’d gathered a small crowd around us in a circle watching us go — probably watching him go, to be honest — and when we ended in a dramatic vogue-y pose, there was a healthy smattering of applause. What could cement a need in two dramatic children more to create a huge splash next year than that?

By the next year, it didn’t seem like the plan would come together. Do you guys even remember how hard it was to keep track of people in the nineties? Right now if I wanted to contact my prom date I could tweet, email, text, message her on Facebook, or, uh, call her; in 1999 I didn’t even have Vanyel’s phone number, let alone an email address. Somehow, somehow! though (I think involving my friend Bob, who had previously been historically entirely straight before meeting Vanyel at one of my parties, falling head over heels, and beginning a relationship with him that lasted almost ten years), we connected again with perilously short time before prom. Operation drag prom was on! System Butterfly ENGAGED.

My parents were nothing but supportive, but my parents have always been nothing but supportive, perhaps even in times when they should have gone ‘no, stop doing that, that is a bad idea.’ My mom took me to the Bittner’s tuxedo rental place in the mall and got me measured up for my tux. I picked a very long jacket that would cover my big ass, though in retrospect I should have gone with something else, since while it hid my curves, it only emphasized the fact that I’m but five foot two. With it I got a very dashing brocade vest and matching bowtie (clip-on), a pair of tuxedo pants (size 40-30), and a pair of very shiny dress shoes (men’s size 4.) The clerk dealt with the situation with aplomb, since I’m sure every prom season brought at least a few girls in tuxes to the store, but my rental slip involved a lot of question marks scrawled over it next to the particulars of the pants and shoe sizes. IS THIS CORRECT? they asked. HAS A MASSIVELY ROTUND MAN WITH CHILD FEET REQUESTED OUR SERVICES, TRULY? Yes, Mr. Bittner, yes, he has.

52849511_fa177076b8_oThe real important part of my evening’s apparel was the undergarment situation. I put on a pair of undersized control-top pantyhose to reduce my hips and behind (god damn it, I could have invented Spanx.) To deal with the big boobs, I followed what I have since learned is pretty much a checklist of How Not to Bind. First step was Saran Wrap, which was my 1 Weird Tip from a Drag Queen; Butterfly told me that queens used Saran Wrap followed by application of heat from a hair dryer around their waists to create an hourglass figure. So of course I did that to my breasts! And then the Ace bandage, because I didn’t think I was flat enough. But then the Ace bandage didn’t feel secure enough, so I got out the duct tape. To be fair, my date also had duct tape as part of her foundation wear. It’s always so cute when couples have matching accessories.

Butterfly showed up on my doorstep on prom night in a cheap black crushed velvet slinky dress with a cutout neckline and a spider brooch on it, matching elbow-length gloves, a blonde wig reminiscent of the Queen of Queens RuPaul herself, and six-inch platform wedge heels. She towered over me and was a stone cold fox. My mom, who spent her youth working in my grandmother’s flower shop, made a lovely corsage to pin on Butterfly’s dress (next to the spider.) Mom went above and beyond, though, also taking two colorful little butterfly-shaped pins acquired from a Claire’s to create a boutonniere for me and a matching hairpin for Butterfly.

In the run up to prom I’d been very loud about my plans. Loud enough that I’d been nominated for both prom queen and prom king, though through some clerical error the vote for the latter had been eliminated. And even though I went to a public high school in middle Tennessee, I ended up with no fallout for bringing a beautiful boy in a dress as my date. I was very lucky, and now, as a grown-ass man (and as the kind of woman who will call herself a grown-ass man), I appreciate how lucky I was.

No one wanted to start shit with me or Butterfly. The boys who didn’t know who I was, well, they just said, ‘hey, who’s that hot blonde chick with that little short dude?’ The girls were a little savvier. More than one of my classmates came up to Butterfly and said something to the extent of, what makes me mad is that you look so much hotter than I would in that. Not a harsh or hateful word, though.

When we did the senior walk, I stood on the ladies’ side, and the principal handed me a red rose. “You give me such problems, Whitney,” he said, and we walked down the promenade to a far, far greater cry of applause than the prom king or queen got at all. I never heard the details of any of his problems. I never heard any problems at all. I was just a girl with way too much shit wrapped around her ribcage rave-dancing with a drag queen and desperate for more punch. We danced, we laughed, we had an entirely normal prom for a couple of dumb teenagers, regardless of the clothes we were wearing or what Home Depot products we’d applied to our sex characteristics.

I was beyond lucky, I realize now. I wasn’t even the only girl in a tux that night. I had just managed to spend my high school years in a surprisingly queer-friendly public high school in middle Tennessee. I know, right? I’ve been written to at least a dozen times since by various organizations and colleges running drag balls, asking advice or asking for use of our photos. I can let them use the pictures all they want, but I don’t really have any wisdom. What can I say, really? Be a popular white kid? Pretty much good advice for anything.

I lost contact with Wayne and Vanyel and Butterfly after graduation. Our drag prom was the culmination of a whole confused adolescence of planning. It was only in the past few years that I found out that that Butterfly had gone into a different cocoon and come out as a full-time Sara. She’s nothing but fabulous now and does a great Katy Perry impersonation. She’s got a boyfriend who’s a transman and a drag performer himself who does a hell of a Justin Bieber. And me? Well, I remained Whitney. All the suits and ties and duct tape and thoughts of other names, and I had just stayed Whitney.

I’ve spent a lot of time looking at the picture of myself in my prom suit since that night. I don’t think I look like a man. I don’t think anyone would look at me and see a man. And for a long time, that was a kick in the face. I spent a long time thinking about my transition, the one that didn’t happen, how I’d never gone for it, how I never would, how it would be so hard for everyone I knew if I did. And in the end, I’d still be that little short dude. And I wouldn’t even be guaranteed the hot blonde chick on my arm. Or even another short dude.

But somewhere, thanks to the stupid internet, thanks to ridiculous places like Tumblr and all the precious babies who live there, thanks to places like The Toast, in only the very very near past few years I’ve learned there’s somewhere between wanting to put your heels on for junior prom and wanting to get Trent Reznor to go to town on your front hole. Every day now that I put on my sensible shoes and my boxer briefs and my raglan shirt and then put on my red lipstick, I want to go back in time and tell teen Whit, hey.

Hey, you know, you’re gonna look great in that tux. You’re going to be a cute little dude. But there’s more choices than being a cute little dude or a cute little chick. I want to tell her that she doesn’t need to spend her life to age thirty lying awake at night thinking about if she should have gone differently, if she should have changed pronouns, if she should have gotten the right shots to grow a totally sweet beard.

There’s something in between, little Whit. There are more than just two paths. And someday, you’ll know it’s okay to feel just as good being the hot blonde chick as it is to be the guy in the tie who has her on his arm. Someday, me in the year 2000, you’ll be your own drag prom date every day.

Photos courtesy of the author.

Whitney Reynolds lives in Brooklyn and can be found on Twitter @whitneyarner.

Add a comment

Skip to the top of the page, search this site, or read the article again