Dress You Up

Sunday, August 7, 2011

My head felt like it was in a vise, with an unfamiliar all-over tightness. And my eyes had been squeezed shut for so long I was beginning to see spots.

“Does this always take so long?”

“Not usually. But the, um, raw material is a little different in your case.” I could hear the smile in K’s voice.

“OK, but can you tell me about how much longer?”

“Just a little more - almost there. You’re doing great.”

I felt another tickling sensation on my eyelids.

“Okay. Let me see those baby blues!”

“Wow. This feels so weird. I feel like my eyelashes gained about 20 pounds each.”

“Yup, makeup will do that. Okay, let me take these curlers out. Sit tight.”

Her hands flew around my scalp, the tightness dissipating bit by bit. I thought I saw a stray blonde curl, but chalked it up to my imagination.

“Last one. Let me just fluff this out really quick, then we can get you dressed and make some adjustments to it.”

She stepped back a moment later, eyes wide.

“Um… I need to make a call in the other room, okay? I’ll… be right back.”


How did I let myself get talked into this? I thought to myself.

Because you wanted to be talked into this, came the reply.


I wasn’t even supposed to be here. Here being this school. This city. This state. This region.

The school, while excellent, wasn’t my first choice, or even in my Top Five. I desperately wanted to go away to school. This was the first sign of a restlessness, a nagging discomfort that I wasn’t where I should be, or doing what I should be doing, that would become a recurring theme in my life.

Although I’d managed to get accepted to the schools I wanted, there had been a glitch. My high school guidance office had misplaced my financial aid paperwork. In the pre-Internet era, this had serious repercussions. By the time they realized it, the submission deadlines at my top choices had passed.

In retrospect, I should have followed my instincts and taken a delayed admission, which would allow me to re-apply for financial aid. But my parents wanted me to start right away, and – another recurring theme – I wanted to make them happy. So I went with the local school.

Because I’d accepted so late, I was living at home, necessitating an hour-long commute each way. I also worked full-time on top of a full class load. This limited my social life, which didn’t bother me all that much – I was a loner, as my guidance counselor told me. (“Not that that’s a bad thing,” he hastened to add, with the slightly perplexed look of a natural extrovert dealing with. J)

It also meant that I had very little free time – something I’d discovered was perilous. Free time meant I had time to…. think. About stuff that I really, really didn’t want to think about.

For instance, like most teenage boys, I was obsessed with girls. But I always knew something was... off about the way I was obsessed with them. I couldn’t place my finger on it for the longest time, until I finally realized that I was both attracted to them and jealous of them. Because they had what I didn’t dare admit I wanted. What I was supposed to have. Long hair. Breasts. A vagina.

Also like most teenage boys, I had dreams about girls. Powerful dreams. Only in my dreams I also had breasts, and a vagina, and was having sex with them as a girl. I would wake up drenched in sweat, feeling terribly confused, troubled, and (to be honest) thrilled, all in almost equal measure. But I quickly realized that none of my friends were having dreams like this.

Similarly, I bit my tongue many, many times when I’d be hanging with my friends, and the de rigeur mixture of braggadocio, homophobia, and misogyny would start up. Especially once the alcohol let loose their inhibitions. They didn’t really feel that way – most of them, anyway – so I always wanted to ask why they felt like being a guy meant being a pig. Maybe they did it because they thought that was what being a guy meant, and never paused to think about whether that was something they actually believed. Or maybe they did think about it, and decided the safest course of action was to just go along. But, again, I didn’t – because I knew the consequences. So I filed it away with all of the other thoughts I had over the years, thoughts I could barely admit I was having, let alone talk about or, even more frightening, acting upon.

The key was control. The stakes were too high to risk ever giving it up. That meant keeping most of my thoughts to myself. It meant avoiding alcohol and drugs – not that I was the type to indulge in them anyway – lest I slip up and let everyone see who I really was. I resolved that the best way to prevent this from happening was to stay in a state of perpetual activity.

So I carried a full course load. And worked a full time job. (In fact, I worked part-time my first two years in high school and full time my last two years, and all four years of college too, as it turned out.) And took an internship. Simultaneously. My secret hope was that I would be so busy that one day I’d realize that these thoughts had just... gone away. If constant motion, chronic exhaustion, and self-imposed isolation were the price I paid, well, so be it.


As part of the required course load, freshmen had one elective class. I wound up taking Contemporary Architecture, mostly because it enabled me to get all of my classes over with in three days, the better to squeeze in more hours working. In addition to being an excellent course, I was the only freshman in the entire class; everyone else was a senior.

I wound up striking up a conversation the first day with a senior, E, who was a nursing student and had family in my hometown. When the professor asked us to form groups to work on a semester-long project, she was nice enough to invite me to join her group, which consisted of her roommates – also seniors, also nursing students, and also beautiful. Since I didn’t know anyone, being a freshman and a commuter, I accepted gratefully.

Needless to say, they were light-years ahead of me socially, being four years younger, chronically shy, and pretty much a social misfit. I still remember how my eyes nearly popped out of my head when E met me at the door for our first meeting wrapped in a towel and nothing else. She just laughed and asked if I’d never seen a towel before. (Not worn like that, I hadn’t.) I wound up becoming a sort of mascot for the rest of the group, as they figured out pretty quickly how much I needed to learn socially. (Four years at an all-boy school will do that.)

One crisp late October day, I panted as I sprinted to their apartment, late for our weekly meeting. I knocked at their door.

“It’s open – come in.” I heard E call from inside.

I walked in, launching into a semi-coherent apology for my lateness, explaining the perils of the local commute. After a few moments, I realized they were all looking at me strangely.

“I’m sorry… is everything OK? Was I supposed to bring something?”

E looked at C.

“So, what did I tell you?” C nodded.

“You’re right.” She turned to me.

“How tall are you, L?”

“How tall? Um… five feet, seven and a half inches.”

“What do you weigh? And what’s your waist size?”

“Uh, I don’t know… 140, maybe? (I was being generous.) And I guess I’m a 30” waist. Why?”

E, C, and D looked at one another.

“This could definitely work.”

 I must have looked completely baffled, because E glanced at me and laughed.

“Sorry we’re being so cryptic. Tell me, what are you doing for Halloween?”

“Hadn’t really thought about it, I guess. Why?”

“Well, we were thinking you could come with us to our sorority’s party.”

“Oh. Well… wait a minute. How am I supposed to go to that? I mean, it’s…”

E looked at me, smiling wryly.

“All girls?”

“Yeah. Guys can’t go.”

Again, silence as they looked at me expectantly.

I felt a chill down my spine – equal parts terror and hope.

“Wait a minute. Are you saying…?”

E nodded. “You can go as a girl? Yup. That’s exactly what we’re saying. With the right makeup and clothes, you’ll look really cute!”

“You’re serious, aren’t you? Makeup? A dress? No way. Uh-uh.”

E walked over.

“C’mon, it will be fun! My sister K is a professional makeup artist for the H- Theatre Company. She already said she’d do it. She’s really looking forward to it, in fact! I think you two would hit it off. She likes U2 and R.E.M. and all those new groups you always talk about.”

“Oh great. I’ll look like one of those chicks with the horned hat on her head, bellowing about Tristan and Isolde, or whatever their names are.”

E giggled.

“First of all, that’s opera, not theatre. And no, she won’t put make you look like a clown, I promise. She’s really talented.”

She paused.

“We really do think you’ll look cute. And we also think it would be cool that a boy would be willing to do it.”

I was tongue-tied. Having one of your deepest most hidden desires handed to you on a silver platter by three gorgeous college seniors will do that, I suppose.

E mistook my stunned silence for indecision. She moved even closer, started rubbing my arm, and locked eyes with me.

“Would you do it for me?”

She smiled.


Unfair Unfair! Using the “do it for me” move. I may have been scared, but I was also an 18-year-old boy who had just escaped four hellish years in an all-boy high school. I could feel a smile tugging at the corners of my mouth, much as I tried to hide it.

“Well…all right, I guess. But I better not look stupid!”

“Yea!” E squealed, giving me a hug. C & D clapped. “This is going to be so much fun!”

I smiled weakly, gulped, and hoped E hadn’t noticed how hard my heart was pounding.


And thus I found myself sitting in E’s living room, hands folded in my lap, with K in the other room whispering on the phone.

She was, as advertised, a professional. We met at E’s apartment the afternoon of the party. We had it to ourselves, as E, C, and D all had classes. She was, if possible, even more beautiful than her sister, but was just as down-to-earth and friendly.

I was visibly nervous – OK, terrified – but she immediately put me at ease. She kept up a steady stream of chatter, about the new bands we both turned out to admire, what I thought of my professors, what my hometown was like… and did it so well that two-plus hours flew by. I even managed to relax a bit.

K had turned around the lone mirror (“No cheating,” she mock-chided me when she saw me glance at it, not realizing I was so hopelessly near-sighted without my glasses that I could barely see her, let alone study her handiwork), so I waited patiently for her return to find out what the next step was. I was dressed in a pair of pink sweatpants and a long-sleeve t-shirt that K had retrieved from E’s closet so my own clothes wouldn’t be ruined. “See? You two are the same size! We’re already half-way there!” she teased me after I’d put them on. I kept blinking, adjusting to the sensation of mascara and eyeliner.

Suddenly I heard the sound of a key in the front door. E bounded into the living room before I could react, shedding her backpack, pocketbook, and coat on the floor in rapid succession.

She looked blankly at me for a moment.

“Oh! Hi. Um, is K around?”

My heart skipped a beat. “Holy s***.” I pointed to her bedroom without speaking.

“Thanks!” She headed off, calling out to her sister.

“Hey K! So where the heck is L?!? I am gonna absolutely strangle him if he chickened – huh?“

K’s reply was all but inaudible.


E emerged from the bedroom a moment later, eyes wide, hand clasped over her mouth, smiling.

“Oh. My. God.”

She shook her head slightly from side to side in disbelief.

“You’re a girl.”

Blood pounding in my head, I attempted to feign indifference.

“Yeah, right. Nice try, E.”

“I’m not kidding. Oh my God. I swear I didn’t recognize you.”

K was behind E now.

“E, slow down. She hasn’t seen herself yet.”


E grabbed my wrist and pulled me up, dragging me to the bathroom.

“C’mon! Time for the grand unveiling!”

K was behind us, protesting.

“Wait! Hold on a sec!”

E ignored her, in true sister fashion. She turned on the bathroom light and pulled me in.

“Ta-da! It’s the new you!”

I stared at my reflection, disbelieving.

She was right. I was a girl.

K was, as advertised, an expert at makeup. My hair had gone from straight light brown to curly blonde. What’s more, I couldn’t even see L when I looked at my face. I tried to place who I seemed to resemble. I sort of looked like… like…

E blurted it out.

“Madonna! She looks just like Madonna! Wow. We are going to have to beat the guys off you with a stick!”

I was having trouble catching my breath. I shook my head violently. Blonde curls bounced in front of my eyes.

“Nope. That’s it. I’m done with this. Take this crap off. I’m out of here!”

K glared at her sister, exasperated.

“God, would you please stop for just one freaking minute?!? You’re scaring her!”

“AND STOP CALLING ME ‘HER’!” I shrieked.

My legs were suddenly wobbly. I swayed slightly.

K moved to my side.

“Are you OK? Do you need to sit down?”

I nodded. She and E helped me back to the living room couch.

“E, get a glass of water, would you?”

“But – “

K just looked at her.

“Please. A glass of water. OK?”

After a moment’s pause, E nodded and headed for the kitchen.

K rubbed my back gently.

“I’m sorry if we upset you. E didn’t mean any harm. She’s just… dramatic.” She shook her head and rolled her eyes. “That’s who I was trying to call before she got back here. But she beat me to the punch.”

E came back with the water and sat down on the couch.

“Here you go.” She paused.

“Please don’t be mad at me. I wasn’t making fun of you, I swear.”

I sipped the water.

“I know you weren’t. I’m sorry I freaked out.”

“It’s OK. I don’t blame you, actually. That must’ve been quite a shock when you saw yourself.” She gestured at K. “I forget sometimes how good she is at her work.”

K said, “Well, it helps when the model is a cutie, like today.”

I could feel my face turning red.

E crinkled her eyes in amusement. “Boy, I thought I blushed a lot!  Oops. OK, no more teasing, I swear.”

She looked again at K, and then turned back to me.

“If you don’t want to go, I totally understand. But I really hope you will. I think it’ll be a lot of fun. Heck, we already did the hard part, right?”

I didn’t say anything. I was torn.

K spoke up.

“If you want, I’ll come too.”

I looked at her gratefully.


“Mm-hmm. And you have my word we won’t let anyone bother you.”

E’s eyes widened.

“But I thought you had plans?”

She shook her head.

“It’s fine. This will be a lot more enjoyable than another boring fundraiser.”

E and K looked at each other for a moment, then E turned back to me.

“Well, I guess it’s settled then! Time for you to put on your outfit. Hope you like mini-skirts and leggings there, kiddo.”

“And crucifixes. Don’t forget crucifixes,” added K.

I sighed.

“Well, there goes ten years of being an altar boy down the drain in one night. This better be worth the extra time in Purgatory.”

“You’re a Red Sox fan, so technically I think you’re already in Purgatory.”

“Good point.”


E & K were right; the party, as it turned out, was a lot of fun. Vanity won out, as it’s prone to do, so at their urging I left my glasses behind at E’s apartment. As a result, I really did need K, E, et al to watch out for me so I wouldn’t walk into walls or in front of oncoming traffic. And I did get asked to dance several times – but other than the first request, all were from girls, oddly enough. (I did dance with the girls.) Alas, as it turns out, having two left feet is unaffected by how you present yourself to the world.


Late that night, we made our way back to E, C, & D’s apartment from the party. E, C, & D were a bit tipsy, while K and I were both teetotalers – she as the designated driver, me by choice. (I didn’t dare lose control like that.) As we pulled into the parking lot outside the security gate, I said good night and started to head for my car.

“Where are you going?” E asked.

“Well, I’m going to head to a motel somewhere so I can take all of this off. I promise I’ll bring it back on Monday.”

“You don’t have to leave. It’s almost 2:00 am. Just stay with us.”

“But this is girls-only after 11:00 pm.”

She looked me up and down, eyebrow arched.

“Oh. Right. Well in that case, I accept.”

Once inside, K waited until E, C, and D called it a night, then offered to remove my makeup.

She worked in silence for a few minutes as I watched her progress in the bathroom mirror.

“Can I ask you something, L? And you don’t have to answer if you don’t want to.”

I nodded. “Sure.”

She hesitated for a moment.

“So… how did it feel to be dressed up like this tonight?”

“I’m not sure I understand.”

She paused again.

“I know I just met you today, so I’m trying not to be pushy. But… did dressing like this… um, excite you? You know…”

“Oh. You mean, did it turn me on?”

She nodded.

I thought about it for a moment.

“Honestly? For a little bit, right after I saw myself. But then, after a while, I sort of… forgot, I guess. It just felt…”


I looked at her reflection in the mirror.

“Yeah,” I said, surprised at my answer. “Exactly.”

She nodded again. “That’s what I thought.” She paused once more. “I’m trying to phrase this the right way. You looked… well, did you see some of the other guys that came in drag?”


“How do you think they looked?”

“Um, like guys in a dress.”

“Right.” Another pause. “Do you think you were different from them?”

“Well, sure. They didn’t have you helping them.”

She smiled. “Thank you. But that isn’t what I mean.”

She put down the cotton swab she was holding. Her dark eyes were wide and earnest.

“I guess what I’m trying to tell you is… it’s OK to enjoy this. There’s nothing wrong with it.”

“I know. It’s Halloween.”

She smiled again, kindly.

“Again, that isn’t what I mean. And I think you know it.”

I looked down, unable to meet her gaze.

She put her hand on mine. “This is important. So I want to say it again: it’s OK to like this. You don’t have to be afraid.”

As it had so often in the past, the familiar flutter appeared in my stomach. My eyes began to water, but I held it all back. Again. But this time, just barely.

“Thank you.”

“You’re welcome.”

“I… I’m not sure…” I looked down, staring at my hands. I started to speak again, then lapsed into silence.

K rested her hand on mine. And so we sat, for what seemed like an eternity. She finally picked up the cotton swab again and began to daub at my eyes. She glanced out the window at the slowly brightening sky.

“Look at that. It’s a brand new day.”

Not a huge Madonna fan, but this was pretty obvious. :c) And it is a pretty good tune too (although I prefer "Into The Groove").


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