That bus stop was as good a place as any. I took out my phone and held it out, making sure to get the big, pretty buildings in the background. I snapped a few shots, and then I heard a voice yell “Instagram!” I spun around and saw a young man wearing big sunglasses, sitting in front of a café with a steaming mug in his hand. He waved at me. I forced a smile back. “What’s your name? I’ll follow you.” He had a big grin on his face. And once again I found myself trying to decipher whether the grin was him mocking me, or him admiring me—and I still hated both the options.
As I was going through the pictures I just took, I noticed a man in the background, looking my way. In one photo in particular, it looked like he was staring right at me, looking down at my ass. I spun around to see if I could spot the man, but he had already disappeared. A chill ran down my spine. I’d only been out in the open for a few minutes and I was already getting more attention than I wanted. But I already had two of my five pictures. I figured I could walk a few blocks snapping photos along the way—then I could grab a coffee, snap a photo in the café, and then maybe zip through the mall, snapping another few photos along the way. Then my task would be done and I could go home.
A strong gust of wind lifted up my skirt as soon as I started walking. I threw my arms down to hold my skirt down, and then I accidentally dropped my purse on the ground. I bent over to pick it up and that’s when I heard the whistling behind me. I looked back to see three guys looking my way with big smiles. I was starting to see why girls were always complaining about sexual harassment. It was surprisingly exhausting—and not to mention discouraging. Every whistle and every catcall and every little glance was just more proof that I was passing as a woman. Miss Barrett was getting the humiliation she wanted. My confidence was nearly non-existent at this point. No young man wants to discover that they make a more attractive woman than they do a man.
I’d never been hit on as a man before. No girl had ever whistled at me from down the street, and no girl had ever shouted a compliment at me. But now, I couldn’t go a single block without getting some kind of attention.
My outfit didn’t help: a short black dress with tall white stockings. It was a sexy outfit. I would have stared at a fit girl walking around wearing the same thing, so I couldn’t blame any of the hungry gazes that were fixated on me now. But that didn’t mean that I liked them, or that I approved of them. I just wanted to get my stupid pictures so I could be done with this torture.
I snapped a couple of photos every block. I already had plenty, but I still needed a bit more variety to ensure I passed Miss Barrett’s assignment. So I slipped into a café and waited in line. While I was in line, I snapped a couple more photos. I quietly ordered myself a coffee, worried my voice would attract too much attention. Maybe my face and body passed the test, but I knew that my voice wasn’t terribly convincing, even when I was at my best. It was one thing to let the barista know that I was actually a man, but I didn’t want to let the twenty other people crammed into that café know my secret.
But even the barista didn’t flinch. She took my order and then she made it, as if she couldn’t tell there was anything off about me. Maybe she was used to getting trannies, or maybe she couldn’t tell, even after hearing my voice. My gut turned as I waited for my order. I wanted to just get a black coffee, but I figured I would stay in character so I ordered a pumpkin spice latte. Unfortunately, a pumpkin spice latte takes much longer to make than a simple cup of coffee, so I ended up having to stand in my little dress, surrounded by people, for nearly ten minutes. And the whole time I could feel the gazes of men and women alike. Still, I had no idea if they were mocking Jake or if they were admiring Jacqueline. I was relieved when my latte was done. I grabbed it and got out of that café in a heartbeat.
The pumpkin spice latte was super tasty. I’d never had one before because I always thought they were too embarrassing to order as a man. So in a way, I’d found the first little perk of being a lady: being able to indulge in feminine treats like pumpkin spice lattes. It was only a few minutes later when I discovered another perk of being a lady.
As I approached the mall entrance, a man leapt in front of me and grabbed the door. He pulled it open and moved aside. “After you,” he said. I felt my cheeks turning rosy. No one had ever gone out of their way to open a door for me before. I hid my face to the side as I passed him, worried he would see that I was really a man and then slam the door into me. Though I was starting to think that no one could tell that I wasn’t actually a woman. I was starting to think that I was tricking the entire downtown population of my city. I was starting to think that the tickling gazes of men on my back were gazes of admiration, men fantasizing about me the way that I often found myself fantasizing about the cuter girls in my classes.
A warm buzzing crept down my spine. I should have been more upset about the revelation, but it was nice to know that all of my hard work wasn’t for nothing. I’d spent two hours that morning doing my hair and makeup. I’d spent the whole week working on my makeup skills and my mannerisms. It was kind of nice to see all of that work coming to fruition.
I walked through the mall for five minutes before stopping to take another selfie. I made sure to get lots of people in the background, so that Miss Barrett would know that I didn’t just sneak around the unpopulated parts of the downtown core. I was doing exactly what she wanted—putting myself into a vulnerable position, going where I was most likely to be found out and humiliated. And I made sure I was smiling in every picture, as if I didn’t care, as if the task didn’t bother me. I tried to tell myself that it was true: that it really didn’t bother me. I didn’t just want Miss Barrett to think that her torture wasn’t bugging me, I really didn’t want her torture to bug me.
And this task, designed to utterly humiliate me, was only making me more comfortable, ruining Miss Barrett’s master plan. So even when I wasn’t snapping pretty photos of myself, I found myself walking around with a smirk on my face. I found myself basking in all of the glances I was getting from strangers. I watched as a woman smacked her husband after catching him looking up and down my body. If only he knew he was checking out a man. I tried not to laugh. I’d become a trap. I was no different from the transgenders who walked around town, except I was probably more convincing than most of them. And in a weird way, it felt good.
CHAPTER VII
I had Sunday off. I’d finished all of my homework and I was confident in my makeup abilities, in case Miss Barrett decided to toss another surprise test my way. All of my friends were busy, unable to hang out, so I was stuck at home, trying to think of things to do. I tried playing video games for a while, for the first time in a few weeks, but I quickly lost interest. I felt like there was something more important I should have been doing, but I couldn’t figure out what.
I assumed I still had some lingering stress from the whole Miss Barrett debacle. So I figured it was probably best that I do some studying for her class. I went over all of my notes, and I was about to go over them a second time but that feeling was still there—as if I wasn’t doing what I was supposed to be doing.
And that’s when I realized that I was still stressed out about my feminizing detention, worried that I hadn’t done enough to impress Miss Barrett. Because it didn’t matter how well I did in her class. If she wasn’t satisfied with my feminization, then she could still fail me for plagiarizing that paper. So I decided to spend a bit more time working on my makeup skills, practising voice inflections, and watching cross-dressing tutorials online. And then I remembered the little bonus she offered: get a boy’s phone number for extra points.
I thought about faking a phone number, but I knew Miss Barrett too well for that. I knew that she wouldn’t just look at a phone number on a piece of paper and assume that it was legitimate. I thought about calling a friend and getting him to help me out, but I could think of ways that could go sour too—and I didn’t exactly want to involve any of my friends on my embarrassing situation. So that only left one
option: go out and try to get a guy’s phone number.
It was around 1:00 PM and my parents had just gone out to the movies. I had the house to myself for at least a couple of hours—more than enough time to get dolled up. I slipped into the bathroom and I started with my makeup. I went with a sexy look that I’d been meaning to try out for days. It was a look I saw online that I fell in love with. It was so pretty, and it actually looked super cute on me too. I used my mom’s hair crimper to give my wig a bit more texture, and then I even nabbed a little bottle of blue nail polish and did my nails. I made sure there was a bottle of nail polish remover before I committed, of course.
The streets were busy with families on their way home from their churches and their brunches, so I slipped out of the back door and went down the alleys until I was a few blocks away from home—far enough away from any neighbours who might recognize me. Then I hopped on a bus and headed downtown. I got my first smile of the day from a well-dressed man sitting at the back of the bus. He nodded his head at me, and I smiled back. I watched as his cheeks turned a shade of pink before taking my seat. Now I was positive guys weren’t looking at me and wondering what a young man was doing in a dress. Now I was sure that I was just another hot girl out on the streets. Once I was able to let go of my ego, it was actually a pretty good feeling.
Getting a phone number wasn’t too hard. I went to that same café that was always so busy. I ordered myself another girly drink, and then I looked around and tried to catch someone gazing in my direction. I found my target: a guy in his mid-twenties, working at a table on his laptop. I sat at a nearby table with a newspaper I snagged from the rack by the cashier. In the span of ten minutes, I caught the man looking my way a few times, always smiling, always with red cheeks. I was hoping he would come and chat me up, but he wasn’t moving from his spot. As soon as I decided I needed to make the first move, my heart started pounding relentlessly, nearly smashing out from my ribcage.
I’d asked girls out before, and I’d been rejected before, so I knew I could handle the rejection (especially because I didn’t actually care if the man liked me or not), but still, the nerves were firing. I wasn’t asking this guy out—I had to convince him that I was a woman, I had to convince him that I was a pretty woman worth dating, and then I had to convince him to give me his number. And I still wasn’t even confident that my voice was fully convincing. But I had to try.
“Hey there,” I said. “What are you working on?”
He looked up at me and his skin was suddenly a shade of red. “A screenplay,” he said, his lips curling into a thinly pressed smile.
“For a movie? Are you a screenwriter?”
He laughed. “If writing a screenplay makes me a screenwriter, then I guess so,” he said as his cheeks turned even redder. “I’ve written a few, but nothing has ever sold—yet.”
“Well that’s still really cool. You look very professional,” I said.
He smiled and gently bit his bottom lip. I watched him closely, trying to decide if he could see through my makeup and my wig, or if he was truly convinced. It seemed like he thought I was a woman. I knew that flustered feeling when talking to a beautiful woman.
“So I assume you like movies,” I said.
“I love movies.”
“I really want to see that new one—you know, the one about that rock band that does drugs out in the woods.”
“The horror movie?”
“Yeah—do you like horror movies?”
He smiled and laughed. “I’m a bit of a chicken, but I still go to see them all the time.” I actually had to admit that he was kind of cute with his red cheeks and his stubble beard. And it was flattering to think that a man in his mid-twenties was flustered with me, an eighteen year old with no relationship experience whatsoever. I stared into his eyes and he stared into mine.
“So are you going to take me to the movie or what?” I said.
His eyes lit up and his lips parted. He became tense and then he snapped out of his strange hypnosis. “Um, yeah. Let’s go. Is it playing now?”
“No, I don’t think it opens until next week,” I said with a grin that I just couldn’t hold back.
“Okay—okay, sure.” He reached into his pocket and pulled out a business card. “Here’s my number. Text me so I have your number. I’d love to see that movie with you. Yeah, totally. Oh, I’m James, by the way—as you can see on that card.”
“Jacqueline,” I said. And I loved the way that name felt flirting off of my tongue. It suited me. It seemed so pretty and so sexy. I left that café with the biggest smile on my face—a smile that just wouldn’t go away, even once I was back home, in my bedroom, out of my dress and wig and makeup.
CHAPTER VIII
Miss Barrett had a look of disappointment on her face as she scrolled through the photos on my phone. I could see that she was looking closely, trying to find evidence of Photoshop manipulation. And then when I handed her the phone number, I watched a grin wipe over her face, and I realized that grin was probably her thinking that she finally had what she needed to fail me. She asked me to e-mail her the photos and then she picked up the phone. I sat patiently while she waited for James to pick up. “Is this James?” she said. “Did you meet a young woman in a café yesterday by chance? No, no, this isn’t her. This is, uh, her friend. I just, um, didn’t believe her. Is she here now? Um, she’s just in the bathroom. Sorry I have to go.”
I watched as Miss Barrett put the phone down with a look of defeat on her face. So I was right: the point of her assignment was to embarrass me and to set me up for failure. She was looking for a reason to give me a zero. She should have just given me a zero when she had a chance, before she went and made up this whole feminization detention. I tried not to show her my smirk when she looked my way. “Is something wrong?” I asked.
“No,” she said. “Nothing at all. He sounds like a nice guy.” She stared closely at her computer screen as she looked through each of the photos I sent her—the five best.
“I only sent five, but I have about fifteen more,” I said.
“Five is fine,” she said. “I like the way you did your makeup.” But she said it as if it pained her to say it. And there I was again, sitting with a smirk on my face, wondering what else she had in store for me. Based on the look on her face, she was out of ideas. She’d thrown everything she had at me and she’d hardly even gotten a rise out of me. The joke was on her now. I just had to survive another week of detention and then another month of her class and I would officially be on my way to college.
The rest of that detention wasn’t any different than the detentions I was used to: sitting at my desk, being told to simply let the time pass while boredom burrowed into my brain. Except this was a little bit more difficult as Miss Barrett made me sit up straight with my legs nicely crossed. “A good woman needs to know how to be patient,” she told me, but I knew that she was just out of ideas. She sent me home without any extra homework or studying.
Maybe I’d hit my feminine limit. Maybe I’d officially mastered the feminine look and the mannerisms—though I felt like I still had a lot of learning to do. I still knew almost nothing about designer clothes and shoes and makeup brands. I still had no women friends to gossip with, the way that girls do—not that I wanted Miss Barrett to introduce anyone else into my detentions. But there was still so much to look forward to, and I was starting to think that it was all stuff I would never get to experience.
When I sat down for Miss Barrett’s class the next day, I was disappointed when she came up next to me and said, “Don’t worry about coming to detention today.” She walked away without even looking me in the eyes. And I wondered: was I off the hook? Was my detention finished early? Had I broken Miss Barrett’s spirit?
I was a bit worried that I’d been too strong in resisting Miss Barrett’s humiliation. Now she seemed bitter, possibly out looking for a new excuse to fail me, waiting for me to slip up again so she could keep me away from college. Maybe I shou
ld have given her a little bit of humiliation. Maybe I should have resisted her game of dress up just a little bit.
It felt weird leaving the school at the same time as the rest of my friends. Terrance asked me if I wanted to come to the mall with him and some other guys, to hit on girls, so I tagged along. I found myself surprised when I saw the line of school busses outside. It had been almost two weeks since I’d last been out of school while the busses were still there.
The mall was crowded with high school kids from the many high schools in the area: girls perusing shops and boys ogling the girls. It was a refreshing change of scenery from Miss Barrett’s bland classroom. It was nice to hang around people my own age instead of a forty-something-year-old woman who hated my guts.
“What about her?” Terrance asked, pointing at a little blonde who was walking in our direction.
“What about her?” I asked.
“Isn’t she hot? Should I ask her out?”
She was cute—maybe a little bit hot. She was wearing too much eye makeup, and her blush was on a bit thick. Also, if I was her, I wouldn’t have worn those green stockings with that off-white dress. Black stockings would have been so much cuter, creating a much better contrast. “Yeah, go for it,” I said.
And then I watched as Terrance froze up as the little blonde walked by.
“Why didn’t you make a move?” I asked.
“I don’t know,” he said, his voice cracking slightly. “Maybe she’s just not my type.” But it was obvious that he’d just become overwhelmed by shyness. And it seemed so strange to me, to be so shy of a girl. She was just a girl—probably hoping a guy would come up and talk to her, probably desperate for a compliment. With all of that eye makeup, she was obviously desperate for a compliment. And if she normally went around wearing mismatched outfits like that one, she probably wasn’t used to receiving too many compliments.
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