An idea occurred to me as I stood naked in the women’s change room next to that warm running shower: if I acted like I wasn’t embarrassed, maybe Miss Barrett would become bored and this whole thing would end without much of a climax. They gave the same advice to victims of bullying: pretend like the bullies aren’t bothering you and they’ll move onto someone else.
So I shaved my legs and the few little hairs I had growing on my chin, and I even shaved my armpits, and I made sure there was no stubble anywhere. I took Miss Barrett’s stupid moisturizer and I coated my whole body in it, making me smell like a girl, and then I slipped back into my clothes and started back towards her classroom. Before walking through the door, I took a deep breath. I was going to be the one with a smirk on my face. I wasn’t going to let her enjoy this.
“What now?” I said as I walked through the doorway with my back straight and my chest out. I took my seat and made my biggest smile.
She looked at me curiously. “Let me see your legs,” she said. So I pulled up my pant leg. She nodded her head. “Looks pretty good. And I assume you got your crotch, too? A good girl keeps her crotch nice and tidy.”
My heart coughed and stuttered. “I got that too,” I said, somehow without my voice cracking. And it was true—I shaved around my cock because it would have looked awfully strange otherwise, with my thighs all smooth.
She handed me the dress. I grabbed it and then I got up to head to the bathroom. But I stopped at the door, remembering the boys’ basketball practise—and not to mention all of the other students who were still lingering around the school, in detentions, in chess club, in debate club, and students who just stuck around to finish their homework because they didn’t want to do it at home for whatever reason. I couldn’t walk that hallway in a dress. So I looked around the classroom and I spotted that little closet. Maybe I could change in there…
“You can change right here,” Miss Barrett said, motioning to her classroom. “It’s nothing I haven’t seen before.”
“I’m not changing in front of you,” I said.
“Okay. Your other option is to go to the change room. Try to be back in five minutes.” She took a seat at her desk, once again with that big smile on her face. I went to the closet and I tried to figure out a way to make it work, but it was too small; I couldn’t fit. So, with a sigh, I changed in the corner, with my back to her. I got down to my undies and then I slipped the dress on. I pulled my boxers down under the skirt of the black dress and then I pulled the panties up. I hated the way that tight lace felt against my crotch. It seemed so unnatural, so taboo, and so degenerate. I straightened the dress and then, after another deep breath, I turned back to Miss Barrett.
“How do I look?” I said with a grin, spinning in a circle, holding the skirt of my dress up as if I was about to do a curtsy.
“You look surprisingly lovely,” she said with an even bigger grin. I looked down at myself and couldn’t help but notice my legs, which really did look feminine. The fact that they were hairless helped, but there was something else about them—something I couldn’t put my finger on. Maybe it was the fact that I didn’t have a lot of muscle. I’d always been thin and a bit soft. Or maybe it was the moisturizer, making my skin shine. Or maybe it was the fact that I had small feet. Girls tend to have smaller feet, right?
I looked away, feeling my face turning red. I bit down on my tongue and forced that grin back onto my face. I couldn’t give her anything—I couldn’t let her mock me the way she clearly wanted to. “So what now?” I said.
“Now let’s get that wig on. And the shoes—and don’t forget the stockings. I think they’ll look super cute on you.” So I took all of the items and I got them on. I was tempted to just slap the wig on my head and make a joke. It would have been less embarrassing if I could have joked around, but I didn’t want to give her an excuse to change her mind about my punishment. I was getting off easy and I needed to keep it that way.
The stockings were tight on my legs, but they looked sleek. The wig was a snug fit. Miss Barrett came up to me once it was on my head and she ruffled it up and adjusted it until she said, “That looks good—just like that.” There was no mirror in the room, so I had no idea if it actually looked good or if it just looked like a silly Halloween wig. Though the hair felt soft and far more realistic than any Halloween wig I’d ever felt. Maybe it was real human hair? Maybe Miss Barrett had gone out and spent a small fortune on the thing.
And the shoes—my feet may have been small, but they weren’t as small as any of the girls’ feet in my class, so why did she have them? Were they her own? Did Miss Barrett have large feet for a woman? I found myself looking, but it was impossible to tell without actually seeing the side printed on the sole of the shoe. So I could only assume that she’d gone out and bought a new pair of shoes specifically for my humiliation.
I wobbled in the heels at first, but I got used to them quickly. They weren’t nearly as uncomfortable or difficult as women always made them out to be. Miss Barrett had me walk a lap around the room. She watched me with a big smile on her face, and I didn’t give her any embarrassment to fuel her revenge. I just kept a straight face, playing along with a smile, but not smiling big enough that she would think I was making a joke out of her punishment.
I caught a bit of a reflection in her window as I walked by. My body actually looked a little bit convincing—as if I was a flat chested girl. But surely any thin guy can put on a dress and have his body look a little bit convincing. Though I had to admit: my hips seemed to be wide in a feminine sort of way, the way a man’s hips shouldn’t be. Maybe it was just an illusion from the pattern on the dress, or maybe it was just some distortion in the glass.
“What now?” I asked.
She threw her finger up into the air, pointed straight. “I don’t want to hear that voice anymore. Now I want to hear your feminine voice. I want to hear Jacqueline’s voice.” Apparently that was me—apparently I was Jacqueline now. The name made me shudder, even though I didn’t mind it. It had a nice ring to it. I’d always liked the name Jacqueline, but not for myself. I never wanted any female name for myself. But if I had to have one, Jacqueline was just fine.
I cleared my throat and did my best female impression. “What can I do now, Miss Barrett?” I knew it sounded ridiculous. It even made her laugh and shake her head.
“Now you need to practise. I’m giving you homework.” She walked over to the closet and fished out another white plastic bag. “Tonight, I want you to learn how to do a basic makeup look. I’ve written down some helpful websites with great tutorials. Spend at least an hour working on the skills. Tomorrow there will be a little test, and if you fail, then I’ll be bringing your paper to the principal.” I felt my heart clenching tight as a nausea filled my stomach.
I wasn’t out of the woods yet. I didn’t just have to play along with her little game; I needed to pass her little game. But a second chance is a second chance—and I wasn’t about to waste it. So the first thing I did when I got home was lock myself in my room. I told my mom that I wasn’t feeling well and that I didn’t want any dinner. I wasn’t happy with just my door locked, so I also dragged a chair in front of the door, for extra security, and of course I closed my blinds.
I got my bag of makeup all unpacked on my desk and then I navigated to the first website on Miss Barrett’s note. It was a video of a young woman explaining how to do the basics: mascara, eyeliner, eye shadow, blush, and so on. It was all straightforward enough. Though I have to admit that it showed me how to properly roll the mascara onto my eyelashes. I tried it right there in my bedroom, and my first attempt wasn’t so bad. But the girl in the video made the eyeliner look easy, so I was surprised when I went to draw on a straight line and I didn’t even come close. I looked around for a tissue to wipe the eyeliner off with, but a tissue didn’t do the job. I scrubbed my eyes hard, but the eyeliner wouldn’t come off.
I needed water, but I had none. The bathroom across the hall had a sink, of
course, but that meant running across the hall while my parents were still away. And I didn’t want to risk having my parents see me wearing eyeliner like a little sissy. But I couldn’t have Miss Barrett fail me. I needed to wash my face so that I could keep practising. I needed to ace my makeup test, which was only about eighteen hours away.
So I opened my door and I casually strolled across the hallway, pretending to rub the sleep out from my eyes with one hand while holding an empty glass with the other hand. I could feel the glow of the living room television on my face, and I could hear my parents chatting. I fought the urge to look over, to see if they were looking my way. I’m sure one of them glanced over at me, and if I would have looked over at the same moment, that would be it for me.
I slipped into the bathroom and closed the door. I quickly ran the sink and started scrubbing my face. I watched as the water swirled black down the drain. And it wasn’t the last time that night. Every forty-five minutes or so I needed to restart, to get a bit more practise, even when I managed to nail the style. I wanted to go into my makeup test with confidence. I wanted to know that I was going to pass. I didn’t want to rely on a fluke. So I just kept practising, going back and forth to the bathroom. I finally went to sleep around 3:00 AM.
CHAPTER V
Miss Barrett waited for the class to empty out before walking over to the door and turning the lock. She turned to me and said, “Get your makeup out on your desk.” And then she went to the closet and retrieved a two-by-two foot mirror that had a little stand. It was a bit of a tight squeeze on the desk, but it fit there with all my makeup. She looked at her watch and said, “You’ve got thirty minutes to impress me,” and then she pressed a button.
And I used everything I had. I drew on every tutorial and every little tip I learned from my own experience. I was especially careful drawing on the eyeliner. That little marker was so finicky. My heart was pounding the whole time. Miss Barrett didn’t keep a clock in her classroom, so I had no idea how much time had elapsed. It could have been four minutes, it could have been twenty-nine minutes. But I couldn’t allow myself to rush—I had to do it right.
When I was finally satisfied with my look, I stood up with a big smile on my face. I knew I’d done a good job. I knew I was going to pass her little test. “All done,” I said in my feminine voice, with my glossy lips curved into a big smile.
She looked at her watch with a grin on her face. “You’ve got ninety seconds left,” she said.
“I guess I’m done early,” I said.
She looked me up and down slowly and then said, “But you’re not even wearing your dress or your shoes—and your hair isn’t done.” My heart suddenly leapt up into my throat. I noticed she had my whole outfit laid out on a nearby desk. I sprung into action, not wasting another second. I fought my thin body into that little dress and then I battled those little shoes onto my feet. I saved the wig for last, bringing it over to my little makeup station and ruffling it up until it looked real. I was fixing a rogue strand when Miss Barrett said, “Time’s up! Hands off the hair.” She walked around me slowly, looking closely at every part of me. She mumbled something to herself and nodded her head slowly. “I think that’s a pass,” she said. “Though there’s still lots of room for improvement. Tomorrow I won’t be so lenient.”
I had a coating of cold sweat on the back of my neck. I was strangely out of breath, but I couldn’t fight the smile from my face. I’d done it—I’d survived another day. I was one day closer to being a college student.
But my day with Miss Barrett wasn’t over. She had more tasks for me—more lessons and more practising. We did a whole hour of walking back and forth in heels. Miss Barrett’s voice echoed in my head for the rest of that night: “One foot in front of the other. Move with your hips. Keep your back straight. Stop slouching! You aren’t stepping with one foot in front of the other,” and so on. But the tips were good ones. I could see my reflection in that classroom window, and by the end of that hour, I really was walking like a woman. It turns out, mannerisms can be learned, even feminine mannerisms.
I was more exhausted after that one hour than I’d ever been after an hour of gym class. Being a woman is surprisingly exhausting—physically and mentally. Your mind has to be firing at all times. There’s so much to remember, constantly.
“Tonight, I want you to keep practising your makeup. I want to see a different style tomorrow. And starting tomorrow, I’ll be marking you on more than just your appearance.”
I smiled and nodded my head and then she let me go. I darted from her classroom to the women’s changing room down the hall, so I could wash the makeup off of my face. Thankfully, there were no students or even teachers around that late—but I wasn’t about to let my guard down. It would just take a single straggler to ruin my whole reputation—just one student who came back to get a book he forgot in his locker.
I scrubbed every last bit of makeup off of my face and then I went home to put some more makeup on. And this was how it went for the rest of the week: long nights practising my mannerisms, voice, hair, and makeup, and long detentions, being tested, absorbing lectures. It was surprisingly hard work—possibly the hardest work I’d ever had to do in my academic career. But I had to do it; I no longer had any other choice if I wanted a shot at college.
Miss Barrett let me take my wig and outfits home for the weekend. Before I left her classroom that late Friday afternoon, she said, “And this weekend I’m giving you a special assignment. I want you to go out, with your whole ensemble. I want you to go downtown and take at least five different selfies in five different places—interior and exterior. And I’ll tell you what—if you can get a man’s phone number, I’ll give you extra points.”
The bus ride home that afternoon was long. I found myself staring blankly out the window, feeling my heart churning in my nauseous stomach. She wanted me to go out dressed like a woman? Not just out, but downtown, which was a fifteen-minute bus from my house. So that meant walking through my neighbourhood in a dress, taking a bus in a dress, wandering around downtown in a dress, and then not to mention the whole trip home.
When I got home, I immediately started to think of ways I could get out of the task. I’d taken a Photoshop class at school the previous year. Maybe I could get dolled up and take selfies in my backyard, and then Photoshop myself into downtown pictures I could take while in my regular guise. Would Miss Barrett ever be able to tell? Were my Photoshop skills good enough? Probably not, but I had all weekend to work on them. I could watch tutorials and take my luck… Or I could just get dolled up and do the task. How likely would it be that I end up running into my friends? And even if I did, would they recognize me?
CHAPTER VI
It was Saturday morning and I was sitting on the bus with very little sleep, but I was more alert than I’d ever been in my life. My legs were cold—my thighs were exposed to fresh January air for the first time, probably ever. I could feel that cold air all the way up to my ass, which was a strange feeling to say the least.
It was only 7:00 AM. I’d already been awake for two hours. My plan was to get downtown before anyone was awake: snap my five photos and be done with the terrible task. I nabbed one of my mom’s old purses from the basement, and now that purse was stuffed with my masculine clothes, which I planned on changing into in a public bathroom, the moment I had my five selfies.
When I set my alarm for 5:00 AM, I figured it would be early enough to beat the general public, but it wasn’t until the bus was pulling up to the bus stop that I realized I would have to face the bus driver. He was a younger guy, only a few years older than me. He stared at me as I stepped onto the bus and handed him my fare. He smiled, making my heart stutter. I looked into his eyes and he looked away quickly, as if he could tell that I wasn’t actually a woman. And of course he could tell, because I wasn’t actually a woman. It was obvious—wasn’t it? My body may have looked feminine all shaved and smooth and in that dress, but what about my face? Surely my face looked ma
sculine, even with all the makeup… But he didn’t say anything. He just waited until I was sitting and then he started towards the next bus stop.
I sat next to the window, and I could see my reflection in that window. I stared at myself, trying to figure out if it really was obvious that I was a man. My eyes looked impressively feminine surrounded by eyeliner, and my cheekbones were surprisingly prominent. What part of my face exactly did I think looked masculine? My lips were full and my facial features were all soft. Growing up, girls were always telling me that they wished they had my nose and they wished they had my eyelashes—so I knew those weren’t my most masculine traits. But what exactly did that leave?
I caught that bus driver looking my way a few times throughout the ride, checking me out at each stop through his big mirror. Was he mocking me, or could he really not tell? I couldn’t decide what was worse. I sunk into my seat, and then we crossed the bridge into downtown.
It was my chance to get my first selfie. I was downtown and technically indoors. So I pulled my phone out from my purse, I held it up, and then I snapped my first shot, smiling. I took a few more shots, trying to get a more flattering picture. The one I liked best had my tongue out and I was winking. It was a bit goofy, but I looked pretty. Miss Barrett would approve.
The bus’ back door wasn’t working, so I had to walk past the driver again to get off. I felt his gaze scanning my body as I stepped past him. I was too afraid to look back and see if he was laughing or drooling. I didn’t want either but I knew he was doing one of those things.
He was slow to pull away, but I never looked back. I found myself on the side of the street, looking around, wishing I wouldn’t have taken so long getting my hair and makeup perfect. The streets were already busy: couples out getting breakfast, girls walking home after their one-night-stands, guys trying to find caffeinated cures for their hangovers, and the go-getter businessmen, trying to get an edge on their co-workers. And then there was me: out to get a few selfies.
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