Though now I was starting to toy with the idea of going to school as a girl in my head. Would everyone make fun of me? Maybe behind closed doors, but not to my face. Like the gym teacher said: I would be immune if I showed up as a transgender. And then I could spend the next few months dolled up, trying out different makeup styles and wearing different outfits. Maybe those girls would even accept me as a friend, the way they did when they thought that I was gay. Maybe, for the first time in a long time, I could have some friends. The idea brought a smile to my face, but it also brought a churning dread into my gut.
I was actually considering the preposterous idea—or was it an amazing idea? My heart was pounding and I found myself looking once again inside of Aunt Fey’s large closet. I found a plaid skirt and a cute grey sweater. The outfit went perfectly with a tiny pair of black flats. It was the perfect schoolgirl outfit—sure to get the attention of at least a few boys.
My heart stuttered again. Why did I care about getting the attention of boys? Why wasn’t I rejecting this idea like it was some terminal disease? Why did I feel so strangely excited? Maybe because I knew no one knew me. I could make up a new name and then cease to exist five minutes after graduation. As I looked into that closet, I was looking at complete freedom: a life I could do whatever I wanted with, with no repercussions. Maybe it wasn’t such a terrible idea after all.
CHAPTER VI
I didn’t go to school the next day—I still had a few things left to get ready. For starters, I didn’t know how to do my makeup. I had access to a lifetime supply in Aunt Fey’s cupboards and drawers, but I had no idea what any of it was for. And then there was the issue of my hair. Sure, my hair was starting to get shaggy, but it wasn’t feminine. I was going to need a wig.
So I took off for town when Aunt Fey thought I was taking off for school, which was my usual routine. I got to town earlier than usual—apparently I was moving quickly as the excitement tingled through my body. I started my trip at the café, getting my seat in the far back corner. The Internet was slow, but it was good enough to get a few YouTube makeup tutorials loaded up. Once the videos were buffered and good to go, I made my way down to the town’s main strip. I was hoping to find a wig store that was willing to cut me a deal, seeing as I only had forty bucks to my name. But I couldn’t find any wig stores. I guess those aren’t really a thing in small towns.
But I did find a clothing store with a number of mannequins in the front window. One of them had a long, straight strawberry blonde wig. The mannequin reminded me a bit of Taylor Swift, whom I always thought was sexy. So I made that plastic humanoid my target. I casually strolled into the store. It was all women’s clothing, so I quickly felt out of place. The cashier was a young woman with her focus down at her phone. “If you need a hand with anything, just ask,” she said without looking up.
I had to move quickly—but not too quickly. I couldn’t draw any suspicion. I moved towards that window and looked back at the cashier. She was still staring down at her phone. I stepped up onto the windowsill. The mannequin’s pretty hair was within reach. Looked back at the cashier again. Then, I quickly reached my hand out and snatched that hair. It slipped easily off of her head. I stuffed it inside of my coat and then looked back again. She was still surfing the net on her phone.
I walked towards the counter. “Do you sell hiking boots? My girlfriend asked me to pick her up a pair while I was in town.”
She looked up at me slowly. “Hiking boots?” she said. “No—we don’t sell those.”
“Okay. Thanks for your time,” I said. And then I got out of that store quickly, jogging down the street before she realized that mannequin was missing its hairdo.
I ended up running home, cutting the hour and a half hike down to just thirty minutes. I was exhausted when I ran through Aunt Fey’s front door, but I was too excited to take a break to catch my breath. I went straight to Aunt Fey’s room, fetched that schoolgirl outfit, and then I went into the bathroom and started getting undressed. I pulled on that white blouse and then I buttoned up that plaid skirt. I pulled a pair of white stockings up my legs and then I carefully buckled up all of the little straps of those black flats. Next, the wig went into my head. It was a surprisingly snug fit. The bangs hung perfectly over my eyebrows. The colour of the hair wasn’t too different from my natural hair, so it blended nicely with the bit of hair on my sideburns. I shook my head from side to side, watching the hair dance, teasing my shoulders just the way I wanted it to.
I hated that I had three hours of makeup tutorials lined up. I wished they were quicker, so I could get to doing my makeup sooner. I wanted to see the finished product badly, but I knew I had to be patient. Still, I followed along with the tutorials, drawing on eyeliner along with the instructors, and then brushing blush onto my cheeks. I could see the look quickly coming together, and with a bit of instruction and guidance, it was an easy look to pull off. I especially liked the red lipstick, which made my lips look plump and kissable.
I did a little spin in front of the mirror, and then I caught myself smiling. Maybe I shouldn’t have been smiling, knowing that I was cross-dressing and getting myself ready to potentially humiliate myself in front of hundreds of people my own age—but I couldn’t help but feel excited over how pretty I looked. I’d never looked pretty before. I’d never even looked handsome. My whole life, I’d always felt average at best. I’d always felt underwhelming and invisible. But now I felt strangely confident. I knew that I would steal the attention of a few guys before word got around that I was really a guy—if word even did get around.
Maybe I could get through the next few months without anyone realizing my reality. Maybe I would fit in perfectly and have everyone fooled. Hell, maybe I would even like it. Maybe this new feminine guise could be my new me.
A cold shudder ran through my body. Now my mind was getting carried away. I was once again having thoughts that didn’t belong in my head. I was just doing this so that I could pass school without being bullied. I just wanted to avoid a lifetime of flipping burgers—and that’s it. Once I had my diploma in my hands, I would be going right back to being Kenny—where I belonged—back in Toronto. Maybe I would even get that growth-spurt I’d been waiting for by then.
I got myself washed up before the sun started to set. I didn’t want Aunt Fey to see me all dolled up in her clothes and makeup. I kept that schoolgirl outfit stashed under my bed, in my schoolbag. I still wasn’t sure how I was going to get changed in the morning if Aunt Fey was there. I could get my outfit on in the woods on my way to the bus stop—but what about my makeup? Would I have to bring along a mirror and all of the supplies, and hope that Aunt Fey didn’t notice anything missing?
Before she got home that evening, I found a little makeup mirror, so I stashed that in my bag as well. I grabbed the makeup supplies that I needed, and then I spent the next hour practising my voice, right up until Aunt Fey was pulling up in the driveway. I knew it would take a few days before I had the voice nailed down, but I knew that if I missed any more school, I wouldn’t be passing. I already had a ton of catching up to do, so I was just going to have to be especially quiet for my first few days back. That was something I was used to: being quiet in the back of the class.
CHAPTER VII
I couldn’t sleep that night. It was almost 1:00 AM and the house was dark and silent, but my mind was busy and loud. I was running through all of the possible nightmares that I could be facing if I really went into that school dressed like a chick. What if word got around to my friends back in Toronto somehow? What if someone posted my picture online in an attempt to publically humiliate me? What if the kids didn’t really care about the zero-tolerance rule, and everyone just made fun of me to my face? They couldn’t expel the whole school, could they?
I carefully got up around 1:30 AM and got that schoolgirl outfit out from my bag. I took off my pyjamas and was about to put the blouse and skirt on when I noticed my chest lumps were bigger once again. They really were growing, an
d they really were starting to look just like tits. I cupped them and squeezed them. Was I going to need a bra soon? Would everyone in the school think that I was a slut, with my nipples pressing against my blouse? It was too late to raid Aunt Fey’s bedroom for a bra, so I was just going to have to take my chances.
I quietly put the outfit on, along with the wig, and then I laid myself down on the bed. I liked the way the outfit felt. They use softer fabrics for women’s clothes—it’s not really fair. I crossed my legs, rubbing my clean-shaven thighs together. I put my hands behind my head, feeling my soft hair through my fingers. Even alone, without a mirror or a camera, I still felt sexy in the little outfit. And why was it possible that I could feel sexy? Surely that was some sort of faulty wiring in my brain. Men aren’t supposed to feel sexy. Men aren’t supposed to grow breasts either.
I closed my eyes and tried to think of some potentially positive scenarios. I imagined guys ogling me, and girls wanting to hang out with me. I imagined myself sitting with one of those blonde chicks, painting our toenails together while gossiping about boys. I imagined one of the football jocks hitting on me, putting his arm over my shoulders, whispering into my ear as his stubble tickled the side of my face. I imagined myself sneaking into an empty classroom with him. I imagined him bending me over and eating out my asshole before sticking his throbbing erection into my body. I imagined him pumping me until cum was dripping out the tip of my cock.
Then I opened my eyes and saw that my plaid skirt was standing up. My cock had escaped my panties and was now throbbing and begging to be jerked off. Was that going to be a problem? What if I got an erection in the middle of class? A little pair of panties wasn’t going to save me the way a tight pair of boxer briefs and jeans could. If the class saw my skirt standing up the way it was now, then I would surely be doomed.
Thankfully, I was alone in my bedroom. I could do whatever I wanted and no one could see me. So I reached down and started stroking myself. Then I looked over at the tall candle on my nightstand. I suddenly had a naughty idea in my head—an idea that would accompany my little fantasy, in which the football jock is fucking me in the ass in the empty classroom. I reached over and grabbed the candle. I gently sucked on the base, getting it lubricated with my saliva. Then, I reached it down and pressed it between my butt cheeks. I used my free hand to hold my panties to the side. Then, with a bit of cramming and squirming, I got that candle pressed into my asshole. I gasped but managed not to make too much noise.
I took a deep breath and started plunging it in and out. I closed my eyes and pictured myself bent over a classroom desk. I could practically feel his throbbing veins inside of me. I could practically feel his shaft swelling up as he held back his warm, wet orgasm. I gripped the edge of my bed. I was fucking myself quickly, plunging that candle down as saliva squished out from my tight hole.
I had my free hand on my cock. I was jerking myself off quickly, but in my mind, the jock was jerking me off. He hand his big, muscular hand wrapped around my shaft and he was pumping ferociously, desperate to see the steamers of cum shooting out from my cock. And I was close. He was about to get what he wanted. I tried holding back, but the cock in my ass just felt too good. I ended up coming, blasting my load into the air. One shot hit my lips, the next few got my blouse, and then the last few got my skirt. I was covered in my hot load.
I sat up quickly. “Shit!” I muttered under my breath. It was the only outfit I had. I grabbed handfuls of tissues and started scrubbing the cum away. “Shit, shit, shit,” I said. I managed to get the cum out from the skirt with a little bit of water from my drinking glass. I could still feel the dried cum on my blouse, but I couldn’t see it. I just hoped that it would be invisible to everyone else as well.
I finally fell asleep around 4:00 AM, which wasn’t ideal, seeing as my alarm was set for 5:30 AM, so that I would have time to get myself dolled up out in those woods before my bus came. Thankfully, Aunt Fey had a pot of her amazing coffee ready for me when I crawled out of bed. For breakfast I only had time to eat a single piece of toast, which seemed like more than enough. It was the coffee that I really needed.
I took a full thermos with me on my hike towards the bus stop. I walked for fifteen minutes before I slipped off the road and found a private spot in the woods where I could get myself ready. I started with the outfit, then the wig, and then I spent the next thirty minutes perfecting my makeup. I would have liked to spend more time, but I was already behind schedule. If I missed my bus, then there would be no school and this whole exhausting morning would have been a giant waste of time.
Thankfully, doing my makeup was easier now that I had a little bit of experience. I was satisfied with what I came up with in those thirty minutes. I slipped back onto the road and continued towards the bus stop. I was all alone, on a back road way out in the woods, but I still felt more exposed than ever. Every little sound made me jump. Whenever a car zipped by, my joints became stiff and I found myself turning my face away, worried the driver would recognize me and mock me. My skin felt cold and beads of cold sweat were already forming on the back of my neck. How was I going to get through a whole school day with this anxiety?
I was walking up to that bus stop just as the bus was coming around the bend. I closed my eyes and made a prayer, even though I wasn’t religious. I bit down on my tongue, and then when I opened my eyes, the bus was in front of me, with its door open. The bus driver was staring at me. “Getting on?” she said.
I managed to force a smile. I took one step onto the bus and then I looked back at all of the students. None of them were looking at me—all preoccupied with their phones and their conversations. “We’re behind schedule, missy, so get to your seat,” the bus driver said. My heart leapt when she said ‘missy’. Did she really think that I looked like a girl, or was she just being condescending? I looked at her. She wasn’t making any strange faces or snickers or grins.
One of the nearby male students looked up at me. I looked at him and then he looked away quickly. Could he tell that I was actually a boy? Or did I make him shy because I was pretty in my little getup? My heart was still racing. I took the nearest seat, next to the potentially shy young man. I looked at him again. He wasn’t looking over at me, but his cheeks were dark red.
“Hi,” I said in my best girly voice. I was surprised that I had enough confidence to even look at the kid, never mind talk to him.
He looked at me with a big, awkward smile. “Hi,” he said.
“I’m Kendra,” I said.
“Danny—I mean Dan,” he said. And his face became redder. He really was flustered. Was he attracted to me?
A couple of guys my age got on the bus at the next stop. As they stepped down the isle, one of them noticed me. His gaze connected with mine, and then he looked down my body. “Hi,” I said, and then he snapped his gaze back up to my eyes. “Hey,” he said with an increasingly familiar flustered look on his face.
I found myself sitting with a smirk on my face. I suddenly wasn’t feeling so vulnerable anymore, even though my legs were still exposed and there was still only a tiny bit of soft fabric between my cock and everyone on that bus. I felt strangely excited and flattered. I was starting to feel like this whole transgender thing was a pretty good idea after all. Maybe the next few months wouldn’t be so bad. Maybe they would even be kind of fun.
CHAPTER VIII
School wasn’t nearly as horrifically awkward as I thought it was going to be. There was only a single gut turning moment, shortly after I arrived.
Before going to my first class, I needed to make sure to buy my immunity, and to make sure my teachers didn’t think a complete stranger was strolling into their classes. So I went to the office and found myself waiting in a line to see the receptionist. I recognized the girl directly ahead of me in the line. She was one of the blonde girls who took me in when they thought I was gay, and then rejected me when they realized they were wrong. She looked back at me, right into my eyes, making my heart skip a beat
, and then she smiled before looking forward again.
Behind me was a guy who looked to be my age. He was dressed for gym class, showing off his arms with the sleeves of his gym t-shirt rolled up to his shoulders. His arms were surprisingly toned and hard not to notice. He smiled at me when I looked back at him.
I was just waiting for the moment everyone in the line realized who I really was. I was preparing myself for the snickering and the whispering—but it never happened. I just kept getting warm smiles from everyone who came and went as I slowly made my way to the front of the line.
“How can I help you?” the receptionist asked.
I leaned over her counter, feeling my skirt riding up—probably showing off my tush to the boy behind me. I could almost feel his gaze drifting down and tickling the soft skin of my shaved bum. “I just want to make sure that the school knows that I’ve changed my name,” I said—my voice was hardly a whisper.
“Changed your name?” the receptionist asked with her regular-volume voice. A cold chill crept down my spine.
“Yes. I’ve changed it to Kendra—Kendra Johnson,” I said.
“Kendra Johnson? What was it before?” she asked.
My gut flopped and churned as my legs began to feel weak. I was tempted to look back at the line of people staring at me—who were all probably just as confused as the receptionist. I bit down on my tongue and tried to swallow the lump that had formed in my throat. My skirt suddenly felt terribly short and my shirt felt awfully tight. “Do you have the attendance for Mr. Jenkins’s class?” I asked.
She slipped a clipboard out from a plastic tray. I reached out and grabbed it from her. Then, I pointed at my name on the list. She leaned forward and squinted. “Jessica Johansson?” she asked.
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