Chapter Two: The Mystery Brunette

I’ll be honest. I was a little too freaked out by the whole thing to mention it to either Annie or Chris. But it was so strange! I’ve definitely been mistaken for a girl before from behind because of my long hair, but this was almost like…an attraction. Did he really think that I was a girl?

The assembly was during the 8th grade lunch period, so we were told to have a quick lunch and then get to our next class. I finished the school day not being able to get that moment out of my head – and with the exciting event of graduation coming up, that’s saying something.

I returned home to find that my parents were out of the house. They traveled a lot and would often go on trips for a whole weekend. Being Friday, they must’ve both left.

My parents trust me a lot though. Being an only child, I’ve grown quite independent. With no bad track record, they’ll give me the house for the weekend without batting an eye.

I ended up inviting Annie and Chris over to hang out. Graduation was next Friday, so I realized this was my last Friday as a middle schooler.

Annie arrived first, and we decided to sit on the couch and talk until Chris came. However, as expected, she would not shut up about the Toned performance.

“And then when they mashed up that One Direction song with the Billie Eilish one? Ahhh!”

Times like these I really wished Chris was here. I needed some to roll my eyes with.

She continued. “I swear, I’m going to all their concerts from now on. Imagine, when we get to high school, we’ll be in the same school as them. I could run into them every day!”

“I think you’re a little too giddy about this guy group,” I replied, a bit annoyed. “You can’t get too excited just because they waved at you.”

“Hey, I didn’t say they all waved at me, but the freshman boy was totally checking me out.”

Her last few words caused my stomach to drop again. It only reminded me further how that boy looked at me.

Just as she said that, the doorbell rang. I jogged to the door. It was Chris.

“Yo yo,” he said, overly casual as always.

The group decided to play Cards against Humanity, which we play a lot. Always gets a bunch of laughs.

“So I got a text from Juan,” Chris said, matter of factly, “My cousin.”

At the sound of “cousin”, Annie dropped her cards. “OOOOH WHAT DID HE SAY?”

“Woah calm down. You’ll actually be happy to hear this.” Chris said.

Annie was squealing with excitement. Chris continued, “So apparently, that freshman singer told him that a really cute girl in the audience caught his attention.”

My heart stopped. But wait – maybe this wasn’t me that Chris is talking about. Maybe it’s Annie! Or heck, anyone else. There were 50-plus girls in the audience during that show, so it easily could’ve been them. Maybe he looked at me in addition to the many other girls.

“Eeeep! That had to be me! When I stood up and waved, he totally looked in my direction. There’s literally no doubt!” Annie said, yelling. She then began to stand up and dance around, celebrating her believed victory.

Chris stood up to calm her down. “Jesus, chill. We don’t know if it was you.” Chris started pacing the room. “I’m actually going to a family party on Sunday. Juan will be there. I could ask him who the mystery girl is.”

“Oooooh this is just like Cinderella!” Annie was beyond giddy.

“Yeah, but in this case you might be the ugly stepsister left holding the bag.” Chris said condescendingly.

I laughed at the analogy, but it was all too possible that perhaps… I was Cinderella.

========

The next week at school I got a chance to talk to Chris at lunch. Annie, Chris, and I always sat together. Usually I would draw while the other two bickered about who knows what. But we all knew that Annie was waiting for one thing in particular.

“What’s the news?” Annie said, as Chris sat down. Chris already looked exhausted by her mood.

“Listen, you’re so crazy about this guy, but you don’t even know his name.”

Chris looked at Annie, awaiting her response.

“Pfft, of course I do,” she said, “It’s…”

We both stared at her.

“Alright, fine! I just think he’s really cute so maybe I’m a bit obsessive. Can you tell me?”

“Well I know two things,” Chris began, “Number one, his name is Scotty Allen. He’s a freshman originally from Highman.”

Highman Middle School. That was the school about a 10-minute drive south of our school, McMillan. I didn’t know too much about it.

Chris continued. “The other thing I learned is that Scotty doesn’t know the name of the girl—obviously. But he kept talking about her when Juan saw him over the weekend. So I guess he’s, like, really smitten.”

“But who is the girl he’s in too! What does she look like?” Annie was on the edge of her seat.

Chris turned toward Annie, as if he was waiting for this moment. “Well unfortunately for you, she was not blonde. She was a brunette.”

Once again, my heart dropped. It had to be me. Scotty Allen has a crush on me.

My face turned red, but nobody seemed to notice. Annie was too busy pouting over the bad news, and Chris was too busy enjoying her pouting.

“Hmm, so he wasn’t into me?” Annie questioned. She shrugged her shoulders, “Oh well, there’s plenty of other cute guys on that stage I could go for!”

Chris sat down and opened up his lunchbox, “The only question now is: Who is this mystery brunette?”

========

The rest of the day went by normally. It was the last week of school, so that was exciting. We continued to watch movies in class and even received our yearbooks. Throughout the day, kids signed each others’, reminiscing of memories of the last three years.

Once I got home for the end of the day, I opened up my yearbook and read some of the notes. As expected, there were a lot of ‘see you in high school’ and ‘have a great summer’ messages. But there were also a few about my hair, mostly from girls, and how they were jealous of it. Ugh, I guess that’s what I signed up for. though.

========

Wednesday was the official last day of school, even though the graduation ceremony was Friday. Lots of tears were shed by the time the bell rang to release us from our final class.

I was at my locker, clearing it out, when Chris approached me. “Hey Jamie, you down to come over after school? I just got this new video game we could play.”

“That sounds good,” I said.

Chris eventually told me the game was the new NBA 2K game. I’m not a big sports person by any means, but I enjoyed the artistic side of basketball: creating plays, weaving bodies, driving to the hoop. Unfortunately though, I was never athletic enough to do it. At 13 years old, I currently stand 5 foot 3 inches, and weigh only 90 pounds, so I’m fairly skinny.

My doctor told me that I entered puberty last year, but still haven’t really seen any effects of it yet. So people’s voices drop a lot, and some people like myself keep a higher voice. I was starting to wonder if I was short, skinny, and hairless for life.

We arrived at the Correa household. I greeted Chris’s mother and father and we went straight to his room. Chris has a really nice family. He and his two brothers are all super outgoing, but like Chris, keep a small tight-knit friend group.

Chris and I sat down on the couch in his room and started to play the game.

“So I did some scouting on who this mystery brunette could be.” Chris said while still looking at the TV screen.

I responded quickly and might have sounded a little too defensive, “Why do you keep trying to figure this out? I thought it was Annie’s obsession.”

He looked at me briefly, and then back at the screen. “Well, Juan mentioned that Scotty brought up the girl again. He told me that he’s looking forward to meeting her in high school.”

“Well that’s not necessarily true,” I said, “She…whoever that person is…could be going to Hinsdale West.”

“Fair enough,” he responded, “but that’s where my sleuthing comes in!”

Chris paused the game and looked at me. He pulled out a notebook filled with writing.

“While signing yearbooks, I took note to ask every girl where they were going to high school.”

“That’s a little creepy,” I told him. He didn’t seem to hear me through his focus.

“As it turns out, out of the 53 girls in the grade, 25 of them are brunettes, and all of them happen to be attending Hinsdale East next year!”
Chris seemed thrilled with his breakthrough. It was totally in his character to get amped about this sort of thing. That didn’t help my nerves though.

“So what’re you saying?” I asked, nervously.

“I’m saying,” he said, focusing his attention, “that Scotty Allen WILL be meeting this girl next year."

========

I've re-edited and picked this story back up after all these years. Look out for a new chapter every week or so :)

Chapter Three: The Graduation Ceremony

It felt like being tied to the railroad tracks watching a train coming in the distance. Sure, I wasn’t screwed now, but regardless of what I did – at least according to Chris – Scotty Allen would find out it was actually a boy he was checking out, and not a girl.

What certainly didn’t help either is the fact that Chris’s cousin, Juan, had now twice mentioned Scotty’s fascination with that ‘girl’ he saw. How was I supposed to get out of this one? I must’ve been an absolute mess the next hour or so hanging out with him.

Enough is enough. I had to tell him. I paused our game and put down the controller.

“Dude! I was winning!” he yelled, quickly changing his tone when he saw my face. “Okay, seriously, what’s up?”

“I have something to confess…” I said solemnly.

“Oh no… don’t tell me you have a crush on Annie. I can’t handle friend drama right now, I just can’t.”

“What? No! Nothing like that!” I shouted back. Chris was always bad at reading the room. “Look, the girl that Scotty Allen saw… It was me.”

He stared at me blankly for a second. Then another second. And as rudely as I would have predicted, Chris started laughing in my face.

“Oh my God no WAY!” Chris was in stitches, rolling on the bed. “The hair! Holy crap it makes perfect sense! Dude, you got the eye of the most popular freshman at East!” Chris couldn’t contain himself. He could barely breathe.

But I was starting to get mad. “This is serious, man! There’s a popular boy who, if he finds out that it was a boy he was making googly eyes at, he’s gonna flip out and end high school for me before I know it! Do you not understand the stakes here??”

Chris was only starting to come down from his immense laugh attack. “I’m sorry, I’m sorry, it’s just so f-u-n-n-y…”

I let him cool down for the next 5 minutes. But each time he said he was done laughing, he’d restart.

Finally, Chris was ready to talk about this like a normal person. “Okay, okay, I’m sorry. So because of your hair, he thought you were a girl. Is that basically it?”

“I think so. There’s not really a reason for Scotty to think that otherwise.”

“Well…” Chris began.

He clearly wanted to say something. “Well…what?” I prodded.

“You’re, uh – and I don’t mean this in a bad way – not exactly the most manly guy in general, right? I mean you gotta admit that.”

As much as I didn’t love admitting he was right, he was right. “I know. I’m small, short, I always hear I have ‘delicate features’, and of course…the hair.”

Chris nodded. While I was an anxious mess, he had a refreshingly calm, curious demeanor. He didn’t have a quick solution. Nobody did. But I strangely trusted his instincts.

“Give me until graduation,” he said. “We’ll think of something.”

========

Lots of people like to hate on middle schools and elementary schools for having graduation ceremonies. “It’s not a real graduation!” they’ll say. But there’s something to be said for closing a loop on a significant period of your life – even if it’s just the early tween years.

Much like the Toned concert (and so many other school events), the graduation was held in our gymnasium. Parents and students alike filled the gym, impressed by the decor and grandeur of the space. Students were seated in folding chairs, and parents and other family were seated in the bleachers behind. My perpetually out-of-town parents even showed up!

Our Principal, Mr. Winters, gave an opening speech and then handed it off to Ms. Reznik, a Spanish teacher and favorite of the students for another ‘go forth!’ type of speech. Lastly, the student council president gave her words of ‘wisdom’, and we soon moved into the presentation of diplomas. The reading of each kid’s name was usually followed by a little ‘woo!’ from the bleachers, likely coming from the proud parents. My parents, however, stayed silent. I didn’t mind it though – it’s not their vibe to be rowdy.

All in all, the ceremony was a quick 75 minutes and we were on our way. Friends and family gathered outside the school for pictures in our little red caps and gowns. Chris, Annie, and I took a picture together as our respective parents looked on at us, all proud and tearful.

I was even approached by some classmate acquaintances, looking to chat about the summer.

“Any plans for the summer, Jamie?” this boy named Thomas asked.

“Honestly, a lot of summer reading. And I’m working on a book of fantasy illustrations.” I explained.

“Oh, that’s super dope,” he said. “Anything in particular you wanna do with it?”

“I’m still not sure. Maybe I’ll turn the characters into a graphic novel some day? Maybe I just let ‘em collect dust. Either works for me!”

We shared a laugh and Thomas shared some stories about all the sports camps he planned to do. On that front I definitely couldn’t relate.

“Well anyway man, if you ever want to hang out over summer, let me know,” he said amiably. “I’m around, and never the worst thing to get some hangs in before heading to East.”

Thomas and I exchanged numbers. I liked that he showed the initiative. Thomas was always in the more ‘popular’ clique of kids, but now that a lot of his friends were going to a different high school, he was clearly looking to expand his group. Whatever the case, it was a nice gesture.

But just as Thomas was walking away, Annie came sprinting up to me. She looked furious. “JAMIE YOU ARE A DEAD MAN!”

I threw my hands up in surrender. “What, what! I didn’t do anything!”

Annie peered left and right to make sure nobody was listening. “Chris just told me that you were the ‘girl’ Scotty Allen was looking at?? Are you kidding me!?”

I rolled my eyes and looked over Annie’s shoulder. Chris was glancing over, shrugging bashfully. “Chris told you, didn’t he…”

“Yes, he told me! I can’t believe you’d try to hide that from me. Ugh! I’m heartbroken.”

“Woah woah woah, I’d appreciate a little sympathy,” I said, checking Annie’s self-centeredness. “You do understand how much of a bind I’m in, right?”

She scoffed. “Yeah, life must be sooo hard for you, having a popular boy interested in you.”

“Yes! It is.” I had to call over Chris.

We reexplained the whole thing to Annie and calmed her down. Though she thought it was the end of the world that an older boy – that she does not know, mind you – wasn’t actually into her, Annie quickly understood the stress this case of mistaken identity was causing me.

“Well, if you hens are done clucking, I think I found a solution to Jamie’s problem,” Chris announced. “Come over tonight and we’ll walk through it, okay?”

========

Chris, Annie, and I all had our respective family celebrations. My parents and I went to Outback Steakhouse for a quiet meal (very much their decision), while Annie’s and Chris’s families had big backyard celebrations. By the time Annie and I got to the Correa household that night, his family party was still raging.

“Grab some punch, water, or whatever, and let’s go to my room,” Chris instructed us, the moment we got there.

We did as told and met Chris in the room. But when we got inside, there was another familiar face.

“Guys, this is my cousin, Juan,” Chris said. “You probably recognize him from Toned.”

I, of course, played it cool. But Annie immediately went into geek-out mode.

“Oh my god, I love love LOVE you guys!” she squealed, barreling into Juan and giving him a big hug.

“Heh, heh, thanks, Annie,” he muttered.

Her eyes went wide. “And you know my name?”

Chris groaned. “Alright, enough of this. I brought Juan in here because we have an idea on how to solve this. And Jamie, you have nothing to fear. He knows everything.”
Are you kidding me?! How could Chris go behind my back and spoil all of this to his cousin – much less his cousin who is friends with Scotty??

“I am so pissed at you right now…” I said through clenched teeth.

But Juan cooled the temperature. “Hey, listen. I’m an ally in this. I know that Scotty’s into you because he thinks you’re a girl. And none of this is your fault, okay?”

I stared at Juan. “Go on…”

“Chris can be an annoying little bastard sometimes, so I was hesitant to help him. But we’ve come up with a… transactional proposition.”

The seriousness of calling it a ‘transactional proposition’ scared me a bit, but maybe that’s just how juniors in high school talk.

Chris jumped in. “Look, we all want to start off on a good foot in high school, right? And Juan is, shall we say, a ‘popular’ guy. So I proposed that he gets us invited to things with the popular kids.”

Annie had a big smile on her face. “Seriously, Juan? You’d do that for us?”

“But I need something in return. I’m not about to just let my annoying cousin into all my parties without something in exchange.”

I had a bad feeling this ‘exchange’ involved me somehow. “What exchange…”

Juan stood up and paced the room. “Toned had a really good year, but the mood of our guys has been… lacking to say the least. And most of that is coming from Scotty.”

Chris was refusing to make eye contact with me throughout Juan’s speech.

“So when Scotty caught the eye of a cute girl that he was actually interested in, we were thrilled! We dreamed that she’d be going to Hinsdale East so he could meet her and be happy. And ever since he saw this girl, his mood has been way up. And therefore, so have his vocals. He sounds incredible! And that’s all with the prospect of meeting her…”

Juan was stumbling a bit. Even a guy of his confidence sometimes had trouble spitting out uncomfortable sentences, so Chris just jumped in. “Jamie, we need you to be that girl.”

I was flabbergasted. “What?! You guys are insane!”

Despite this clearly abhorrent request, nobody was really sharing in my shock.

“We do have a plan for this, you know. And I think it’s fair.” Juan said. “All you have to do is come to a few parties and events, pretending to be a girl. I’ll introduce you to Scotty where you guys will chat, have fun, and do whatever freshmen and sophomores do to become friends.”

I fervently shook my head. “But I’m going to high school with him next year. And I’m attending as me. Jamie. A BOY.”

Chris leaped up with his finger in the air. “But aha! Here’s the kicker. The girl version of you won’t be attending. Because this ‘girl’ is your ‘cousin’ that’s moving away. We’re thinking from Texas.”

This story was getting wilder and wilder. “Texas?” I wailed. “Are you guys insane? Seriously. We need to get a psychiatrist in here.”

“Or honestly, any lie will do.” Juan brushed off my fear with surprising ease. “Look, the whole point is this: we get Scotty’s confidence up, you get your connections at cool parties for high school. And at the end of all of that, everyone forgets all about the cousin, you’ll cut your hair–”

“I cut my hair?” I said, cutting off Juan.

“Yeah… I mean, we need a way to differentiate you for the new school year. Cut your hair in a few weeks when your cousin ‘leaves’. Then ‘boy Jamie’ can start attending the parties, and nobody will ever think you were anyone else. You’ll still have, like, most of the summer to grow your friendships and get all set for high school.”

I paused. Despite the absurd nature of this whole arrangement, I did envision a world where this all worked out.

“Well, what if I refuse?”

Juan looked over at Chris. “Then Toned will suck, and you guys will go back to being lame.”

Annie grabbed my shoulders. “This is a win-win for everybody. I desperately need Toned in my life.”

I thought about it some more. Silently.

“Three events,” Chris said, then appealing to Juan, who agreed. “Just three events. That’s all you need to do. Go to three events as a girl. Talk to Scotty, get him out of his funk, and then your ‘cousin’ can leave town forever. Toned gets its guy back, we get a whole new bunch of friends for high school, and you get to enter high school as a fresh-faced freshman with a cool new men’s haircut. I’ll even help you pick it out!”

In a life full of sighing, I don’t think I ever sighed this intensely. But trust me, it was warranted.

“...Fine. I’ll do it. I’ll be your girl.”

========

I've re-edited and picked this story back up after all these years. Look out for a new chapter every week or so :)

-Jennifer

Chapter Four: Girl Practice

My friends are the luckiest people in the world. Why? Because their good friend Jamie is willing to do all the heavy lifting, apparently.

I can’t believe I agreed to their dumb request. Pretend to be a girl? What the heck do I know about being a girl? As far as I can tell, in each of my 14 years on this Earth I’ve been a genuine, 100% BOY.

Thankfully, Chris promised it’d only be three events. And it better be. Three times I’d pretend to be a girl, hang out with Scotty, and then my ‘cousin’ gets to leave forever. Chris, Annie, and myself will be rewarded with a fun, interesting group of friends heading into high school. And maybe it’ll end up being super easy.

However, I spent much of the weekend not worrying about any of that. My true passion was drawing and illustrating. Did I want to be a book illustrator, a graphic designer, or a painter? I wasn’t sure yet. But much of this summer – outside of spending time making friends – I plan to draw freely, create characters and designs, and hopefully gain a little direction on where my art interests lie.

My favorite thing to draw was young, male protagonists. Much like myself. I was always enamored with the recluse teen that everyone doubted could save the day. I’d create these stories in my head where a seemingly unpopular, uninteresting young boy defies expectations and saves the day. They go from weak to strong, feeble to powerful. That sort of stuff. Hey, who knows – maybe I can channel some of that energy into my task.

========

At the onset of summer break, everyone rejoices in their newfound freedom. No school, little to no responsibility. But tale as old as time, about a week in, we all get bored. So I reached out to Chris about knocking off my first assignment. We decided to hang out that afternoon. And in the middle of a Madden game, Chris finally dropped some ‘good’ news.

“So listen, Juan told me one of the Toned guys is hosting a party tonight,” he said, mid-Cheetoh munch.

“Wait, seriously? That’s perfect! Can we get an invite?”

“Probably. I’ll check with Juan.” Chris reached for his phone. “Let’s hit up Annie too. She’ll wanna come.”

So while we waited for a response from Juan, Chris called Annie and invited her over. However, she seemed angry and stressed about it over her phone. Very unlike her. She insisted we come over to her house immediately.

When we arrived at Annie’s, she was shaking her head with utter disappointment.

Chris kicked off his shoes in the mud room. “Annie, what’s the deal? Why are you so pissed off?”

She didn’t reply. Just gestured to us to follow to her room. Once we sat down and she locked her door, she finally spoke.

“What do you think you guys are doing? Are you trying to get Jamie blackballed forever?”

Chris and I looked at each other, perplexed.

“You don’t see the problem here?” she reiterated.

I had to get a straight answer out of her. “No, Annie. We don’t. Would you care to tell us?”

“You want to go to a Toned party. Tonight.”

We nodded.

“Well thank god I’m here to stop you. Because if you go to this party without prep work, the whole operation will implode,” Annie was in full ridicule mode. “Tell me, what exactly was your plan?”

I shrugged and looked at Chris. “I dunno, I was gonna, like, borrow one of my Mom’s dresses and give it to Jamie? That should work.”

“My god, you guys are so dumb. You can’t just throw on a dress and call yourself a girl! There’s a nuance to it. An art. Does Jamie have long hair and feminine features? Yes he does. But do you think the moment he starts walking and talking that anybody will buy he’s a real girl?”

I guess we hadn’t thought that far. She totally had a point.

“That’s what I thought,” Annie replied proudly. “That’s why you’re gonna decline the party invite today so we can practice.”

“Woah, practice?” I quickly jumped in. “That sounds a lot to me like extra sessions. In other words… more than THREE.”

She nodded, unfazed. “Of course. If an actor agrees to do a show, do they not also agree to rehearsals?”

“I mean… I guess.”

“Perfect. Then today we’ll practice. Chris, you can stick around or not, but I’m mostly going to be paying attention to Juliette.”

“Excuse me, Juliette?” I asked.

Annie smiled. “Mhmm. I decided just now. You’re officially Juliette. Okay sweetie?”

Chris started to chuckle, but I shot him a mean glare. He stopped.

“While clothes aren’t everything, it’s important for a girl to be dressed as such. It’ll best get you in the proper mindset,” Annie said, digging through her closet. She pulled something out. “Here, try these on.”

She tossed me a pink pleated skirt and a white tank top.

I groaned. “Ugh. Pink. Seriously?”

Annie laughed. “Really? I’m handing you a skirt and your issue is that it’s pink? You know what, just for that, I’m gonna make you wear these too.”

Annie reached into a bin in her closet and threw a pair of white panties at me as well.

“No no no! I’m not wearing your underwear.” I protested.

Chris was starting to look uncomfortable. “Maybe I should leave…”

Annie was starting to lose it. “AGH! You guys are ridiculous! Do you want this to work or not? Tell me. RIGHT now.”

Chris and I were silent. Annie was dead serious.

“Juan is graciously giving us this opportunity to start high school on the right foot,” she began. “We’ll get a great group of friends. Cool friends. All we have to do is get Scotty Allen to believe Jamie is a girl. And despite this gift, you guys are making every step of the way as frustrating as possible!”

Annie turned back to me. “Jamie, who knows the most about being a girl in the room?”

“You do.”

“Exactly. So are you gonna do as I say, or are you gonna let us sulk back to the bottom of popularity…Juliette?”

Annie was right. I knew it, and so did Chris. We had to be all in if this was going to work.

Without saying a word, I respectfully picked up the skirt, top, and panties, and took them into the bathroom to change.

I took my pants off and stared at myself in the full-length mirror – naked and fearful of what was to come. But I denied every naturally male instinct of mine and slid on the panties. They fit snug around my package and were, well… actually comfortable.

The skirt was a little less so, and took me a few minutes to figure out how to position it properly with the tank top tucked underneath.

I re-emerged from the bathroom to an approving nod from Chris and Annie.

“You look adorable, Juliette.” Annie said confidently. “Now we can get to work.”

Over the next several hours, Annie gave me a complete crash course on girlhood. Much of it was aesthetic, but so much more was about demeanor, character, and attitude.

Girls move differently than guys. That’s a fact I believed, but never quite understood. Annie had me try on all different kinds of her shoes and did a full lap around the house wearing each of them. She showed me how my steps should be shorter, my upper-body posture tighter, and my hips more fluid. Thankfully her parents were out of the house for the day, otherwise they’d have seen me prancing through the halls every 20 minutes with a new outfit and shoes.

And I tried on ALL sorts of outfits. Over the roughly six hours of ‘training’ I wore androgynous items like sweaters, hoodies, shorts, and pants, as well as significantly more feminine items like dresses, stockings, nighties, and bras and panties. We’d practically cycled through her entire wardrobe.

Though skeptical at first, I found that my demeanor changed drastically based on the outfit I was wearing. With Annie’s blue tracksuit on, I felt powerful and agile. When I wore her pantsuit, I felt like a total ‘boss bitch’ (as Chris put it), ready to take down the patriarchy.

Alternatively, when Annie had me wear her soft pink panties and flowy pink nightie, I’d never felt so dainty. Just lying back on her cushy bed, stroking the satiny duvet cover with my bare, hairless legs felt like a dream.

“A woman is many things,” Annie reiterated. “Clothes aren’t all of it, but so much of a woman’s being can come from what she’s wearing. I hope that you learned that today, Juliette.”

I nodded and thanked Annie with a hug. Chris stayed surprisingly active during this whole process, chiming in with his opinions, both critical and complimentary.

It was getting late so I decided to change back into my boy clothes and head home for the night. Chris told us that Juan was confused why we weren’t coming tonight, but understood that some ‘girl practice’ might be necessary.

“What’re you guys doing tomorrow?” Annie asked us as we put our shoes on. “Because I’ve got some ideas for Lesson #2.”

“Wait, there’s a–” I began to say, but quickly cut off my protest. I promised Annie that I’d trust her with the girl prep. I was but her humble servant.

“I’m free if you are,” I replied instead.

Great. Then be at my place tomorrow at 10 AM.

Ten o’clock in the morning felt especially early in the morning for another practice session, but it’s not like I had anything else going on. Chris said he couldn’t make it, but Annie said his presence wouldn’t be necessary.

“Lastly,” she said. “I want you sleeping in these.” Annie had handed me one of the pairs of panties I’d worn earlier in the day. The pink satin ones I’d worn with her nightie.

“Are… are you sure?” I asked. “You know I’m not being Juliette full time.”

“I know, Jamie. But think of it as ‘passive training’. We only have a short time to get in as much girl practice as we can. Just try it.”

I reluctantly took her panties, but agreed nonetheless.

========

My parents were home when I returned, but were fully occupied watching some violent drama series in the living room, sipping their new bottle of whiskey. I decided not to bother them.

I still had a little of the night left to myself, so I opened back up my sketchbook. Flipping through the pages I saw a soldier, a giant robot, a sword-wielding teenage boy – each in a different art style. I also had a half-finished cyborg teenage boy that I’d been trying out.

But tonight I didn’t feel like finishing that one. Instead, I flipped to a blank page. I began with a sketch of an androgynous face and body shape. It’s usually at this point that I then add a suit of armor, a fierce weapon, or a mighty animal sidekick.

…but not this time. I graced my new character not with a masculine crew cut, but rather a long, elegant hairstyle. And I didn’t have the character attack an enemy. I had them lying on a bed, wearing a soft, feminine nightie. Was it a boy? Was it a girl? Perhaps something in between.

It wasn’t too in-depth of a sketch, and I only spent about 20 minutes on it. But it was a creative expression that grew organically from my day’s experiences.

Maybe that brief but genuine creative expression of femininity will benefit me in tomorrow’s lesson...

Chapter Five: A Trip Outside

Not that she normally does this, but it would’ve been the absolute worst for my Mom to come into my room to wake me up this morning. I think she would've about died from shock had she seen her only son sleeping in his bed wearing women’s panties. I wouldn’t even know where to begin to explain the ridiculous clothing choice.

But this is one of the sacrifices I agreed to make. Annie was totally right – there’s a lot of prep work that goes into being a girl. I couldn’t just expect to show up in some ill-fitting dress at one of the parties and expect Scotty to believe I was a real girl.

So I left my house just before 10 AM to meet Annie for the second day of practice. Funny, she never mentioned how many days of ‘girl practice’ I’d need. I guess I’m just along for the ride.

When I arrived at her place she grabbed me and quickly pulled me upstairs. “My parents are home,” she said, quickly shutting the door behind her.

“Cool… why does that matter?” I asked.

She looked at me like I was a total ditz. “Because I don’t want them to see what we’re doing.”

“I mean, yeah.” I shrugged. “Let’s just do girl practice in your room then. If they knock, I hide and you say I left.”

“Hmm… so, I was gonna wait to tell you this til you were dressed up, but it seems relevant now… I made 11 AM brunch reservations for us.”

“You what??” I nearly screamed, praying her parents didn’t hear me… or her.

Annie sat me down on her chair. “It’s okay, it’s fine. It’s only at Café Soleil. You’ll be fine.”

I couldn’t believe how matter-of-fact she was acting. “Are you insane? Café Soleil is packed like all the time! Don’t you think somebody’s gonna recognize us?”

She snapped her fingers. “Way ahead of you. I already called ahead and asked for a back booth. They said it’s where they put their ‘celebrities’.” Pfft. As if any real celebrities lived in the suburbs of Chicago… the occasional pro athlete, maybe. But still.

But with time, I started calming down. Annie pleaded and pleaded and reminded me how convincing I looked yesterday and how much of a natural I was wearing girls clothes. Maybe – just maybe – we can pull this off.

She picked out a conservative, girly-but-not-flashy, light-pink sundress for me to wear, paired with white summer sandals. I was also given a white bra and panties set to wear underneath. Annie decided to somewhat match me with her own sundress, but hers was light green and she wore navy blue summer sandals.

“My nails are already painted… but I don’t think we have time to do yours. Sorry, Juliette,” she playfully cried, knowing full well I was happy about that.

She also applied a little bit of makeup to my face for the first time. Super subtle, but she insisted makeup would only help hide my identity and make me feel more confident as a girl. Not so sure about the latter, but I rolled with it. Annie even handed me a pair of large, feminine sunglasses as an extra layer of recognition protection.

Soon enough, I was fully dolled up. Annie even took a mirror selfie of us, much to my displeasure. “God, you make for such a cutie!” she squealed.

We left the house without running into her parents, and she told them we were off to meet more friends at brunch.

========

Café Soleil isn’t too far from Annie’s house – only a 10 minute walk – but damn did it feel like a marathon. The sandals were comfortable, and I’d gotten a lot of practice yesterday with women’s shoes, but the fear that I’d run into someone was immense. We were in my hometown after all. Not on vacation, not in some fake virtual game. Nope. The real world

Annie gave me physicality tips on posture and poise along the way, up to and including arriving at the restaurant. Annie agreed to peek inside first, and if she saw any of our classmates, we’d be allowed to abort the mission. Once the coast was clear, we entered and were seated at our back booth. I wanted to keep my sunglasses on the whole meal, but Annie said doing so would probably attract more attention than if I didn’t. I think she was right.

“Okay, I see the server heading over,” Annie whispered. “Have you practiced your girl voice?”

“My girl–what? No, I haven’t practiced my girl voice!!”

“Oh… she muttered. Maybe we should have…”

But it was too late, the server had already arrived. She was a middle-aged woman with kind eyes. “What can I get for you, hons?”

Annie spoke up first. “I’ll do an omelet with cheese and spinach please.”

The server nodded. “And for you?”

She was staring at me, awaiting my response. It was my moment of truth. “Uhhh, the same please.”

The server smiled, nodded, and walked away. I let out another HUGE sigh of relief.

“Great job!!” Annie whispered. “I mean, you only said like three words, but you sounded just like a girl. Weird, I didn’t think you liked spinach though.”

“I don’t. I just thought that was the way I could order using the fewest words…”

Annie laughed. “Cheater!”

But we’d done it. We’d gotten through the toughest test.

========

The rest of brunch went super smoothly. Nobody bothered us, nobody really looked at us. We walked out of the restaurant feeling on top of the world. Hey, maybe this girl stuff isn’t going to be that hard after all. Walking home, I even had a little pep in my step for the first time.

Annie looked at me, impressed. “I gotta say, Juliette. You’re taking this so well. I mean, can you imagine if we asked Chris to take this on?”

I laughed. “He’d never. He’s too stubborn and thinks he’s soooo macho.”

“I just love that you’re sweet and sensitive. That’s a quality that’ll take you far in life.”

I kind of raised an eyebrow to that. Is it? Everything I’ve been told about men – at least from my parents – is that they’re supposed to be strong, confident, family-focused guys. I always felt a little bad about myself, knowing I wasn’t on that path. I’m not into sports. I like art. I’m scrawny with long hair. And now… this? I guess it’s something to consider. Things could get dangerous if I don’t keep my mind focused on the task: I pretend to be a girl, I cheer up Scotty and let him down easy, and boom! We have popular friends for high school.

Annie did her job scouting out her house’s foyer, and smuggled me back upstairs to her room.

“I’m probably good to get this dress off, right? Why risk things any further?”

Annie immediately pouted. “Aww, really? I was having fun with Juliette...”

“Yeah, yeah. Well you can have more fun with her at the first party, assuming we’re done with girl practice for now?”

I think reluctantly agreed with me. “I must admit, you’ve been killing it. Granted, you said three words to the waitress…but even hearing you practice your girl voice on the walk back… it’s pretty stellar.”

“That sounds like a successful day then.” We high-fived, and I went into Annie’s bathroom to change out of the dress and remove the makeup.

“I have wipes in the top right drawer. It’s super easy, you’ll figure it out.”

Annie was right. It was pretty easy to remove the makeup. But it’s interesting, even taking it off, I still saw myself as unbelievably girly in the mirror. The way my hair was hung, the fact I was wearing a dress. Kinda crazy that I probably didn’t even need makeup.

But then there was a very concerning KNOCK on the door. Not the bathroom, but the bedroom door. “Annie, did everything go okay at brunch?”

CRAP! Her mom was right there. If I weren’t in the bathroom, I’d be totally screwed. Pleeeease just send her away, Annie. But Annie waited a few seconds, then answered.

“Come on in, Mom!”

WHAT THE HELL! Annie, you’re such a dope! Did she forget I was in the bathroom or something?

I couldn’t see from my perspective, but I could sense her Mom was exploring the room.
“Do you have a friend over?” she asked.

“Mmhmm.” Annie answered confidently. “Juliette. She’s in the bathroom.”

“Hmm, I’m not sure I know Juliette.”

“Well, you can meet her in just a sec,” Annie said cheerfully. What the hell was she doing? Was she trying to screw me over?

“Oh, okay,” her Mom said. I don’t think I’ve heard you mention her before.

“Yeah, I met her through Chris,” she said normally, but then her tone sounded a lot more pointed. “I thought I’d invite her back to TRY OUT THE NEW SHEET MASKS we bought.”

What? I wasn’t trying any sheet– wait a sec… this was her way of giving me an out!

“Why are you raising your voice?” her mom asked.

“Oh, no reason,” Annie said. “I just really like the SHEET MASKS IN THE UPPER RIGHT HAND DRAWER.”

“Okay, jeez…” her mom was clearly confused.

But that was all I needed to hear. I frantically opened the drawer and found the pack of sheet masks, which I realized were those things used for facial cleansing and to remove blackheads. While Annie made small talk with her mom, I quickly scanned the instructions on how to apply it. I rinsed my face, pressed the mask on… and perfect! My face was perfectly concealed under a white sheet.

“What’s taking Juliette so long? Does she need help?”

“No, she’ll be out in a sec,” Annie said. As much as I was pissed at her, I mustered up the courage to leave the bathroom after quickly tying my hair up in a bun.

“No worries,” I said, terrified but flawlessly faking confidence. “Hi, I’m Juliette.”

Fortunately, Annie’s mom didn’t stick around too long, and only asked a few questions about how I ‘knew Chris’. Thanks to my girl voice, the dress I still had on, and the concealing white mask, she didn’t suspect a thing. And a couple minutes later, she left the room.

Never having been so stressed in my life, I collapsed straight on the bed. Annie burst out laughing. Once I recovered, I shot back up wanting nothing more than to tackle her like a linebacker. But she held her hand up.

“Nuh-uh-uh,” she motioned me back. “I told you, those three words you said to the waitress weren’t enough.”

“...what?”

“I needed to give you a real test. A real world scenario. My mom didn’t recognize you for you. And congrats, you passed.”

I stared blankly at her, but I finally realized her game. All of my anger washed away and turned into genuine respect. Holy crap, that was maybe the smartest thing she could’ve done.

“NOW you’re done with girl practice. I think you’re ready to meet Scotty.”

Chapter Six: Juliette's First Party

Annie totally played me, but I’m kind of glad she did. I had to ‘perform’ under the utmost pressure while pretending to be Juliette in front of her mom. Sure, I had my face concealed by a sheet mask, but I still had to fake a girl’s voice, move femininely, and make sure I gave off zero male impressions. Looks like I passed.

And thank God I did, because otherwise I definitely wouldn’t be confident enough to meet Scotty in person and convince him that I’m a girl named Juliette, rather than a boy named Jamie.

Chris got a huge kick out of my frighteningly stressful encounter with Annie’s mom, but he too was glad I’d be prepared for my first of three promised interactions with Scotty.

“Dude, I still can’t believe you got away with that,” he said in the middle of munching on Cheetos.

I rolled my eyes, even though we were playing video games and he couldn’t see me. “Chris, it was a week ago. Why do you keep bugging me about it?”

“I’m not bugging you,” Chris insisted. “I just think it’s hilarious that she didn’t recognize you. I mean, how many times have you talked with her mom? How many times have you been in that very house? And she still thought you were a different person – a freaking girl, even!”

Annie never even told her mom that it was actually me. In fact, we didn’t even give Chris all the details about girl practice. Sure, he knew that I was practicing walking, talking, and acting like a girl, but I conveniently left out that I was wearing panties on the daily underneath my boy jeans. Annie thought it’d be good to ‘always keep a bit of Juliette with me’. I actually kind of agreed, as much as it scared me that someone might notice a frilly yellow band poking out of my jeans if they looked at me from the wrong angle.

But to this day, still only Annie, Chris, and Juan knew about our plan to get popular. Juan, of course, being the catalyst and one who’d actually be getting us into these parties. And as it turns out, it looks like this weekend would be the time.

It was Saturday, and Annie had just arrived at Chris’s when he read out the text from Juan.

“Ben Grumman is having a party tonight. Can we make this a Juliette night?” Chris read from his phone. “Well, Jamie… is it gametime?”

It didn’t take much discussion. I was ready to debut publicly as Juliette and get one of my three parties out of the way.

“Tonight’s the night! Yes!!” she squealed. “What do you think you’re gonna wear?”

“I haven’t thought about it,” I replied honestly. “I was just gonna defer to you.”

Annie scoffed. “That’s right, you haven’t been a girl long enough to figure out your own style.”

We decided to meet at Annie’s at 7:30 to get ready for the party.

========

As we’ve done in the past, Annie scooted Chris and me up to her room without her parents noticing. But now that ‘Juliette’ has been established, if we ever got caught, she’d simply claim I’m somebody else.

Annie had already laid out three complete outfits for me to choose from.

“Damn, dude! You’re gonna look smokin’!” Chris joked.

“What’s the easiest one to walk around in?” I said, brushing off Chris’s weird remarks. “Comfort should be prioritized for the first night.

Annie stared at her selections for a bit, then settled on the middle option. “I’d say the leggings and top.”

She was referring to a pair of black leggings and a slouchy sweater. It wasn’t too girly, which I liked, and looked far more comfortable than the other two options, which looked like tighter skirts.

We decided on the leggings and sweater, and I was sent into the bathroom to change. Annie insisted I wear and stuff a bra to accentuate my figure just a bit. My ‘cute butt’ (Annie’s words), needed no such enhancement with the leggings.

Chris was impressed. “Holy shit, how do you look hot without even putting on makeup?”

“Can you quit with the objectification?” I grunted back at him. It better not be like this all night.

However, he had a point. I hadn’t done anything to my hair or face yet, and still looked almost 100% girl. Should I be proud of my naturally feminine look? Or maybe, concerned…

Nevertheless, Annie went to work on my face, giving me the works. Foundation, concealer, blush, penciling in my eyebrows, adding mascara, and a fruity, sparkly lip gloss that she claims ‘always make me feel extra femme.’

My hair was brushed, then straightened, and then run through a curling iron to add some loose waves. She topped me off with a few spritzes of perfume and the girl transformation was complete.

“You look gorgeous, Juliette,” Annie said, giving me a big hug. Objectively she wasn’t wrong. I looked like the cute girl-next-door a guy like myself would want to date.

Chris read a new text from his phone. “Juan says we should head over now. Scotty’s arrived.”

========

Ben Grumman was an incoming senior and a bass vocalist in Toned. He wasn’t the leader, partier, or particularly notable guy by any stretch. But his parents were super loaded and didn’t give a shit about parties. The ideal friend for anyone in high school.

He lived in a massive, upscale colonial-style home parked on a ton of land. But as we walked up, we noticed the party wasn’t happening in the house, but rather the gigantic, barn-like garage in the back.

The outfit was comfortable, but my nerves were bouncing off the walls. The closer we got to the backyard down the long, gravel driveway, the more I felt like I was making the biggest mistake of my life.

I violently grabbed the arms of my friends and stopped us dead in our tracks.

“Am I gonna die?” I spat out, clearly startling them both.

“Why would you die?” Chris said. “All we’re doing is attending a party.”

“But like, if someone finds out I’m a boy… they’re obviously gonna scream it out to the party. I’ll die of embarrassment.”

Annie held my shoulders and looked me right in the eyes. “Juliette, you are a beautiful, confident, outgoing girl. Keep telling yourself that. Chris and I will look out for you. Juan too. You’ll be fine.”

I guess her words calmed me a bit. Enough to make it into the barn.

As it turns out, I’m really glad she did. This place looked insane. It was a two-level barn converted into a garage. Dozens upon dozens of high-schoolers crowded the space. Some dancing, some drinking, some just chatting, but everyone was having an awesome time. String lights were strung across the ceiling, and the space was accented with vintage posters, old street signs, and other sick memorabilia.

Juan approached and dapped up Chris.

“It begins!!” Juan shouted, quickly lowering his voice. Not that anyone would know what he’s talking about. “Let me introduce you to some friends.” He did a double-take looking at me. “Damn, Jamie, you clean up nice!” I rolled my eyes.

Never before had I been so welcomed into a party. Juan was such a popular guy that his word was plenty to vouch for our coolness.

For the first 20 minutes, I mostly stuck in a group with Chris and Annie, meeting sophomores, juniors, a few seniors, but notably no other incoming freshman. My heart dropped a few times when I saw a few faces I recognized, but I guess my feminine disguise was good enough that they didn’t clock me. Amazing, the power of makeup and a good outfit!

“Hey, Juliette,” Juan came up behind me. “I got someone you should meet.”

Juan turned me around and pointed exactly where I thought: Scotty Allen, standing alone by the drinks.

“Scotty!” Juan shouted, waving him over. When Scotty looked up and over, recognizing who I was, his face lit up. The kind of excitement that you get when talking to your crush? That was the look he was giving me. It hurt me knowing that I’d have to be letting him down eventually. Who’d want to ruin a wonderful emotional rush like that?

“Meet Juliette,” Juan said, stepping away smoothly to leave me alone with Scotty.

The trance he fell into was just like the one on stage. Despite the girly clothes, hair, and makeup this time around he clearly recognized me as the girl from before. The same one who caught his eye at the Toned concert.

“Juliette,” he said. “Nice to meet you.”

I smiled back, shaking his hand. “Nice to meet you too.” There wasn’t much to say outside of an awkward pause. “I really love your music.”

“Thanks,” he smiled back, not furthering the conversation. Maybe there was a reason this guy couldn’t get girls. He was kind of awkward.

It took a while for me to pry out some answers, but we eventually got to talking about music and interests.

“So, remind me, you’re going to Hinsdale East this fall?”

“No, no,” I explained, having to keep my lies straight. “My cousin, Jamie, is. I’m moving back to Texas at the end of the summer. Love a good trip with my ‘ol Aunt and Uncle!”

Ugh. That was a lame thing to say.

I went on explaining my fictitious backstory: That I’m up here for the summer for a few weeks to hang out, but my ‘cousin Jamie’ is kind of a quiet, art-loving recluse (hey, not an entire lie) so I’m hanging out with his friends and going to parties. I may have messed up a few details here and there, but Scotty totally bought my story.

As it turns out, Scotty just needed a little loosening up. Admittedly, I was far more obsequious than I normally am. After all, my job was to get Scotty’s confidence back up – not to strike up an actual friendship. So I continued asking questions about his music, his family, his views on life, etc. He was definitely coming out of his shell. At least enough to share some more personal details.

“You seem like an honest, reliable person, Juliette,” he began. Ohhhh, the irony… “Do you ever just, ya know, feel like the stuff you’re doing now, isn’t the stuff you’re meant to do?”

“How so?”

“Well, I dunno... I’m super grateful that Toned wanted me as a freshman. They, like, never do that. But as much as I enjoy singing, it feels like I have other interests I should be trying out. Maybe I’ve, like, gone too deep into music.”

This right here was my purpose. It was exactly my job to plant in Scotty’s head that ‘NO, you DO like music!’. Maybe a pretty girl telling him that could solve it all.

But before I could muster a word, somebody called his name.

“Hey, my buddy’s calling me. I think he needs help,” he twiddled his thumbs for a moment before stepping away. “Sorry, I didn’t mean to drop all my woes on you like that.”

“It’s okay, don’t wor–”

“Could I like, get your number, maybe?”

His request totally caught me off guard for some reason. “My what?”

“Your, like, phone number. So I can… I dunno. Text you? Sorry, maybe that’s dumb. I just kinda liked talking to you is all.”

Crap. Was he really asking for my number? This wasn’t part of my agreement with Juan, but I guess it falls under the umbrella of ‘get a girl to boost his confidence’.

“Sure,” I said, reaching for his phone. I input my number, making sure to write ‘Juliette’ and not ‘Jamie’.

“I…will…text you,” he said, not really looking up at me as he left. God, was this his first time asking for a girl’s number? I’m not the smoothest guy, but even I’m not that clunky.

I caught up with Chris and Annie who were chatting with separate people of the opposite sex. It didn’t look like either of them was doing too well, so I came to the rescue.

“What? I was doing fine!” Chris insisted as Annie and I yanked him away. We found a spot in the barn to break down what happened.

I filled them in on my surprisingly awkward but overall manageable conversation with Scotty.

“Do you think he likes you?” Annie asked.

“Definitely. His face lit up when he saw me. But listen, I don’t think confidence is really this guy’s issue. At least not completely.”

Chris and Annie stared at me.

“I think he may just… not like music anymore.”

Annie gasped. Chris threw his arms up. “What!? How can he not like singing? He’s so good at it!”

“Yeah, I know. But he mentioned something about ‘other interests’…”

Chris stopped me right there. “No no no. He can’t have other interests. Because if he has other interests, he drops out of Toned. If he drops out of Toned, that means we did the exact opposite of what Juan asked us to do!”

“And if we don’t have Juan on our side, there goes our party hook-up. I mean look at this place! Do we really wanna lose all this?”

I sighed. This was becoming a lot more complicated than I thought. “Look, I gave him my number–”

“Whaaat?” Annie squealed. “Juliette, that’s adorable!”

“Shut up, okay?” I cut her off. “He asked for my number, so maybe I still have some influence on him. Maybe it’s not too late to stop him from quitting music.” I looked across the barn at Scotty chumming it up with some friends. “He said he’ll text me tomorrow, so I’ll craft a logical, persuasive text–”

Annie was furiously shaking her head. “Nuh-uh. Now way I’m leaving this high-stakes job in the hands of you texting.”

“Well, what other ideas did you have?”

“I think once he texts you tomorrow, you set a time to meet in person to discuss this. Outside of school, outside of parties.”

“Wait, like, just the two of us?”

“Yes, obviously… Pick a park or a restaurant or whatever.”

I couldn’t believe what she was insinuating. “So like… a date?”

Annie smiled. “Exactly.”

========

If you're enjoying this story, check out any of my newest release on Kindle, In Rotation! ~41,000 words, 23 chapters!

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