Chapter One: A Sister’s Request

I always thought that September was the best month. Not just because it had my birthday in it (in fact I just turned 15) or because high school had just started for me. Rather, it was the leaves falling all around that always looked so nice.

The autumn scenery is so great for writing poetry, and now that I'm taking a poetry class this semester, I'll have plenty of inspiration.

Yeah, I know, poetry isn't really the most masculine attribute, but I really enjoy it. To be honest, I don't exactly have the most masculine attributes anyway. I'm 5'5" (I haven't hit puberty yet), I have long brunette hair past my shoulders, and I don't have big muscles.

I guess one masculine thing about me though is that I'm a pretty decent runner (I run on my own, not on the cross country team), so that helps me get toned.

It was my second week of school and I haven't made too many new friends yet. However, I'm still close with my best friend from middle school, Daisy. We've been friends since we were three years old, and our families do a lot together to this day.

So I'd say my life is pretty typical and boring. As of now…

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I get home from school on a Tuesday and walk in to be greeted by my Mom, Dad, and sister, Jenna, sitting in the living room. It's the same thing every day, except this time Jenna said something pretty atypical.

"Hey Sam, can you meet me up in my room in a minute? I need a favor."

I hesitated due to the strangeness of her request. "Uhhh sure. Yeah I can help, I guess."

It was weird. Jenna had never really asked me to go into her room before. I mean we definitely have a good relationship with each other — my whole family does — but Jenna usually reserves her room as her own personal space.

I walk up the stairs and open her door. She's sitting down at her desk with a bunch of notebooks out. There are sketches on them of different clothes and hairstyles.

"Oh there you are! So you said you'd help me?" Jenna asked.

"Well I guess that depends on what it's for," I replied, unsure.

"It's for a class. Trust me, it'll take like 10 minutes."

"Sure, but what is it you need help with?"

Jenna continued to look down and sketched out something. "It's for my fashion class. Our first unit is on hairstyles: what looks good, what doesn't, and why. Just typical stuff."

Jenna then pulled out a clamp looking thing.

"So basically… I was wondering if I could style your hair and take a few pictures!"

I was shocked! Why does she need to take pictures of me? A boy!

"Aren't these girls' hairstyles you're working on?" I asked concertedly.

"Well... not necessarily..." she began, "I was just hoping I could straighten your hair and show some of the pictures in class. Most of the girls are using their own, but since I have a short pixie cut, I can't."

I paused for a second. Do I really need to do this? I mean, I already know I'm not that masculine, and this certainly isn't going to help.

"Ehhh...I don't know," I said, "I feel like people will make fun of me if they know I'm getting my hair done in a girly style."

Jenna finally looked up from her notebook and looked at me. "Nobody has to know it's you. I mean, all the people who would be seeing this are other seniors in high school, and they probably don't even know I have a freshman little brother. Plus, if they ask, I'll just say it's my cousin or sister or something."

I still felt uneasy. Jenna smiled at me pleading. She's always been so nice to me and I see her as a good sister and friend.
"...I guess I'll help," I said regretfully, but with a weak grin.

Jenna jumped up. "Yay! You're such a help!" She then immediately picked up that clamp thing (which I learned is called a flat iron) and sat me down at her vanity.

"So I know you have pretty wavy and messy hair," she began, "but I believe there's a lot of potential. You have a lot of volume and once this straightening iron does its job, it should look really good."

She got right to work and explained the steps to me as she went.

First, Jenna put some dry shampoo powder on my roots to absorb any oils that start to develop. Then, she started sectioning off my hair, after she put up part of it in a scrunchie. She would take sections of it at a time and run the flat iron through it a few times over. It took about 25 minutes, but by the end, my hair was completely straightened and shiny.
"Voila!" Jenna exclaimed, "So...what do you think?"

I stared at it for a little while, kind of surprised at how I looked. I'd never seen my hair so shiny before. I shook my head and my hair gracefully swayed across my face, neck, and head.

"...and a finishing touch." Jenna said, as she put a flowery, black clip in my hair. I gave her a semi-mean look, but let her leave it in.

"It actually doesn't look half-bad," I said, a bit impressed and surprised at myself.

"I figured you'd like it. Everyone likes being pampered from time to time." She smiled at me and I smiled back. "Oh! And now the pictures of course!"

Jenna pulled out her phone and stood about 5 feet away. I turned around, as I did NOT want my face being seen in these pictures. She took a few from the back, the top, and even a few from the side, but I made sure it was clear that you couldn't tell it was me in the pictures.

"All done...sis!" Jenna joked. I shot her another glare but she just laughed it off.

Right as we finished, our mom called us down for dinner. We went downstairs right away, as we were very hungry.

"Well well well, who do we have here?" Mom said. I looked back at Jenna but she just smiled. Then I realized that she meant me! Right as that happened, I blushed.

"Uhh...Jenna was..." I stammered.

"It's okay honey, I think it looks good." My mom said as she walked over and kissed me on the forehead.

All I could do was blush. I began to explain but then Jenna spoke up.

"It was for my fashion class project," Jenna explained. "Since I have my pixie cut, I needed someone with long hair to style and take pictures of."

"I guess your brother is a good resource..." Mom said.

"Even if it makes you look a bit girly." my dad pitched in.

Both my parents and Jenna laughed. I laughed nervously with embarrassment.

We ate dinner and afterwards, I went up to my room to do homework.

So many weird feelings went through my head today. I had straightened my hair for the first time, and it didn't actually make me feel that bad. I wouldn't say it was a good feeling, but I definitely learned more about what girls go through when they do their hair. I mean it takes a good half hour (if you know what you're doing) to get your hair all straightened and ready for the day. To relax, I wrote a brief poem about my feelings for the day:

a different experience

like none i'd felt before

soft hair cross'd my neck

causing tingling galore

t'is usually known

by girls alone

but tonight an exception

for me in my home

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The next morning, my hair had lost most of the straightening, but I could still tell it was like that a bit.

School was pretty average as always, and I luckily didn't get any comments on my hair.

When I returned home, Jenna was waiting at the door with a big smile on her face.

"I'm assuming you want to know how my class went??" Jenna said excitedly.

"Uhm sure...I guess. The pictures worked well?" I responded.

"My class loved it! They adored how shiny your hair was and thought that they'd never seen anyone pull off straightened hair that well! Isn't that cool?"

"I suppose that's good for you, right?"

"Well yeah I got full points on the assignment, but what was really interesting was that everyone wanted to know who I took the photos of."

My heart dropped for a second. "You...you didn't tell, did you?" I said, freaking out.

Jenna sighed, "No, I didn't. I said that they were from my cousin."

I breathed a sigh of relief. "Thanks, Jenna," I said, "I'm just glad that I could help and keep my anonymity at the same time."

"Yes, thanks again. However, I'd like to stress that even my teacher was blown away by what your hair could look like. If they knew it was a boy's hair, I'm sure they'd flip out."

"I can imagine," I said. There was a brief pause. "Well, I think I'm gonna go for a run. But I'm really happy the pictures worked well."

I started walking past my sister but she grabbed my shoulder. "That actually brings me to my next point...Would you mind doing me another huge favor?"

I stopped and a skeptical look creeped on my face. "What kind of favor...?"

"...can I do your hair again?" Jenna said sheepishly.

I sighed. "Listen, I was going to go for a run..."

"Oh please Sam! You were so helpful last time!" she pleaded.

"Ugh. Fine." I said. I guess I could put off the run.

Jenna squealed and told me to run up to her room. I guess I'm just too nice sometimes.

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I went to my room to drop off my backpack and put some things away and then walked over to Jenna's room. When I walked in, I assumed that she'd just be needing to straighten my hair again, but this time, there were MANY more products and items out on the table than before.

"What...what's this?" I asked.

"Oh yeah..." Jenna responded, "I need to do a bit more this time. Our requirement is to use curlers this time. It might take a bit longer...could you still help...?"

I guess I'd already committed, and I'm in her room now...so I nodded and sat down.

"You are going to be so pretty!" Jenna cooed, as she ran her fingers through my hair. I gulped nervously. She then caught herself, "I mean, your hair will look pretty." She smiled and giggled.

She started by spraying my hair with some sort of fragrance. "What does this do for the process?" I asked.

"Oh, nothing. It's just always nice if hair smells nice." She said, giggling girlishly.

I sighed and just accepted it. She ran the flat iron through my hair briefly to straighten it out again. It didn't take as long as last time because it was still straight enough from yesterday. She then went to work with a curling rod. She started with a few sections of my hair, the same way as she did with the flat iron, but this time, she just curled it.

She went to work on all my hair and within a half hour she was done. It was a weird sight. My hair was always kind of wavy in a messy way, but this time it was a 'coordinated wavy.'

Jenna stepped back from me to admire my hair, "I think it looks great. What do you think Sam?"

"I guess it looks...nice." I said. I mean what else am I supposed to say? 'It looks adorable' is not something a guy would ever say.

"Just nice?" Jenna asked. "Ugh boys know nothing about hair... Alright! Picture time!"

She had me stand up this time.

"Wait. That plaid button-down looks awkward," she said, "do you have an undershirt underneath?"

"Uh, yeah I do." I said, confused. I took off my plaid button down and now had my white undershirt on."

"Thanks. You can tell in the picture that that isn't a girl's shirt. See? I am looking out for you."

We both laughed and she was about to take the picture of my hair, but she had one more correction. Jenna grabbed a peach infinity scarf lying on her bed.

"Put this on. It'll look much cuter in the photo." She said, tossing the scarf toward me.

I caught the scarf. "Ehhh, I don't think so...This is too girly."

"Too girly? But nobody knows it's a guy in the picture. If anything, it'll assure that nobody will suspect it's a boy's hair."

She had a good point. She helped me put on the scarf. It was positioned delicately around my neck. It was a very feminine scarf, and it felt really weird to be wearing it. Once it was finally positioned well, Jenna readjusted my curled hair so it cascaded over my shoulders and the scarf.

With everything set, she snapped the pictures, and uploaded them to the computer on powerpoint for the class assignment.
Watching the pictures get uploaded, I noticed that they looked very good. Even though you couldn't tell it was a boy, it was weird to see the hair—my hair—look that feminine.

"Thanks again little bro. They look fantastic," Jenna said with a smile.

I hesitated, still staring at the pictures on the computer screen. I told her "no problem at all," but did I really mean that? I mean, was I doing the right thing, trying out such a girly hairstyle?

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The first five chapters of this 33 chapter novel are available here, but the remainder has been moved to my Kindle page. Thanks as always for reading and supporting me! :)

Link: https://www.amazon.com/dp/B0BPZCV3KT