“C’mon down Tom!” Mom yelled. I looked at my alarm clock and it said 7:35. Dang! School was gonna start in 10 minutes!
“I made you some eggs,” she yelled again. I look around my bedroom for some pants and found some old, baggy 90’s-style jeans. I throw them on and grabs an old Nirvana t-shirt and sprint downstairs.
“Jesus Christ Tom, your hair looks terrible! Would it kill you to run a comb through it every once in a while?” she said as she tossed the plate of scrambled eggs in front of my spot at the kitchen table.
Mom was always complaining about the condition of my hair. My shoulder-length dirty blonde hair was washed about once every few days, and I bathed regularly, but I never even considered combing it before school.
“It looks fine” I said, annoyed, grabbing my backpack and consuming the last of my scrambled eggs. I think the reason that my hair really bugs my mom is because my older sister’s is absolutely stunning. Her golden-blonde locks hang about 5 inches below her shoulders and have a beautiful natural shine to them.
MY hair kinda just hangs there.
I got home from school at around 3:30, only to see my mother greeting me at the door.
“Well I got a call from the school today, Tom. They said that there was some bullying going on from the kids at school? Care to explain?”
First off I’d like to mention that I attend a school in the Northern suburbs of Chicago called Thornwood College Prep. It is a very wealthy private school. And it shows.
A typical look for the boys there is button-down shirt, sweater, khakis, and boat-shoes. And the girls always wear skirts or dresses.
I was never one to wear nice clothes. Jeans and a tee-shirt have been fine for me for most of my life. But most of my freshman classmates have begun to notice and shun the likes of me. Surprisingly I don’t really care that much though. I’m just a messy-look kind of guy.
“Mom, its fine, trust me. I really don’t care what the others think of me.”
“Well you should! When your grandfather went there, he was always known as a respectable young gentleman. All of the girls at the school loved how he looked and all of the boys envied him. We would love if you didn’t ruin the Reginald name.”
“Mom, with all do respect, I could care less about what Grandpa and his old Thornwood contemporaries think of me.”
“Tom you are being ridiculous! The family name will not be tainted just because you prefer to dress like a lazy bum! I don’t expect you to wear a full tuxedo, just look a little nicer. Okay?”
“Good. Now I asked your sister, Faith, to help you out with your look. She’s in her room so go meet her now.”
I went up to my sisters room and walked in. The smell of perfume was overwhelming. She wasn’t an overly girly-girl, but there is no way, from the pink walls, etc, that you wouldn’t guess this wasn’t a girl’s room”
“Hey Tom! My told me you needed some help with your look?” Faith asked.
“I guess so…” I breathed a deep sigh.
“Well Tom, I’m a Junior at Thornwood, and being a student there I can tell why people make fun of you” she said as she ran her fingers through my messy hair.
“Take a seat”
I sat down at her vanity and she pulled out a big hair brush. She loosed my blonde hair from the ponytail and it fell down to my shoulders.
“You know, you could actually have nice hair if you just took care of it. You know what, before I brush it, go wash it.” she said as she handed me a light green bottle of conditioner and shampoo that had a bundle of flowers on the front logo. “Shampoo, then condition, and let me know when you’re done.
I did what she asked and then called her into the bathroom to meet me. She grabbed a blow drier and blew it completely dry. I then followed her to the vanity where she began to brush out my hair.
“Wow Tom your hair is Beautiful!” she exclaimed. “I love how naturally straight it is!”
I took a look in the mirror and was very surprised. It was quite nice and very straight, hanging a few inches below my shoulders.
“You know, from behind, you’re hair looks just like Elle Fanning!” Faith joked.
I blushed when she said that and continued admiring my hair in the mirror.
“Here, lets move on to your clothes. You need to lose the baggy jeans right now, as well as the t-shirts. Those things don’t fly at Thornwood. Go change into something school-appropriate.:
I went back to my room and put on a plain white button-down shirt, and some older khakis. They were nice, just a little tight. I returned to my sister’s room.
“MUCH better!” she said. "Now since a lot of guys wear cardigans at school, you should go grab one as well”
I told her I don’t have one so she went straight to her closet and grabbed a light blue argyle sweater.
“This is a girls’ sweater Faith…” I said uncomfortably.
“True, but it’s really not that feminine. Just put it on.”
She was right. I put it on over my button-down shirt and admired it.
“That should please the kids at school. Feel free to wear that tomorrow and let me know how it goes!” She said excitedly.
Well at school the next day things were much better. I actually got complements on my washed and brushed hair. And most of them were even from some girls! I walked in the front door to see my sister sitting in the family room.
“How did school go?” she said excitedly.
“Actually pretty well! I got a lot of compliments from girls,” I responded.
“Great! Hey can you actually come up to my room real quick? I want to show you something.”
Faith seemed really giddy as I followed her to her room.
“So I had a lot of fun helping you with your look yesterday, and I was wondering…”
“Wondering what?" I asked.
“Well it was a lot of fun yesterday, so I was wondering…could I do your hair again?”
I was kinda confused because she didn’t REALLY “do my hair” yesterday. She just brushed it. However, she seemed like she really wanted to, so I thought, what the hell.”
“Yay!” she squealed. “I know a great style that you could use for this weekend!” Faith then told me to wash my hair again, and make sure to condition and shampoo too.
I did as she asked, and then returned to her room. She pulled out a blow drier as she did last time, and then pulled out a curling iron.
“What’re you doing Faith?” I asked concerningly.
“Oh I’m just adding a few loose waves to your hair. It should look pretty.”
“Pretty…what?” I asked.
“Just pretty!” She happily responded!
I awkwardly just let her do her thing. She HAS been at Thornwood longer than I, so I guess she knows what’s cool and what’s not. She then stepped away from me smiling.
“Wow! Your hair looks incredible!”
I took a good look in the mirror and she was right. My blonde hair beautifully cascaded down just past my shoulders. Faith’s eyes lit up and went over to her dresser and grabbed a white flower barrette. She clipped it on near my temple without my permission and the excitedly squealed.
“You’re hair looks so cute now!”
I don’t know why, but I didn’t immediately reach to pull it out. I weirdly agreed with her, because it did look pretty good on me. I’ve always been told I have feminine-ish facial features, and the way the hair was shaped with my head, it did look pretty stellar.
Well Faith and I just sat in her room for the next hour or two talking, and I guess I was so consumed in the conversation, that I totally forgot I had made a Friday night dinner with my friend Kate! I explained to my sister that I had already made plans and she said that I should go.
I went back to my room to change out of my school clothes. I left the khakis on, but could not for the life of me find a t-shirt.
I guess Faith saw me struggling and she decided to help.
“Hey Tom if you need a shirt you could always borrow one from me.”
I thought about it, and then figured that it would be alright. It’d be a good conversation starter with Kate. She then led me back into her room and pulled out a plain white blouse. It was a long-sleeve cotton piece with a v-neck at the top.
“It’s not too feminine, so you should be fine,” she said.
I put on the shirt and then walked out the door. The restaurant, called Sally’s, was just a few blocks down and I saw Kate sitting down at the table.
“Hey you weirdo!” I said as I walked up to her jokingly.
“Um excuse me!" She said glaring at me. Her face then relaxed and she started blushing. “Oh my gosh Tom? I hardly recognized you! You’re hair is so…different!”
I too began to blush. “I mean…do you like it?”
“Tom, I love it! Actually not that…I’m IN love with it! That is some of the most beautiful hair I’ve ever seen!”
I blushed more than I ever have in my life. “Well my sister just kinda wanted to try something out…”
“Seriously Tom you should do that more often. And I love your barrette that you put in it as well! It’s adorable!”
I completely forgot about the barrette! I thought I had taken it out when I left the house! I rushed to take it out but Kate grabbed my hand to stop me.
“No! Please keep it in, Tom. It makes your look really cute.”
I couldn’t believe it! I had never been called cute by a girl before! Was Kate hitting on me?
Well we finished our dinner at around 7:30 and we began to walk out the restaurant just as Kate asked me something.
“Hey Tom, would you wanna come back to my place? It’s still early in the night and you know we can just hang out or whatever…”
In my mind I was going crazy! A girl was asking me over! And not just any girl…I mean I’ve been friends with Kate for a few years now, but I’ve always had a crush on her. She’s simply a beautiful, pure, loving girl. I love everything from her innocent wide eyes to the cute little nose she has. Her gorgeous, wavy brown locks always are perfectly groomed and add to her unworldly beauty.
We arrive at her house and immediately head to her room. She sits me down on the bed and tells me to close my eyes. She tells me that she loves my lips and tells me to wait. I’m dying with anticipation right now!
After about 15 seconds (that felt like 15 minutes), I feel something on my lips. But it isn’t HER lips…
I feel the pressing up against my lips and realize that it is not her LIPS that are touching me. I open up my eyes and see are holding a container of very light pink lip gloss in her left hand, and a lip brush in her right, applying it to my lips.
I jump back, startled, and she asks whats wrong.
“What’s wrong! You’re putting lipstick on me!”
“It’s not lipstick, it’s lipgloss, and I just HAD to see what you looked like with it on. I just got it at Macy’s last weekend, and I thought it would look fabulous on you with your new hairstyle!”
“But Kate, I’m not a girl! I shouldn’t be wearing lip gloss…right?”
“Not just girls have to wear lip-gloss,” she said convincingly, “Guys can wear lip gloss and other make-up.”
“Really…” I said sarcastically, “Please, tell me who.”
“Well have you heard of the band KISS?”
KISS actually happens to be one of my favorite bands in the world. “Shout it out Loud”, “Detroit Rock City”, and “I Was Made For Loving You” are three of my favorite songs ever recorded.
“I guess they do wear make-up…”
“Exactly. So why shouldn’t you be able to, And even so, this is much less make-up then them. It’s just a little lip-gloss and mascara.”
“Oh! I forgot to mention! I got this great new max-volume, ultra-black mascara last weekend too! I was hoping to try that on you as well.”
Before I could respond she had the tube of mascara ready to go. She told me to steady my eyes and she began to apply it. After a few minutes she told me to take a look in the mirror. Even without mascara, my naturally long eyelashes look a little girlish. But WITH it, they look even prettier than your typical girl.
“You look beautiful Tom!” Kate said.
Beautiful wasn’t really the word I was looking for, but I guess I did look pretty good…
Hell, not good. I looked like a girl! With my wavy blonde hair (accented with the flower barrette), light make-up, and my white blouse and skinny khakis, I looked a LOT like a girl that would be in my grade. Being thin and 5’7” only added to that notion.
Kate and I ended up talking about school for the next few hours until I went home later that night. I walked home and when I got in the door, I tried to sneak up to my bathroom (to wash off the make-up) but was cut off in the hallway by my sister Faith.
“Hey Tom, can I talk to your for a second?”
“Sure” I said with my head down, so she couldn’t really see my face.
“So I was at home and Scott (Faith’s boyfriend) came by. He sat me down and with brutal honesty, he dumped me.”
“Oh dear…Faith…I’m so sorry….” I said with extreme sadness.
“(sighing) I know, me too…I’m just feeling really down that’s all. Can… can I have a hug?”
I couldn’t say no, so I went in and hugged her for a while.
“Thanks Tom. That at least helps a lit-“ she cut herself off, “are… are you wearing makeup?”
I blushed in a very obvious way and tried to pass her up and get to my sink, but she stepped in front of me.
“Tom, I don’t have to know why or where you did this, but I just want to tell you that you look like a beautiful girl.”
She then walked downstairs to the family room to watch TV. All with a warm smile.
I started to continue on my way back to the bathroom but stopped once I reached the hallway mirror. Taking a long look at myself in the mirror, I sighed. I really have no opinion on my look, but It seems to make Faith really happy. After a few minutes I walked back to my room, turned the lights out and went to sleep.
Waking up Saturday morning, I knew what I had to do. Faith was out volunteering at the Animal Shelter for the next two hours, so I knew I had plenty of time. Faith needed to be cheered up due to her boyfriend, and if seeing me dressed as a girl will help, then so be it.
After showering, I walked into Faith’s room after my shower and began to blow dry my hair. Once that was finished, I sat down at her vanity, grabbed the curling iron and went to work. I did a surprisingly good job, basing off what I had seen her do the other day, and once I finished, I had a head of long, loose, golden curls. I even added a similar pink flower barrette like the one from yesterday.
There were multiple drawers underneath her vanity, and looked through them until I found the ones with makeup. I took mascara, a tube of Light Pink Lipstick, shimmery lip gloss, foundation, blush, and even a little glitter. I began with the foundation. Now I had never put on makeup myself before, but I had seen my sister and mom do it TONS of times, so I new all the tricks. Once the foundation was applied, I added blush. Before I used the mascara though, I picked up an eyelash curler and curled them to a girlish length. Then the mascara.
The lipstick was next, and after that the lip gloss. I paused for a second, remembering last night when Kate applied it on me, and what a weird, good feeling that was.
My makeup was now complete. In the end, I think I did a very good job, as I looked even prettier and more girly than I did yesterday. Which I suppose qualifies as a good job.
And now for the clothes…
Having a sister, I know how girls dress. I took off my t-shirt and jeans, stripping down to my underwear. At this point, I basically have a girl head and a boy body. A thin, small body, but a boys body nonetheless. I went into here drawers and grabbed out a pair of white cotton panties. Very basic, as no one was going to see them any way. I started for the closet, but then realized nothing would fit well if I didn’t have a bra. So i went back to the drawers and put on a lace, white brassiere.
There I am, standing in my sister’s girly room, with my face and hair dolled up, and wearing a bra and panties. I know most boys would never be doing this, but am I really like most boys…
I quickly threw that thought out and remembered the task at hand: cheering up my sister.
Now that I had her bra and panties on, I went over to her closet. Knowing how most girls style themselves, a dress would be most appropriate. And boy did Faith have dresses…
Inside her closet there were ALL TYPES of dresses: maxi, mini, wrap, sheath, peplum, you name it.
I decided on a white, flowy summer dress with blue and pink flowers. I stepped into the dress, and adjusted it to my fitting. The feeling was something that I had never experienced before.The air could rush up my legs and my lower half just felt so…free. (Don’t tell anyone, but I even twirled around a few times because it felt so good!)
There were some blue flats by her bed that I slipped on (a little small, but they still fit), and I walked back over to the vanity. I sprayed on some Anna Sui perfume to give me a girly smell (To be completely honest, it smelled magical).
So there I stood; I was completely girl from head to toe. Looking at myself in the mirror, I had another strange feeling: comfort. Like I actually enjoyed this…
I also removed that thought from my mind quickly.
Just then I heard the front door close. Faith was home. I could hear her talking to my mom in the kitchen downstairs, and she still sounded very gloomy from last night.
In a hurry, I cleaned up her room and walked into mine, closing the door till just a crack open. I called for my sister, excited to show her the surprise.
“Hey Faith!” I yelled, “I have something to show you in my room!”
“Be right there,” she said gloomily.
I waited for 15 seconds and then the door creaked open.
She stood at the doorway, looking confused at first. But then her face slowly started to change. A smile was growing and her eyes began to water. The smile grew and grew, and while watching this, I began to tear up.
Tearing up, she said “Don’t cry, you’ll ruin you’re mascara.”
We both laughed. And with that she ran and emotionally embraced the feminized me.
“I thought you needed some cheering up,” I said, “and I figured this would help.”
She pulled out of the hug and looked me in the eyes. “You’re…beautiful. Purely beautiful."
To possibly be continued or sequel-ed...
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