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A Guy With Girly Hair - Becoming A High School Girl

 ALL STORY LIST

CHAPTERS - CH2 | CH3 | CH4 | CH5 | CH6 | CH7 | CH8 | CH9 | CH10 | CH11 | CH12 | CH13 | CH14 | CH15 | CH16 | CH17 | CH18 | CH19 | CH20 | CH21 | CH22 | CH23 | CH24 | CH25 | CH26 | CH27 | CH28 | CH29 | CH30 | CH31 | CH32 | CH33 | CH34 | CH35 | CH36 | CH37 | CH38 | CH39 | CH40 | CH41 | CH42 | CH43 | CH44 | CH45 | CH46.1 | CH46.2 | Epilogue 

NOTE - Not a continuation but very similar to A Boy With Girly Hair - The Contest.

Many of you were very disappointed with the ending of (A Boy With Girly Hair - The Contest); I am really sorry for that; thinking about the comments, I was very restless, so I was thinking overnight about how will I continue with this story and then started writing this story; I promise this will be a long story and will not rush for the end. I hope you will like it because it will be a long journey to cover. 

Not A Intro

Hi, I really don't know how to start this. My friends and family recommend that I put this all down on paper, so I've put this together based on my journals and memories.

Please be patient with me.

I've decided to focus on my senior year at Central High School. It seems appropriate, as it was the year in which my entire life turned around. 2002 would become be a very monumental year for me.

At the time, my name was Eric Alexander Walters, age 17. I was 5'-10" and weighed around 140 lbs.; yes, I was a stick, a stick with shoulder-length light brown hair. Entering my senior year of high school, I could be best described as a pretty good student, well-liked, and a first-class runner; I was, to all appearances, a normal, average teenage boy.

I can still remember when I registered at my new high school. Looking back, it started me on a path that I would have never thought possible.

Mom and I had just moved into this little town. We had been living in San Diego, but the job market forced us to relocate. Mom got a great job offer that was too good to pass up. She would now be in management, and the money was tremendous compared to what she'd earned before.

The problem was that we had to move to a town called Golden Hill, located in the middle of Pennsylvania. The computer program company that had hired my mom had selected it for their new headquarters just because it was so "quaint." I had looked at the map and found that it was located perfectly so that it was an equal distance away from anywhere interesting. There was a small liberal arts college nearby, but not much else. I tried to be upbeat and supportive, but it was difficult. I was about to enter my senior year in school, and now I would be the outsider.

Like I said, I tried to be supportive of the move, even though I dreaded it. My mom's happiness was important to me. She had raised me as a single mother. I never knew my father, and she never said much about him. Mom always was there for me, and I never felt like I was missing anything. The move, however, was hard for me to accept. I had hoped, up to the minute that the movers arrived, that a miracle would occur and we wouldn't have to leave San Diego.

I guess I should explain a few more things concerning the move. I mentioned earlier that I was an average student. Actually, I was slightly better than average but not good enough to get an academic scholarship. I was also a good athlete, but again, not spectacular enough to earn a scholarship. While we were never wanting, there was never any extra money to put away for college. Something always seemed to come up whenever we got a little bit ahead.

I desperately wanted to go to college. But considering our money situation, I had resigned myself to working part-time and attending community college. I had often dreamed of some miracle happening that would solve all our money problems.

Mom was very frustrated with her inability to help me. She really wanted me to make something with my life, which led to her taking the job in Golden Hill. That's what made a move even more frustrating for me. I was leaving my life behind; at the same time, I knew that Mom was doing this for me. I also realized that she was also going to be experiencing a whole new life.

The drive itself excited me, giving me a chance to see the country. We crossed the landscape in a roundabout route, which gave us a chance to talk about the new job, new town, and new school. She told me that our new house was really nice. She had already rented a house in one of the newer developments.

Our neighbor, Terri Hawkins, was one of her future co-workers, and they had hit it off from the start. Terri was divorced and had a daughter my age named Caitlin. Terri sent us a lot of stuff on the town and the school. I had even traded a few e-mails with Cat, and she told me to call her. Maybe it wouldn't be so bad after all, I thought.

Terri and Cat helped us get settled in our new home. In some magical way, Cat and I instantly became friends. I guess I should tell a little about her. The cat was a little taller, and at the time, she kept her long brown hair in a ponytail. She was very athletic, but you wouldn't consider her a "tomboy." She loved dressing up and usually wore long skirts that seemed to flow down her long legs. And her personality! She had the same warped sense of humor that I have. I guess I fell in love with her the minute we met; however, it took me several months to tell her. Sorry, I am getting ahead of myself.

Anyway, back to the story.

On our first night in town, we ate dinner with the Hawkins. Terri told us that I would need to register for high school, and Cat volunteered to take me over there in the morning. Terri then asked my mom if I was going to enter the Senior Scholarship competition. Cat smiled at me and said that I definitely should, that it was worth competing for. I asked her if she was going to apply, and both Cat and Terri laughed. Terri told me that it was only open to boys.

I was thinking about how they never would allow such a thing back in California when my mom asked Terri about the contest. It turns out that the winner would get a fully paid four-year scholarship at the college of their choice; additionally, they would get a monthly stipend to pay for living expenses. It sounded too good to be true!

"So, what do I have to do to win this?" I asked as I took a sip from my soda.

Terri looked at Cat and smiled. "Why don't you tell him, dear?"

"It is a simple competition that starts on the first day of school. It's a contest of elimination. You're in it until you either quit or violate a rule. The last one wins," explained Cat.

"The last one wins? By doing what?" I asked. I sensed that it was something difficult.

"You dress and act like a girl, twenty-four hours a day, seven days a week. Everything from the tip of your head to your painted toenails" answered Cat. "I hope you enter. I know that, with my help, you'll win!"

"That's not exactly true, Eric. You won't just dress as a girl; you'll be treated like a girl too," added Terri.

I sat there, unable to speak. I was hoping this was a joke. I looked at Terri and could tell she was serious. Cat got up and brought back an application package, and handed it to me. I opened it up and looked at the pamphlet. Sure enough, the rules required the competitors to dress completely as female. Applicants were also to have a female name and take courses appropriate for their gender. Each applicant was encouraged to go out for extra-curricular activities or get a job in their new gender.

"They have been doing this here for the past seventeen years. The woman who started it was married to the president of Dewey College. She had inherited a huge amount of money and decided that she would put it all into a scholarship program. She offered it as a way of teaching gender equality. It is now considered an honor to win it. When it first started, the competition only lasted three weeks. Last year, it ended just before the winter holiday break," explained Cat.

"What happens if the school year ends before someone wins?" asked Mom.

"Well, that hasn't happened yet, but the rules say that all those still in the competition would get a scholarship," noted Terri.

"Last year, there were nearly forty entries at the start, and there should be about the same this year," added Cat.

I was still reading the rules. During the contest, all competitors would be officially considered female in all aspects of their lives. I showed this to Terri and Cat.

"What exactly does this mean?" I asked as I pointed to the paragraph in question.

"It means, among other things, that you would be fair game when it came to dating. No one would consider it immoral or gay when you dated, as long as you were dating a boy. Almost everyone around here just accepts the scholarship contestants as girls," explained Terri, "not just at school, but all over town."

"Everybody? I wouldn't consider it normal," I mumbled.

"It's considered part of the competition, Eric. First, you don't have to date. If you want to date, then it's cool. Second, it's just a date; you don't have to kiss or anything like that. Think of it as gaining a new view of the world," continued Terri.

I nodded as I absorbed what she was saying.

"Come on, Erika, it would be so much fun. I would help you!" chided Cat, "Besides, I think that you'd look really cute."

I glared back at her for the "Erika" crack. I looked at my mom, and she was looking intently at the pamphlet with Terri.

I wasn't sure if she was serious or not. Part of me still thought this was a joke that was being played at my expense. But, if it was a joke, then it was pretty well played. The form looked very official.

"Well, at least think about it. They will explain it to you again tomorrow at school when you register," replied Cat.

When we got home, Mom asked me if I wanted to talk about the scholarship. I shrugged my shoulders and tried to give the impression that I didn't care one way or another. We sat down at the kitchen table.

She asked me what I thought about the idea. I looked at her and stated. "I don't want you to think I'm gay."

She smiled and reached over and hugged me. "Honey, doing this has nothing to do with your sexual orientation. There are straight people who dress in the clothing of the opposite sex, just as there are gays who don't. And I'll always love you, no matter what you do."

I sat there for a minute, trying to think of something to say. It's funny, but even now, I can still remember those same feelings of denial that I did back then.

"You know that this is a great opportunity for you," she continued. "I know how badly you want to go to college. You know that our finances aren't great; we had to move here because I couldn't afford to turn down the job. Sometimes, you have to do something you don't want to. And sometimes, it turns out for the best."

I thought about the sacrifices that she had made over the years for me. Would it really be that bad to dress as a girl for a few weeks? If I won, then she wouldn't have to worry about paying for college. I also thought about Cat. She really seemed to want me to enter, and maybe this would allow me to get closer to her.

"Even with my new salary, it will be very difficult to pay for college," explained Mom.

She didn't have to go into detail. The move had been expensive.

"I want to think about this before I make my decision," I replied softly.

"I also want you to know that I knew nothing about this scholarship contest," continued Mom.

I nodded again. I knew that she was telling me the truth, as she had never lied to me. There were things she wouldn't tell me, especially relating to my father, but she never lied to me.

Mom leaned over and gave me a kiss. "You know, Cat is right! You could make a very pretty girl!"

I laughed at myself.

I had a very restless night. I tossed and turned, thinking about my life, the scholarship, and what I would have to do to win it.

A Guy With Girly Hair - Becoming A High School Girl

Comments

I have no idea which story this “other one” is referring to - that said, I love the premise, the opening, and the huge potential for another of Urban’s novela works I have rapidly come to love, having only discovered Urban’s work a few months ago. She is already my favorite on Patreon as it is…. These longer well developed works are the reason i near instantly went for top tier. Please keep up the awesome storytelling

Annah Rourke

I'm reading and listening to this story again I don't know our many times I've enjoyed it but this time the story won't play

Brett Schuhkraft

This is the 6th time I'm enjoying this. I wished so much that I had started my transition when I was in school, and now I'm kind of living it through this story. I love everything about this story, even the voice.

Leloine

No matter how many times I try to access the new chapter 44 the system takes me to 36!

Laura OLacy

Come on guys, Urban just started this story and you are already complaining about it? Give her a chance to get into it. The last story was about a boy-girl beauty contest and she ended it when the contest was over. The new story is a school year long contest to see who makes it to the end. Let’s see how it goes.

Julia Miller

This story has lots of promise, a great intro chapter. Hopefully Eric/Erica and Cat date each other

Kylie Boucher

Really sounds a lot like the last story . hopefully we are not equally disappointed.

Shane Olson

I’m holding comment as it’s a bit convenient for my full liking

Clive hooks

I love the start of this story. Go Erika.

Brianna Demonet

This story has a promising start. Our boy Eric really wants to go to college but mom can’t afford it. In their new town he has a chance to win a scholarship, but must dress as a girl. What’s the worst that could happen to our boy? 😊 I guess we will find out. 🧑🏻‍🦱🔜👩🏻‍🦰

Julia Miller


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