Brothers Keeper

Brother’s Keeper
A Short Story
By Maryanne Peters

I adored my brother Jason, and I wanted nothing more than to hang around with him. But I knew that I was an embarrassment. I was less than two years younger than him, but I was half his size. He was born to be big, and I was born to be small. He was born to be strong – a natural athlete, and I was born to be … not that. He liked to hang around with his pals – the jocks – Kevin, Brad and Hans. They were guys like him. Guys to be admired by guys like I was.

Most brothers would just push me away, but Jason was not like that. It was because Dad had disappeared years before (he was a jock too, but an asshole) and Mom was working hard to bring up two teenage boys. From when I was very young Jason understood that he had a role in looking after me, so he let me tag along. That was the kind of brother he was.

I knew that I did not fit in. When we were at the Shake Shop I would sit at a different table to the four of them – the Jocks. I would sit at the table next to it and read a book. I liked to read fantasy stories – powerful men and beautiful women, on a mission. They would do their thing. It was good just to be around them.

I suppose things changed when the jocks started to chase girls.

They talked about girls all the time before then, but sport took up all their time. The fact is that I knew more girls than they did. I even had a girlfriend or even more than one, but it was never sexual. I had friends who were girls – more like that.

The guys spoke about the girls they would like to date, and I remember Kevin saying – “Hey Miles, you are really cramping our style here. How can we pull the babes with the kid brother hanging around?”

I remember him saying it because I was sitting at the table behind the jocks when two girls that I knew came over and sat with me. They chatted with me, but I knew that they were interested in the guys in my brother’s group by the way the girls set about deliberately ignoring them.

“It would be more useful if you were the kid sister instead of the kid brother,” said Brad

“I would pay money to see that,” said Hans. It was a common line with him, because his family had money and was always laying down challenges or bets.

“Leave him alone,” said Jason, protective as ever. “A younger sister would have been great, but that it not what I have.” He fluffed my hair when he did it. He cared about me, and I adored him. I only wanted to do good for him

“How much money are we talking?” I asked. There was something about the way that Jason spoke that made me say it. It was like I was a burden. A sister would have brought girls to our house. Instead, he had to put up with me.

Could I bring in the girls for the jocks? The thought came into my mind that I might be able to. Although I could never be a girl, maybe if I was a wannabe girl? A transgender person transitioning to female? I had read somewhere that such a person can be subject to special protection and empathy by girls in the same class as they are.

“I’d give you a grand and pay for the makeover,” said Hans. “But you would have to get in with some pretty girls. At least 4 of them.”

They all laughed. Including Jason. It riled me a bit. Not Jason, but the others would make fun of me sometimes. It never mattered too much to me, but I started to consider how things might change if I took up his challenge. If I could become a special friend of a group of girls – a project for them even – then the attitude of Jason’s jock pals to me, might change significantly.

“Shake on it,” I said, walking over and putting my hand in front of Hans. He looked at me then his pals, and then grabbed my hand and crushed it, making me wince. It made me think that he would never do that to a girl.

“Thanks for the offer, Miles, but you don’t have to listen to these guys,” said Jason. He always had my back.

“No, I want to Jase,” I said. “I can do it for a few months. Maybe I can set you guys up. I want to be useful, and I don’t have a reputation to protect.”

It was really that simple. I just had to run it past Mom.

“If you are transgender then I need to know,” she said. She was busy and so she was practical.

“It’s not that simple these days, Mom,” I said. “Young people like me are exploring gender. You don’t have to choose – at least, not yet. I would like to find out how deep the feminine in mem, runs.”

It was nothing to do with that, but I knew enough about gender fluidity to run out a few of the arguments. All that she wanted to know was that before I made any decisions with permanent consequences, she would be involved, and I promised that she would be.

“Having a daughter around for a few months might be quite nice,” she said. “God knows your brother is no good around the house.”

“Mom, that’s a sexist comment,” I said, but then we both laughed.

I read up about what it meant to be transgender and then I arranged a meeting with the principal to explain what I was going to do after the Christmas break. Mom went along and I announced that I was going to come to school as Milly. I think that the principal was not surprised. He did not know me at all, but it was like he was ready to have a transgender student come forward one day.

“I want the school to protect her from bullying,” Mom said, using the pronoun for the first time. “Her brother will do his best, but students need to be told not to make fun of my daughter.”

She gave Jason a lecture when we got home too, but it was not like it was needed. Jason was there for me as a brother, and he would be if I was a sister as well.

“Are you sure that you are not taking this too far,” he whispered to me. “I know what this is about, but you have to be able to unwind it all when you have done what you want to do.”

“I am in control of this,” I told him. “Just tell Hans that I have booked the makeover at that little salon on Maplewood Street for the weekend before school goes back, and they want payment in advance.”

“Okay Miles, I mean Milly,” he said. I think he may even have given me a nod of approval. It was a big thing that I was doing, and he knew it.

I went to that salon with Mom, and she took the opportunity to have her hair done too. But what she and the hairdresser were at pains to point out was that presenting as female would not be easy, but it needed to be complete. The salon recommended waxing and hair extensions, plus a facial, eyebrow threading and makeup plus a course in doing it all myself.

“Who is paying for this?” asked Mom. “Don’t tell me that you have a boyfriend already.”

“Hans is paying. Maybe he wants to be,” I said it, but just because I did not want to tell her much more.

When it was all done I think the whole three of us, Mom, the hairdresser and me, were startled that I looked so good. I guess that where Jason took after my dad, I looked more like my Mom, who was known as a beauty in her school days. That did not escape her attention.

“If you are interested in boys, then make sure you pick the right one,” she said. “Don’t make the mistake I did.” Mom rarely put Dad down, but she could never forgive him for walking away from her and his family.

I walked out of the salon looking fabulous but in a sweat suit. Still, Mom had sorted out some clothes for me to wear to school on Monday, starting with feminine underwear.

“Perhaps just wear jeans and a shirt for your first day at school, with your wonderful hair tied up,” she said. “But wear these under whatever you are wearing to remind you that you are a woman … if that is what you are?”

“I’m doing this Mom,” I said. “Who knows where it will lead?”

I was looking at myself in the mirror as I said it. It was supposed to be a fabrication – an excuse to cover the bet and the favor I was giving to Jason and his pals, but as I saw those pretty lips saying those words I realized that there was already doubt. I did not know where I was going with this.

Mom and I practiced me being a girl, sometimes with Jason looking on in amusement.

“Well done with the walking, Sis,” he might say. Encouraging perhaps, but skeptical.

On the first day of school I dressed as Mom suggested – jeans and a shirt – but embroidered jeans and a floral print shirt, and that underwear underneath despite not having the body for it.

I had to wait in the principal’s office until he made the announcement, and then I swallowed deeply and went to my first class.

Of course, I knew everybody there, and they knew me, or they knew who I had been. The teacher mentioned that there had been a change over the break and that – “a certain student here has proven to be a very brave young woman”. I just shrank into my chair. I had prepared myself for this moment yet it still seemed to be the most embarrassing moment in my life. Then some of the girls in my class started clapping and pretty soon everybody was looking at me and applauding.

Looking back on it, this moment should have been a great one in the life of a young transwoman, but I was still not yet that. But I was grateful for the support and I smiled in the direction of those that seemed to be clapping the hardest – the pretty girls. They were why I was there. To make friends with them and help out the boys.

And by the end of the first day as Milly, I had pretty much done that. Some of the girls came up to me afterwards to ask me questions – When did I first realize I was trans? How had I been able to last so long living as a boy? Did I want to have an operation? I had prepared answers to these. Did I like to wear dresses? Where did I get my hair extensions done? Was I on hormones?

When I said no to the last question, all the girls seemed surprised. I just said that I was considered too young – it was something that I could look forward too.

Alyssa, who was the effective leader of the prettiest girls, said that she had been planning a sleepover party for the weekend, and maybe I should come along? The other girls looked at one another and agreed.

“You’re a girl now,” was the consensus. “You should come. We will just do girl stuff – do one another’s hair and make-up and watch back-to-back romcoms.” From that moment I was accepted. I guess that day made me realize that I was never really accepted by any group of guys in my class, and now any of them who might have been considered a friend wanted to distance themselves from “the tranny”.

The school had warned every student that name-calling and general intolerance would not be tolerated, but we all know that spoken words are not required to shun a person, and many guys did that. I told myself that the only guy whose opinion mattered was my brother Jason, and those around him. But I was pleased when some of the guys in my class started talking to me again. I guess one of the best things about radically changing who you are sorts out the people who matter.

But it was the girls that I wanted to be close to, and as they pointed out, they were the people I needed.

“I guess it will be difficult for you, but we’ll help you to join the female sex,” said Chloe, another of the popular crowd. “There is a lot for you to learn, but it will be fun.”

I said that I was thankful, and I was. The last thing I wanted to do was be a guy in drag. I wanted to be a serious transitioner, at least until the job was done. After that, I could simply detransition and put it down to “an adolescent experiment in gender fluidity”, or something like that.

But before the week was out, Alyssa came back to me and said that her parents were concerned about a guest at their daughter’s all-girl pyjama party actually being a boy.

“I told them that you were on hormones and could no longer function as a male,” she said. “I managed to get you some hormones. I know that you have been told that you are too young, but that is bullshit. I have read up on it. Everybody in your position can’t wait to get on them – right? You must be thrilled?”

What could I do? The worst thing was that they were patches, and not the kind of patch that could be taken off and then stuck back on. One under each nipple stayed there for two weeks, and she said that I should be proud to show everybody. I had to appear deliriously happy and stick them on then and there. But I told myself that I could handle this and that the effects could only be minor given the dose was short term.

The party at Alyssa’s was a great success and I learned so much about being a girl there. When I told them that I really felt a part of a group for the first time, I also learned something about boys too.

“Don’t you understand that boys are lone wolves,” said Chloe. “Even if they hang in a pack it is only to get what they want. They still compete with one another. Their friendships are different. Female friendships are real and sometimes closer than family. Women love to be in groups. It is part of our biology. Child birth and child raising need the support of others. Even if you never have that chance it’s now the way that you live – among friends.”

I have to say that I burst into tears at that point. It may have been the hormones. It may have been the raw emotion of having been told that you might be among friends perhaps closer than family. But there was also a strange tinge of sadness that I could never truly be one of them because I could not bear children. That was the kind of thought that did not belong in my head. It was transgender thinking, and that was not who I was – or so I thought.

Then we got on to a discussion about boys. I had to join in as if I was interested because I wanted to talk to them about my brother and his friends.

“Your brother Jason is a babe,” said Alyssa, “But I really like his friend Kevin.”

“He has another friend called Brad, right? What is he like?” another asked.

I spoke positively about all of them, including Hans.

“He is a little bit weird,” said Alyssa. “Good looking, but strange somehow.”

I suppose I understood what they were saying. Hans was different, but as we talked I felt an urge to stick up for him quite strongly, but I didn’t say much.

After the weekend Jason said that I should go down to the Shake Shop with him as he was getting together with the guys.

“Why don’t you wear a dress? That will give them a real shock when they see you,” he said.

I suppose that they might have seen me at school although they were two years above me and did not mix much with juniors. I agreed to wear a dress, and when I had it on I was very happy to see myself in it, and spin around a bit in front of the mirror.

We arrived late. Jason took a seat and I sat at another table. I had brought a book but also a compact mirror to inspect my hair and makeup – which is what I did.

“Is that you, Miles,” said Kev.

“It’s Milly, not Miles,” I said curtly, in my feminine voice.

“You’re really pretty Milly,” said Brad. “Don’t you think so, Hans? Take a good look, Pal. You paid for this look. Hans turned to look at me, and the expression on his face startled me for a moment. It was amazement I guess, but it was as if he was fighting something within himself. It is strange that you can see so much in a person’s face when you have known them as long as I did Hans, but he was looking at me like a stranger – one who fascinated him.

I was only just starting to recognize desire in the face of men, but this was something different. I think that Kevin was amused, and Brad curious. Jason just saw me, as a brother should. But Hans was mixed up. It’s a bit weird, perhaps. But I like the feeling seeing my effect on him gave me.

“So, Milly has made friends with a bunch of girls who might be interested in meeting guys like us,” said Jason. “Why don’t you come on over and sit with us, Sis. Tell us whether we have any admirers that we should know about.”

It was the first time I had ever been invited over. It was also the first and last time I accepted. By the time I had done my bit and done what I had promised I would, I realized that I did not really belong with these guys. I had spent years wanting to be sitting at that table with them, and now I knew that while they had not changed, I had.

But I had some pairings in mind and I agreed to act as go-between and arrange some date.

“Remember that you owe me a grand if everybody gets a date,” I said to Hans. He simply nodded. He was strangely quiet the whole evening.

I decided to pair Jason with Chloe, who was both beautiful and clever. Alyssa likes Kevin and he was a guy who could follow her lead. I had Brad to date Madison who was super sexy and even looked a little like him. But I could not find anybody to date Hans.

“He is super good-looking, has a great body and he is rich,” I implored.

“He is a catch, all right,” said Alyssa. “He is yours.”

I was thinking about how to collect my money, but I figured she was right. I could turn up as his date. I was a girl just as much as my friends. Jason just needed to explain to Hans that his partner for their meal as 4 couples was going to be a blind date. He might be a little pissed when he discovered that it was me, but I would still be expecting him to pay up, and I figured his pals would tell him that he had to do it.

So, the big date came around and I went around to Alyssa’s place for the four of us to get ready. We all agreed that we needed to hit the ball out of the park with our looks – hair, makeup and sexy clothes. It was that night that I discovered that the hormone patches had already had an effect on my body. They were not yet breasts but there was flesh to work with in making a cleavage of a kind. I was shocked, but I could not show it. I had to show joy, and I found that strangely easy to do.

We all got an uber to meet the boys at the restaurant. I could see almost immediately that the pairings I had arranged were going to work, but I also had to face Hans, and deal with likely dismay. But instead he just smiled.

“I was hoping you would be my date,” he said. “I find you the most fascinating creature I have ever met, and I really feel I have only met you twice.

“Just remember that you owe me some money Hans,” I said, giving him the smile I had practiced in the mirror. “But then I owe you for …, for being as I am.”

“I like the way you are, and I am happy to pay,” he said. He came forward and kissed me on the cheek. I swear a jolt of electricity passed through my body. Even in the years since, he has the same effect on me when I am in his arms.

The End

© Maryanne Peters 2025

Author’s Notes:

This story was as a result of a chat with somebody and I can’t remember who. I only have the note: “This sounds like a good story line to me. It is simple and I can see the brother/sister and the brother/friend relationships and also others in the brother's group reaction to his transformation and the aftermath. Can't wait to read it!” Who was that?

More importantly, this story is from my latest anthology of short stories on Amazon entitled "Romance we Must" themed around gender change out of some sense of obligation as opposed to voluntary, forced or otherwise compelled change. I will post a blog with links.