Aunt Katherine
A Short Story
By Maryanne Peters

My mother’s aunt Katherine had always hated men. She had never married, and that had served her well. She thought that her sister had married badly – to a man of course. The wealth that they had inherited was frittered away by my grandparents, where she had kept hers and multiplied it many times.

“No man will ever get his hands on my money,” she would say. And she meant it.

My mother’s older sister Geraldine (Gerri) had three children – two boys and a girl, Maddie, who was only a little older than me.

“Those boys will get nothing,” Aunt Katherine would say to Aunt Gerri. “Everything that will go to you will go to little Maddie”.

My mother had two children – a boy and a girl. Well, that is a lie. She had two sons. I am not really a girl.

It is just that as far as Aunt Katherine was concerned, we could never say that.

We knew all about this from the very beginning. I was given the name “Ashley” because it was what we would now call “gender-neutral”. My mother would always refer to me as “she”. So would Aunt Gerri and my cousins. The whole family was agreed that when she died, the estate would be split between the family of the two sisters, or if they died first for any reason, between Maddie and me. That way the wealth would pass on fairly. Maddie and I would be committed to looking after our brothers.

Then there were the occasions in my youth when I would visit Aunt Katherine, or the two or three occasions when she deigned to visit us. I would need to appear as the female version of myself. My mother had me keep my hair long throughout my youth to cover this eventuality. It could be a boy’s style all the time, but could be styled and have barrettes or ribbons added for encounters with my great aunt.

I wore dresses for the early visits, but I guess that she understood that I was a bit of a tomboy, so I could get away with pants if I wore a feminine top and something nice in my hair. I could not be too boyish because, well, my aunt hated boys as well as men.

As I got older and more frail, she stopped visiting us, but we still had to visit her every now and again, including staying over for Thanksgiving. She had a big house with a room for each of her nieces and each of their daughters, to stay over for at least one night. Boys were not encouraged to visit.

The problem was that she was still very much alive when I started approaching puberty. My mother was terrified that I would be found out. Aunt Gerri shared her concerns because we were all agreed that the eventual inheritance should be shared, but we did not want to risk her giving any part of it away.

Gerri and Maddie came around to our house a few weeks before Thanksgiving to discuss the problem. Aunt Gerri suggested that we needed to hold off puberty. She said that it could be done chemically. She ought to know as she worked in a drugstore. My mother seemed to be agreeing, but I was horrified.

“Hey, all the guys at school are about to go through this and you are talking about shutting me out of it?” I complained.

“Every boy has the change at a different time,” said Mom. “You might just be a bit later.”

Somehow it was understood that if Aunt Katherine’s estate could not be split into two equal shares, a chunk would go to charity. So, it meant a lot that I stay as the beneficiary on my side of the family. So much so that delaying my puberty seemed (to Mom and Aunt Gerri anyway) a small price to pay.

When I started taking the pills. What none of us were aware of was that my body would change, but in a different way. You see, the spiro-something drugs neutralizes male hormones, but male puberty includes a whole bunch of hormones including the ones that the spiro does not affect. I am talking about the estrogen hormones. The female ones.

Anyway, I was still neutral, I guess, when we went to Aunt Katherines for Thanksgiving. We stayed two nights in the big house. Aunt Katherine, like she always did, said that she was not long for this world and that we were her hope for the future, intelligent young women. That was us, Maddie and me. But this time she gave some jewellery items to us, split evenly. She gave me earrings and said that I should have my ears pierced so that I could wear them for the thanksgiving dinner.

She also said that both of us should have our hair put up and be dressed like proper young ladies for the occasion. It would be her treat. She would arrange a makeover and two classy party dresses. For both of our moms too. A proper ladies’ dinner, with five of us in our finery. In fact, there would be six, because she had invited her lawyer, Miss Jade Lowe.

Miss Lowe was a spinster like Aunt Katherine. I understood that they were around the same age, but whereas Aunt Katherine was thin and wrinkled, Miss Lowe had a round face and quite smooth skin, but blotchy. She was a big lady with a belly and bosom that filled her green dress. Her hair was white and thin, and wound into a bun on top of her head.

Jade Lowe could be very Jolly and funny, and she told clever jokes in her husky voice. But she could also be very serious when the topic was business, or matters concerning Aunt Katherine’s will.

“Jade will be acting as my Trustee and tending to the education and welfare of the heiresses to my fortune after my death,” Aunt Katherine announced. “I am concerned to see that these you carry my fortune forward with grace and class, and I know of nobody better that my lawyer and oldest friend, Jade Lowe, to see than done.”

It seemed like even after she was in the ground, she would be trying to control us from the grave. I wondered if I would ever be free just to be a normal guy.

It got even worse when we went in to the salon to get prepared for “The Ladies’ Dinner”. Aunt Katherine was very specific. We were to wear cocktail dresses that she would pay for, and shoes with heels, and our hair and makeup were to be done professionally. And I had my ears pierced. That would require some explaining at school. But it was not as bad as the eyebrows. Mom said that we might have to shave them off afterwards. It seemed like a nightmare.

I had my earrings in and a necklace around my neck, and my hair pulled up, and there was no mistake that I looked very classy. I sort of liked the look.

At the dinner, Maddie and I were allowed to drink wine. We were only just teenagers but we were throwing back glasses of wine called Sauterne – it was sweet and tasted really good, and I was told that it was expensive too. We actually had fun. Aunt Katherine talked about all the places she had visited and all the fine people she had met in her life (all women) and Miss Lowe told jokes and funny stories about her clients.

Aunt Katherine got a bit sad when she said that it would be the last Thanksgiving we would have together. She hugged us before we went up to bed. She had never done that before.

It turns out that she must have known something, because by the end of the winter she was dead. If you had had asked me six months before I would have been happy with that news, but after getting to know her at that dinner I found that I was quite sad. She was an intelligent woman who had done well because she had good judgment, and she always looked classy, even in old age.

Jade Lowe did not delay in making contact with us. She said that the will left the entire estate to Maddie and me, but on trust until we reached the age of 18. And in the meantime, Aunt Katherine had set out some rules. It was as we feared, the old woman wanted to keep tabs on us, even after death. At least until we were 18.

Maddie and I were enrolled to attend a Swiss finishing school for our high school years. It was the same school that she had attended, and so had our grandmother. We had to go there too. Graduation was a condition in the will. Graduation required that we meet standards of behavior rather than academic milestones. It would see us graduate at 16 so we still had the option to come back home to do a final year at high school in the US.

But what it meant for me was three years living as a girl. And Miss Lowe would be checking up on us.

The other condition that Aunt Katherine had imposed was that we were not to have any sexual relations with males until we collected our inheritance. Maddie sighed, but that was one thing I could live with. Sex with females was not ruled out.

What I had a problem with was that not only would I be sent away to an all girl’s school in Europe, but that I would need to postpone puberty for a full five years – quite possibly the most important 5 years in a young person’s life.

We had some private family meetings to discuss what we could do. My mother had asked Miss Lowe what would happen if either of the nieces declined to go to the school. The will had made provision for that. The inheritance would go to charities.

We even talked about just accepting half and splitting it. But there were complications with the gift so that that looked problematic too. No, I would have to bite the bullet and spend most of my high school years in drag. But everybody recognized that this was asking a lot of me, and that I deserved a proper reward for my sacrifices. Would anything be enough?

Could a boy hide in a girl’s only swiss finishing school? You would not think so, but then those hormones that I was talking about kicked in. I started to grow breasts. In fact, I started to show all of the signs of female puberty except menses. It was weird, but in a way convenient.

The only thing I had to worry about was what was in my underpants, but that had become only a little problem. I mean, it had become little, so much of a problem. Every guy at my school was getting hairy and had big swinging dicks on display in the changing room, and I was wearing binding under my shirt to hide my titties, and I had the groin of a 10-year-old.

To be honest, when I got on the plane to Zurich, I was happy to be going somewhere where nobody knew me, and where I could just disappear in the disguise that I needed to adopt.

I will never know what my high school years could have been like, but it turned out that high school in Switzerland was pretty cool. The fact is that it was not really a finishing school at all. They were a thing of the past. The school that my Grandmother and Aunt Katherine had attended had become an “International School” with presentation and etiquette only being a small part of it. Classes were in English and there were girls from all over the world there. French and German were taught and widely spoken, and also Italian. All four of those languages are widely spoken in Switzerland.

Maddie and I had a full five year education there, and we shared a two bedroom room throughout, as Aunt Katherine had arranged and paid for. Not only did I manage to conceal my male genitals for all that time, but I hardly even gave them a thought.

Our term allowed a summer break and a Christmas break when I could go home. When I was home I could go back to being boy Ashley, but I have to say that it got harder and harder to drop the girl Ashley. One reason is that my circle of friends had changed. I hardly knew the people that I went to middle school with. When I met them they would look at me oddly. I guess that I must have looked childlike or gay, or something, even in jeans and a baggy shirt that hid my breasts.

Also, some of the girls from my Swiss school lived nearby. Maddie and I could get together with them. So if we did, I would need to change into girl clothes to go out, then come back home and … why bother changing? Vacation time was supposed to be boy time, but I didn’t miss it if it didn’t happen.

Also, Aunt Katherine had set aside money for my Mom and my aunt to come to Europe for the short spring and autumn breaks, and when they did, we just travelled around as four women. Maddie learned German and I learned Italian, and we both learned French. They were just a week or so, but we travelled all around on money from the estate. It was great. What high school kid, boy or girl, could claim better school years than that.

I suppose the only thing that was a bit confusing for me was boys. I mean relationships. The girls from the US were always talking about boys. I learned that it was the drug I was on that kept my sex drive way low, so I was not that interested anyway, but I suppose I sought refuge with other girls. In particular I made friends with two Arab girls – Miriam and Latifah. Our school remained a single sex international school, unlike the others, so it was popular with Arabs and other traditional societies. I mean, Miriam and me still played around with short dresses and hairstyles and makeup and stuff, but boys were off limits. That suited me.

Miriam and Latifah are still firm friends, and whenever they are in America they tear off those robes and we go out together, sometimes with Maddie.

But I suppose that I was also a bit worried that I was not attracted to any of the girls either. I mean, there were some gorgeous girls there. The daughters of the rich and famous can have pretty good genes from the trophy wife side. I admired some of them, but not in a sexual way. It did concern me, but also without the distraction I was able to be very successful at school.

I graduated. That meant that I just had to go home with the diploma and collect the cash.

There was only one intervening complication, and his name was Norris Carter. Maddie and I had decided to fly home through Paris. We could legally drink in France so we went out on the town to celebrate. Jade Lowe (she asked us to call her Jade rather than Miss Lowe) had sent us some money to buy some nice outfits and we decided to wear them out to a very high class bar in Paris, one serving $50 cocktails. We were going to put our properly finished charms to the test after 5 years or study and practice.

We did not have to buy a single cocktail. Norris and his friend gave us the time of our young lives. Do not ask for details as I would be hard pressed to remember, but the vivid memory is the kiss. It was my first. Man or woman, I had never had a single erotic experience until that night. I was completely unprepared, probably because I had always assumed that my first such kiss would be one that I planted on a girl. Instead I was the girl, and I loved it.

He would have gone further, but he was American, like me, and I was only 17 and still a schoolgirl – enrolled until the following day. Then there was the unpleasant fact hiding in my panties that he would never know about.

Still, the experience was formative, as I now know.

So, I went to see Jade Lowe the day after my eighteenth birthday

She sat down in the chair opposite me, smoothing out her dress over her knees. I was wearing a dress too, but it did not go down that far.

“I was most particular that you be described in the will as “my sister’s grandchildren” and not as “The daughters of my niece”,” said Jade. “Because we would not want the distribution under the will to be questioned should your secret come out.”

I was gobsmacked. I said: “Secret, what secret?” How could she know? What is more, she seemed to be saying that she had known all along. Since the time that Aunt Katherine had signed the will, some years ago at least.

“Well you see, Ashley,” she said. “I have a secret too. In fact, we have the same secret you and I. Exactly the same secret. And rather than explain, and I am going to do something rather crass and unladylike, and I am going to show you.”

And with that she spread out her legs and pulled back her dress to reveal a pair of rather robust looking neutral colored underpants. Then she pulled those aside to reveal a small but obvious penis. There was no scrotum. Just a penis.

I was so shocked that I just made a noise, sort of like a mumble with your mouth open, I guess.

“You see, I loved your Aunt Katherine,” Jade said. “I always have. But she had no eyes for me. She has always despised men. I could not bear to have her despise me. So, I had to adapt, you see. It was hard to be a lady lawyer when I first reappeared as that, back in those days. There were not many women practising law. Nothing like it is now. But I had Katherine and her parents as my cornerstone client, and then there were others who sought out the advice of a woman rather than a man. I specialized in estate work. I did very well.

“Did Aunt Katherine know?” I asked, still in disbelief. “Did she know that you were … not a woman?”

“Goodness no,” Jade said. “She would have hated me had she …”. Jade paused for a moment to think. “You know, now that you ask it, I cannot say for sure, but she never said anything. She never noticed me as a man, so when I came before her as a woman, she accepted me as one. That’s it how it appeared to me anyway. We were just two old spinsters, she and I, growing old together. We talked to one another every day, and every week we would share at least one meal together. And every Christmas…”.

There were tears in her eyes.

“I had no idea,” I said.

“We had a happy life,” she said. “All I want is that you should have a life at least as happy as ours. I want to help you to do that. Nowadays there are so many surgical options …”.

“Oh no,” I stopped her. “I think that you misunderstand.”

“I don’t think so,” she said. “You don’t get to live as long as I have straddling the sexes not to recognize and kindred spirit. You can never live as a man. You know that, don’t you?”

“Yes,” I said to her. “I think you are right.”

The End

© Maryanne Peters 2019

Author's Note:
Here is one from two years ago that I missed posting. Thanks again to Bronwen for her editing and helping me sort out my stories muddle!