Working for Aunt Sophie
A Short Story
By Maryanne Peters

When my mother passed away, I had no choice but to go live with my Aunt Sophie who lived some distance away, separating me from the few friends I had. Aunt Sophie lived in Springfield and ran a small ladies clothing store below her modest home on the floor above. She was an expert seamstress and had an eye for what was truly fashionable and tasteful. She sold some factory-made stock, but she also made clever modifications and she made some tailored garments for discerning clients.

Even though she was much admired by her customers, she was barely getting by. One day, as she came into the living area - she seemed distraught, and I asked her what was the matter.

“Oh, I’m really concerned about making ends meet,” she said.

I had not yet found a job despite some effort (although admittedly not too much) so I asked if there was not something I could do to help. She thought for a moment, then asked if I could do basic accounting.

“Well, I was good at math in school,” I said. That was good enough for her. I became involved in my aunt’s business. I started working from the office at the top of the stairs where I had a desk and I could deal with credit card receipts, stock invoices and all financials. All seemed to go pretty well. After the first week I started to see that there were simple things that my aunt was missing by being full time in the store or on her sewing machine. There were double payments and finished goods delivered to customers but not paid for. In the first week I recovered $3,000.00 and had shown how we could add a regular sum to the bottom line.

“And I have so much more time to make and sell because you have taken over all that accounting stuff,” Aunt Sophie said. But really it was the responsibility to do what she did not understand which was the burden. In no time at all I was indispensable.

She paid me, but I said to her that as I was earning, I should pay some board. She refused, saying that she was in my mother’s place, but I restocked the larder. In return she said that I should never pay for clothes – she would make shirts and pants from fabric she had.

The clothes were OK around the house and the store, but somehow, they did not look quite right for going to town. Aunt Sophie said she had no experience making men’s clothes, and I suppose the fabric and the cut was not quite right for a guy, but it worked for work. It was not as if I had any friends in Springfield.

But then she had the problem with Mrs. Bollington, one of her best customers. I was always darting in and out of the store and the stockroom behind when I was not upstairs. I burst in on Mrs. Bollington in the change room by mistake. I did not say a word, I just grabbed the stock and shot out.

Aunt Sophie told me afterwards what had happened and what she did about it.

Mrs. Bollington was not just embarrassed, she was mortified. She said: “A young man burst in on me while I was in a state of undress. I can no longer trust your establishment.” But before she could finish Aunt Sophie felt she needed to act quickly to keep her customer.

“Oh no, not a young man,” she said. “That was my niece … Daisy. She is a bit of a tomboy. My late sister’s daughter. Off a farm, you know. But not a man. Oh no.”

As she said afterwards, the thought just popped into her head, along with that awful name. Anyway, it was supposed to calm Mrs. Bollington down, and it did – immediately.

“Your clothes are like you, so pretty and feminine,” Mrs. Bollington remarked to Aunt Sophie. “Your niece really needs to make some changes to fit in here. She cannot rush around wearing boys’ clothes.”

“I am so busy I don’t have time to take her in hand.” That was what Aunt Sophie said. It was what came next that caused the problem.

“I understand completely, my dear. Please introduce me to her. I have the time and the money to knock off those rough edges.”

And that was how it began. I could not believe Aunt Sophie when she told me. But she said that all I needed to do was to meet with Mrs. Bollington, pretend to be the tomboy Daisy, and convince her that I was female, but an incorrigible tomboy.

Aunt Sophie suggested that just in case, I should shave my legs and wear some shape wear under my clothes. That meant a filled bra and a pair of panties that held everything in. On top I wore some of the work clothes that Aunt Sophie had made for me – a loose shirt in a floral pattern and a pair of loose-fitting harem pants in a pastel shade, which were just so comfortable if you are staying inside.

I had worn those clothes before around the store, but somehow when I wore then over that underwear it seemed to me that everything was different. The clothes hung differently, and the absence of tight crotch fabric, and my smooth legs made the pants feel so light and liberating. It seemed to me that I had changed somehow, even just wearing the same clothes as the day before. And I liked the feeling.

Aunt Sophie said that I would need to practice how to speak like a girl. It is all about singing to reach the notes and then turning a song into conversation – not a falsetto but just a higher tone. I practiced all night with a sound recorder until I was happy.

The following day Aunt Sophie called up to my office: “Daisy, there’s somebody I would like you to meet.”

I came down the stairs with a blank look on my face. The trick was to look female without looking feminine. I was a tomboy after all, and I did not want to be anything else. All I said, to cover my aunt, in my girly voice, was – “I think we have met before, when I caught you out in the change room.”

“Oh that. It’s nothing between girls,” said Mrs. Bollington. “And please call me Marge. Now turn around for me, my dear, let’s have a look at you. Heavy footed and lacking in grace; hair needs work, and makeup would do wonders for you. Would you be prepared to humor me, Daisy? It would be at my expense of course. Didn’t you ever play dress-up as a little girl? I really think that you could be a very beautiful young woman.”

I knew what I had to do. Just say no. Or rather politely explain that I am not the girly type. More the practical woman. A lesbian in fact. Lipstick would be wasted on me.

Instead, I found myself saying: “That sounds like fun.” Because somehow, it did. Who doesn’t like a transformation story? Even a guy can appreciate something like that. It was almost as if I was expecting to watch it from the sidelines without any thought that it was going to happen to me.

It was my fault. I had to admit that after she had gone. After that my aunt was only concerned to see that I did not make a mistake and give myself away. She could not afford to lose Mrs. Bollington’s custom.

So with some further preparation, on Saturday after work, as arranged, I went around to Mrs. Bollington’s house.

It was a large home, and she lived alone in it. There were five bedrooms with only one bed, her own, being slept in; but every closet seemed full of clothes. It was clear why Marge was Aunt Sophie’s best customer. But it seemed that she might be the best customer of several other boutiques.

“I love clothes and pretty things,” she said, opening drawers to display what seemed like hundreds of panties, bras and slips. “I am sure that you can find something to fit, but because you seem a bit smaller in the bust than me, I have taken the liberty of buying some inserts, just to fill the bra cups.”

I had to smile. This woman was completely taken in, which was amusing. For Aunt Sophie’s sake I could humor her, but I had to ask for privacy before I put on the underwear, and I had to choose items that concealed the fact that I had no breasts, but instead had something further down that was distinctly unfeminine.

I was able to find a sheer bra decorated black lace and a pair of panties with strong enough fabric to hold everything solidly between my legs.

But curiously as I cupped my bra and felt the inserts jiggle perfectly, the work I had done in my panties seemed to be becoming undone. My cock was straining. I was so turned on that I had to jack myself off. I did it looking at myself in the mirror – not me but Daisy the sexy tomboy.

I must have been flushed when I came out to see what Mrs. Bollington had for me next, but at least my crotch was now smooth. There was still a little oozing, but I had found a panty-liner in the adjoining bathroom.

She held up a dress, and a pair of shoes. This was the very opposite of what a tomboy would wear. The obvious response was to give her a disapproving look and politely decline. But that is not what I did. I wanted to wear those things, despite who I was. Somehow all my masculinity seemed to have been put to one side, just for the moment. If I was reluctant, it was just because of that realization.

“I checked with your aunt. She gave me the sizes. You will recognize the dress as one of hers, but I bought the shoes for you, so you must humor me by putting both on for me.”

My mother brought me up properly. She would say: “Politeness costs you nothing but will earn you plenty.” Generosity demands a polite response. So, I had to agree. But in reality I wanted to wear this stuff, with increasing desperation.

Perhaps there are others who will understand what was going on, because I didn’t. There was a part of me that was saying that this was weird and perverted and definitely not what I should be doing, but the part of me that longed to see myself wearing this was much stronger. I was not a tomboy. I was quite the opposite.

I just needed to try to conceal from Marge how thrilled I was to be wearing such gorgeous clothes.

She then led me away from the full length mirror to the dressing table.

“Longer hair would suit you, my Dear,” she said. “But for now, there is enough for a nice style using a bit of product, until I book a time for you at my favorite salon.”

The thought of that sounded exciting too. My mind seemed to have been taken over by someone else.

She came at me with a lipstick. I thought that it was time to put on a show of protest, so I pretended to object, but I was thrilled. The taste of the lipstick was like my first kiss, although I could not remember the girl who was wearing it. For now, the girl in the dressing table mirror was my dream woman.

“And a little mascara,” she said. “We’re taking it slowly. I know that this may not be your thing, but I just want to show you how good you can look if you want to. Maybe if you agree we can move to another level of beauty. I just think that it is such a shame that a girl as pretty as you should hide her beauty away.”

Just lipstick and mascara, and my eyebrows shaped with a small brush. Before she had even started on my hair, that was all it took. There I sat in my dress and with my feminine face looking back at me.

“I should have started with foundation,” she said. “But frankly you need a full facial, and some attention to a few stray hairs. Don’t worry my dear, even somebody of your youth still has to fight such things, but permanent solutions are at hand.”

I was hardly listening. I was in love. The face in the mirror enchanted me. I was not sure if I wanted her or I wanted to be her, but I knew then that she would never be going away.

She just played around with my hair a little using some product and a brush to create some volume. A pixie cut I suppose. Well, I know that now.

“You have enough hair for those girls to put those extensions in,” she said. “How long would you like it? Down to here? Or here? You are fair so it should be blonde, or honey blonde?”

I was just thinking how wonderful it would be to be able to choose.

“Tell me that you don’t like the way you look,” she challenged. “Are you truly a tomboy not concerned with being beautiful, or do you now understand what it means to be a pretty woman? At least tell me that you are beginning to understand.”

I mumbled. I was in a corner. What could I say? I could not upset her after all the work she had done, and buying shoes in my size. She was Aunt Sophie’s best customer. But it was time for the truth.

“I love it. I love the way I look.” I did.

“Very well, now leave those clothes on and head home, and dress that way again for Monday morning and I will arrange you an appointment. And Daisy, try to work on your walk a little on the way home. Those shoes have a heel, but not too high. Walk the way you look, young lady. And don’t swing your arms. Keep your elbows bent. That’s it.”

I walked out of her house and down the street all the way back to Aunt Sophie’s store. It was a Saturday and Main Street was quite busy. I could see people watching me, but I felt that the best policy was to look straight ahead.

It seemed like people might be smiling at me because they were amused to see a boy dressed as a girl walking down the street, but as I glanced in a shop window and saw my reflection it dawned on me that they were smiling just because I was a pretty girl out for a walk in a pretty dress. Pretty things make people smile. I was that.

This is something that men can never appreciate, but suddenly I had learned it. I was admired and desired – two things that I had never experienced in my life before. And all I had done was to walk down the street in a pretty dress.

I walked into Aunt Sophie’s shop by the front door, which was something I rarely did. She was with a customer, but she looked over at me and gasped. I gave her a little wave instinctively, but as I did so I caught sight of myself in the mirror. It was a very feminine gesture by a very pretty and happy looking young woman. I almost did a double take to confirm that it was me.

I just flicked through the racks while I waited for Aunt Sophie to finish, and the satisfied customer had left the shop.

“Sweetheart, you look wonderful,” she said. She was positively fizzing. I felt very pleased with myself. “But that outfit simply cries out for earrings. We will need to get your ears pierced. Actually, I could do it for you.”

It did not seem like a big deal. Men have their ears pierced. It is only what you wear in your ears that might be gender specific. She obviously knew what she was doing even though it was only a needle and disinfectant. She put in hollow studs so that I could wear what she had for me from a huge box of jewelry. Drop earrings that were about as specific to the feminine gender as they could be.

There were so many mirrors in her store, as there should be. As the last customer left, I found myself parading through the store and catching a thousand glimpses of the beautiful young woman strutting past the racks. Her short blonde hair shimmered in the light as those dangling earrings sparkled and danced.

I knew then that I had found my true calling.

“If you need any help in the shop, then perhaps I could come down and help you?” I said to Aunt Sophie. “So long as you will let me wear the product.”

“Oh Daisy,” she said. “You are not a tomboy anymore, or any kind of boy at all, it seems to me.”

The End

© Maryanne Peters 2022

Author's Note: This story was inspired by a review on a story I posted on Fictionmania by a fan Stephie - a sissy.