The start

10 year old orphan comes to live with his Aunt, and gets transformed

The short letter arrived on a Friday, and simply read:

“Dear Julia.

I am sorry to have to tell you that Christine and her husband John are dead. They had a fatal automobile accident this afternoon, in which they, due to heavy rain, skidded off the road and into a tree. Miraculously their child, Sam, escaped with only a few scrapes and bruises; but has been checked at the hospital, just in case. As he has no close relatives but you, I have appointed you as his guardian, and will bring him over on Monday. I hope you don’t mind?

I am enclosing a photograph, so you will know what he looks like.”

The photo showed a boy; maybe 10 years old, with blonde hair, quite long for a boy, slim, with delicate features.

“Poor boy;” I thought, “losing his parents in such a terrible way, at such a young age!” At the same time, however, a plan started to take shape. What if I could---? No, it was unthinkable, inconceivable, and yet; oh, so tempting.

I grabbed my plastic card and my shopping bag, and set my plan in motion.


Monday arrived, and so did Sam, still looking quite dazed and confused. Having taken care of the extensive paperwork, I put my arm around his shoulder, and carefully guided him to his new bedroom, which I had spent the whole weekend decorating, filling all the drawers and the wardrobe with his new clothes.

I took his bags and put them in a closet, grabbed his hands, sat down on his new bed, and tried to look him straight in the eyes.

“Do you like Fancy-dress games? Or at least trying new kinds of clothes?” I asked.

He looked down at the floor, shrugged and replied: “I guess,” in a dull voice.

“Would you like to try some, right now?” I asked.

Still looking at the floor, he shrugged again, and gave me the same, dull reply.

“Tell you what,” I said, “I’ve got some clothes in a closet and I need to know if they’ll fit someone your size. Wanno help me by trying them on?” another shrug and still the same sullen expression.

”I guess,” he whispered.

“Excuse me,” I said, “I didn’t quite hear you?”

He looked at me, and what I saw in his eyes almost made me take a step back; it was nothingness and sadness of such intensity, I had never seen before.

“You heard me,” as all he said.

I tried to shake off the uneasy feeling I got when I looked into his eyes, by taking him to his room, where I had prepared for the first step of his transformation, by putting a pair of knickers, plain, red wool pantyhose, and a denim knee-length skirt on the bed.

I told him to change into it, and give me a shout when he had. I walked out and waited, anxious to see the result. A couple of minutes later, when he called my name, I went in and was blown away by the result. Not only did the clothes fit him, they actually enhanced the impression of him actually being a girl.

“How do you feel wearing them?” I asked.

“They’re O.K, I suppose, except for the skirt.” he answered looking a bit self-conscious. “I had a look in the closet and saw a dress I thought was real cute, but it’s more a Sunday kind of a dress. As for the rest of the clothes; let’s just say they’re a mixed bag. Some even I could consider wearing, some of them I don’t think a girl my age would touch with a ten foot pair of pliers.”


I tried to hide my astonishment as best I could, and asked if he could pick out the dresses and skirts he liked, and then we’d go buy some new ones.

“Sure,” he said, “would you mind if I changed back to my own clothes one last time before we go, or do you want me to keep these on?”

Still confused, I replied he could wear whatever he wanted.

“Right,” he said; “then I’ll keep on wearing these clothes when we go shopping. With my looks, no one will be able to see I’m a boy in a skirt anyway.” He turned around to start sorting out the clothes he wanted to keep.

“I’m curious,” I said, “What made you say you thought I wanted you to start wearing other clothes?”

“Well, Aunt Julia, it’s kind of obvious; isn’t it? It is way too much clothes to give away, and they’re all roughly my size.” He smiled for the first time since he arrived as he turned around and started sorting though the piles. As I was about to close the door, he timidly said; “Would you mind if I kept the panties and pantyhose?”

“No, of course not,” I replied, satisfied things had gone as smooth as they had, but baffled he seemed to take things so in his stride. “It has to be he shock.” I thought to myself.

In the end, he kept most of the clothes I had bought.

That evening, when he had changed into a yellow and pale pink, floor-length cotton nightgown, I asked him about it. The answer he gave me astonished me once again;

“You’re my mother’s sister, aren’t you? She used to make me wear dresses and skirts sometimes, so I figured you’d do the same, although I must admit I have never worn them full time before.”

“What a strange boy you are!” I said. “Most boys would’ve run away, at the merest mention of them having to wear a skirt; but you seem to like it!”

“I don’t know if the phrase “like it” is entirely correct; it’s more like” having gotten used to”, he told me, in that charming, precious way of his. Then he seemed to remember something. ”By the way, I sometimes wet the bed. I have some diapers in my bag; would you mind diapering me every night? And there are some mittens there too. Would you mind putting them on me too, as I have a tendency to try to take the diaper off in my sleep?”

“Of course I can, but you do realize this is all a bit much for an old lady like me to take, in all at once?” I said, probably looking every bit as confused as I felt.

“Sure,” he confidently said,“ but I’m sure you’ll get used to it; eventually.”

The End

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