My Stepsister
A Short Story
By Maryanne Peters

I have to say that when my Dad married Dawn, I was a bit unsure. I could see why he did. She is a good-looking woman, and I mean a really good-looking woman. The problem was that her son Mark looked just like her – a younger version that is.

Every time I looked at Mark, I could imagine him with tits. Is that weird? He had long hair and he was scrawny, and he acted like any other guy, but I just could not see him as a guy.

I didn’t feel that I was gay. I am only into girls. I just wished that he was one. Like, all the time.

It got to the point that it was driving me nuts. What I wanted to do was to see him in a dress. I figured that he would have to be the same size as Dawn and I had a dress that she used to wear that looked really good.

I figure that it is not healthy to have erotic thoughts about your stepmother. I mean not because she is my mother, because she is not. But she is my Dad’s girl. That is betrayal on so many fronts. It’s wrong.

But then you have a copy of her, but my age, but just short of a couple of vital ingredients. Somehow it seems less wrong to desire her. By ‘her’ I mean the girl Mark could be.

I had to do something about it, and that is what led to the bet.

I am bigger than him so the bet was that if I could wrestle him to the ground with one arm tied behind my back, he would have to dress as a girl for the weekend.

“If you can’t win a wrestle against a one-armed guy, then you don’t deserve to be a guy,” I said.

“And if I win, you promise that you will stop constantly stop staring at me?” he said.

Well, he lost. I guess I am still entitled to stare, especially after the shave down and slipping on that dress over the stuffed bra. He screamed blue murder, but I told him that dressing as a girl means undressing as a guy, and body hair has to be shed – not that he had much to speak of anyway.

I called him May.

I told him that we were going out, so he had better get himself looking as feminine as possible.

“I don’t want to be walking around with a tranny,” I said. “And you don’t want to be laughed at by everyone, so put some effort into your appearance and practice some lady-like moves.”

She pouted, but somehow that made her even prettier. I couldn’t think of using “he” to refer to her from then on.

I found the dress in Dawn’s closet. As I said Dawn had not worn it for ages. May looked great in it. I raided Dawn’s stash for shoes too.

“Everything seems too small except these heels,” May complained.

“They are perfect,” I said. They made her freshly shaved legs look a mile long.

She found earrings and makeup, and a hairbrush and a clip for her freshly washed hair. Then I drove us across town to the Northside Mall so that we could hang out, with her looking like a woman.

I said that she should go into the cosmetics store and get a makeover – I am paying. There was still something about the way she walked that was not right. She needed to make up for that, or get rid of any Mark still left in her.

“You’re shitting me,” she said.

“Now watch your tongue pretty lady,” I scolded her. “Like I said, if you walk around looking like some gay fem boy that looks good for neither of us.”

I told the beauty girls to do it right. They knew their stuff – false eyelashes and coloring but not too much. There was beauty in that face. I knew that much. It just needed to be put on display.

I went across to the sports store, to wait. It seemed like a while before I heard a voice behind me. It was not Mark’s voice – it was May’s.

“Is this what you wanted?”

When I turned around she must have heard me gasp. I knew that she would be beautiful, but I was not ready for what I saw. Dawn was a warthog next to her daughter. This was incredible! They say the heart is the organ that feels love, and I never understood that until that moment.

And the organ of lust … that is somewhere else, and that was talking to me too.

“Baby May,” I said. “That is everything I wanted and more.”

To me it seemed the way it should be. As I said, I was uncertain about the whole ‘strange feelings for my stepbrother’ thing. But now it seemed that he was gone and I was walking with May. When I looked across at her it seemed to me that this was a woman that I desired. I was relieved. I was not gay. I had just fallen for one of those transwomen.

May said that she was not one of those. But I am a patient guy. I can wait for it all to sink in. I know what she is. That is what she has to be. One of those women born with a dick, that needs to be … whatever those surgeons do.

May is scared. Who wouldn’t be? Nobody likes the thought of pain, let alone where it really hurts.

But I am not gay. May needs to understand that.

When she has doubts, I just have to point out how easily she “transitioned” from Mark to May. When she sees herself in the mirror she has to fix her hair or her makeup. A whisker on her chin horrifies her.

I have arranged to fix that with the hormones. I heard that they are most effective administered anally with suppositories. I put one of those puppies on the end of my cock and I administer it as deeply as I can. I don’t want my girl growing whiskers. I want her growing tits.

I broke the news to Dawn and she was shocked.

“How could I not know this of my own son?” she wailed.

I had to correct her: “You mean your daughter. She has been struggling. But it was hard for her to talk to you, but I am here. I am helping her through it.”

Dad doesn’t care. His son is a man. He knows it like I know it. Just like I knew Mark wasn’t one.

“Help your little sister,” he said. “Like a brother should.”

Well, I don’t suppose a brother should be donkey deep in his sister’s butthole. But she is a stepsister. It’s not the same thing.

May says that she is afraid of me, more so as the hormones weaken her further. I joke that I could now probably wrestle her down with both arms tied back. But I tell her everyday that I love her and want her to be a complete woman so we can marry.

We have to run away to do both of those things. But for now she needs to come to terms with her position. It’s under me, in every sense.

The End

© Maryanne Peters 2020