First Date

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Mom arranges a first date for a sissy son, as a girl!
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"I have arranged a date for you with Mrs. Davis son Matt, he's a handsome young man you should count yourself lucky".

"But Mother I don't know I'm ready to date a boy, does he know about me? Does he know that I'm a sissy, that I'm really a boy?"

"Oh nonsense, of course you're ready to date and I think you've long ago passed that line of being a sissy, you will never be a boy again, I think sissies are feminine boys, but you are not a boy anymore. I think the hormones and having your little testicles removed proves that. You're a young lady now in body and mind and you'll make a wonderful wife someday. You are no longer Andrew - you are and will always be, Amanda. And yes, Matt has been shown pictures of your transformation and thinks you make a beautiful girl."

"He's got pictures of me? What have you done Mommy? But ... I guess he is handsome. I just hope I'll be able to please him like a normal girl"

"Oh honey, you'll have your operation soon enough to make you a real girl, but until then you'll have to learn to please him in other ways, I'm sure you'll figure it out".

My mother had always been best friends with Mrs. Davis, who lived two doors down the street. After my Dad left us Mrs. Davis was very supportive. The same thing had happened to her. She was left alone with a son to look after.

Her son Matt was older than me, so I knew who he was, but we had never really talked. We had not even been at school together. He had a job by the time I started high school -- a good one working in IT. He was good-looking but Mrs. Davis complained that he was too shy to get a girlfriend. My mother told me that before she often wished that she had a daughter so that she and Mrs. Davis could become grandparents together. Weird, right?

Well, if you think that is weird, wait until you hear what happened next. But first, I should explain how I got here.

I guess I had a hard time at school and some of the guys called me a sissy. It was not as if I was gay or limp-wristed or anything like that, I was just pale and weak and not capable in sports. I was more artistic, and I liked neatness.

My mother said to me that if that is being a sissy, I should be proud to be one. She encouraged me to express my creativity at home with collage and scrapbooking, and she even taught me about embroidery and quilting. She told me that I was a natural at these things, and that made me feel good. And it was not a lie. My mother sent some of my crafts through to a competition and I won a prize.

My mother told me that when she had sent the stuff in, she had told them that the work had been done by her daughter Amanda rather than her son Andrew. She said that it was easier that way because all of the other submissions had been sent in by girls and that the contest needed to be "between equals". I guess that sounded OK, but then how was I going to collect the prize at the County Fair?

"You will have to go as Amanda," my mother said.

How could she suggest that? How could she even get me into this mess? I mean, she agreed that it was her fault, but she said that I should collect the prize, and she would fix it so that I could. It just meant dressing as a girl for the day.

It helped that my mother was the same size as me, but her clothes are a bit old fashioned. Still, she managed to put an outfit together for me. It was pants with some padding in the butt, and a bright floral top, and I wore a scarf and a fall of blond hair at the back.

Then she made up my face. Of course, I had never worn make up before, but when she was done, I could not believe that I looked so good. It kind of changed me. I had been dreading going to the fair, but now as I saw myself, I got quite excited. Nobody would recognize me that was for sure.

My mother and I went to the fair and had a really good time. We met Mrs. Davis there. She looked at me with a look of confusion. It took her a while before she recognized me.

"My God, Sweetheart you are gorgeous!" she said. I have to say that when I heard those words, I felt really good. I mean, at school I am a zero achiever. No good at sports, average in all my studies, not a standout in anything. I honestly thought that this might have been the first compliment I had ever received from somebody other than my mother.

Then I picked up the prize and I was flooded with compliments by the judges. Of the 5 prize winners in my category I received the grand prize and another bunch of praise. It was one of the happiest days of my life, and it just happened that it was the day at the fair when I was dressed as a girl.

Anyway, that was ages ago. Could that be how it happened? Could that be why I accepted my mother's suggestion to adopt girls' clothes at home? I think it is more likely that it was manipulation by my mother. I think she liked the idea of me being a girl, even a part time one. I wouldn't go so far as to say she forced me. But really, she did. I mean, she never told me about the hormones.

She told me that the morning smoothie was about building some volume on my skinny frame. I certainly had that effect, but all the volume came in the wrong places. I never noticed at first, maybe because when I started to swell, she praised me.

"Oh, what a wonderful shape you are developing. Your clothes are going to look so much better with some shape underneath them. We need to get you a training bra."

But she was right. I was wearing her stuff, but it never looked good on a flat chest. I guess I realized that I had turned a corner. I wanted breasts, just like a girl. I spent every night putting cream on to help them to swell, and even massaging them. It worked.

At about this time I started to grow my hair and experiment with makeup as well. People at school, mainly boys, called me a sissy. But I remembered what Mom had said to me. People who don't do boyish things and are more interested in being clean and tidy and making beautiful things ... well, I didn't tell them I was a sissy, but I didn't try to fight them either. That's not any way to behave.

But it did make me a bit sad. My mother suggested that if I didn't want to be a sissy then I really had only one course open to me. I was never going to be a proper boy, so maybe I could be a girl.

"It seems to me that you are transgender," she said. "You have gender dysphoria. You are clearly more of a girl than a boy, but you are in the wrong body. You need to take steps to remedy the situation."

"What would I need to do Mom?" I asked.

"Well, we need you to get some injections to fix your body chemistry," she said, without telling me that had already started. "And girls don't have testicles, so they will have to go," she said.

I had to go to visit a doctor -- a gender specialist. Mom had told me what to say. He said that if I wanted to make permanent changes, I would need to sign off on it and my mother would need to as well. She could not do that fast enough. Before I knew it, they were gone.

When the swelling had gone down then that was when she arranged the date with Matt.

"Matt is not gay, so he won't date boys, but now that you have removed the crucial boy parts then he will accept you as a girl," she said. "He will look after you." I sort of liked the idea of being looked after, and Matt is a guy who could do that.

Mom helped me to get ready and Matt came to pick me up. He sure was shy, but I did a lot of the talking. The first question he asked me was whether it was true.

"You sure don't look like you used to. You look like a girl. So, is it true that you have been castrated?"

"My testicles have been removed so that I can become a girl. And when I do, you're going to look after me."

That's what I told him. He looked really happy. I told him that the operation needed to wait another year or so, but that was ready to start being a girl anytime he liked.

He says he has got some ideas. He says that they might be a bit messy. I really prefer things to be clean and tidy, but if he is going to be my boyfriend, I guess I need to compromise. He says that it might involve flushing out my butthole with warm water and soap. That sounds clean. I like clean. I am not sure what else is involved but I have bought the baby oil and I do like the smell.

Anyway, I am nutless and clean, and in my best pink angora, so I feel ready for anything. I have made up my face and put some curls in my hair and I know that gets Matt really excited. Mom says we will figure it all out, so here goes. Wish me luck.

The End

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5 Comments
AnonymousAnonymous2 months ago

A different kind of story. I like it. Well done!

300bowler300300bowler3002 months ago
WISH

Wish my mother had done this to me when I was young...She did a little

that turn me into sissy, but this would have been a dream world for me...

Hugs and Kisses Betty jo xoxo

pstg65pstg652 months ago

Nice one. Will we be getting a chapter 2?

AardieAardie2 months ago

His mother should be in prison.

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