Pool Boy Ch. 01: His Transformation

The following is one story but broken into two parts. I hope you enjoy them both.

Part I

The Pool Boy's Diary

Hi. My name is Chris and I'm a professional Aquatica maintenance specialist. I'm five feet three inches tall. I have long black hair and pale skin. Some would even say I'm kind of dainty. The following are important excerpts from my journal spanning the last six months. Looking back now, it's obvious to me that I had no idea what lay in store for me when I met Miss Grant.

Day 1

Today was a great day. I took a new client named Mrs. Grant. Everyone I talked to said that I shouldn't take the job and that she was hard to work with. Nothing could have been further from the truth. She is so nice. I mean she is a shrewd negotiator, but in my book that just makes her even better. We agreed that I could start working for her on a trial basis for 75% of my bid and that after two weeks if she was pleased with my work, she would hire me at my full bid price after that. She also said there would be a chance for me to earn a bonus.

She was a little mysterious about what she meant by 'earning a bonus' but said we could discuss that later. I'm not worried. I'm one of the best pool guys around and I know that I will be able to please her. The Customer is always right.

Day 15

Mrs. Grant, who insisted I start calling her Carrie, told me today that she was very pleased with my work and that she wanted me to sign a one-year contract with her. I am so excited, but also a little scared as I have never had a long-term client like her. Most of my current clients are month-to-month. I guess I'm moving up in this world.

I'm also a little concerned as I have to admit that I find her very attractive. I have always had a particular attraction to strong, intelligent, older women and Miss Gra.. I mean Carrie is all those. This will be a real test of my professionalism and willpower.

Day 30

I got my first bonus today. Well in a way it's a bonus. Carrie doesn't want me to have to worry about bringing my lunch, so she is providing me with one. The idea seemed a little odd to me but after she explained how she was saving me on my food bill it all started making more sense to me. The food is top knock. The weird thing is that she watches me eat and insists that I eat everything. She said it was because if I don't the balance of the meal with be thrown off. I guess I don't mind her watching. If anything, it's kind of nice she is thinking of me.

Day 44

Carrie apologized for the whole watching me eat rule. She said she used to be a nurse in an elderly care facility, and she missed having someone to care for. I told her it was not that big of a deal and that if she wanted to keep bringing me lunch that was ok. She beamed at my response and told me I was such a 'good boy.' It was kind of strange being called a 'good boy' like I was a child but maybe that is what she used to tell her residents.

Day 60

I have been feeling so weird lately. My emotions have been all over the place. I can't eat one day and then I just devour everything in sight the next. My chest hurts and my nipples seem to be hard all the time. Carrie thinks it might be a vitamin deficiency. I said she was probably right and that I would go and see the doctor. She just laughed and said, 'Those quacks don't know their ass from their elbow. And they will charge you a fortune. I know what you need, sweetie.'

Later that day she brought me a protein smoothie and had me drink it. It tasted great. She said she would make me one every day and then send two home with me on Friday for the weekends. I thanked her perfuse.

Day 80

I'm still not feel like I did before I started working for Carrie, but at least I'm getting used to the changes. I told Carrie that I was thinking of going to see a doctor again and she got pretty mad. 'Fine waste your time and money. See if I care.' She yelled. For a minute I was afraid that she was going to fire me. to save my job, I apologized and said she was right and that I wouldn't go. For this, I was rewarded with a smile and another 'good boy.'

I don't know why, but her calling me a good boy didn't seem so weird this time. it felt kind of good, actually. Like a warm hug but with words.

Day 100

I am starting to get a little worried. Many of my other clients have told me that my services are no longer required. When I asked them why all of a sudden, they were not happy with my service most refused to answer. I pressed one long-time client and all she said was that she was not comfortable with a person like me around her kids.

I told Carrie and she said that some people in this world are so ignorant they are afraid of any kind of change and anyone that doesn't fit into their little ideal mold. The good news is that Carrie said she had more than just pool work for me to do if I was interested. I told her I might be soon if things don't change. All she said was 'Good' and then she gave me a little smile.

Day 105

Carrie said I was looking tired and wanted to know if I was sleeping well. I told her I was but she saw through the lie in an instant. She gave me an old MP3 player and said that I should listen to it every night. I asked her what it was and she said it was soothing white noise with a subliminal track that would help me relax and become the person she knew I could be. That seemed a little odd but I was desperate at that point so I took it and will start listening tonight.

Day 110

Wow, I'm not sure what is on that mp3 program but I have been sleeping great lately. For which I thanked Carrie. She seemed so happy. What I didn't tell her is that I have also been having very erotic dreams. Most of them involve me just doing my job at Carrie's except for she is watching me while I work, and I'm completely naked save for a dog collar.

Day 120

Carrie asked me how I was feeling and I finally broke down and told her how my chest hurt and she asked if she could see my chest. I was so embarrassed as in the last 100 days I had grown myself a nice set of man breasts.

She wasn't shocked or surprised. What she was, was supportive. She went inside and came back with a bra. I was hesitant at first but once she had it on me it felt so right. It also felt so right to listen to her. She gave me five more bras and told me to start wearing them under my shirt every day. Then before I could stop myself, I responded, "Yes mistress."

I expected her to fire me on the spot but instead, she just gave me a pleased grin. She patted me on the head and said, "It looks like someone has been listening to his night music like a good boy."

It was then that I confessed I had not been listening to the music for a long time. I expected her to be mad but all she said was, "Even better."

Day 150

I have only a few customers left. I know I should be worried but I'm not. With few people to service it leaves me more time to spend with Mistress. Carrie said it was OK for me to call her that but only when we are alone. I should call her Miss any other time. She opened my eyes to how good it can feel to serve a person. Each day she rewards me with a new task to perform. It's so much fun. In return, I am learning about makeup, hair, and women's undergarments. The rest of the world is bleak and dark and falling apart, but when I am with Mistress, everything just feels so right. I don't have to think or plan, I just have to obey.

Day 175

Mistress confessed to me that she was giving me testosterone blockers and estrogen in my food today. I hugged her and thanked her for knowing what I wanted before I did. She then spent the whole day teaching me about makeup, hair, and nails. She says I have a real gift for blending and shading and she is so proud of me. To reward me she bought me my own makeup set and took me to the hairdresser. I also got a 'good girl' from her which had me walking on air all day.

Day 180

All of my other customers have fired me. Jerks. I lost my apartment and I thought I was going to have to live in my car. That was until Carrie offered me a new job as her live-in personal assistant. I was so happy I cried for ten minutes. Now, I can spend every day with Mistress Carrie.

And just when I thought the day could get any better it did. She told me she didn't want everyone to talk and say that she was only hiring me because I was a cute guy and she wanted a boy toy, so to take care of that she is going to have me transition from male to female completely.

It's as if she can see into my soul. It's like she knows exactly what will make me the happiest. She is going to have all my body hair, what little I have permanently removed with lasers. I'm going to get to wear dresses, and other women's clothes all the time and change my name to Kim. And she is going to set up a separate fund for me so that if and or when I decide I want to have my little man taken off I can.

That was the last entry written by Chris the pool boy. All future entries will be written by Kim the very personal assistant.

This story is continued in Pool Boy Ch 02: Bad, Pool boy. Bad.