The Pool Guy Diaries (A Guest Story) (Patreon)

This story is written by a very personal freind of mine-going under the pen name Michael A. Richardson.

(who helped write the eBook edit of the Ballet Dad)

I hope you enjoy this.

Part I

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.

PART II

Bad, Pool Boy. Bad!

“You are a sissy sub. (pause) Obey. (pause) Submit. (pause) Mistress is always right,” is all Carrie could hear as she lifted the large earphones off the head of Kim, her form pool man turned very personal female assistant.

Carrie reached over and stopped the recording. But Kim kept repeating “I will obey. I will submit. Mistress is always right,” even without being prompted.

She was very pleased to hear Kim’s repeating the training video over and over again even with the recording stopped. It gave her hope that the last twelve hours of listening to the submission reinforcement training recording may have had the desired impact on Kim’s subconscious. Kim had disobeyed her for the first time last night, and that could not be allowed to happen again. Normally, Carrie wouldn’t have given Kim another chance, but she liked the submissive very much and had convinced herself Kim was worth a little reconditioning.

Carrie took the key from around her neck and unlocked the restraints holding Kim’s body to the bed she had been lying on for the last day. “Good morning sleepy head,” said Carrie in a motherly tone.

Kim smiled, up at her, and said in a gravelly voice, “Oh, Mistress. I was just thinking of you.”

“As you should have been,” responded Carrie sharply.

Kim flinched away. Her eyes began to well up with tears and she began to weep, “I’m so sorry Mistress, I was so…”

Carrie pressed her forefinger to Kim’s lips causing her assistant to stop. “Drink,” ordered Carrie putting a straw to her lips.

Kim obeyed.

Once Kim had drained the cup, Carrie rewarded her with a pat on the head and a “Good girl.”

Kim opened her mouth to speak but was silenced by a look from Carrie. “We need to talk about yesterday,” said Carrie sternly. “I was very displeased by your behavior.” Kim began to whimper. “I think I should discharge you,” said Carrie without emotion.

This was a test of course. If Kim remained silent there was hope for her, but if she spoke that would mean her submissive nature was too badly damaged to be salvaged. Kim didn’t speak. She whimpered a little more but then sniffled and fell silent. Carrie’s heart leaped with joy.

After a few minutes of silence, Carrie figured she had passed the test and patted Kim on the head again and said, “Good girl.”

Kim sniffled again and remained frozen. “Now, why did you disobey me?” asked Carrie.

“I got scared, Mistress,” answered Kim.

“Do you trust me?”

“Yes, of course, Mistress.”

“Have I ever let anything happen to you?”

“No.”

“Who transformed you into the lovely creature that you are today,” Asked Carrie.

“You did.”

“I gave you the choice between cash or a collar,” said Carrie, grabbing the D ring of Kim’s collar pulled her off the bed a little, and let her fall back. “Which did you choose?”

“Collar.”

“Would you make the same choice?”

“Oh, yes, Mistress,” said Kim. “I live to serve you.”

“That’s hard to believe after last night.”

The comment hit Kim harder than any blow ever could. “Yes, Mistress.”

“I had to punish you!”

“Yes, you did, Mistress,” Responded Kim. Then she dared to speak a little more. “Thank you, Mistress.”

“So, what am I to do with you?” asked Carrie rhetorically. “Do you want me to stop giving you your hormone shot?”

“No, Mistress.”

“Do you want me to let your clit dick out of its pretty pink plastic cage?” asked Carrie moving to unlock him.

“NO, Mistress,” responded Kim in a panic.

“Then we need to figure out what happened last night,” said Carrie putting the key back around her neck. “Because my guest left here last night not satisfied and that is something that can never,” she moved to get right in Kim’s face before continuing, “never happen again.”

“Yes, Mistress.”

“Do you have any idea how much business my company does with Arron?” asked Carrie pulling back.

“Yes, Mistress,” answered Kim still staring at the ceiling.

Carrie walked away from the bed. Then she called over her shoulder, “How much?”

“Nearly a third, Mistress,” Replied Kim.

“Wow,” said Carrie, turning back to face Kim’s still prone form. “That much?”

“Yes, Mistress,” answered Kim meekly. “One of his shell companies recently bought out Springfield Industries.”

“So, you do know how important it is that we keep him happy?”

“Oh, yes Mistress,” answered Kim.

“Then why did you not take care of him?” asks Carrie staring daggers at Kim. “We spent weeks making sure your blow job skills were top notch and you know how much I love watching you work.”

“Because he wanted more than just a blow job, Mistress,” said Kim sitting up. “I could tell.”

Carrie began to tap her forefinger against her chin. “I see,” she eventually said, and then exited the room.

Not knowing what else to do, Kim put the headphones back on, turned the recording back on, and laid back down on the bed. A big grin began to form on her face as her mistress’s voice filled her ears. Kim was in heaven again as her mistress's voice berated her for being such a sissy, such a sub, and such a slut. A few minutes later Kim was once again surprised when the headphones were pulled off her head again. “Stand up, wimp,” ordered Carrie.

“Yes, Mistress.”

“You are just such an adorably, pathetic, little sissy,” said Carrie, who then leaned in and kissed her sub square on the lips, hard. Their tongues played tag and then Carrie put her leather-gloved hands, on Kim’s shoulders and pushed her down to her knees.

It was then that Kim noticed that her mistress had dawned a green crushed velvet corset, a pleated leather skirt, and a set of sheer black stockings. Carrie had pulled her jet-black hair back into a ponytail and she had traded her glasses for contacts. Kim could also see a small bulge under her skirt which filled her heart with both anticipation and fear.

“Lift my skirt,” said Carrie with a smile. “I have a surprise for you.”

“Yes, Mistress,” responded Kim.

She lifted the leather skirt to discover a long thick purple strap on, staring back at her. Kim was well acquainted with this particular toy as it was the strap-on she had learned how to deep-throat a man with. “Professor Plum, misses your affections,” said Carrie, swaying her hips back and forth which caused the fake cock to quiver. “Open up, slut.”

Kim kissed the big shaft. Then she spit on it. Next, she gave it a good rub from tip to base, all the while looking up at Carrie. She then opened her mouth as much as she could and waited. Carrie counted to 30 in her head and then gave Kim a slight nod. This was their established signal for, “go.”

The black snake disappeared into Kim’s mouth and she off. The first time Kim had sucked a cock she had no idea what to do. She had gagged several times. She was so eager to please her mistress that she had almost caused herself to throw up. Now, after several months of practice, she was an expert.

Carrie closed her eyes and just took in the sound of her sissy sub-sucking her artificial cock. Lord how she loved the slurp-slurp sound that Kim made when feasted on a cock, real or silicone. The pressure of said cock being pushed against her lady parts was nice of course, but nothing could compare with that sinful sound. It was driving Carrie wild.

“Enough,” cried Carrie as she felt her control beginning to slip. Kim looked up, her eyes begging to know what she had done wrong. “On your feet, bitch,” ordered Carrie, the sound of Kim sucking the dildo still echoing in her head. Once she was standing, Carrie reached out with her right hand and grabbed Kim’s right wrist. She then spun the surprised girl and pressed her down on the bed. Carrie then whispered into Kim’s ear, “Don’t move, pet.”

“Yes, Mistress,” answered Kim.

Kim’s heart began to pound in anticipation. She could not see what Carrie was doing so she fell back on her other senses. She could hear the clicking of Carrie’s heels on the floor. She felt Carrie’s gloved hand begin to rub her arse. She heard the creak of a draw opening and closing, and she could smell how aroused her mistress was becoming. She felt the fur of the restraints go around her left and right wrists. Her breathing quickened as Carrie brought her hands back and secured them even tighter together.

“If you move, you will be punished,” Carrie advised her in a cold tone. She then demonstrated what kind of punishment she would receive by patting Kim on the left butt cheek. “Please don’t make me punish you, sweetie,” Carrie said in a plaintiff tone. “You know how much I hate punishing you.”

“Yes, Mistress. Thank you, Mistress.”

Carrie spread some lube onto the forefinger of her glove. She put the tip of her finger at the top of Kim’s ass crack and slowly she ran down. This sent a shiver through Kim. Carrie repeated the process once, then twice and then a third time. Kim quivered each time. “Do you like that, slut?”

“Yes, mistress. Very much, mistress. Thank you, mistress.”

“Good girl,” complimented Carrie, which sent an electric charge through Kim’s chest. “You are such a good girl,” said Carrie as she began to play with Kim’s rosebud.

Kim tried but couldn’t stop herself as Carrie started to probe her arse with her forefinger. “Bad girl,” exclaimed Carrie as she slapped Kim’s left butt cheek. “I said not to move.” Then she slapped Kim on the other cheek and finally gave her a could blow on her pink clit cage. “You stupid sissy. I hate it when you make me punish you,” added Carrie as she walked away.

Kim began to weep, not because it hurt but because she had once again displeased her mistress. “Don’t you understand I am trying to make you a better sub?”

“Yes mistress,” sobbed Kim. “Thank you, Mistress. I want to be a better sub.”

“You mean a better bottom?”

“Yes, mistress.”

“A better faggot?”

“Yes, mistress.”

“A better toy for my personal use and the use of my friends?”

“Yes, mistress. I want to be that more than anything,” confessed Kim.

“OK, then,” said Carrie taking a noisy deep breath. “Let’s start again.”

With that, Carrie applied more lube to her finger. Kim turned her head and pulled a bit of the sheet under her into her mouth. She resolved not to move again. She wanted to please her mistress. She was going to please her mistress.

Carrie started to play with Kim’s crack again. Then without warning, she stuck a single finger into Kim’s hole. Kim’s scream was muffled by the sheet. She squirmed a little, but Mistress Carrie decided to tolerate that. She pulled her forefinger out, lubed another finger, and began to push into Kim’s ass again. Kim began wiggling again and this time received a light pat on her left cheek for it. Kim froze and Carrie continued inserting her fingers. “Just relax,” cooed Carrie in a supportive tone. “You’re doing great. Deep breathes.”

Carrie pulled her fingers out and slid them back in a couple more times. Kim whimpered but didn’t cry like before. She was trying to hold an image of Mistress Carrie’s smiling face in her mind. That always helped her relax. “That’s it, slut. Let my fingers in. Your ass is pretty tight so we will go slow today. You know I will always take care of you, right?”

“Yes Mistress,” responded Kim through gritted teeth.

“Good girl,” said Carrie, rewarding her pet. “You will have to add cleaning yourself out, to your morning routine. I want you clean and ready to offer your ass on demand from now on, understood?”

“Yes, Mistress.”

“I will get you some toys to practice with and some to wear all day to stretch yourself out. I may even get you a couple with tails. Would you like that?”

Kim’s little clit dick twitched at the fantasy of a vibrating butt plug. “Yes, Mistress.”

Carrie shivered with delight at the thought of Kim getting spit-roasted by a married couple she had over from time to time. “Oh, you would look so cute with a fox tail sticking out from under your skirt.” Carrie pulled her fingers out entirely and let Kim have a break. “I’ll order those right after we are done here,” added Carrie, removing her solid gloves, and dropping them on the floor for Kim to collect, and clean later.

Carrie moved behind Kim and sprinkled more lube into his ass crack and then began to coat her strap-on with lube. She then started to tap the tip of the dildo against Kim’s ass. “OK, baby, time to be bred like the bitch we both know you are.”

Kim pulled more of the sheet into her mouth and tried to relax. ‘I want to please mistress. I want to please mistress’ she kept repeating to herself in her head. She felt the head of the dildo go in and she clenched her teeth. Carrie slowly pushed in more, stopping and even pulling back a little when she hit resistance.

“You’re doing so good, pet,” Carried said in encouragement. “Your little ass is taking my big cock so well.”

Kim didn’t like pain. She didn’t like being in pain, but she loved pleasing Mistress, so she bit down harder on the sheet and tried to relax. She was just about to give up when her discomfort began to ebb. “You’ve taken the whole thing,” announced Carrie. “Good girl, Kim. Very good girl.”

“Thank you, mistress.”

Carrie just stood there, her strap-on impaling Kim's ass for a minute. She then poured more lube on her hand and down Kim’s ass crack and began to pull the dildo out. She wrapped her glistening hand around the shaft of the dildo as she pulled it out, to make sure that it was ready for immediate reinsertion. She pulled all the way out and then slowly began to push back into Kim’s ass. Far more prepared for the probe this time, Kim’s hole opened wide and took the strap-on in with little resistance.

“Oh, my goodness Kim,” chuckled Carrie. “I didn’t know your ass was so hungry. If I had, I would have started feeding it dicks a long time ago.”

“Thank you, mistress.”

“How does it feel?”

“It still hurts a little,” said Kim looking over her shoulder, “but it’s also starting to feel good.”

“The first time is always the roughest,” advised Carrie, as she pushed her cock into Kim’s behind. “From here on, it should get better.”

“It already is,” said Kim, before she had a chance to stop herself.

“Good,” responded Carrie, as she began to pull out and push back in faster. “How about, now?”

“That feels nice, Mistress” answered Kim.

Carrie then sped up her pegging a little more. “And now?”

“Good,” answered Kim, as she started to push back against her mistress’s cock. “Thank you, Mistress.”

Noticing Kim’s response, Carrie increases her speed again and reached around Carrie’s hips, and gives her clit cage a tap. “I think you’re beginning to like this.”

“I am, Mistress,” answered Kim in a dreamy tone. “Thank you so much, Mistress.”

“You’re welcome,” said Carrie as he climaxed. “Have you cum?”

“Did you want me to cum, Mistress?” asked Kim.

Carrie had to think about it for a minute before she decided to deny her submissive and pulled out, “Not today.”

Kim humped empty air once before stopping and simply lying on the bed. She spit out the sheet and a smile grew across her face. She was tired and her ass hurt a little, but all of her aches and pains were completely masked by how good she felt. Not only had she overcome her fear, but she had also pleased her Mistress and opened a door to a whole new world of pleasure. She couldn't wait to be given another chance to please Aaron and every other man or woman Mistress told her to pleasure.

“I think you have learned your lesson,” said Carrie, while unlocking Kim’s restraints.

The moment she was free, Kim fell at Carrie’s feet. “Yes, Mistress. I’m so sorry about this, Mistress.”

“I consider the subject closed,” said Carrie in a nonchalant tone. “Take a shower get cleaned up and get to your chores.”

Carrie watched Kim run out of the room. She then sat on the bed. A wave of relief washed over her. She was ecstatic that she wasn’t going to have to lose her favorite pet.