Mom knows best for son Ch. 01

After returning home, and bringing in the groceries, I asked Katya what was she to do next. "I am to dress in my maid's uniform Mistress."

"That is correct. So why have you not done it yet?" I made my stare harder then necessary.

She ran immediately to her room. She was back in the kitchen in less than 5 minutes.

"Put the groceries away. Then I will give you a cooking lesson." I left immediately for my office. I needed to check my email to see if any problems arose over the weekend. Also, I wanted to continue to do more research on her transition.

Katya came into my office, a half hour later, to inform me that she was done putting groceries away.

We went back into the kitchen, and I taught her how I like to cook chicken breasts. We had that for dinner, along with rice and vegetables. We cooked a few extra breasts for salads. She picked up quickly in learning her new skills.

Event though her uniform was not soiled, we cleaned it anyway, with a home dry cleaning product. I did this to teach her how to use the product. She did very well, and fully understood. She was an A or B student throughout high school.

Before I left for work the following morning, I watched Katya apply her make up. I only needed to do very little touch-up. She has learned very well. She dressed in her uniform, and then gave her a list of things that I wanted done.

The week started smoothly. The reports that were received, showed that the disaster crews were getting the claims done quickly and correctly. Maybe I won't need to fire anyone.

I called the doctor's office and made an appointment for Katya in the morning. I also spoke with my secretary Karen, about her and the idea of farming out Katya. She liked it a lot. In fact, she wanted to try her out. I invited her to the house on Saturday.

On the way home, I picked up some special items for Katya. I decided to advance her training. When I walked through the door, I was met with a very pleasing site. The house was clean, and Katya was kneeling in the living room waiting for me.

"Mistress, I hope that you are pleased with the way that the house looks?" She had her head down.

"Yes, but you have missed something." I had a stern tone to my voice.

"Mistress, what is it. I will take care of it immediately." She had a nervous tone to her girly voice.

I walked to the couch, pulled my skirt up, then sat down. "This!" I opened my legs so she could see my pussy.

She quickly crawled over and began to service me, just like she did the first time. I did not let her stop after my first orgasm. In fact, she brought me off 3 more times.

During her act of passion and love, I thought that I was in syzygy, with my mind, body and soul, before I had her stop. Only because I was about to stop breathing.

It took several minutes for my breathing to return to normal. "Katya, I could make a lot of money from your ability to eat pussy. So I think that you should also learn to suck cock." I noticed a slight shiver run through her.

I had her bring the shopping bag to me. I reached in, and pulled out a cock like dildo. "Now, you will learn to suck cock. I want you to service men, as well as, women." I looked directly into her eyes.

"Yes, Mistress." She had a gleam in her eyes. "I have watched videos on how to do it."

I showed her first how to hold a cock. "Stick your tongue out, and lick the head. Now, flick the tip over the head. Now kiss it. Keep doing each of those until I tell you to stop." She did that for about 2 minutes.

"Good. You did that very well. Now suck just on the head .....gently. .....Take it into your mouth. .....Go back and forth. Just the head, ....in and out." Katya did that for a couple of minutes. Her excitement level was increasing. She began to drip saliva.

"Very good. Very good. You will make an excellent cock sucker. Now take more of it. ......Keep pushing as much as you can into your mouth. .....Go until you make yourself gag.

"Now, go in and out .......keep your tongue out along the bottom....as you suck it into your mouth. Keep sucking all of the time." I looked down at her groin. Her little 2'' clit was sticking straight out.

"Keep going until you make your clit spit." It only took another minute, of increased speed, until her excitement overflowed. She splashed all over the carpet. She pulled off of the dildo.

"Bend down and lick that up, then use the spray carpet cleaner. Make sure you wash your dildo. When you are done, we will talk about this." In my reading, I remembered coming across a passage that stated that to use humiliation, helps train a sissy.

I was sitting at my desk, when Katya came in. "Mistress, I have finished cleaning the carpet." I snapped my fingers, and pointed a finger down, to indicate that she should kneel.

"Did you notice that I called your male part a clit?" I asked matter-of factually.

"Yes, Mistress. Is it not my male part?" She had the most adorable expression.

"No. When you get your surgery, it will become your clit. So we will refer to it as such. It is way to small to be called a cock." There is that humiliation again.

"Yes, Mistress. When will I have the surgery for you?" She asked that with a little bit too much excitement.

"When I think you are ready. First, we need to fully train you as a sissy. Part of that is to get your male pussy ready to take a cock. We will do that tomorrow. Now I want my dinner." I was starting to become annoyed. I already knew that it will be 2 years until she will be able to have the surgery.

"Yes, Mistress." I sent her away to finish preparing my meal.

After a decently good meal, prepared by Katya, I returned to my office and stored the remaining items from my shopping. Three sizes of butt plugs, 2 large bottles of lube, a box of rubber gloves, a box of condoms, and an 8'' strap-on dildo. The clerk said that if you are going to train someone to take it there, you might as well go big.

In the morning I took Katya into the doctor's office. She did a complete exam, and determined that Katya could go on the drug therapy. She also arranged an appointment for the psychologist. We filled her first prescription immediately. I returned home and had Katya dress in her uniform and take her first dose, while I went into work.

I stopped on the way home that evening, and purchased a case of pre-made enemas. I don't want a mess when she starts taking it there. As soon as I walked through the door, Katya was in the same position as the previous night. I had her go out to the car and retrieve the box.

"Store the box in your bathroom, then take 2 bottles out. Use them as directed. Then come into my bedroom naked." She did as she was told. She was back in just over an hour.

"Alright Katya. Bend over the bed on your stomach. It is time to get you ready for whomever I wish for you to service." She took her position. I put on a glove, and squeezed some lube onto her pink rosebud. I spread the lube around the opening, then inserted a finger. Katya let out a moan.

As I increased the number of fingers, her moans became louder. "Do you like this?"

"Oh, yes Mistress. I can't wait to feel a real cock in there." Her ass was wiggling to stimulate the felling some more.

I pulled the three fingers out, that I had gotten up to, then pushed the small butt plug in. It was a good thing that I had put a towel down first. Katya's little clit just spit all over it. That confirmed that my former son was now my sissy.

"You will keep that in until you go to bed. I will put it back in tomorrow morning, and you will keep it in all day." I pulled the glove off, had her stand, threw the glove on the towel and had her clean the mess up. I then went into the living room to have a glass of wine.

In the morning, Katya was waiting for me, in uniform, with her panties down around her knees. I put a glove on, lubed up her rosebud, and reinserted the clean plug. She pulled her panties back up, knelt and reached for my hand and kissed it.

Each night Katya practiced sucking the cock dildo, and I increased the size of the plug every day. Then on Friday night, after her appointment with the psychologist, it was time for her to take the strap-on. Katya went and cleaned herself out again, then came into my bedroom naked.

"Katya, kneel in front of me. Pretend that you are servicing a man. Then I will fuck your male pussy with it." I was feeling some excitement myself from this.

Katya knelt in front of me and started her now semi expert cock sucking. She was getting better each time. She was running her tongue along the entire shaft. Sucking the head, and taking just about the whole 8'' of the devise. Her saliva was dripping down her chin and soaking her chest. I kept encouraging her to look up at me.

Finally, I had her take as much as she could, hold it, then back off. "Katya, stand and take the same position again on the bed." She laid down on her stomach. Then I put a glove on, and lubed her butt and the strap-on. Taking a hold of it, I ran it up and down her crack. She moaned.

I placed the head at her entrance, and pushed. The head met some resistance, but slid in slowly. Shortly the head popped past her outer ring. Katya let out a small whimper of pain. I held my position for a moment. I wanted her to enjoy this. She was, after all, going to be my cash machine.

I started to push again. Katya's whimpering turned to moans. Soon I found myself with only just a few inches left. "How does that feel?"

"Oh, ...Mistress. ..... I never knew that I could feel this wonderful." Her joy was very evident.

I pulled back slowly, until just the head was left. Then just as slowly, pushed back in. Katya was starting to push back against me.

"Alright Katya. I want you to take over and fuck yourself." Did she ever. I had to lean forward to prevent from being knocked over, due to the powerful strokes she was fucking herself with.

She was slamming her ass into my groin. Each time that she hit against me, her ass would jiggle, just like she was twerking. She kept that up for several minutes. I was approaching my own orgasm, when Katya said that she was approaching hers.

"You need to ask permission first." I commanded.

"Mistress, ....may I cum?" Her voice was straining.

"No. ....Keep fucking me." I wanted to add a new element of domination to this.

A few more strokes later, "Please ...may I cum Mistress. ....I am about to explode."

"No. ....I will tell you when you can cum." I was having difficulty holding my own orgasm back.

I reached around her waist to feel her clit. It was hard as steel. She really was ready to explode. I grabbed her hips and started to pound her pussy. She was moaning and sighing with each stroke. They started to sound more like crying pleas.

"Cum, ....Now!" I yelled. Katya let out a wailing moan, as she spit all over the towel.

My own climax hit me at the same time. My juices squirting out of me. That was something that I had never done.

We both had trouble breathing. The exertion was equal to running a long sprint. I slowly pulled out, turned and sat on the bed. Katya stayed were she was.

Shortly, she looked up and smiled. "Thank you ....Mistress. I did not know that..... it could feel this great." She then knelt down and surprised me by taking the strap-on into her mouth and sucking on it. That sent a shiver through me, and I was hit with a small, post coital orgasm. I pushed her head back and smiled at her.

"Where did you learn that?" My curiosity piqued.

"On one of the sites that I found about sucking cock Mistress. They said that this is the one act that truly shows the love a woman has for their lover." Her face reflected that love.

"You honor me with your love. But I don't want you doing that. You may become ill, and I don't want to lose you." I gently ran my fingers over her cheek as I spoke softly..

"Yes, Mistress."

"That is enough for today. Take all of this and clean it up. Tomorrow you will need to prepare a meal for a guest. Make sure that it is a good one. I will assist you in preparing it. Make sure that your uniform is clean, and your make up is perfect. I will do your nails."

"Yes Mistress." She stated happily.

I went into my bathroom and had a long hot soak in my tub. I needed to soak all of the tension from the week away. I finished the bottle of wine that I had brought into the bedroom earlier. I had a delicious buzz going when I stepped out of the tub. Sleep came quickly.

***************

Ch 3 The entertainment begins

I had Katya dress in the floral sheath dress, so that her uniform could be clean for this evening. I still had her wear the girdle and garter belt, along with her hosiery and heels. After lunch, we prepared a roast chicken. There will be parsley potatoes and a green salad to accompany it.

After the chicken was in the oven, I sent Katya to take her shower. When she was done, I inserted a plug and started on her nails. She sat in front of me naked, as I did both fingers and toes.

As we waited for her nails to dry, we talked about things in general. Usually just girl talk. Different shading options with make up, new styles of dresses, as well as, shoe styles. It felt good to have a mother/daughter type talk.

When the nails were dry, we did her make up and eye lashes. I went with red for both lips and nails. Then she was allowed to dress.

We first put on her tummy tucker girdle. I needed her to continue to develop an hour glass figure. Then her garter belt, and hosiery. After putting on her bra, I put the latex cups in it. Katya finally had breasts.

I had her put the uniform on, then styled her hair. It more than covered her shoulders. I put her maid's cap on. Then there was one final surprise for her. A new pair of blush rose colored 2'' kitten heels. I also put on a jeweled choker. She was now ready for my guest.

I had her put a full apron on over her uniform and start the potatoes. I went and started on the wine. It felt good to have a servant. I received a text from my secretary at 3:30 pm that she will be there by 4.

I called Katya into the living room. "Katya, please come in here."

"Yes, Mistress." She stumbled a little with her new shoes and the butt plug in place. Her apron showed the progress made in meal preparations.

"Do you know how to curtsy?" I asked calmly.

"No, Mistress."

I then showed her how to do it. I had her do it several times. Each time, a little deeper. "My guest will be here shortly. You will curtsy when she comes in the door."

"Yes, Mistress. May I go back into the kitchen? I don't want to burn the potatoes." I quickly dismissed her. I heard her continue to practice curtsying.

Right at 4, my secretary Karen, was at the door. I had Katya greet her. "Please come in. Mistress is in the living room." She did a perfect curtsy.

"Rachel, I am completely impressed. What has it been, not even a couple of weeks?" Karen was smiling broadly.

"Yes. It turns out that she is a complete submissive. Katya, do you have a few minutes?"

"Yes, Mistress. How can I serve you?"

"Show Miss Karen your talents." I snapped my fingers, and she went straight to her knees in front of her. Karen sat on the couch, pulled her skirt up, spreading her legs.

Katya then spent the next 5 minutes servicing her pussy. I sat there jealous that it was not me. I never saw Karen so happy. A continuous chorus of 'yes', 'oh God', and 'eat me' came from her mouth.

When she climaxed, she squirted, right into Katya's mouth. Katya then had a face full of female cum. She ran her tongue out as far as she could, to lick as much as she could reach.

I sent Katya back into the kitchen to finish dinner. "Rachel, you have ......a gold mine in her. I know of .....at least 5 women who would ......pay at least $50 each to .....have that done to them." She was still trying to catch her breath.

"That is what I want to talk about. We will need to work out the details on Monday. Be sure to block out at least an hour for that meeting. She will be able to service both men and women with both holes now." Just then, Katya said that dinner was ready. I had her stand in the corner, while we ate.

Karen and I returned to the living room after dinner. We just talked about things in general and who could we get to pay for Katya's services. We also enjoyed the wine and each others company. Karen does a good job of eating pussy as well.

When she left, Katya opened the door for her and bid her good evening by once again doing a deep curtsy.

I removed the plug and gave it to her to clean. I then went to my bedroom, showered and went to sleep. Katya closed the house up, then did the same.

In the morning, the aroma of coffee drifted through the house. When I got out of bed, I just put a robe on. Just as I reached the kitchen, Katya was fully dressed waiting for me. When I sat down, she placed a cup at my seat. "Get a cup for yourself, if you wish, then have a seat."

"Thank you, Mistress."

"We will need to go to the mall today to get you some more nice dresses. From time to time, you will accompany me to work. There, you will service whomever I tell you to do. Whenever I tell you to.

"The money you earn, will go towards your support of this house. This is not going to be a free ride. You will earn your keep. Do you understand?" There was no anger or commanding tone to my voice.

"Yes, Mistress. It is a pleasure to serve you." Her head and eyes were down cast.

"Then make us some breakfast and we will leave." She hopped up, and whipped up some eggs and toast. I dressed, Katya changed out of her uniform, and were out the door in under an hour.

We went to the better dress shops. I am not going to have her looking cheap. I initially stayed with styles that fit her current body type. They each ended at or just above the knee.

I purchased a Peplum style one, in blue with white and black trim. A black sheath dress, for a more business look, when she is working for me in the office. As well as, an apron one. This was in case I had her do any serving of drinks at meetings, or parties in the office.

I picked up a few pair of shoes, as well. A pair of 3'' peep toe with sling backs, and black 3'' pumps for the sheath dress. Also, a pair of rose colored 4'' decorative heels for her uniform. She will wear those in the house, when she learns how to walk in them.

That will give her 5 pair to chose from. Depending on the occasion for now. I also picked up a few more pair of hosiery, just in case.

All total, I dropped over $2,000. She was shocked at the amount of money that I just spent. "Just make sure that you are worth it." I also had her ears and tongue pierced, along with some of the accompanying jewelry for her ears and tongue.

"Yes, Mistress. I will not disappoint you."

"Start learning how to walk in the 3'' heels, during the day. I don't need you tripping over someone with a drink in your hand." I made sure that she understood.

"Yes, Mistress."

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Ch 4 Going to the office

In the morning, Karen and I spent over an hour going over how we could utilize Katya best. We knew that it would not be safe to have her continuously performing here at work. So Karen said that she would look for a safe place.

In the afternoon, I was briefed on the amount of claims so far submitted. It was going to be an expensive one. At present, there were more than 15,000 claims, with a price tag of just over $ 2 billion dollars. I notified the boys in the corporate office. That sent them into their normal parsimonious rant of spending money.

What do they think as to the reason why people buy insurance in the first place. "You know Bill, you are one sanctimonious ass hole." That caught his attention. He started laughing at that. I told him that this is a preliminary report. That I was still waiting for 2 other offices to report on their claims.