Mom knows best for son Ch. 01

There are things in life, when they occur, are totally shocking. Things that exist, right under our noses. Here, a mother, finds out that her 19 year old son has questioned his sexuality his entire life.

Follow the journey of this young man, as he changes, and how mom takes advantage of it.

This is the introductory chapter to this story. In order for the reader to understand fully the life altering changes that will occur, there must be background information given to be able to obtain that understanding.

Flashbacks will occur in following chapters, that will fill in abbreviated scenes.

All persons in this story are over the age of 18. This author abhors, and is totally against, pedophilia.

*

Ch 1 The discovery

I was finally home from a very grueling day. The office was nuts from the moment I walked through the door. I am a regional department manager for a large insurance company. My office is in central Florida, on the top floor of the largest bank in the state.

Due to downsizing, and flattening of the organizational structure, I now manage offices in this state, as well as, other offices in surrounding states, in the casualty and disaster areas.

A category 5 hurricane had just hit the Gulf coast over night, doing major damage in all of the states that are in my region. Wind speeds were constantly reported at over 150 mph.

I was continually holding video conference meetings with each offsite office. This was being done on one cell phone, while holding another. When the office manager was able to find cell service.

I was constantly running down the hall to another meeting with my boss in this building, continuously putting out fires.

It seemed that on this day, no one had the common sense to organize, and send disaster relief crews out to the scenes of these incidents on their own. In other words, to do their own fucking jobs, without being told. I guess it's time to do some replacing.

I was exhausted from calling the other offices all day. Reminding people of the proper protocols to follow. By the time I walked through the front door of my house, my feet were killing me. I kicked my 4'' heels off, and just left them there.

I walked to the bar, opened the little fridge, pulled out a bottle, and poured myself a large glass of white wine. I wanted to get drunk, but it was only Thursday. I still needed to work in the morning. I took a cool soothing drink, then took the bottle back to the couch.

I was just finishing my second glass, when I heard a noise from my son's room. I heard him run from his room into the hall bathroom. He was mumbling something that I did not understand. Then a strange, sweet smell was detected by my olfactory.

I immediately thought grass. But there was no smoke. I placed my glass down, and quietly walked down the carpeted hallway to his room. He was just coming out of the bathroom, when I reached his door. The scene shocked me to the core.

My now 19 year old son, was wearing a pair of my panties. He also had his face covered in make up. He looked more like a circus clown, then a woman. "What .....the fuck ....are you doing?" I yelled quite loudly.

I think he had a heart attack at the sound of my voice. He just stood there with his mouth open, and an ashen expression on his face. "Mo.....mom, ......I....I....oh shit." He stuttered out, while his lips quivered. I looked into his room and on the bed was a bottle of lube and my dildo.

"Clean yourself up, .....then come into the living room. .....I will give you time to think of an explanation. ......Just make sure that it is the truth." I stated angrily, then walked back to have another glass of wine. I just might have to get drunk.

I have been on my own for the last 12 years. Since I kicked my useless husband out, and divorced his ass. He spent more time at the casino, with a bimbo at his arm, then he did at a job. The only thing he did right, was to be the sperm donor for my son.

I met the useless son of a bitch during the later part of our junior year in college. We dated briefly over the following summer, then needed to marry after a drunken mistake, because I became pregnant.

I made sure that I graduated, but the SOB dropped out and got a job. Lost that one, then another job. Lost that one. You get the picture.

I am a strong, dominant, independent woman, who is a workaholic. At 5' 10'', I stand as tall as some of the men I work with. I take no bullshit from anyone, including upper management. They appreciate that. My long flowing auburn hair can be seen most days flying down the hallway, while being led by my 36C chest.

Since the divorce, it has been just the two of us, Kevin and I. As he walked into the living room, I indicated that he sit next to me on the couch. His shoulder length auburn hair was wet with tears and sweat.

I took a deep breath and a large gulp of wine before I spoke. "Alright Kevin, what the fuck is going on." My anger was still very evident.

"Mom, ....I am so....sorry. ......I am just not sure.....who I am.....suppose to be." The tears were flowing from his grayish blue eyes. His usual light, soft voice was now heavy with emotion.

"What do you mean....that you don't know. You are my son, .....who just graduated from high school ......and about to enter into college." His assertion did not make sense to me.

"I don't mean ....what I will be .....studying in college,......but what am I. ....A man or .....a woman." Now I know that I definitely need to get drunk. I thought that I was shocked before, but this just floored me.

I needed time to fully digest this. "Kevin, are you telling me that .....you are not sure of ......your sex?" I almost asked it incredulously.

"Yes..... I have not....been sure....if I am.....male or...female....all of....my life." He said while sobbing out each syllable. The time I needed now, was time to either get totally wasted, or sit with the Dali Lama, for the next year, to figure this out. He continued to speak.

"All during when I .....was going through puberty, .............I did not grow any body hair. My male parts ..........did not grow. I have the same size .............dick, as when I was ......6 years old." He choked out with some difficulty. I decided to continue this tomorrow.

"Alright, tell you what. .... Go and finish washing up. .....Over the weekend we will discuss this further and come up with a solution." I spoke with a motherly tone, while taking him into my arms and hugging him. At least now I know what I am facing. I just needed to stall for time.

I finished off that third glass of wine and went to put the bottle back. If I didn't, I would have gotten drunk. As I was putting the bottle in the fridge, a very bad thought came to mind. 'Did I neglect my son that much these past 12 years, that I did not even notice his issue?'

I still had a small hangover the following morning. Due in large part to my son's confession, and a very restless night. As the morning fog cleared, I knew that I needed to set my mind to helping my son.

The day went better than the day before. At least, there were not as many problems. All offices had crews on the ground, to areas that could be reached. I was even able to do a little research on Kevin's issue.

At least it was Friday, and I was able to leave a little early, in spite of the situation on the ground. I stopped by the store, and picked up something for dinner. I also stopped by the liquor store for a few more bottles of wine. Just in case I needed to stew my brain.

Our meal was simple, a bucket of fried chicken and sides. I wanted to start on Kevin's problem as quickly as possible. I had Kevin clean the kitchen, while I went into the living room, to start to think on how to start approaching the problem. When he was done, I had him sit next to me.

"So the omphalos to this, is that you feel you are a female. How long have you felt this way?" I asked this calmly.

"Seriously, ...for about ....the last 2 years. ....Since my .....junior year." His voice was a quivering raspy, girly tone. "But I have ...always had a ....strange feeling ....that I am living .....in the wrong .....body.....all of my life."

I began to realize that his grades did begin to fall off starting at the end of his sophomore year. He just did not recognize his sexuality issue fully, until the following school year.

"Then you would want to be a girl, ....rather then a boy? Is that correct?" Asked with a calm and inquisitive voice.

"Yes. .... I would ....feel more...comfortable....as a....girl." His tone did not change.

"When you are around girls, what attracts you? Is it the girl, or what they are wearing?" This is to dig a little deeper to get to the root of the problem.

"When I see girls ...in pretty dresses, .....I really like to see what they are wearing. ..... I picture myself wearing those dresses. .....The girls do nothing for me." There was a small amount of excitement in his voice.

"When you are in gym class, .......have you looked at the ......other boys dicks?" I noticed a small shiver from him.

"Ye ...yes. I get a little hard ....when we are.... in the shower." He bowed his head and turned red. "But I have to hide my private parts, because they are so small."

"Did you use my dildo in your ass and ......think that another boy .....was fucking you?" I needed to know how far he went or was willing to go.

"No. That is when you came home .....and I had made a mess with the lube. But I have dreamed ......of being fucked there." There was brightness in his eyes as he said that.

"Alright Kevin. Then I will help you to transition into a woman. I will teach you everything you will need to know. ......But it will come at a cost." He perked up.

"College is out the window. .....You will become my sissy. .....You will do everything that I tell you to do. If you don't, ....you are out on the street. Do I make myself clear?" My tone changed to the same when I am dressing down an employee.

"Yes. ......I understand." His demeanor changed to a very submissive one. There was a note of excitement on his face.

"Alright then. You can no longer go by your name of Kevin, since you want to be a girl. From now on, I will call you .......Katya." I proudly put forth. Using humiliation and name change was some of the things that I discovered earlier.

"I like that name." The new Katya exclaimed.

"Also, I think that you should no longer call me mom. ...You will call me ......Mistress." I used the same down dressing tone.

"Yes, Mistress." He smiled for the first time.

"Tomorrow we will go shopping for your new clothes. We will need everything. From undergarments, to dresses and shoes. We will have the sales clerk measure you so that we get the right sizes." Good time to present the new female in public.

"So now go to your room and search for how to walk in high heels, as well as, dress and shoe types and styles." I made sure that he understood what to do. "Katya, ....shave all of your body hair off as well." His body hair was very light in amount, but somewhat dark in color. I will decide later if he needed laser removal.

"Yes, Mistress." I pulled my laptop out, when he left, but after first retrieving another bottle of wine. I needed to fully learn how to make him into a real sissy.

I awoke the following morning, just before 7 am, still on the couch, with the laptop still on the small tray table for my lap. An empty wine glass and bottle, by my side.

The battery indicator was flashing. I plugged the computer in, and went to take a shower. When I was done, I only put on a robe and went into the kitchen and made myself some much needed coffee. Took some pain pills, then resumed my search.

Over the course of the next couple of hours, I learned that the person changing into a girl, must think and act like one. They must refer to themselves as one, in every way and everything they do. That is the only way that the transition will be effective.

Besides the clothes and the mental change, there was also the prospect of the physical change. This would be accomplished through hormone drug therapy. I definitely needed to think about that. I will need to check my insurance coverage to see if this whole thing was covered.

I called Katya back into the living room. "Alright Katya, from now on you will refer to yourself as a female. I know that you already think that way, but you must always act just like a girl. You must believe that you are ......a girl. Do you understand?" I asked this as if I was passing knowledge.

"Yes, Mistress. What I have found thus far is very interesting as well." She said very excitedly.

"Good. Now, you will be responsible for doing the housework and cooking the meals. You will perform all other duties that a stay at home housewife does." I waited for acknowledgment.

"Yes, Mistress."

"Good. Now go make something for breakfast and plan dinner afterwards." I waved my hand in a dismissive way.

"Yes, Mistress."

The rest of the morning was quiet. Katya did a good job with breakfast. I will still need to give her more cooking lessons with dinner. Especially since she will be cooking for anyone I bring home.

After a light lunch, I found more information on the drug therapy. Also came across the information and a video on the surgery to have the male parts changed into female ones. A very interesting concept.

We dressed and left for the mall right after reading about that.

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

Ch 2 The transition begins

We spent the better part of 5 hours at the mall getting Katya her new things. She will wear an 8 and half shoe. We purchased several pair of different colored hosiery, along with a girdle and garter belt.

She will wear a dress size of 8. She is only 5' 5'' and 110 lbs. I decided not to have her auburn hair done at a salon just yet. It was still a little too short and unruly.

The only formal dress I purchased, was a maid's outfit. It is pink with white ruffled trim, with an apron and a white ruffled hat. The shoes were also pink with 2'' block heels. A second pair was black, to go with the other dresses, which were shift and sheath style.

I purchased a full make up kit, along with replacing the ones she used up on me. I also picked up 6 additional shades of lip stick, as well as, lip gloss.

I had Katya sit for a make up demonstration to begin to learn how to apply her own. I will finish instructing her at home. I had the sales clerk put fake eye lashes on Katya. She went through each step demonstrating the complete process, from trimming the correct end, to applying the adhesive, to properly applying pressure to secure it to the eye lid.

The sales clerk did a fine job of transforming her face, from a boy, to a girl. The clerk even brushed out her hair a little and styled it. She also did her nails. I bought 3 more sets of eye lashes.

Katya wanted to buy perfume, but I told her not yet.

I had her change into one of the floral summer dresses in the store, we just purchased, along with the proper undergarments, hosiery and shoes. Along with the make up job, she easily passed for a girl.

We finished our shopping by walking through the mall again with Katya completely dressed as a woman. I did not buy a wig. The quick brush and style was more than enough.

I treated her to dinner out. She was very nervous that someone she knew would recognize her. "If you are truly committed to changing into a woman, then you need not worry about someone seeing you."

"Yes, ....Mistress." Her voice cracking with nervousness and humiliation.

When we arrived back home, I had her change into her new maid's outfit. Which included the girdle, garter belt, white hosiery and hat, along with the pink 2'' heels. When she returned into the living room, I gave my instructions to her. "Katya, you are to dress in that everyday. It is to be clean and neat.

"Since we did not know the type of material of your outfit, we will go to the store tomorrow, and get the proper cleaning products for it, as well as, doing the grocery shopping."

"Yes, Mistress." She stood there waiting for further instructions.

"I think that I will call for an appointment for you to see the doctor. I need to ask about wanting to put you on hormone therapy, so that we can have you begin to change your sex." I said thoughtfully.

"Oh yes, ....yes Mistress. That is what I truly have been wishing for all along. ....Thank you Mistress. I will do what ever you wish of me." She then dropped down and started kissing my feet.

"Anything Katya?" I asked inquisitively. Since I was new to this whole thing of being a mistress, might as well take advantage of it.

"Yes, Mistress. Anything." That is interesting. As Kevin, I could hardly get him to clean his room. But as Katya, her true submissive nature has been released.

"Then put your mouth to better use and lick my pussy." I spread my legs to give her the needed room.

Katya moved to between my legs and started to lick my pussy through my panties. She eagerly sucked my lips, through the material, into her mouth. This sent an large electric charge to my brain. My legs shook from the shear force of it.

She backed off, moving to my thighs. Placing kisses from my groin, to my knees. First working down one leg, then up the other.

She used her fingers to move the material to one side. She licked my lips, flicking her tongue on the outer lips. Then stuck her tongue as far into me as possible, along with a couple of fingers. She moved them all around, as well as, in and out very quickly.

My juices were flowing freely because of this. My breathing started to come in short gasps. Fireworks were going off in my head. This girl is good for being so new.

Then her tongue made contact with my clit, as she sucked it into her mouth. This brought my hips off of the couch. My orgasm hit me with the force of a tidal wave. I have never cum that quickly. But then again, it had been months since my last sexual encounter.

My breathing was coming in hard, short, gasping breaths. It took a minute for me to be able to speak. "Katya, that was ....amazing. You have a ......very talented tongue." I was almost dizzy from the experience.

"I think that ....I will need to make .....use of it more often." I know some others who just might benefit from her tongue.

"Thank you Mistress. It is my pleasure to serve you." Her face was covered in my secretions.

"Where did you learn that?" I had to know.

"On the internet. I have been researching anything to do with being a girl." The smile on her face, was priceless.

"Go and shower now, and be sure to remove all of the make up. Be sure to hang your uniform, and all of your other clothes up.

"I will get you a bottle of my skin lotion. Put that on before you go to sleep. Also, brush your hair at least 100 times every night before bed, as well." If Katya was to successfully transition, then we needed to get rid of her old boy hair, and soften her skin.

The thought of the financial benefits of hiring her out to others, was becoming enticing. I will need to discretely look into it. Besides, she can start working for me in the office, after she is trained.

In the morning, I had Katya shower again and reapply the skin lotion. Then I did her make up, I put a bright pink lip stick on her. I dressed her in a blue sheath dress, with undergarments and white hosiery and her black heels. She looked adorable.

While we were in the grocery store, I had her push the cart. I did not allow her to try to hide behind it. I made sure that she was standing straight at all times. She received some very nice glances. One boy even came up to her and asked her out. She smiled at him, but I had her decline. Maybe after she is trained.