The Lost Soul

My name is Mark, I'm 29-years-old, and I'm a self-made man. I married my childhood sweetheart at 19, and life was good, or so I thought.

I had worked hard to build my business, and provide a comfortable lifestyle for my wife. But I neglected to give her something she really wanted, me.

After I made my first million, me moved into a nice neighbourhood, in the North London suburbs. At first, she was happy, but only 23-years-old she quickly found out she had nothing in common with the 40-somethings housewives that lived in our area.

This, and my continued absence due to working my arse off, led her to become lonely.

This leads us to the events of 4 years ago, two young 14-year-old boys were canvasing the area looking for gardening work. Most of my snobby neighbours told them to piss off, as they already hired professional gardeners to landscape their gardens.

I on the other hand appreciated their young entrepreneurial spirit, been an entrepreneur myself.

Tim was the leader of the duo, he was well on his way to manhood when they started to work for me, Josh on the other hand was still very much a boy, though he was 3-months older than Tim.

The boys worked hard, and they would come round at least once a week to tend to my garden.

Fast forward 4 years, and now aged 18, the young men were now making a fulltime living from their landscaping business. Tim had filled out to a whopping 6ft 1, but Josh never grew passed 5ft 7.

This is where my trouble started, you see Tim started to tend to more than my garden, and was now fucking my wife regularly.

Their affair was well into its 6th month, when I came home early and caught them.

The betrayal, led to the inevitable divorce, and at 29-years-old I was a broken man.

To my ex-wife's credit she only demanded 1 million pounds of my fortune. She was sorry she cheated, but wanted to be with Tim. I later heard that they had a couple of kids, and got married. Tim had used the money from the divorce to build his business, and they were doing very well.

I should have been angry at her, but I knew deep down that this was my doing by neglecting her. I vowed never to put work ahead of love again.

I reorganised the leadership structure of my company, I was still the president, but I had delegated the day-to-day operations to my deputies. I would mostly work from home from now on.

I quickly learned that Josh had quit working with Tim, when he was refused an equal share of their business.

I obviously had fired Tim for fucking my wife, there were no real hard feelings, but I did not want to see him around my house. I have talked to him at several business conferences, and though we were not friends, we were on semi friendly terms.

I kept Josh on, it felt like the right thing to do. I also decided I would need some staff to run the household, my ex did all the housework before.

About 3 months after my divorce, on a hot summer's day, I was working in my home office. I decided to take Josh a cold drink out, since the suns heat was crippling today.

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As I approached him, I could tell he was weeping.

"Josh, are you OK?" I asked him.

"Oh," he replied noticing me approach, "Yes Mr Lawrence, I'm good."

The young man was not convincing no one.

"Please tell me what is wrong," I insisted.

He could not hold back the tears any longer and started to bawl.

I put the drink down and hugged him.

I repeated, "What is wrong?"

"My Father has thrown me out, I have been living in my car," he said between sobs.

"Why?" I asked.

"I can't say, or you will fire me," he wailed, "And this job is all I have left."

"I promise I will not get mad," I said, trying to reassure him.

"Promise," he replied, almost pleading.

"I promise," I replied, giving him a more tighter reassuring hug.

He broke our embrace, but would not look me in the eye, "My Dad a caught me dressed like a girl."

"Wait, what?" I said in disbelief.

"I'm a transvestite," he said meekly.

I paused for a moment, trying to process this information, "OK, well that is not so bad."

Josh nodded, "My Dad thinks so, and tossed me out of the house."

"Well, I'm not your father, am I?" I said, trying to sound comforting.

He could only muster a meek, "No sir."

"OK, finish up hear and come up to the house for a chat," I told him.

Again, he replied with a meek, "Yes sir."

I headed back to my office; my brain was flustered. I had no real experience of a transvestite, other than watching Raul Paul's Drag race.

20 minutes later, John knocked on the patio doors of my office. I waved him in.

He stood in front of my desk like a schoolboy sent to the head masters office.

"Josh, first off, please relax," I said with a smile, "You are not in any trouble here."

He managed a smile.

"I have a proposal for you," I said, leaning onto my desk, "Since Karen left, I have a need for a housekeeper."

He nodded, not really sure where I was going with this.

I continued, "I was just writing up the advert, before I came out to see you."

Again, he nodded.

"Well, to be frank, if you want the job of housekeeper, it is yours," I spelled it out for him, "It is a live in appointment, so you will get your own room."

His young face lit up, "Really, you mean it?"

"Yes," I said, "We have both been through a tough time recently, I will be happy to help you out."

"Thank you, Mr Lawrence, I will work very hard for you," He said thrilled, then his face turned sombre, "I promise never to dress up in your home."

"Nonscience," I replied, with a dismissive wave of the hand, "You can be your true self here, if you want to dress in women's clothes, that is fine with me."

His smile returned, but I was not sure he believed me.

I showed him to his new room, and left him to get settled in.

I returned to my office and typed up a list of duties for him to perform. And over a takeaway dinner, we went over the points.

The next day Josh was up bright and early, and had breakfast ready for me.

He then spent the rest of the day tidying the house, and catching up on my laundry. I had neglected to keep on top of the house chores since Karen left.

After a week, Josh had the house back in perfect order. I had gone over the property finances, and he now had access to pay the bills, and run the other household admin.

One evening, after I had finished work, I had invited him out to the patio for a beer.

"You've done an amazing job Josh, the house looks fantastic," I praised him.

"Thank you, sir," He replied.

"I think we can drop the sir when you are off duty," I told him, "You can call me Mike."

He smiled, "OK Mike."

We sat in an eerie silence until I had to say something, "So Josh, I've not seen you dressed in anything but your male clothes?"

"Oh, erm, I did not want to embarrass you," he replied sheepishly.

"Nonscience," I replied, "I told you, you can be yourself here."

He just replied, "OK."

"In fact, why don't you go get changed now," I told him.

"No, I can't," he said with a look of panic on his face.

I smiled at him, "Relax, I won't judge you, please, go change."

He set his beer down, and went into the house.

I relaxed in the garden, taking in the warmth of the summer evening sun.

About 15-minutes later, Josh returned. He was wearing a floral summer dress, a bad blonde wig the still showed his brown hair beneath, and he still wore his trainers.

He looked like a boy who had lost a bet, and forced to wear this outfit. His legs were hairy, and there was no sign of any makeup.

I decided to play it with some diplomacy, "Nice, now please relax."

With a timid smile, he sat back down and picked up his beer.

"So how long have you been dressing?" I asked him casually.

"Since I was 15," he replied.

I was now getting very curious, "So is it just the desire to wear the clothes, or do you want to be treated as a woman?"

He shrugged his shoulders, "I don't know, all I do know is it feels right to wear female clothing."

I thought for a moment, "From tomorrow, I want you dressed as a woman when you do your chores."

"Really?" he replied.

"Yes," I continued, "I want you to start feeling comfortable wearing what you like in my home."

"Yes sir," he said, before correcting himself, "I mean yes Mike."

"Do you have a female name for when you are in girl mode?" I asked.

Josh looked a little perplexed, "No, I never really thought about it."

"OK, from tomorrow when you are working, you will be referred to as Jane," I informed him.

"Jane, I like it," he said smiling.

And so that is how we carried on for the next couple of weeks. Jane would have my food ready, my house cleaned and my laundry done.

One afternoon I called Jane into my study.

"I'm hosting a dinner party for some prospective clients next Tuesday evening, please arrange for the catering." I informed her.

"Yes Sir," she replied, "How many guests?"

"5 including myself, and I want you to be our server," I replied.

She frowned, "I will have to purchase a new suit for Josh for the evening."

"No Jane, you will be our server," I told her.

"No," she said in a panic, "I cannot have anyone else seeing me like this!"

I had already thought this through, and to be honest the dinner party was just an excuse to push Jane down this path. Though I was happy for her to be herself, she really had no clue on how to dress properly as a girl. I had already made arrangements to get her some help in the tranny department.

"Jane, I agree that you are not very passable as a girl," I laid it out for her, "I have arranged for a madam to come here and give you some lessons on how to look, and act like a lady."

"But Sir, I cannot afford that," Jane said.

"I have already taken care of that; Madam MacManus will be her tomorrow at 8am to begin your training."

"Yes Sir," Jane replied, her head in a spin.

I dismissed her, and returned to my work.

I had found Madam Debbie MacManus online; information is my business and there is little I cannot find out about someone online.

Her website lists her as 26-years-old, but after digging a little deeper, I discovered she was actually 32, and she was born Angus MacDonald. She appeared to have transitioned 8-years ago, and started her tranny training company 5-years ago.

There are some positive testimonials on she website, and after digging into the clients that made these statements, they are for the most part true.

Debbie MacManus arrived at 8am sharp the next day, Jane was incredibly nervous and was very fidgety as she prepared my breakfast.

Debbie was a beautiful woman, and there were no traces that she was once a man, I knew I had hired the right woman for the job.

"I will spend the morning observing the student, and I will make notes on the best direction of her training," Debbie said as we drank coffee.

Jane was hovering near the table listening to our conversation.

Debbie turned to her and commanded her, her Scottish accent piecing, "You have chores to do?"

"Yes," Jane replied.

"You will address me as Madam, is that clear," Debbie said, asserting her dominance over Jane.

Jane straightened up, and replied, "Yes Madam."

"Good," Debbie commented, "You are dismissed to start your chores."

Jane left, and Debbie's demeanour relaxed. She dropped the madam act with me as I was her employer.

"So," Debbie said, in a warm and friendly tone, "What are you wanting Jane to become?"

"Sorry, I don't understand?" I replied.

"Do you want her to be completely sissified, or just trained to be a woman?" she asked.

"Oh, I just want you to help her be herself," I said, "She clearly is a transvestite, I just want you to help her with her appearance and behaviour."

"So, you're not looking for a sissy slave?" Debbie enquired.

"No, no," I insisted, "I just want her to be passable as a woman, so she can live as one if she wants."

"Does she have many clothes?" Debbie asked.

I shrugged my shoulders, "In the few weeks she has been dressing here, she has only worn two dresses."

"OK," she said, "We will need to expand her wardrobe then."

"Wait a minute," I said, "My ex-wife left some clothes behind; they might fit Jane?"

"Lead on," Debbie said.

I took Debbie up to my bedroom.

"That was her wardrobe," I said pointing to the large walking wardrobe.

Karen had taken most of her stuff, but there was still plenty left behind. Debbie slid the door open and disappeared inside.

I sat on my bed and started to flick through my phone.

"Oh, very nice, some good stuff in here," Debbie commented, "Oh wait, what have we here?"

I looked up from my phone, as Debbie exited the wardrobe.

She held up the two hangers, one had a complete catholic schoolgirl uniform, and the other a complete WPc police uniform.

I turned a little red, as Debbie asked, "Into a little role play, are we?"

"I have a thing for shirt and tie uniforms, and my ex-wife indulged me a bit," I replied embarrassed.

"A little bit," Debbie replied, "There are at least half a dozen women's uniforms in there."

I felt a ping of regret for neglecting Karen, she was a good sport for indulging my uniform fetish, and really got into the role of the uniform she was wearing. As a policewoman, she oozed authority, and as a schoolgirl, she was timid and shy.

Debbie shook her head, "Well nothing wrong with some harmless fun."

She then ducked back into the wardrobe, and reappeared holding a in red dress, with matching heels.

"I'll see if these will fit Jane," she said, and then went off to find Jane.

I headed to my office to do some work, but the images of Karen dressed up kept flooding my memory.

I opened a folder on my private home network, it was full of pictures and videos of Karen wearing various uniforms.

I hit play on one, Karen appeared on the monitor, she was dressed as a British Airways stewardess. She said some corny lines to me, before fishing my cock out and blowing it.

I opened my trousers and started to wank to the video, it had been a while since I last masturbated. Karen, now had her uniform shirt open, her nice C cup breasts jiggling up and down, as she rode my cock. I grunted as I ejaculated into a tissue.

I cleaned myself up and got back to work.

It was lunch time before I saw Jane and Debbie again. Jane was now wearing Karen's old red dress and shoes. It hugged her frame better than the dress she was wearing earlier, but she still looked like a bloke in a dress.

Jane served Debbie and I lunch.

"If it is OK with you, I will be taking Jane away from her chores this afternoon?" Debbie asked me.

"Sure," I replied, "What are you two girls up to?"

Debbie took a sip of her water, "I'm going to take Jane to a salon run by a friend of mine, we are going to give her a makeover."

"Nice," I said finishing my food, "Enjoy ladies."

I left them to their lunch, and returned to work.

I knocked off work around 4.30pm, and headed to my home gym. I changed into my workout clothes, turned on the 60-inch tv on the wall, and started my exercise routine.

After a steam and shower, I got dressed and went to the tv room, and relaxed watching some of my favourite shows.

I heard the front door open, and Debbie announced their return.

I heard her distinct Scottish accent give Jane a command, "Go up to your room, I will join you shortly."

"Yes Madam," Jane replied obediently.

Debbie came and found me in the tv room, "The makeover went well, as soon as Jane as squared away her new makeup purchases, she can start dinner."

"Make sure you charge all her supplies to me, the poor kid is broke," I asked her.

"No problem," Debbie said, "I'm sure you will be pleased with her."

Debbie left, and I returned to my programs.

I lost track of time, when I heard Jane calling me from the kitchen, "Sir, dinner is served."

As I entered the kitchen, I was nearly floored at the sight that greeted me.

Laying the plates of food on the table, was a gorgeous brunette. Her long smooth legs disappeared under the hem line of the red dress she was wearing. Her hair, was long and style very feminine, with long curls cascading down her back, and framing her face. She had C cupped breasts, where a few short hours ago she had nothing.

She was made up like a supermodel, showing all the right contours to give her the look of a sexy goddess. Her plump kissable lips pouting beneath the long fake eye lashes, framing her eyes, gateways to the innocents of youth within.

"Fuck me," was all I could muster.

"Now, now Mr Lawrence, that is not how we address a pretty young lady is it?" Debbie said.

I snapped out of my daze, when I realised, I had been staring at Jane for far too long.

Jane stood, and gave me a twirl, "What do you think Sir?"

As she spun, her hair bellowed around her, her perfect arse came into view. I had to force myself from gawking at her.

"Excellent work Debbie, the transformation is fantastic," I said to Debbie in awe of her work.

"It helps when you have a good canvas, she only needed some help to realise her potential," Debbie replied, clearly proud of her work.

Debbie and I sat down to eat, as Jane served us.

"So, the next question, is how far do you want to go with this?" Debbie asked.

I again was confused, "Sorry, you've lost me again?"

"Do you want to leave her like this, a part time girl," she took a sip of her wine, "Or do you want her to start a permanent transition?"

I looked over at Jane, standing ready for her next instruction.

I turned back to Debbie, "Well that is up to her, she is my housekeeper, not my slave."

Debbie moved her head to the side, "Are you sure?"

"What, no," I said as I started to protest, "Yes she is beautiful, and any man would desire her, but I'm not going to force myself on her, that is not right."

"So, if she found herself a boyfriend, you would be OK with it?" Debbie asked.

"Of course, if that is what she wants," I replied, but part of me regretted saying so.

Debbie looked at Jane, and then back to me, "Well what if she chose you, to serve with her body and soul."

My eyes widened in shock, I noticed Jane had a coy smile, and had blushed with embarrassment.

"But she is just a kid, it would not be right," I said, trying to talk my way out of this situation.

I was not gay, I had no attraction towards Josh, why would they think I would be open to this. But then the young lady stood in my kitchen did not look like Josh, did not even act like Josh. My cock had started to stiffen when I first set eyes on her.

I was in a real state of confusion.

I turned to Jane, "What do you want, do you want to transition?"

"Yes Sir, with all my heart I want to be Jane forever," Jane replied, almost pleaded.

I turned back to Debbie, "How do we go about doing this?"

Debbie took another sip of wine, "First, hormone treatments to stop any further male development, and to start her body down the female path."

"So, we need a doctor?" I asked.

"I can take care of all that," Debbie replied, "I will also get the ball rolling to change her ID from Josh to Jane officially."

"How long will it take?" I spoke.

"Well, it all depends on funding, the hormones will take time to alter her," Debbie said, "But with money, we can help the process along with surgeries."

She turned to Jane again and said, "It all depends on how far you want to go; I can make you look like a woman to the outside world, but do you want to take that final step?"

Jane looked confused, "Final step?"

"Gender reassignment," Debbie confirmed, "Everything is reversable, until they cut your cock off."

"Oh," was all Jane could say as the gravity of her situation sunk in.

Debbie reassured her, "You don't have to decide about the final step for a while, you have to live as a woman for at least a year before you legally qualify for a gender reassignment."