The Lost Soul Pt. 02

I awoke the next morning, and I was riddled with guilt. I only had honourable intentions in helping Josh feel comfortable as a transvestite. I hired Debbie because she was highly recommended, and it was never my intention for her to change Josh into a sissy sex slave for me.

Last night, in my study, Jane had caught me wanking, and I let her give me a blowjob. I could have easily have stopped her, but in the heat of the moment I was getting a blowjob from a girl wearing my own personal Kryptonite, a shirt and tie.

I did my best to avoid Jane this morning, I went straight into my study, skipping breakfast.

Around 10am, there was a knock on my door, my heart started to pound as I said, "Come in."

The door opened, and Debbie entered the room.

"Good morning, Mark," she said, in a tone that hid a small level of sarcasm, "I heard your dinner party went well?"

"You know exactly how it went last night," I snapped back, "You groomed that young man to be the object of my desire."

"Tosh," she replied, her Scottish accent taken a stern tone, "I have not forced her to do anything she does not want to do."

I shook my head, "He just wanted to be a transvestite, not a full-time girl."

Debbie was clearly getting angry with me, "How dare you, I would never 'groom' as you put it a young girl."

I flinched as she carried on ripping into me, "After I had transformed her for the first time, she asked me to help her go all the way."

I meekly replied, "OK."

"Jane asked me to help her seduce you, she is attracted to you, you numb nuts," her tirade continued, "You may not have set out to make her your sissy lover, but she told me she wants you."

"First of all, I'm sorry for accusing you," I replied, "But this is too much for me, I like women, real women, I'm not sure I can love her the way she wants me too."

Debbie's tone softened, "I can make her as real a woman as you like, when I'm done with her the only thing, she will be incapable of doing as a woman, will be to bare your children."

"This is too fucking much to handle," I said putting my face into my hands, "I care for the kid, but she is just a kid."

Debbie stepped over to me and put a reassuring hand on my shoulder, "She has her shit together more than you know, she knows what she wants."

"And that is?" I said starting to sob into my hands.

"You, you dumb arse," she said in a light hearted tone, "She told me she wants to be your woman, she loves you."

"Jesus Christ, how can she love me, we hardly know each other!" I replied, my tears stopping.

"She was infatuated with you for several years," she carried on, "Your acceptance of her transvestism, and taking her in when her world collapsed pushed her in to loving you."

I raised my head and looked at her in desperation, "Shit, what am I supposed to do?"

Debbie cuddled me for comfort, "Do what your heart tells you."

"I'm in conflict, my brain says back off," I replied, "My heart cares deeply for her, and my cock lusts after her."

Debbie let me go, and took a few steps away, "Perhaps we need to approach this from a different angle?"

"OK," I said.

"I think you are scared of jumping into bed with her because it makes you look like a pervert," she said, "But, what if you took her out on a date, and see if a relationship develops?"

"But the age gap," I rationalised.

"That is bollocks, and you know it," she cut me off, "She is attracted to you, and you to her, so why not see if something happens."

I just stared at her, not knowing what to say as I had a thousand things swirling around in my mind.

"Anyway, think about it and let me know what you want me to do," she said, before turning on her heels and walking out of the room.

All thoughts of work fell by the wayside, as I tried to process Debbie's words, could I love Jane? Yes, but she was still very much a boy under the cute exterior, but would I freak if I saw her cock?

Would I be selfish enough to let her mutilate her body to please me? I decided the best course of action was to talk it out with Jane.

I left my study, and went to go find her.

I heard whistling coming from my bedroom, and when I entered, I was stopped dead in my tracks.

Jane was whistling a happy tune, as she made my bed. The thing that shocked me, was the fact she was once again dressed in her server's uniform from last night. The tight collar and tie, had my cock twitching.

Jane stopped her work and smiled at me, "Good morning Sir, I hope you don't mind, but I've decided to adopt this outfit for my everyday uniform."

I smiled back, "And very nice you look in it to."

Fuck, I thought to myself, I was flirting with her, and she blushed.

"Ah, I mean very well," I stammered trying to regain my composure, "I wanted to talk to you about last night."

The colour of her face drained, as did her smile.

"Look, I have had a chat with Debbie, and she has told me you have feelings for me," I continued, "And though I do not love you, I do care for you deeply."

I could see her eyes starting to well up, "Yes Sir, I understand."

"I think last night, we both got caught up in the moment," I said, keeping my tone even, "And though I enjoyed it very much, I feel I have taken advantage of you, and I'm sorry."

She took a step towards me, then stopped, "Oh no Sir, please don't feel that way, I wanted to please you."

"Well, that being said, it was not the right time for such things," I continued, "So I propose, that you and I go out for dinner together, and really get to know each other."

"Like a date?" she said excitedly.

"Yes, but no promises it will lead to a relationship, but I want to get to know the real Jane, and see how it goes," I said with a smile.

She nodded her head, "Yes Sir, that sounds lovely."

"OK then, I'll make arrangements for tonight," I said, as I left the room.

I made reservations at a restaurant, and later when I was passing Jane, I told her to be ready for 7pm.

After work, I had a quick workout, before hitting the shower. As the water cascaded over me, my belly was full of nerves. I had not been on a 'date' in over 10-years, will I make a fool of myself, what would people think of me with such a young girl!

But then a strange calm befell me, and I actually started to look forward to the date.

I dried off, and put on a dark blue 3-piece suit, white shirt, and blue tie. And when I was ready, I headed to the lounge to await Jane.

I was looking out the window, lost in thought when there was a cough from behind me. I slowly turned, and was greeted by a beautiful sight.

Jane stood in the doorway, she wore a black dress, the was off one shoulder, and fell just above her knees. Her hair was styled in a French plait, with two bangs cascading down each side of her face, framing it perfectly.

"You look beautiful," I complimented her.

"You look very handsome too Sir," she replied

I laughed, "I think we can drop the sir for tonight."

"OK Mark," she said, looking so coy, Princess Diana would be proud.

I put my arm out, and she fed hers through it, and we walked out of the house.

I had arranged a car for the evening, and I could tell she was impressed with what lengths I had gone to for our date.

"This is all very special," she said.

I laughed, "The last first date I went on was to a MacDonalds."

"As long as I'm out with you, I would have been happy with MacDonalds too," she replied, and squeezed my arm tighter.

It was my turn to give a coy smile.

After we had ordered our food, I decided to get serious with her.

"Jane, here is my problem," I said, looking directly at her, "A week ago you were happy as Josh, just a boy in a dress."

She looked nervous as I continued, "I am finding it hard to accept, that after a week with Debbie, you now want to transition into a woman full-time?"

Jane took a sip of her wine, and said, "It is crazy I know, but when I first started dressing up, even when you let me in your home, I was holding back."

"Holding back?" I asked.

"Yes, part of me was scared I would not be accepted as the real me," She carried on, "Debbie helped unlock the real girl within, and the look on your face when she presented me to you gave me hope."

I frowned, "Hope for what?"

She looked away, not meeting my gaze, "Hope that you could fully accept me as a woman, and most of all love me the way I love you."

"You love me, fuck," was all I could muster.

Jane started to well up, "I know it is too much to ask, but over the last few weeks I have been staying with you, your kindness and acceptance, I could not help but fall in love with you."

"Jane, I do care for you," I said, taking her hand in mine, "But I'm not sure I can love you that way."

"You don't find me attractive?" she asked.

"Shit, you are the most beautiful girl I know," I said to her pleading eyes, "That being said, I can't shake that you are still a man underneath the gorgeous exterior, and I'm not sure I can handle a partner with a cock."

"So, if I was born a girl, you would love me?" she asked sounding a little annoyed.

"No," I snapped back, "There is more to love than what we have, your age bothers me, and I cannot help but feel you are only infatuated with me."

Her fist came down on the table, drawing a few glances from the other diners, "I do love you, do not treat me like a love-struck teenager."

My heart went out to her, I just wanted to swop her up in my arms and protect her. I did not feel romantic love towards her, more of a paternal love.

I gave her a smile, "Let's start again."

Jane relaxed, and the waitress arrived with our food.

For the next hour we had a relaxed and free flowing conversation. After a while, I forgot I was chatting to Josh in drag, and got to know the smart and intelligent you woman that Jane was.

When we returned home, there was an awkward moment as we said goodnight. I leaned in and kissed her on the cheek.

Later when I laid in my bed, my brain would not let me sleep. I hated to admit that my feelings were starting to change towards her, but I had trouble shaking the thought that she had a cock between her legs. It wasn't until the wee hours of the morning when I finally managed to get off to sleep.

I was awoken by the sunlight that suddenly rushed through the window as the curtains were pulled open.

"Good morning, sir," Jane said cheerfully.

I tried to cover myself, as my morning wood was rock hard, not helped that Jane was wearing her waitress uniform.

"Ah, Good morning," I replied when the fog of sleep started to clear.

Jane handed me a cup of coffee, "Sorry to wake you sir, but a Mr Jennings called from your office, he needs to talk to you ASAP."

Bob Jennings was one of the directors I appointed when I decided to step back from my company.

"OK, I will shower then come down for breakfast." I told her.

"Sure thing Sir," she said before leaving my room.

My eyes lingered on her perfect arse, wonderfully shown off by the tight pencil skirt.

I shook my head out of its daze, hit the shower before dressing in a light blue shirt, and dark grey trousers.

Debbie was also in the kitchen when I entered.

"Sounds like you two had a nice time last night," she said as I sat down at the table.

"Yes, Jane is a very sweet young lady," I replied, sipping my orange juice.

Jane placed a plate of food in front of me, "Thank you Sir, I had a wonderful time."

"Perhaps a second date is on the cards?" Debbie fished.

I thought fuck it, "Yes, I think I'd like to take her out again."

"I'll start picking a hat out for the wedding," Debbie teased.

I hated to admit, but I was starting to see Jane in a different light after our date. Was the age gap to big, I was definitely coming around to a romantic relationship with her.

I pushed those thoughts out of my head, as I went to my office to call Bob.

For the next few hours, I was busy in my office dealing with a difficult client. I was bushed when I finally emerged, I had managed to pacify him.

I went into the lounge and Debbie was sat watching TV.

I slumped down onto one of the couches.

Debbie paused her program and turned to me, "I'm leaving tomorrow."

"Wait, what?" I said processing her words.

"I have taught Jane all she needs to know for now," she answered, "I will still take care of her transition, but I do not need to coach her everyday anymore."

I nodded, "Where are you off to?"

"New York, I have a client there that is getting ready for the final stage of transition," she said, before putting her program back on.

I went off, changed in to my workout clothes and hit the home gym. After I showered and changed into a pair of jeans and a t-shirt.

Jane served Debbie and I dinner, and dutifully waited for us to finish and leave, before eating herself.

Debbie and I went into the lounge, and I poured us both a brandy.

"I have to say my feelings for her are changing," I said to her.

"I'm still sensing a but?" she replied.

I rolled the glass around in my hands, as I pondered my response, "I'm not sure I can get round her having a dick."

Debbie shook her head, "Have you ever pegged a girl in the arse?"

"Yes," I replied, "With my ex."

"Did you like it?" she asked.

"It was great, what is your point?" I asked her.

She took a sip of her brandy, "My point is you can have that pleasure with Jane, and if one day she goes all the way she too will have a functional vagina."

We sat in silence as I mulled over her statement.

"Let me send you a link to a little film that might help you," Debbie said, downing the last of her brandy and leaving.

A couple of minutes later my phone pinged, there was a message from Debbie with a link.

I clicked on the link and a film started to play, it looked old, maybe from the 90's by the grainy quality.

As the film played out, it was set in a classroom with several girls all prim and proper in their blue and gold school uniforms. My cock instantly tented in my jeans.

All but one girl left, and she approached the teacher. She said something about getting her grades up, and then proceeded to seduce him.

My eyes nearly fell out of my head when the teacher pulled her white panties down and a 6-inch cock fell out.

I subconsciously had pulled my cock out and started to jerk off, as the teacher pegged the tranny schoolgirl.

I came when she did, but I kept rubbing until he unloaded his jism on her face.

I closed the video and started to stuff my cock away, I looked over towards the door and Jane was standing there watching me. She had lust in her eyes, and when I noticed her, she ran away.

I had a feeling my life was going to get even more complicated than it already was.