This is the second part of a 4 part story from my short series entitled 'Purely a Business Arrangement'.
Copyright - Lorna Elizabeth Black 2004

None of this work may be distributed as original by any other person or group. Permission is given to redistribute this work in its entirety and any credit is given to me as the original author.
Any resemblance between characters in this work and persons living or dead is purely coincidental.

Be also advised, some of the storylines contain adult themes including sex. If you are underage or if this offends, then please go elsewhere.

 

Purely a Business Arrangement – Anna

by

Lorna Elizabeth Black

part 2

 

The tale continues, where the business flourishes and so do relationships.

The story so far-

Whether by some action instigated by myself or some plan on behalf of my landlady, I have been persuaded to completely dress in women's clothes. I can honestly say that I enjoyed the experience. My landlady, Janet, then made the proposal that I could rent a spare room as business premises but there was a catch. She said that because of criticism from her relatives about taking in a male lodger, let alone renting a room as business premises to a man, she had come up with the plan that should I now present myself as female, things could be a lot easier. Purely a business arrangement, as she put it.

Now read on.

 

Chapter 3 – Quandaries

 

Janet and I had a few drinks; we talked a little, mainly about her family and the difficulties she was put under by taking in a lodger, me. She never made any further reference to the way I looked or called me by the name Anna, this name she had 'christened' me with. I felt she was allowing me to become comfortable in this new role, this female role. But a decision would have to be made and I really was in a quandary.

What should I do?

Should I say yes or no?

Should I say yes and submit without any fight?

Am I Andrew and not Anna?

Am I not a man?

Should I say no and say I don't want to be dressed like this when in reality I wasn't sure?

I had just been given the offer of business premises, which I desperately needed. What I had been asked to do could be considered a small sacrifice to make. So perhaps I should be pragmatic and take the offer. Really, I was in no position to argue. After all I had allowed myself to get into this situation. I was the only one wearing a short red skirt, white blouse, black stockings, high-heeled shoes and lacy underwear. Even Janet wasn't wearing a skirt. She had on trousers and a shirt.

 

Curiosity was now taking over. If I were to accept this offer, would I be expected to be dressed as a woman all the time or was it only for short periods of time, just for appearances sake? Before I could even ask any questions, Janet said,

"Rather than pressure you into a decision now, why don't you sleep on it and you can give me your decision in the morning."

"That's probably a good idea," I replied.

"Oh, and by the way, make sure you remove all your makeup before you get into bed."

Janet kissed me on the cheek and said, "Goodnight."

This was also a first. In all the time I had stayed with Janet, there had never been any physical contact between us. It was a small gesture, but nevertheless it was still a first.

 

Anyway, I made my way to my room and finding I was actually getting quite used to walking in high-heeled shoes. I opened the door to my room; put the light on to see lying on my bed a beautiful long white satin nightdress and on the chair at the side of the bed a matching negligee. There was a note lying on top of the nightdress. It read,

Why don't you try it on and see if it fits?

Wear it to sleep in, if you want to.

Janet.

 

I removed my makeup and my clothes, but I left on my bra and wig and yes, I wore the nightdress in bed that night just to see how it felt, you understand.

 

In the morning, when I awoke, rather than spoil the illusion I had created for myself, I went to the bathroom and sat to relieve myself. I had a very close shave, not trying to look at myself and see someone in a satin nightdress and wig having a shave. After cleaning my teeth, I made my way back to my room, brushed my hair, or should I say my wig, put on the negligee and the women's slippers that seemed to have appeared by my bed and went downstairs for breakfast. As I entered the kitchen, Janet saw me and said,

"I think I know what you answer is. It's yes, isn't it?"

I nodded my head in reply.

"Good," she said. "However I think we've got some planning to do."

"What do you mean?"

"Well, you know how nosey the neighbours are around here."

"Are they?"

"Yes, very nosey. I think they would notice if my lodger suddenly changed sex."

"Isn't that what's going to happen anyway?"

"Yes, but it's got to be seen, for the neighbours benefit, that one person leaves and another arrives."

"Well, what do we do about it?"

"For a start, I want you to resume your normal daily activity as a man."

That statement actually threw me for a moment. I actually felt disappointment at the thought of becoming a man again. Reality then kicked in, I knew, of course that I had to resume my daily life as that man.

"We'll talk about this tonight when you come home from work."

The rest of the time we sat and ate our breakfast in almost total silence. When finished, I went upstairs to change back into the person I had been all these years instead of the person I had become last night.

 

The day was really dragging. I just couldn't concentrate on work. The thing on my mind was the thought of being in women's clothes again. It just would not escape from my mind. So what I did do for most of that day was to surf the internet for cross dressing and transgender sights. These sights were a real eye opener, showing me many new things.

 

When I eventually returned from work, Janet greeted me with a kiss on the cheek and said,

"Why don't you go and get changed. I've laid some things out for you on your bed."

Strange thoughts went through my mind.

Was this reality?

Why was Janet really doing this?

Did she have other plans for me that I knew nothing about?

Am I to become female full time?

All I could say to Janet was, "Thank you" and rushed up stairs as quick as possible, but not so quick as to give the impression I was desperate.

On the bed were a bra, panties and suspender belt all in black, all very lacy, all very sexy. There was a black full slip with lots of lace trim. A dress lay there which was blue in colour. It had a mandarin style collar and the material looked as if it was satin. It was absolutely gorgeous to the touch, so cool, smooth and sensual. The shoes were black sandals with about a three-inch heel. The wig I wore the previous evening was there as well. There was also a box which I picked up and removed the lid. Inside was a pair of silicon breastforms and some form of adhesive, presumably to fix them in position. There was a leaflet in the box as well. I lifted it out and quickly read it. It was indeed the instructions on the proper way to position and fix the breastforms. It looks like I'm going to have a decent sized bust, I thought. On top of the clothes was another of Janet's notes. It read,

 

Anna

I thought you might like to try on these things tonight.

Give me a shout if you want any help with your makeup.

Love Janet

 

I turned round and looked at the dressing table in my room. It had acquired the makeup items that were used on me last night.

Of course, Janet had assumed I would want to dress in women's clothes again and in reality, this is what I had been wishing for all day, perhaps this is what I had been wishing for all my life.

 

 

Chapter 4 – Dressing for Dinner

 

I couldn't wait to change. So it was off with the clothes I wore all day and into 'my' negligee which was where I had left it in the morning. Next, the bathroom for a shower and a very close shave. If I was going to wear these pretty clothes, then the appropriate preparations were required. I was going to look as feminine as possible. My visit to the bathroom completed, it was back to my room to bring Anna back to life.

 

My wig was first to give me at least some illusion of femininity to begin with. Next it was to slip off my negligee and on with my panties. I was hoping the thing between my legs wasn't going to cause a problem. These panties were not going to allow it, however. These were control panties, firm control panties. My suspender belt was next but I struggled with my suspender belt straps pushing them through my panties. A girl needs to go to the toilet every so often and there is no point in making things more difficult then they need be. Having eventually succeeded with my suspender straps, it was the stockings next. They were the same ones as the previous night, black with a lace top and again they felt absolutely fantastic when I got them on. Now breastforms are things I had heard of, certainly after surfing the Internet earlier, but obviously never worn up to now that was, so I thought I should study the instructions carefully. But, I was too excited at the thought of wearing them, I just glanced over the instructions. I did notice that they could be worn with or without the special adhesive supplied in the box. At first I wasn't sure if I was going to use the adhesive, but I thought,

"In for a penny, in for a pound."

So, I applied the necessary amount of adhesive and placed each breast form in position in accordance with the instructions. I put my bra on and allowed my newly acquired breasts to nestle into the cups. I looked at myself in the mirror at this point and, even without makeup, I thought I was looking good. But it was makeup next and because I couldn't see what Janet was doing when she applied my makeup the previous evening, I realised I would need help. So I put on my slip followed by my negligee and finally my slippers and made my way downstairs to find Janet. When she saw me, she jokingly said,

"Who are you? I thought there was a man staying here, not an attractive woman who's going around the house in her lingerie."

I chose to ignore that remark.

"Will you help me with my makeup, please?"

"Of course I will, Anna dear. Oh, by the way, are you wearing the breastforms?"

"Yes."

"How do they feel?"

"Nice."

"You didn't use the adhesive, did you?"

"Yes, I thought that what it was there for?"

"Did you read all the instructions?"

"I quickly glanced over them."

"So, you didn't read about the special adhesive remover to take them off?"

"No, I didn't see that."

"Well, let's put it this way you're going to be stuck with breasts for a while, if you'll pardon the pun,"

"Why?"

"Because there is no adhesive remover."

"Oh well, so be it."

 

So we both went upstairs to my room. This time I paid particular attention to what Janet was doing. Anyway Janet let me see the result of each stage of my makeup being applied and how to apply it. Last night was all a bit of a blur and my makeup was applied without me seeing it until it was all on. If I thought I looked fairly good without makeup, with makeup, it was a different story. Even if I said it myself, I looked good. I looked all feminine and girly and I liked what I saw.

Have I been missing out in this up to now?

It certainly felt like that.

Should I have been born female?

I was beginning to think I should have.

No time to stand and stare, I had to finish dressing. Janet stayed so that she could zip up my dress. I think it was the tightness of the skirt of the dress that got to me. I realised that my movements were restricted and I could now only take small steps. This appealed to me. Janet noticed I liked this idea and said,

"You like that dress, don't you? Is it the colour or style that appeals?"

"Yes, yes and yes."

"I now see the type of things you like to wear. I think you would enjoy wearing a corset."

"Yes, I think I would like to try."

Lastly it was the shoes, high heeled shoes and as soon as I had the straps fastened on each, I stood up and looked at myself in the mirror. Under my breath, I said,

"Yes."

I was ready. I was ready to be Anna.

Janet broke my flight of fancy by saying,

"Come Anna dear, dinner is almost ready."

"Er, right," I replied.

This time we didn't have dinner in our usual places in the kitchen. Tonight dinner was served in the dining room with candles and wine. In fact, you could say a romantic meal for two.

That is what it was and the way that Janet acted throughout was to treat me like a lady. It crossed my mind what might happen afterwards and I thought I would just go with the flow. After all, I had come this far.

 

 

Chapter 5 – No Quandaries

 

Next morning as I awoke, next to Janet, I remembered with a smile what had gone before. There was I lying next to Janet, both in beautiful nightdresses having consummated our relationship, here in this bed, the night before. We had now become lovers, lesbian lovers. Now I had to ask myself some questions.

Should I become Anna full time?

Should I become Anna full time from this precise moment? This might have to be the case purely from a practical view. I had, after all, stuck my breastforms on and had no adhesive removal solution.

Could I become Anna part time and because of my breasts, wear baggy clothing while I was not Anna?

It didn't me long to formulate my answer. After what happened last night and what I was feeling at that precise moment, I wanted to become Anna now, this instant, permanently. Janet was still sleeping, so I crept quietly out of the bed and made my way to the bathroom. Regardless of what happened last night and how I felt about my sexuality, I was still a man and unfortunately things like beard growth still occurs. So my idea was to have a shave before Janet woke, so at least I could present myself without a five o'clock shadow. So I followed the routine I created for myself the previous morning by hanging on to as much of my female side while I did the necessary to keep that illusion. Once done, I crept back into bed, Janet stirred, turned and said,

"Good morning Anna dear."

"Good morning dearest Janet and thank you again."

"What for?"

"You know what for."

"I, I mean you just found the woman inside you. I just helped you along a bit."

"I know."

Janet stretched over and gave me a kiss.

 

At breakfast, Janet said,

"We have to make plans from where we go on from here."

"Yes, I know."

 

End of part 2

  

  

  

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