Copyright - Lorna Elizabeth Black 2002

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.

A man is guided into a new life by two influential women.

 

Jane

by

Lorna Elizabeth Black

 

Chapter 1

New Beginning

 

Two years ago, I was, to my mind, in a bad way. My marriage had just ended in divorce and I had lost my job through redundancy about the same time. So all in all, I was, what you might say, in a fairly desperate state at this time.

However things were beginning to improve slightly, I did manage to get another job as a clerk in an accountant's office in another town. Although I had spent most of working career in the insurance industry, this was the only job available to me at this time and frankly, I was glad of just being able to get another job.

So, here I was, in the situation of starting a new job in a strange town and desperately needing somewhere to stay. However, my new employer gave me address of a suitable house with a room to rent. I gave the phone number a ring and a female voice at the other end answered. I queried about the room, which was available, and was invited round to view although I did sense a degree of reluctance on her part.

 

I arrived at this fairly large Victorian, terraced, house, in a very quiet, leafy street, and rang the doorbell. After a few seconds a woman came to the door and I introduced myself as John the person who had called earlier on the telephone. She in turn introduced herself as Barbara and invited me inside to view the room.

I was shown to the room, which turned out to be perfect for me in my present situation and decided to take it there and then. The reluctance on the part of Barbara I had sensed when I originally phoned seemed to have disappeared. I also discovered that Barbara lived on her own, although she had a tenant before me.

Now Barbara was a divorcee, about five years or so older than myself and to me, she was attractive with a nice rounded figure. So that made two divorcees, about to live in the same house, but for me, and at this particular time in my life, I was feeling quite low.

 

So a few days later, I moved in with all my bits and pieces, the remnants of my recently broken marriage and tried to re-start my life.

 

 

Chapter 2

Dinner for Two

 

A month had passed and I found myself getting more and more attracted to Barbara, although I had done absolutely nothing to express these feelings. These were feelings I either thought, or used my hand to dampen them in the privacy of my room. I felt that Barbara may have had some feelings for me, but again, if she had, she was keeping them to herself.

Anyway it was Friday night and I had finished work for the week, in fact on this Friday night, not only did I have the weekend off, I also had the following week off as holidays. I had no particular plans for that coming week, until I told Barbara. She suggested that we could perhaps spend some time in each other's company, if as she put it, 'If things work out.' This sounded like an excellent suggestion and so now I was looking forward to the coming week, although I had no real idea what she meant about things working out. I took it to mean whether she could get time off from her part time job.

 

When I arrived back at the house on this particular Friday, and as soon as I had closed the front door behind me, Barbara called to me to come through to the dining room. What I saw was the dining table set for a meal, for two and I immediately thought that Barbara was expecting company. She was also dressed beautifully in a rather attractive black cocktail dress, this actually being the first time in all the time I had stayed here; I had seen Barbara in anything else but trousers. She said,

"Would you care to join me for dinner?"

I was really taken aback, because although we had dined together, it was always in the kitchen, never in the setting before my eyes.

Pulling myself together, I replied,

"I thought you were expecting company and were wanting me to make myself scarce or something."

"No, I don't want you to make yourself scarce because the only company I'm expecting is you. So will you join me for dinner?"

I was honestly taken aback. I know I was looking forward to the coming week but from what I could see before me, it looked like it could be better than I expected.

"Thank you, I would be delighted. But first I need to shower and change."

"Dinner will be ready in about an hour," she answered.

So that's just what I did, I showered, changed and descended the stairs to my surprise dinner date.

 

Barbara had really gone to town on the meal. For starters there was melon cocktail that was followed by coq au vin, new potatoes, fresh runner beans, salad and crusty bread and to finish, fresh fruit salad. On top of this there were two bottles of a rather nice red wine to wash it all down.

 

 

Chapter 3

Surprise Desserts

 

With dinner over, I helped Barbara load the dishwasher, and with the remains of the second bottle of wine and our glasses in her hands, she invited me through to the lounge and asked me to sit beside her on the settee. This of course, I was only too happy to do.

We had drunk a lot of wine that evening which certainly loosened the inhibitions, so much so that I thought the time might be right to make a pass and see where that took us. I did try but all she said was, "Perhaps later." Instead she seemed more interested in my background and the strangest thing, she asked me when I had gone bald. I really thought this was weird, and frankly a bit off putting, but she kept asking about it and other things like, "Would you like to have your hair restored." I replied that of course I would, but then the most bizarre thing happened, she said,

"How about now?"

"What do you mean, now?" I replied rather puzzled. "How about seeing how you would look with a full head of hair now?" she went on.

Really, I was in no mood to argue or protest. The wine had taken effect and to be honest I couldn't really care less. So I replied, not knowing what she had in mind,

"If you like."

So she got up from the settee and went upstairs. A few seconds later she returned with a box and a hairbrush. Opening the box revealed a wig with the hair the same colour as my own. Barbara said,

"Here we are. Let's see how you look in this."

The wig was all very well but to me, it didn't look like a wig for a man, this looked more like a wig for a woman. Before I could say anything it was on my head and was being brushed into place. I was a little surprised at all this, but Barbara just stepped back and looked and said,

"Yes, just as I thought, that really suits you."

Of course, I hadn't seen myself at this point, so Barbara said,

"Why don't you come upstairs and have a look at yourself in the mirror?"

So, upstairs we went, me with my newly acquired head of hair, and I was invited into Barbara's bedroom, which was a first. I was guided towards the dressing table mirror and when I saw myself, I was shocked. Instead of seeing myself as I was some ten years ago, as I might of thought I was going to see, what I was seeing was someone who looked decidedly female. Barbara said,

"So, what do you think?"

"It's a bit girly, isn't it?" were the first words that came into my head.

"Yes, but that's just the point, putting on that wig changes you completely."

"But it makes me look like a woman in man's clothes."

"That may be so, but let me ask you this question?"

"Go on."

"When you look at yourself in the mirror as a man, do you like what you see?"

"Frankly, no."

"Now when you look in the mirror, do you like what you see?"

"I don't know, this is all a bit weird."

"Let me put it another way. From what you are seeing now, do you think you look you look better as a man or a woman?"

"Putting it that way, and if I have to choose, I suppose I would have to admit that, I actually look better as a woman."

"Good, that's what I think as well which leads me on to my next question. Would you like to go a bit further?"

"What do you mean, go a bit further?"

"You know, make you look even more like a woman."

"What are you getting at?"

"You know, maybe put on some make-up, try on a dress, things like that."

"Why?"

"Because I think you might enjoy it."

"Will I?"

"I think you will. Anyway, you never know what might happen later on."

To me this was Barbara saying that she would be receptive to any further moves on my part. So as far as I was concerned, I would go along with what she had planned and anyway, for some reason, I was quite enjoying what was unfolding. I replied,

"OK I'm all yours."

"Fine, the first thing I'm going to ask you to do, I hope you don't mind, is to shave your legs, chest, arms and underarms."

"Why all that? Isn't that all a bit drastic just to prove a point?"

"Well, not really. For one thing, I just don't like hairy bodies and for another, I think you'll look better and like I said, you never know what might happen later."

Again there was that invitation and I just couldn't ignore it. So what did I do? I did as she asked. I went to the bathroom and using copious amounts of shaving foam, I literally covered my body and shaved of every hair I could see. I still had the wig on, and every time I looked at myself in the mirror, the strangest feeling came over me almost as if I was seeing another side of me, a female side. During my hair removal session, I did leave a triangle of hair around my now constantly erect penis. Even if in my own mind, I wasn't absolutely sure what was going on, the thing between my legs certainly seemed to know. For some reason, just after I had finished my hair removal, I put one hand in front of my cock, to hide it, and my other arm over my chest, as if I was shielding my breasts and looked at myself in the bathroom mirror. What I saw rather shocked me, because to all intents and purposes, at that point, I definitely looked female.

 

Before I had gone to the bathroom, Barbara had said that when I had finished, I should put on the robe hanging on the hook in the bathroom and I should wear nothing underneath. So that's just what I did. I put on Barbara's long silk dressing gown and tied it at the front and all that was underneath was my extremely rampant cock.

 

Barbara heard me as I emerged from the bathroom and beckoned me to come back into her bedroom. I was invited to sit down at the dressing table and now in my present state, wearing a woman's dressing gown and seeing myself in the mirror, I realised I did now look like a woman. The real reason I was asked to sit down at the dressing table was to allow Barbara to apply some make-up to my face. I was still questioning in my mind, why I was doing this, but every time I did, something was telling me just to submit to Barbara's wishes, so that's what I did.

I let Barbara pluck my eyebrows, which was extremely painful.

I let Barbara apply liquid foundation over my face to hide any semblance of beard growth.

I let Barbara apply eye shadow on my eyelids and mascara on my eyelashes.

I let Barbara apply blusher to my cheeks.

I let Barbara apply bright red lipstick to my lips.

And finally, I let Barbara apply some very expensive perfume to my wrists and neck.

It was at this point I saw myself, still in the robe and frankly, I had great difficulty in recognising myself. What I was seeing was a woman reflected in the mirror.

Barbara looked and pondered and finally said,

"Yes, that looks nice, don't you think so?"

"I don't know what to think. I'm lost for words."

"Never mind, shall we carry on?"

"Why not, I've gone this far."

So carry on we did.

The first thing was the application of bright red nail varnish to each and every nail, including my toenails.

The first item of clothing was a pair of white control panties with a pretty lace trim down the sides. For modesty, I turned my back to Barbara and slipped them on underneath my robe, notice, I was now referring to my robe. They did tame my rampant cock and I'm sure that's why I was given them to wear. I was asked to take off my robe and sit down. Barbara guided my arms into a white Wonderbra, clipped it at the back and with her hands from above my shoulders, pulled the fleshy part of my chest into the cups of the bra to create a small but noticeable bust. I was asked now to stand up and I saw myself in the mirror. My feminisation by my landlady was being taken further and further and I didn't seem to be resisting and I kept asking myself, why this was so and every time my answer was, why not.

 

A white suspender belt was clipped into place and Barbara instructed me into how the suspender straps should lie inside my panties. This I did, noticing that as I guided them through, my cock was still as rampant as ever, but being tamed in its satin and Lycra prison. A pair of sheer black, lace topped, stockings were removed from their packaging and with me sitting down once more, Barbara showed me how to roll them up my legs and clip them to my suspenders. I stood up once more as Barbara put a white, full length, slip over my head, through my arms and let it fall down over my body. That was the point when all my questioning why I was doing this finally disappeared. I think it was the feeling of that slip; soft and silken, falling over my body convinced me that I was doing the right thing. Barbara noticed my reaction as the slip fell over my body and just smiled. The dress that Barbara had decided I was to wear was red in colour, in a satin type material with a Chinese Mandarin type collar. It had slits up either side and was zipped up the back. I had one thought that when I'm in this dress, there was no way I was going to get it off again without Barbara's help. So, what did I do? I stepped into the dress, put my arms through the sleeves and Barbara zipped it up the back. To finish off my transformation, Barbara clipped a pair of earrings into place and produced a pair of strappy, black, high heeled, shoes, which seemed to fit my feet like a glove. I wondered why this was, because it certainly looked as if I had bigger feet than she. As well as that, the clothes I was now wearing fitted me and fitted me well. They certainly would not have fitted Barbara, as she must have been about two sizes smaller than me. I stood up, the new me a bit unsteady in my high heels but full of confidence and seeing myself in the full length mirror.

"How do you feel?" Barbara queried.

"How do I feel?" I thought to myself.

I certainly know what I feel.

I feel hair falling down over my face for the first time in ten years.

I feel the earrings dangling from my ears.

I feel these stockings I am wearing, soft and cool, encasing my newly, shaved legs in nylon and Lycra.

I feel a complete sense of freedom wearing this dress even with the restraints round my cock and chest.

I feel female from smelling the perfume I am wearing.

That's what I feel and how does this make me feel?

Well, I feel bloody marvellous, but all I said to Barbara was,

"It's OK"

"Is that all? Is it only OK? Because to me you look super."

What should I say, should I admit what I was really feeling or carry on being non- committal. I could see the disappointment when I said it was OK, so I decided to be truthful and replied,

"Well, it's actually more than OK, it's good, it's very good, in fact it's bloody marvellous."

"Thank you, and you look bloody marvellous as well."

"What do we do now?" I said.

"What we do is we have a drink together to welcome the new you and give you a new name."

"Do I need a new name?"

"Oh yes, you certainly don't look like a John now, do you? What about Jane?"

"Yes, why not."

So from thinking that I was going to have a boring Friday night, all of a sudden it turned into something I would never have expected in a thousand years.

Barbara said,

"Now that you've become Jane and since you've got all next week off, what about staying as Jane for the next week? We could do things together, go out, go shopping, things like that."

"I would like that, I think."

I wondered if this is what Barbara really meant when she said, "If things work out."

 

The rest of the evening was spent chatting about what I would be expected to do as Jane. Things like, what I should carry in a handbag if we were out and even things like visiting the ladies toilets. Of course things like this had all been a mystery to me up to now. We even spent some time looking through a mail order catalogue at the women's clothes with Barbara suggesting things that might suit me.

 

 

Chapter 4

Bedtime

 

It was getting late and Barbara suggested it was near bedtime. I suppose by this time, the idea of me making a pass at Barbara had gone, now that so much had changed in the past few hours. So, in some ways, I would have been quite happy just to go to my own room, and perhaps become Jane in the morning. Barbara, however, had other ideas. She said,

"I would like you to spend the night with me, with me in my bed."

I had no idea what she was expecting of me, whether she wanted me to revert to John and have sex with her as man and woman or, whether she wanted me to stay as Jane, perhaps just to even keep her company. There was one thing though, there was no way I was going to turn her down. So I decided I would accept and go along with whatever the night had in store. I replied,

"Thank you."

So, between us, we switched off the lights in the other rooms and made sure the house was secure before we climbed the stairs to bed. To be honest, when I entered Barbara's bedroom, this being the umpteenth time in this particular evening, I just stood there not knowing what to do. Barbara, meantime, had gone to one of the drawers in her dressing table and took out a beautiful, white, satin nightdress and matching negligee. She turned to me and said,

"For you Jane."

So there it was, she wanted me to stay as Jane and presumably that would be as far as things would go. Barbara then suggested that I take off my dress, slip, stockings and suspenders, but leave my bra and panties on and put my nightdress on top. This I did as Barbara unzipped my dress and showed me how to take off my make-up. Even without make-up, wearing this nightdress and negligee, I still looked more female than male, which now I was, of course, revelling in. While all this was going on, Barbara had removed her clothes allowing me to see her naked body for the first time. She, too, had been wearing stockings and suspenders under her dress, just like me. She seemed completely unabashed at me seeing her naked. Perhaps she now perceived she was in the company of another female and didn't have to bother how much she showed. Her nightwear was not like mine; she put on a pair of black silk pyjamas. I was still standing there in my nightdress and negligee, when Barbara came over to me and slipped off my negligee. She put her arms around me and gave me a big kiss, full on the mouth. This was the first real physical contact Barbara and I had since I moved in. Drawing back from the kiss, she said softly,

"Jane, it's time to lose your virginity."

I'm not going to say what happened that night; I leave it up to the imagination. I will say this. I experienced things that I could never have imagined as a man because I was taken, sexually, as a woman. It was incredible.

 

 

Chapter 5

Good Morning Jane

 

Morning came and I still couldn't take in all that had happened the previous evening and in bed that night. However I just needed to look at myself to see that it was reality, because there I was dressed in a beautiful satin nightdress with a bra and panties on underneath. Barbara was still asleep, so I decided I would rise and make myself more presentable because regardless of the beautiful feminine clothing I was wearing, my beard still grew. I knew that this was the first thing I had to see about. So that is just what I did, I slipped on my negligee and put on the fluffy slippers that seemed to have appeared at my side of the bed, combed my new hair, went to the bathroom and had a very close shave. When that was done to my satisfaction, I went down stairs to prepare breakfast. This was the least I could do. With coffee, croissants and orange juice all on a tray, I climbed the stairs to the bedroom to be greeted by Barbara just stirring from sleep. She opened her eyes and seeing me there, just said,

"Good morning Jane, this is nice."

I replied,

"It's to thank you for last night, for me, for Jane."

"Don't mention it. I take it then you want to carry on being Jane then?"

"If you don't mind?"

"Of course I don't mind, but if you are going to stay as Jane then there are things you will need to get, and get today."

"What things?"

"Underwear, like bras, panties, stockings and the like."

"Do I?"

"Oh, yes. If you're going to be Jane, then there are lots of things to get. I'll tell you what, when we've finished breakfast, we'll get dressed and go to town to do some shopping."

"Is that such a good idea? After all I am a man dressed in woman's clothes."

"You'll get away with. Look at yourself, you make a really nice woman."

"I don't know how I should take that."

"Take it as a compliment, my dear Jane."

It was time to get ready. We both showered and Barbara suggested I put on my negligee while I re-applied my make-up. This time I did most of it myself under Barbara's guidance and again, I was seeing my female side dominating when I looked at myself in the mirror.

 

I was really getting into my new role as Jane and I felt there was no going back, although it was still early days. My next thought was what I was going to wear. I said to Barbara,

"I haven't a thing to wear."

Barbara replied,

"Well if I'd never heard it with my own ears, I would never have believed it. What you just said made you sound as if you had always been a woman."

"Well I don't have anything suitable to wear. I can hardly go out in the dress I was wearing last night. Can I?"

"No, I suppose you're right. First you'll need clean panties. I'll lend you another pair of mine but after today you'll have to wear your own. You can wear the bra, suspender belt, stockings and slip you had on last night. Now for outerwear. Let's see what I've got in my wardrobe."

Barbara opened her wardrobe, pondered for a few moments, had a rummage about all the clothes that were hanging there and finally produced a fairly short, straight black skirt, a cream satin blouse and the black jacket, to match the skirt."

"Try these on for size?" handing them to me.

By this time I had put on the clean pair of control panties, my bra, suspender belt, stockings and slip. The blouse, skirt and jacket fitted me perfectly, which again mystified me, like the previous evening about Barbara being about two sizes smaller than me. I said to her,

"These clothes, which fit me perfectly, would surely be far too big for you?"

"I'll tell you all about it sometime."

 

I finished dressing. I put on my shoes and my earrings, Barbara gave me a bracelet to wear and handed me a shoulder bag."

"You'll need this," she said.

Barbara showed me what things I should carry in my new bag. Things like lipstick, powder, comb, tissues and a tampon. She even gave me a purse to carry my money.

"Why the tampon?" I asked.

"A girl has to ready for any eventuality," was the reply I got.

"Oh," I said.

"Ready?" Barbara said.

"As ready as I'm going to be," I replied.

"Right, let's get going."

"Are you sure I'll get away with it?" as doubts began creeping back into my mind.

"Of course you will. Just act calmly and coolly and no one will ever notice."

Well it was too late to change my mind now, with our bags on our shoulders, Barbara opened the front door and I stepped outside for the first time as Jane. Because of the seclusion of the house, I wasn't too worried about anyone seeing me at this point. The thing that did get me when I stepped outside was feeling of the wind blowing up my skirt and around the bare flesh of my stocking tops. Barbara saw my reaction to this, smiled and said,

"You'll get used to it."

"What's there to get used to, it's nice."

And it was nice, it was lovely.

Anyway we got into Barbara's car, me in the passenger seat, not without some difficulty wearing a straight skirt, and headed off to town for my first shopping expedition as Jane. This was going to be a trip to departments in shops I had never ventured before, because the first things I needed, and needed urgently was lingerie and a lot of it, because this is what I was now wearing and wanted to wear from now on.

 

Chapter 6

Shopping

 

We arrived at a multi-storey car park some fifteen minutes later and again I found a bit of difficulty getting out of the car in the skirt I was wearing. I struggled and if anyone had passed just at that moment they would have got an eyeful of stocking tops and bare thighs. Anyway I got to my feet and straightened my skirt, put my bag on my shoulder, and together with Barbara, we headed for the shops.

 

The first department store we entered, Barbara literally dragged me to the lingerie department. We looked at panties of all shapes and sizes, some were plain, and some were lacy and silky.

Guess what types I bought?

Put it this way, it wasn't the plain variety. Actually, mostly they were control type panties as I still had a problem with that thing between my legs. Barbara had suggested that, as I probably would be wearing stockings and suspenders most of the time then for a change I might like to wear French knickers on occasions. So along with around a dozen pairs of control panties, in various colours, I also bought two pairs of French knickers, one pair in white and the other pair in black. As well as these I also bought a few pairs of bikini briefs in black as well as a panty girdle. Barbara said that there might be times when pantyhose were the more appropriate things to wear. So, since I was only a trainee female at this time and Barbara was the expert, I bowed to her experience.

 

That lingerie department did a roaring trade that day, for not only did I buy many pairs of panties, I bought two Wonderbras, one in black and one in white, two very lacy suspender belts and many pairs of stockings and a couple of pairs of pantyhose, mainly in black. It didn't stop there. Barbara said I needed nightdresses and slips, so that is what I bought.

I have to say that on entering the shop and making our way to the lingerie department as we did, I thought that I would have found the whole thing quite scary, because there was me, a man dressed as a woman buying women's clothes. This was not the case, I felt excited but content doing what I was doing. It actually felt I was doing the right thing.

 

 

Chapter 7

A Tale of Two Lives

 

Life now fell into a routine, by day, at the office I was John but as soon as I got behind the front door of the house, I immediately, or as quick as humanly possible, became Jane. It was usual for Barbara to lay out the clothes I would wear in the evening. I would always trust her judgement on this and it was always either, skirts and blouses or dresses. I never wore trousers again in the evenings or at weekends. Stockings and suspenders were always laid out, never pantyhose. In other words the clothes I wore in the evenings and at weekends was always as feminine as possible.

 

One evening, Barbara and I had just finished our evening meal. This particular evening I was wearing a red skirt, which came just above the knee, a cream satin blouse, black stockings and black high-heeled shoes. Barbara for her part was dressed in black trousers and a white shirt. She suddenly said,

"It really is time you let your boss at the office know."

"Know what?" I replied.

"About Jane."

"Why?"

"Because you're getting more and more frustrated about leading two lives."

 

Well my boss happened to be female, a rather formidable lady called Alison, who was head of the firm. She was about my age and also about the same height and build as me. If you like, with me as Jane then Alison and I would be the same dress size. There were two other people that worked in the office, one was Margaret a lady in her fifties who was Alison's business partner in the firm and Laura who, like myself, was a clerk.

I replied to Barbara's last statement,

"I don't think Alison would understand."

"You might be surprised."

"Do you think so?"

"Definitely. So will you do it?"

"I suppose I really would like to, but how do you tell someone, the man you have been working with would rather be female. She would likely sack me on the spot."

"Not necessarily, not if we set this up properly."

"What have you in mind?"

"Well, why don't you invite Alison round here for dinner on Saturday night and if she looks like she might be receptive to the idea, we'll break to her then. By the way does she have a partner?"

"Well if you think that might be best and as far as I know, she lives alone."

"Good, I do think it's for the best. Then you invite her tomorrow."

The next day, after much thought and much rehearsal of what I was going to say, I nervously knocked on her office door and was invited in. I did, eventually, invite her for dinner on Saturday night with Barbara and myself. I suppose I was hoping she was going to turn me down, but instead she said she would be delighted.

 

Saturday came and Barbara and I made the preparations for the evening. Barbara then suggested that we plan how we would conduct the evening. She drew up the scenario that we would follow.

1. I would answer the door as John when Alison arrived.

2. I would introduce Alison to Barbara and serve drinks for the two of them.

3. If all seemed well, I would disappear and change, meanwhile Barbara would try to prime Alison about what was to follow.

4. I would make my entrance as Jane on cue from Barbara.

To say I was nervous at this point was an understatement.

 

The time of Alison's arrival came and precisely on seven o'clock, the doorbell rang. As planned, I went to the door and opened it to Alison standing, looking tall and elegant in a blue two-piece suit. In her hands was a beautiful bunch of flowers.

"Hello Alison, come in please."

She handed me the bunch of flowers and said,

"Thank you John but you seem a little nervous."

"Well we don't do things like this very often," was the only reply I could think of.

So far so good, I thought as I took Alison through to the lounge and introduced her to Barbara as my landlady and friend. The next part of the plan was to serve drinks, which I did. Alison did wonder why I was not drinking but Barbara chipped in and said that I had to go and change. This would appear to be my cue to become Jane although I had no idea how Barbara could possibly perceive that the time was right for this. As I left the lounge all I could hear was Barbara saying,

"What lovely flowers. Thank you."

Upstairs my clothes were all waiting for me; Barbara had laid out what I was to wear. There was my Wonderbra, control panties and suspender belt, all in black. A new pair of lace topped black stockings, still in their packaging, my black high-heeled sandals, my wig and finally my red Chinese style dress, the dress I had worn on my first night as Jane. I stripped naked. There was no need these days to remove my body hair because it was never allowed to grow. I had a very close shave on my face just before Alison arrived, so it was really just a matter of changing my clothes, putting on my make-up and nail varnish. I suppose this took about twice as long as I normally would have taken partly because I was extremely nervous and I suppose I was trying to put off the inevitable confrontation for as long as possible. Anyway I was now dressed, I had my make-up on and I couldn't really put it off any longer, so slowly I went down stairs to see what fate was in store for me. I stood outside the lounge door not wanting to go in but Barbara saw me and said,

"Ah Jane, there you are. Come and meet your boss."

What could I do, I had nowhere else to go, so in I went and stood in front of Barbara and Alison. Alison looked at me intently and for about thirty seconds and said nothing. I was expecting her to burst out laughing or call me a pervert or something. But when she did eventually speak, all she said was,

"It's about time."

I immediately thought, for some strange reason, this was a comment on the time I had taken to change, so I said,

"I was as quick as I could."

"I didn't mean the time it took you to get changed. I meant the time it has taken you to admit who you are."

"Then you knew?"

"Yes I knew"

"How?"

"Let's just say I knew. The important thing really was for you to admit it to me."

"So what do I do now?"

"About what?"

"Well, me. Do I still have a job for instance?"

"Of course you do. There were changes I was about to make anyway."

"What changes?"

"Well, for a start, John doesn't have a job anymore."

"What?"

"To repeat, John doesn't have a job anymore. I don't want John back in the office ever. I want Jane to be there instead and on a permanent basis. You see, one of the changes I was about to make was that I want the firm to become female only. So what do you say?"

"Are you sure?"

"Of course I'm sure. Well is to be Jane who comes into the office on Monday?"

"Yes, of course. But may I ask you a question?"

"Yes, go ahead."

"You said you wanted the firm to become female only. What would have happened to me if I hadn't decided to go the way you now see me?"

"You would have been given the choice to stay as a female member of staff or resign."

"So even with me going through torment how I was going to tell you that I liked to wear women's clothes, you had all this planned already?"

"Not quite true."

"What do you mean?"

"Ask Barbara."

"I still don't know what you mean?"

At this point Barbara intervened and said, "Jane, I have a confession to make."

"Yes."

"Well, Alison and I have known each other for quite some time."

"And."

"Well, Alison knows about your preference for wearing women's clothes."

"So that's what you meant when you said that you knew."

"Yes."

"I suppose you had a great laugh at my expense about it all?"

Alison said, "No, you've got it all wrong. It's true that Barbara and I have known each other for a long time, which, I suppose, we should have said. However, I only learnt about you dressing in women's clothes by accident."

Barbara followed on by saying, "It was really all my fault. Actually, what happened was that Alison and I were having coffee on one of those days when you had gone to sort out something with your ex-wife, and Alison was showing me a new suit she had just bought. I just let slip that John would like that. Before I realised what I had said, Alison had questioned the fact that you would like it. By my reaction, Alison realised that I had said something that I shouldn't have and I'm afraid I admitted your preference for wearing women's clothes."

I felt, at this point, I had the upper hand, even although there I was dressed to the nines in all my feminine finery. I said,

"Well go on, I'm listening."

Alison continued,

"Don't blame Barbara, you should know I'm like when I'm trying to get information out of someone."

"True," I replied.

Alison went on,

"Believe me, when I heard I was not laughing, fascinated, yes, but certainly not laughing. When Barbara told me, I just had to find out more. She told me the type of clothes you like and how you become Jane in the evenings and at weekends. I even did some research in the local library to find out more. So, all in all, I'm now glad to meet Jane, at long last."

"Are you?"

"Definitely, look at yourself; you're now a stylish confident woman, not a rather self-conscious man that I once knew. You look good as a woman, no you look great as a woman, a woman is what you should be."

"You're not winding me up are you?"

"No I'm not." Alison retorted rather indignantly.

I was taken aback by this feeling I had just lost the upper hand I had a few minutes earlier.

Alison said,

"Then will it be Jane I see in the office on Monday morning?"

"Yes it will be Jane you will see in the office on Monday. Only one thing, though, what about Margaret and Laura?"

"They know what to expect."

This confrontation, as Jane had expected, was over. In fact it never really took place, so Jane felt "she" could now relax, because "she" realised that Jane could now be there twenty four hours a day, seven days a week.

"Just one other thing, I want you, Jane, and Barbara to come to my house next Saturday for dinner."

"Thank you," I said.

"Thank you, we would be delighted," said Barbara.

 

 

Chapter 8

The New Girl at the Office

 

Monday morning came and to be honest I was nervous about going into work as Jane for the first time. Anyway I had no option, Alison had said she didn't want to see John back in the office, she wanted Jane.

 

I rose early from bed that morning, not having slept particularly well. I left Barbara still sleeping at her side of the bed as I slipped into the bathroom. I ran my bath while I shaved my face. This was now becoming a chore I was resenting more and more, but it still had to be done and done extremely thoroughly. The shaving finished, I slipped off my nightdress and got myself into the bath. While in the bath I checked that no stray hairs had started to grow on my legs, arms or body. With my bath over, I dried myself with a large fluffy towel, put on my dressing gown and made my way back to the bedroom. Barbara had risen by the time I returned and had laid out my clothes for my first day at the office as Jane. She had chosen a white Wonderbra, matching panties and suspender belt. Along with these were a white panty girdle, full white slip, white satin blouse, black straight skirt, black stockings and black high-heeled shoes. I queried the girdle with Barbara.

She replied, "Just a bit of insurance."

I really had no idea what she meant at that time, it was later on in the day I was to realise what she actually meant.

 

At least one thing I thought, I didn't need to strip off my red nail varnish I've been wearing over the weekend and I didn't have to worry about being discovered that my toe-nails have also been varnished, which I also have been doing, and not stripping it off during the week.

 

So I got myself dressed for work, not as John in a suit, white shirt and tie but as Jane, still in a suit, but a suit consisting of a skirt and jacket, along with a white blouse, black stockings and high heels. Dressing was inevitably going to take longer each day because now I was going to have to apply full make-up before I went out the front door. This really did not concern me, as the ritual of applying my make-up was something I enjoyed anyway, part of my transformation to female form, if you like. Barbara made sure that all the necessary accessories were added like, a pair of my clip on earrings, a gold bracelet and chain and the ladies wristwatch, a present from Barbara for my last birthday. Finally a couple of squirts of my favourite perfume were added to my neck, so that at least I felt and smelt female, even if I still wasn't one.

 

Since this was my first day in the office as Jane, Barbara decided to drive me there, so leaving the house, I got into the passenger side of the car, making sure my skirt wasn't riding up showing my suspenders. On arrival, Barbara parked the car quite far from the office door, which meant I would have to walk about a hundred yards on my own. This would normally not have been a problem as I had walked along the street a number of times as Jane but always in Barbara's company. This time, I was expected to walk along the street on my own and into a building I had only ever been in as John. I knew I would have to do this and get myself from the house to the office as Jane from now on if I were expected to keep my job.

So Barbara gave me a kiss on the cheek and said, "Good luck," as I got myself out of the car. I straightened my skirt so it lay properly, put my bag on my shoulder, said goodbye to Barbara, shut the car door and started on my journey to the office. The things that still got me about being outside as Jane were,

I still thought that people were looking at me and saying to each other, that there's a man dressed as a woman. In actual fact, no one knew, because I made a good woman and I suppose no one could really give a damn, they were more interested in their own lives. No one stared, no one looked, to everyone else around, I was just another woman going off to work.

The other thing that still got me about being outside was the fact that the wind blew up underneath my skirt on to my bare thighs. I always remember the first time I went out as Jane when this happened and it felt wonderful then. It still got me now.

 

I was nervous, but I just kept going to the door of the office, opened it and entered, not sure what sort of reception awaited me there. The first person that saw me was Margaret and before I could anything, she said,

"Good morning madam, can I help you?"

What could I do? Did she know who I was and was winding me up, or had Alison not told her about me and she, genuinely, didn't know who I was? I just about turned and went back outside when I heard all this. However she continued,

"Sorry, I was only joking. Actually, welcome. Alison has told me everything. May I have a look at you?"

Again I felt she was mocking, but actually she was serious. So she looked and the only thing she said was,

"My goodness, you do look good. In fact you look better as a woman than I do."

Was this a complement from the woman who in the past would think nothing of slagging me off? It certainly sounded like one, so that's what I would take it to be. Margaret continued,

"Would you go straight into Alison's office. She wants to see you the minute you came in."

I was still nervous. Was what she said on Saturday a big joke? Now was the time to find out. I tapped on her door, from the other side there was, "Come in," so gingerly I opened the door and went in.

"Ah, Jane there you are, you're looking nice today. Will you sit down, please?"

I sat down adjusting my skirt as I did so. I got the impression from Alison's tone of voice, she had known me for ages as Jane and this was just a routine meeting. In fact it seemed to carry on just like that, with Alison giving some of the tasks that I was to carry out for the day. Finally she said,

"I'm really glad you've found yourself in Jane and just as a small welcoming gift, I would like you to accept this."

She had handed me a small box. I said, "Thank you," and opened it. Inside was a pair of expensive drop pearl earrings, for pierced ears. Before I could say anything Alison said,

"You're just about to say that your ears aren't pierced, aren't you?"

"Something like that."

"Well, we'll remedy that later on."

Come lunchtime, I was about to do what I had always done since I worked here was to go along to a local supermarket and buy a sandwich. Alison had other ideas though. She said,

"I'm going to take you out to lunch today Jane, but first I want to take you somewhere."

Well this somewhere turned out to be a jeweller's shop where, Alison took me, to have my ears pierced. She paid for everything. Now I knew why Barbara had insisted I wore my panty girdle because that feeling of vulnerability and pain of getting my ears pierced, I could feel a definite rising from between my legs. As it turned out, Barbara knew all about the ear piercing. Apparently this was another thing she and Alison had arranged.

Anyway I now had pierced ears with a pair of gold studs in them. I would not be able to wear my new earrings for about three weeks. This didn't worry me too much because I felt I had moved a further stage down the road to being a full woman, which was now my ambition in life.

Discussing this with Barbara, she realised that I would have to progress this way. For her part, she wanted me to do this because as we had become closer, she realised in herself she had fallen in love with Jane. She didn't want a man, in fact she realised she never wanted a man and that her marriage had been a sham. Barbara revealed that she was reluctant to rent me the room when I had first phoned. She was hoping for a female tenant but between feeling sorry for, and seeing me, as I should have been, she took me in. We are now lovers, yes lesbian lovers, and that's the way we both want it.

 

It was around this time, my curiosity was aroused and I asked Barbara about the clothes and shoes she produced when I first put on women's clothes. This was the fact they were obviously too big for her. What transpired was she had bought them for her then husband to put on as part of sexual experimentation. He never wore these clothes; Barbara said she could never persuade him. As she saw it, she was trying to bring out his female side and as far as he was concerned that part of him never existed. Ultimately this led to the break-up of their marriage and I suppose that is where I came in.

 

 

Chapter 9

Another Dinner Party

 

I had now spent my first week at work as Jane; actually I was now Jane full time. There were still things I had to get used to as a female but as far as Alison, Margaret and Laura were concerned, they would appear to have got used to Jane. The one thing I was still working on was my voice. It was now becoming more female. After all there was no need for me to sound like a man anymore. Laura gave me tips on how I should not allow my voice to drop in pitch at the end of a sentence but to allow the pitch to come up slightly. This surprisingly went a long way in changing my voice from sounding male to sounding female.

Before I knew it, it was Saturday and time for our return dinner date to Alison. So it was into my red Chinese style dress again, because I didn't really have anything else to wear. Not that I was complaining though because I loved that dress and anyway it was that dress that first brought out Jane in the first place. It had a very special place in my life.

So, it was into the car, Barbara drove the short distance to Alison's luxury flat on the other side of town. She rang the appropriate doorbell and after a few seconds a voice came over the intercom.

"Hello, who is it?" Alison's voice said.

"It's Barbara and Jane," Barbara replied.

There was a buzz, Barbara pushed the door open and we entered the hallway. Alison's flat was on the first floor so we just climbed the stair instead of using the lift. By the time we had got to the first floor landing, Alison was waiting for us by her front door. She smiled warmly and invited us in. This really was a beautiful flat with the best of everything inside.

I presented Alison with a bottle of red wine we had brought with us a welcoming gift. Alison thanked us and gave me a peck on the cheek.

"Dinner is nearly ready," Alison said as she showed us into the lounge. Drinks were offered and I chose a gin and tonic, my tipple nowadays. When I was John, beer was my drink, not anymore, as my style of dressing had changed so my style of drinking had changed as well.

 

Anyway, it was into dinner to a gorgeous meal Alison had taken most of the day to prepare. Most of the chat over the meal was small talk but when it came to coffee, Alison seemed to adopt a more businesslike tone to her voice.

"There are two other reasons I invited you here tonight," Alison said.

She continued, "Jane, do you have a lot of clothes?"

"Well, not really," I replied.

"Would you like more?" Alison queried.

"Of course."

"Well come with me because I think I can help you."

I was beginning to understand why we were invited here and with Barbara giving a knowing smile, I had the feeling this was all planned. I also realised that because Alison and myself were about the same size where the clothes would be coming from. Not that I was complaining, because over the time I had worked with Alison she always dressed elegantly and stylish and I even, perhaps, had pangs of jealousy about the way she dressed long before I even knew that Jane ever existed inside myself. So if some of these clothes were to come my way, then I would be delighted. What I didn't realise was the amount of clothes I was to receive and not only that, I had to try on each and every dress, skirt, blouse and every other garment and show myself to the women present for their approval.

 

Not everything I tried on that night suited me, certainly according to the women present. Anything that did meet with their approval, I had to put it into a cardboard box for taking home. The result was, I now would have a wardrobe of clothes that many women would be jealous of. I had everything.

I had skirts of various colours, styles and lengths from very long to some so short there was no way I could wear with stockings and suspenders.

I had blouses of various colours and styles. Some were of cotton but there were many of silk.

I had dresses of various colours, styles and lengths from very long to some so short and again, there was no way I could wear with stockings and suspenders. But I did now have a variety of dresses. Dresses for summer, flowery and flowing, dresses for formal occasions, and even some little black dresses. I now had a ball-gown in silk with a wide skirt and net petticoat. When I was ever going to wear it, I had no idea. However, trying it on gave me a new sensation of the net underskirt rubbing against my stocking clad legs. It was certainly not unpleasant.

The most surprising thing of all was that Alison insisted that I tried on a wedding dress with all the accessories including white stockings and shoes, head-dress and veil. The nods of approval indicated to me that it definitely had to be included in my wardrobe. Again I had no idea when I was ever going to wear it. There is one thing, though, about that wedding dress, it felt really lovely to wear and I felt really wonderful wearing it.

There were various other bits and pieces obtained that evening, like scarves, belts, jumpers, handbags and even some jewellery. Everything was put into what had now become two cardboard boxes of clothes.

The fashion show now over, I put back on the dress I had come in that evening and joined the other women for a drink in the lounge.

 

The other reason Alison gave for inviting us over completely took me by surprise.

She said, "Now I've had a little chat with Barbara and what I'm going to suggest to you has her approval."

I looked at Barbara and she just smiled and nodded.

Alison continued, "What are your boobs like?"

"My what?"

"Your boobs, your breasts."

"I don't really have much up there. It's my Wonderbra that helps."

"Would you like to have a proper pair of breasts?"

"I had not really thought about it too much up to now, but thinking about it I suppose I would."

"Good."

"What do you mean, good?"

"Well, next Wednesday you've an appointment to see a plastic surgeon to insert breast implants. It's a small operation and before you say anything, I'm paying for them to be done."

I was taken aback. I felt elated but extremely nervous. I felt other people were beginning to take over the running of my life. All I could reply was, "I don't know."

This was the cue for the two women to start persuading me and I knew I did not have a strong enough will to resist for long. It didn't take me long to say yes.

 

Chapter 10

Nowadays

 

That was all two years ago, so what of me now. Well I still live with Barbara, not as landlady and tenant, but as partners. We went through, what would be best described as a form of marriage ceremony with me as the bride, wearing that wedding dress given to me by Alison that night two years ago when I got all these clothes.

I still work for Alison who is a great friend and influence on me. Oh and Margaret is still there but Laura left to get married. As far as John is concerned, he died two years ago, and yes, I am Jane full time. Although it was Barbara who originally showed me in my true self, it was Alison, who over the past period has guided me more in the true ways of a woman. I now think of myself as a woman and I suppose think like a woman.

My doctor diagnosed me as transsexual, which came as no surprise to me, and recommended my present course of treatment. So now that the female hormones, I have been prescribed, are beginning to kick in, my waist is slimming down and along with my breast implants which I've had for some time now, I feel I am developing a proper feminine body, which is absolutely delightful. Barbara says I am treating all this as a bit of a novelty. Well after all it is a bit of a novelty because, if you like I'm going through my version of female puberty, better late than never.

My sex change operation is due in the next few months, and to be honest, I can't wait to get rid of that thing between my legs.

 

The End

  

  

  

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