Companions

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COMPANIONS

Hannah Nicolson

Copyright – Hannah Nicolson 2019

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.

The story begins with an off-chance visit to a female friend, now a widow, and what followed.

Chapter 1 – The Reunion

I rang the doorbell, not really expecting her to be at home. I heard footsteps inside, the front door opened and there stood Jane, just as I remembered.
“Hello William, this is a surprise. It’s so nice to see you. Please come in.”
“Thank-you, I wasn’t sure you would be at home.”
Jane kissed me on the cheek before I was ushered through to the lounge, offered a seat while she made coffee.
With coffee and biscuits served and us both sitting down, Jane said,
“It’s ages since I’ve seen you, so, what’s been happening?”
“Well you know since Maria and I left this town because of my job, what is it now, ten years ago, much has happened.”
“Go on.”
“Well, for a start, I’ve taken early retirement and I am now on my own because Maria died last year.”
“Yes, I had heard and I am sorry I couldn’t get to the funeral. If it’s not too painful, please tell me about it.”
“It was last September at our home. She was diagnosed with cancer the previous year. Unfortunately, it was too far advanced to do anything effective. However, she went through all the available treatments which really only delayed the inevitable.”
“Why didn’t you get in touch earlier to say she was ill?”
“Well, there was so much going on in our personal lives at the time, and to tell the honest truth, I was distracted.”
“No pressure, but if you want to tell me about it now, feel free.”
“Yes, I think I would like to tell someone about what went on.”
“Thank-you.”
“Well, here goes. Just before Maria was diagnosed, we had actually separated, our marriage was in tatters and she had thrown me out of the house.”
“That’s a surprise, I always thought you were such a devoted couple.”
“It was my fault that caused the break up.”
“So, what did you do, rob a bank or have an affair or something?”
“No, nothing like that.”
“There must have been a good reason why you were thrown out.”
“If I tell you, you’ll probably throw me out as well.”
“Try me?”
“Are you quite sure?”
“Yes.”
“Well, OK, here goes. I was caught by Maria wearing women’s clothes.”
“Her clothes?”
“No, my clothes.”
“Is that all?”
“Isn’t that enough?”
“It sounds like, to me at least, she may have over-reacted.”
“That is definitely not the reaction I was expecting from you.”
“So, were you completely dressed, you know, panties, brassiere, stockings or tights, petticoat, dress or skirt and blouse?”
“Yes, the lot, with stockings and suspenders rather than tights.”
“So, what is your style?”
“Is that relevant?”
“Definitely.”
“Well, I really don’t know because ‘my wardrobe’ as it were, is really bits and pieces bought online, or from supermarkets and charity shops mainly. So, I suppose more tarty than practical and probably too young for my age.”
“So, what happened next?”
“Well, soon after her discovery of my cross-dressing, Maria was diagnosed with cancer. We had a sort of reconciliation and I moved back into the house primarily to look after her. Like I said before, Maria went through all the available treatments which really only delayed the inevitable. I was there with her when she died at home. Despite all the drama that had gone on, I think she appreciated me being there at her bedside.”
“I am so glad you had at least some form of reconciliation and I presume you never cross-dressed while Maria was ill?”
“Definitely not.”
“Since Maria died, have you dressed again?”
“Yes, I have but, I find it a truly lonely and frustrating existence.”
“It is obvious you like wearing women’s clothes but you feel there is no future just doing as you are.”
“Exactly.”
Please answer this question with a yes or no, but only if you feel you can or want to. You like wearing women’s clothes, so would you like to wear women’s clothes all the time if you could?”
“In a word, yes.”
“Good, maybe, it was what you were wearing that caused the problem with Maria.”
“Isn’t that what I just said?”
“No, what I meant was your style.”
“Do you think if I dressed like a woman more of my age, it would have been better?”
“Who knows.”
Jane continued, “Do you have any pictures?
I opened my wallet, took out a photograph of me as my alter ego, this picture taken by myself using the delayed timer on my camera which was mounted on a tripod.
I handed it to Jane and said, “Please don’t laugh.”
She looked closely at it before saying.
“Well, looking at this picture tells me a number of things, and before I say anything more, I am not going to laugh, because there is nothing to laugh about. I will make the following observations however.
1. That outfit you’re wearing is far too young for you.
2. Your hairstyle / wig is also far too young for you.
3. You may be a blonde, but definitely not that hairstyle.
4. You are deliberately showing your stocking tops, not very ladylike.
5. Lastly, you have fantastic legs and look much better in a skirt than Maria ever did.”

“So, what you are saying, apart from my style being all wrong, I can pass as a woman?”
“In a word, yes.”
“I would have thought you would want to condemn me.”
“Why would I want to do that?”
“Well, surely I’m some sort of a pervert. Most people would probably think so.”
“I’m not most people, so don’t be silly. All that is wrong, you look like ‘mutton dressed as lamb’.”
“Is that all?”
“Yes, that is all. Another question, do you think you would prefer to live as a woman?”
“This is all getting a bit personal, but if I think about it, I suppose the answer would have to be yes.”
“Well here’s another personal question, would you prefer to be an actual woman?”
“Yes, but that is just an impossible dream.”
“So, have you always felt this way?”
“Again, I suppose, I have.”
“Thank you for being honest with me.”
“So, what do I do now that I have bared my soul?”
“Well, if you will let me, I will guide you towards being the woman you should be.”
“I don’t understand. Why would you want to help me in this way?”
“Because, you mean more to me than you might realise.”
“Oh!”
“So, will let me guide you to be the woman you should be?”
“Yes, that would nice, but how are you going to do it?”
“For a start I would like you to try on some clothes.”
“Are you sure?”
“Of course, but you should be aware, these clothes are very feminine and for women of our age.”
The lingerie, as she put it, also belonged to another age, an age of glamour and extreme femininity. Overawed by all this, all I could say was,
“I think I would like that.”
So, we went upstairs to Jane’s bedroom, there she asked me to strip, which I did, reluctantly, to my Y-fronts. The bulge in the front of my underpants was beginning to become obvious. All Jane commented on was the lack of hair on my body, arms and legs.
I responded by saying, “I like to keep it that way.”
First was a pair of nylon full cut pink panties. They felt gorgeous as I, having turned my back to Jane, slipped off my Y-fronts and pulled on the panties. These were so much nicer than the panties I had bought in the supermarket. This was followed by a type of open corselette, white in colour with four suspender straps. This corselette was tight but not constricting, more like a firm embrace rather than squeezing the breath out of me. It allowed me to adjust things ‘down below’ so that the bulge I had earlier was minimised. Jane adjusted the shoulder straps to fit and as if by magic, produced a pair of flesh coloured breast-forms for the brassiere cups. I now had a prominent chest/bust and the semblance of a womanly figure. Jane said she nearly always wore foundation garments like that, and always with stockings and suspenders where necessary. Hold-up stockings and tights were only worn where there was no option.
Stockings were next, fully fashioned and tan in colour. They were beautiful, obviously not from a supermarket, more like from an exclusive ladies’ wear shop.
I was given a long sheer white peignoir to put on. Again, another gorgeous garment. I was beginning to realise all the things I had missed in my dressing sessions in the past. I just never thought of things like girdles, peignoirs and the like in the past. Maria never wore things like that in all the time we were together. If anything, her underwear was always plain, almost utilitarian.
I was now guided over to the dressing table where I was asked to sit.
“How are your make-up skills?” said Jane.
“Basic, very basic,” I replied.
“Well, time to learn.”
I was now given a master class on how to apply make-up, suitable for my age and skin type and that included my finger nails. The results were outstanding, only they didn’t look quite right since the head that had been made up had male pattern baldness, not a great look. However, this was remedied when Jane produced a dark brown styled wig. First, a wig cap was placed on my head, followed by the wig itself which was tugged and pulled into place, brushed into a neat style to show me my new look. I really couldn’t believe this reflection I was seeing. Before me was a woman of my age who could have been my sister, if I had one that was, sitting at her dressing table in her lingerie, doing her make-up.
“Well what do you think?” said Jane.
I just couldn’t contain myself because I burst into tears, something I never did.
“What’s the matter?” said Jane, rather concerned.
“I feel absolutely gorgeous, but I know, when I take off the clothes and make-up, I will just be plain old William again.”
“It doesn’t have to be like that.”
“What do you mean?”
“Well you have already said you’re retired now and have no family and living in that house all by yourself, I presume.”
“Yes, that is all true and I am lonely as well.”
“Well, I’m going to make a suggestion and please say no if you think I’m getting ahead of myself.”
“Please go ahead.”
“Why don’t you come and live with me?”
“What do you mean?”
“I said, why don’t you come and live with me?”
“Are you serious?”
“Yes, I’ve never been more serious.”
“I never expected that. To say I’m gobsmacked would be an understatement.”
“Well, gobsmacked you may be, but what I am offering is for you to become my live-in companion, my female companion that is, because I’m lonely too.”
“Do you really mean it?”
“I really mean it. I’ve never been more serious.”
“You’ve just me an offer I can’t possibly refuse and of course, I accept.”
“When I say ‘female companion’, I mean female permanently. It is important that you understand what I am saying, because we might as well stop now, if you think you might want to go back to living as a man sometime into the future?”
“You have just given me the most wonderful opportunity and the last thing I would ever want to do is to go back to living as a man having been given this wonderful opportunity to live as a woman. I accept all your conditions. I just can’t think of anything nicer.”
“Good, but I think we should repair your makeup and you should finish getting dressed. I have your skirt and blouse here for you.”
I noticed the word ‘your’ when Jane referred to the skirt and blouse. The skirt was light beige in colour, fully lined, straight and quite short, shorter than I might have expected.
The blouse had a sheen to it, light gold in colour and a ruffle in front. It was gorgeous to wear. A pair of high heeled shoes, black in colour with a narrow heel of about three inches in height was produced. They fitted extremely well which surprised me, because Jane’s feet looked somewhat smaller than mine. I queried this and Jane, in a very matter of fact way, explained that they belonged to her late husband who was also a cross-dresser. Jane’s attitude towards me now began to make sense, the breast forms, the wig and now the shoes.
Final touches included clip on ear rings, a string of pearls, a bracelet on my right wrist and a lady’s watch on my left followed by perfume, expensive perfume. It smelt absolutely divine.
Fully dressed, I looked in the long mirror and I just about burst into tears again seeing the new me.
Jane said, “With you looking like that, you will need a new name, a female name that is. How about Willamina or perhaps Wilma, you know a female version of William?”
“Oh no, none of these, my new name will be Hannah.”
“Why Hannah?”
“Hannah is the name I would have been given had I been born in the correct gender, a girl, so now, better late than never.”
“Hannah it is then, and may I say that is a lovely name.”

Chapter 2 – The Explanation
Jane said, “I would like you to stay here overnight and you can sleep in the guest bedroom. I will give you one of your nightdresses to wear and tomorrow, why don’t we both travel to your place so that you can pick up things you might need for the next few days, at least.”
I noted again the reference to ‘your’ nightdresses.
Jane continued, “Not to get ahead of ourselves, I think you should leave things like the selling of your house for now. Let’s just see that we are both happy with our new arrangement. You can perhaps think of selling if and when you are ready.”
“I think that’s a great idea.”
“Good.”
“And do you mean me go as Hannah.”
“That’s up to you, but when we return, you must become Hannah, full time if that is acceptable?”
“Yes, of course, but can I decide who I will be in the morning?
“No problem.”
“Thank-you.”
“At this point I think you deserve an explanation about my attitude and the lifestyle I had with my late husband, John.”
“I would like that.”
We both made their way downstairs to the lounge, where Jane offered me a drink. I opted for a gin and tonic and Jane had a whisky and soda. We made ourselves comfortable, making sure I swept my skirt under before sitting. Jane related her tale.
“Well, when I first discovered John in women’s clothes, I suppose my attitude was a bit like Maria’s. There were the usual recriminations, and the sort of questions I put to him were like,
How long has this been going on?
Are you bored with our sex life?
Do you prefer men to women, in other words, are you gay?
Do you want to become a woman?
Was this all my fault?
Really, all sorts of things like that. We had a blazing row, with him saying that it allowed him to get rid of some of the stress from his job and life and also gave him a feeling of contentment. He said he definitely wasn’t gay and did not want to become a woman, it was just the clothes. I was in tears and he went into the guest bedroom that night. For my part, I couldn’t sleep with all that had happened turning over in my mind. It was during this time I rationalised the situation and realised it was not such a big problem after all. You see, the thought of my husband dressed as a woman was causing a strange feeling inside me, a feeling of attraction towards him and not revulsion.
Was I thinking, what would it be like to have an affair with another woman?
What I did next was rise from my bed and go through to the guest bedroom where he was. He too was not asleep, also he was a bit frightened to see me coming into the room. I asked him if he had a nightdress, to which he said no. So, I asked him to come through to master bedroom, which he did, reluctantly, where I handed him one of my nightdresses, a long dark blue satin nightdress. This, of course surprised him especially when I asked him to put it on and come to bed with me. I cuddled him that night and he wept.
From that night on, John always wore a nightdress in bed, initially mine, then his own and eventually, our sex life resumed but with me now taking the dominant position. Our sex life went from, what was in the past, at best, mundane to absolutely magnificent. John became a willing submissive partner. We had, what you might say, become passionate lesbian lovers because, John now always wore a nightdress, or lingerie, or both, when we made love. In other words, he always took on a female role.
There were other changes with John’s underwear, where he started to wear panties occasionally, to wearing them full time including under his business suit at work.
Since that night we never looked back. By day he was John, but behind closed doors, he was Johanna. Unless we had a social commitment, every evening when John returned from work, he would become Johanna. This would also happen at weekends and occasionally when we were on holiday where he was Johanna all the time. You see he could pass as a woman quite easily. The only problem was John had to live a double life and he hated it, we hated it.
Since he was due to retire, our plan was to carry on as we were, then after he retired, move away where John could become Johanna full time. However, it was not to be, because, as you know, John died before he reached retirement.”
“Wow, I had no idea. All the years we knew you and John as a couple, the height of respectability on the outside, but behind closed doors, well?
You must have been absolutely devastated when he died?”
“I was. I literally cried for weeks.”
“I know you became a bit of a recluse for a long time after that. To be honest, many of us were getting quite worried about you.”
“I am now going to tell you something which I have never told anyone before. When John was laid to rest at his funeral, he was dressed fully as Johanna. There are only two other people that know this, namely our doctor and the undertaker. You see John was undergoing hormone therapy before he died. He was taking female hormones under the supervision of our doctor and after my suggestion, to which he readily agreed. His breasts were beginning to develop which delighted both of us. I should say, the reason for his death had absolutely nothing to do with his hormone treatment. Let me put it this way, I just wished that he hadn’t smoked.”
“But you said earlier that he said, it was only the clothes, because it made him feel contented, so why did he start taking female hormones?”
“That’s true about the clothes, but really it was more than that. John admitted he wished he had been born a girl and surprisingly, this did not upset me because seeing John as Johanna, I saw how natural he was as Johanna, and that was how he should have been.”
“That is amazing, like I said, you never know what goes on behind closed doors. One thing, though, I hope you are not trying to make me take Johanna’s place.”
“No Hannah, I had no idea until earlier today, you even cross-dressed, but when you agreed to move in with me and be Hannah full time, all I am hoping for, is companionship. You are lonely, I am lonely and we have been friends for a long time. The idea of two mature ladies living together is quite respectable whereas a man moving in would set tongues wagging.
I know it’s a detail, but after you move in, I would like you to meet, and for that matter register with, my doctor. My reasoning is that you need to have the obvious security about your health. You should also admit your lifestyle choice to her. She is totally non-judgemental. Should, at some time in the future, you want to go the same way as John, you will find her very cooperative as you will with me.”
“Thank-you, I will do that.”
We spent the remainder of the evening looking through clothes, predominately Johanna’s clothes because Jane had kept them and she now wanted me to have them. This made me slightly uneasy but I let it pass.
Jane also showed me lots of photographs taken by her of John as Johanna and she was right, he looked good as a woman. I certainly would never recognize him as John dressed the way he was. What also was noticeable, was his / her expression, total and utter contentment as Johanna. He was meant to be Johanna. Certain pictures of John were at the best questionable, especially the outfits he was wearing. I looked but said nothing.
Jane then brought up the suggestion that she would like to photograph me, that is Hannah. I was wary but Jane assured me the pictures would only be viewed by us unless I gave permission otherwise. She argued; they would be a useful record of my progress into womanhood. I could see the logic in that.
Anyway, photography is a hobby of Jane’s and with the invention of the digital camera now allowed her to take certain photographs that would, to put it mildly, cause a bit of a stir at the film processors. I was shown some of these pictures, especially of Johanna, but also some of Jane and Johanna together. I was surprised I was shown them because I would consider them, to put it mildly, extremely private.

Chapter 3 – The Next Day
Yes, I decided to go back to my old place as Hannah, it being in a quiet location with no prying eyes. Jane said that my outfit from the previous evening was not really suitable, more evening wear than day wear, so she looked out another ensemble for me from my ‘new’ wardrobe.
The skirt I wore was, black in colour with box pleats and a slight flare.
My underwear consisted of a white, full cup lace trimmed bra over my breast-forms with white nylon full cut panties and white suspender belt with six straps. Jane suggested no girdle today, why, I had no idea, but I was soon to find out.
Actually, my breast forms were glued into place using a medical adhesive since I had decided to be Hannah permanently. Now, there was absolutely no reason to remove them. After all a woman does not remove her breasts when she takes her clothes off, does she? However, the breast forms would have to be removed at certain periods for cleaning and to allow my skin to recover.
Stockings, black in colour, were rolled up my legs into place and attached to my suspender tabs. Since my skirt was not lined, I wore a full white slip which had a beautiful lace trim all round. It was gorgeous. My blouse was white in colour and had a large bow in front, a pussy bow. A pair of high heeled pumps, black in colour with fairly narrow heels and about two inches in height was my footwear of choice.
Final touches included a bracelet on my right wrist and a lady’s watch on my left followed by perfume, that expensive perfume.
Fully dressed, I looked in the long mirror and said under my breath, “Yes.”
As well as this new wardrobe of mine, I now became the owner of many accessories suitable for a woman of my years. These included quite a number of jewellery items and some items were of good quality, not cheap costume jewellery. Most of my new earrings were for pierced ears, so there was something I needed to do urgently, that was, get my ears pierced, this being something I’ve wanted to do for years, then not practical, now essential. Scarves, gloves, handbags and shoulder bags made up the rest of my collection.
Jane suggested while we were out, we should do some shopping for cosmetics and other make-up items, plus get my ears pierced, this of course being my suggestion. I needed everything and there was no time like the present. For extra security, Jane also suggested I purchase a supply of panty pads. I queried this but all Jane said,
“You’ll see and I think you should wear one today.”
So, Jane handed me one of the said items, and never having worn one before, it was fairly obvious what to do. So, I pulled up my skirt and pulled down my panties, removed the backing paper and stuck the panty pad into place on the gusset of my panties. I pulled up my panties, tucking ‘things’ into place so that I was comfortable. It felt good. So, it was on with one of my ‘new’ scarves followed by my coat which was fairly short with a fake fur collar which felt lovely and warm.
For some reason, I felt completely at ease crossing the threshold of the front door and stepping out into the ‘big bad world’ as Hannah since the only time I had been out dressed before was briefly out in my car into the countryside during summer time. This was different, this was November and there was a cold breeze blowing. I don’t know where that breeze was coming from, but I knew where it was going, and that was blowing up under my skirt and around my stocking tops. This was not unpleasant, in fact rather pleasurable. I now realised the need for the panty pad. Jane looked at me and just smiled seeing my expression at that exact moment.
We made our way to my car which was parked some fifty metres away. I now had to remember how to get in and out a car without exposing myself to the whole world. I may have been wearing pretty lingerie, but I still preferred to keep its viewing a private matter. So it was, sit down on the car seat and keeping my legs together, swing them into the car. The heels I was wearing, they being about two inches, allowed me to drive in comfort. So, it was off to my old place, the journey would take around two hours. We stopped off at a roadside coffee shop about half way into the journey for a short break.
Again, I had no problem stepping out of the car and mingling with other people in the coffee shop. If anyone had ‘read’ me it was not obvious, because I never noticed anyone staring, pointing or whispering for instance. I did let Jane do the ordering in the coffee shop, as I still needed to work on my voice, it being still far too male.
Before we departed the coffee shop, Jane suggested we visit the ‘Ladies’ to ’powder our noses’ as it were. Now this was definitely my first time in a ladies’ toilet, so it was with some trepidation I crossed that particular threshold. Again, no one stared or screamed, so that was another one of these progression to womanhood tasks struck off the list. I now realised the full reason for not wearing a girdle especially when it came to the manoeuvring required within the toilet stall. Another piece of my training you could say.
All the necessary tasks in the ‘Ladies’ completed, including touching up my lip stick, it was back to the car to complete the journey back to my place.
I needed to pick up things like my laptop computer, certain personal documents plus various bits and pieces I might need for the next few weeks.
What I did not pick up were any of my male clothes. If I was going to make a success of Hannah, then male clothing definitely played no part.
That part of the list completed, it was off to the city centre shopping mall, but, having arrived and sitting in the car park, Jane asked,
"How do you feel? Do you want to go on?"

"Yes, so where to first?"

"Do you still want to get your ears pierced?"

"Yes, very much."

"Right, let's do that first then."

There was a suitable jeweller just a few yards from the entrance we had just come into the mall. Jane said,

"How about here?"

"Fine."

"Let me do most of the talking."

"Fair enough."

Into the shop we went, the shop assistant asking,

"Can I help you ladies?"

"Yes, my friend would like her ears pierced, if you don't mind."

"Certainly, if you would like to follow me."

We were ushered into a small room where the shop assistant explained what would happen and the instructions I was to follow while the holes healed. I was to have two small gold studs inserted, one in each earlobe, and they would have to remain in place until everything healed. In fact, the studs were inserted with what looked like a gun which ‘fired’ the stud through the earlobe.

"Ow," was my reply from as each stud was ‘fired’ into my earlobes.

Once the studs were in place, a small ‘butterfly’ catch was put on to the end to keep them falling out.

This job now done; we all made our way to the front of the shop. Jane said, as she opened her handbag,

"Let me pay, my treat."

"Thank you."

The shop assistant looked as she took the money, ever so slightly suspicious.

Next, Jane asked me once we had come out of the jewellers,

"Do you want to go on?"

"Yes. Let’s make the most of this day."

"OK, you really need some more cosmetics and especially things like nail varnish and perhaps more perfume. Actually, you really need to start afresh because you need to establish your preferences and not rely what is already in the house."

"Yes I do, don't I?"

We made our way back to the large department store in the mall and headed for the cosmetics counters. I really loved this as we were both pampered with samples of this and that before deciding on the products I wanted and for that matter, Jane as well.

More shops and more shopping and with our arms now laden with carrier bags, we decided to call it a day and made our way back to the car park for our journey home.

On entering the house, Jane asked,

"Well?"

"Well, what?"

"What did you think of your proper first day out as a woman?"

"Great, I suppose I was a bit nervous to start with but I soon got over it."

"So, do you want to do it again?"

"Of course, I'm a woman now and there is a big wide world of retail therapy out there."

Jane laughed and said,

“Typical woman and I should know because, I’m one as well.”

Chapter 4 - Lovers

I now lived as Hannah, Jane and I were companions as originally planned but we were getting closer emotionally. The inevitable happened of course, we made love, and before long, became a couple, a lesbian couple and yes, we became lovers. It took only about two weeks of me being Hannah to becoming Jane’s lover. We now share Jane’s bed and although I present myself to the outside world as a woman, the plan was, Jane would make use of the thing between my legs to our mutual enjoyment, with Jane always on top.
Well, not exactly true, apart from Jane on top, you see it was the ‘old’ problem, namely my age and trying to maintain an erection. I was able the first few times, perhaps it was the excitement of something new, but after these first few times, I was back to the ‘old’ problem. Jane had the solution of course by producing a strap-on-dildo for me to wear, this being yet another thing that was used by John on Jane. So, I was not alone in my condition. Jane craved penetration which the dildo provided, however it left me somewhat frustrated, and no doubt John as well.
To give some relief, Jane would give me a hand job. This went on for a number of times until Jane suggested something completely different.
What was it?
It was that she would wear the strap-on-dildo and penetrate me up my rear end. Jane asked if I had done this before, to which I had said ‘no’.
Jane said, “So, you a virgin?”
My answer was, “Yes, I suppose I am.”
I was extremely reluctant to go there but Jane set about persuading me in the nicest possible way, including using a smaller dildo rather than the one I was using on her. You see, the strap-on belt could take different sized dildos and Jane seemed to have a full set. She also said the dildo would be well lubricated.
So, I reluctantly agreed.
Come the hour, the bedroom, our boudoir was discretely lit with perfumed candles, I made sure I was extremely clean ‘inside’ and was dressed in my long white night dress, soft white lacy bra over my glued-on breast forms and no panties, as requested by Jane. She presented me with, and asked me to put on, a pair of special white lace panties with an opening at the rear. I did as she asked without hesitation. She said they were especially for ‘girls’ just like me. Jane said she wanted me to look virginal, all in white. I also wore my long-haired wig, Jane saying it made me look that bit younger and innocent, in her eyes at least. Who am I to argue about looking younger and innocent?
Jane was dressed in a similar nightdress to me but in black and the strap-on-dildo, which was also black, for my ‘deflowering’.
I was taken by the hand, led to our bed and was sat down. I changed my position to lying and Jane came on top of me spreading my legs in the process. She hooked her arms under my legs lifting them clear. My ‘entrance’ was now exposed as that ‘invader’ attached to Jane came nearer. Finding the spot, Jane said, “just relax,” and very gently pushed and slow but sure, I was entered. These was pain but nothing too bad as I was fully entered.
I was no longer a virgin.
What was it like?
Well, for a start, I was not too happy.
At first there was that pain as I was penetrated and,
I felt a degree of humiliation.
Then there was that feeling of fullness as Jane pumped the dildo in and out.
Well I came and I came big time. I hadn’t expected it, but it happened.
So, what next?
The more I rationalised it, the whole idea filled me with strange thoughts like;
This is not a position a man should be in.
But I no longer wished to be a man.
This was humiliating, or was it?
If I was a woman, this is what I would want. I now realised I craved penetration.
Having done this once, what I wanted was to do it all again, as soon as possible, if not sooner.
Over time, I graduated, if that is the word, to larger dildos, my anus now able to comfortably accommodate these larger sizes. This was, without a doubt, my preference as far as any sexual act was concerned.
Jane suggested we spice things up a bit with some costume play, mainly by me. So, there were times when I might be dressed as a little girl, a schoolgirl or a hooker, always with the same end result, full blown sex. These costumes weren’t bought specially for me to share, they were already in the house. It seemed that Jane and John had a very interesting, if not unusual, sex life and it looked like I was now about to be the inheritor.
Was I objecting?
Not a bit of it.
Certain items, in particularly the hosiery was different from my usual wear. Although there were stockings, there were also pairs of tights, mostly white in colour as well as long white and coloured socks, all the sort of stuff young girls might wear but in larger sizes.
Jane reasoned that I might like to dress as a little girl or schoolgirl occasionally as I had, after all, missed out on that part of my life.
She was absolutely correct of course, as I loved being the little girl I never was. If we had no plans to go out, sometimes I would spend the whole day dressed as a little girl or schoolgirl.
As a complete contrast, I loved wearing the hooker costume because in many ways I was becoming a bit of a nymphomaniac, Jane being little better and all this, of course, happening behind our front door. Regardless of which costume we wore, the end result was always the same, complete and utter sexual gratification for both of us. It was amazing.
As a couple, I was always the more submissive partner to which Jane said I was very much like Johanna in that respect. I said that I preferred being that submissive partner.
Jane would now wear a double ended dildo, with one end inside her, so sex was always mutually satisfying.
What can I say, up to now I never knew such lifestyles existed, but they do, us being a prime example. I just loved it.
So, life and love went on, generally good with fantastic sex, and all the time, to the outside world, we were two ‘mature’ widows living together, all very respectable.
If only they knew.

Chapter 5 – The Change
As mentioned already, I suppose, regardless of earlier plans and ideas, there is always the tendency for them to get put aside or even forgotten as time goes on, and this is what happened to us, well me. Although we had talked about taking my transition further, nothing actually happened or was done about it. There had to come a day when a change would occur, but rather than planning for this, it came because of events out with our control, or more precisely, illness.
What seemed to be a bad cold I had contracted, and rather than get better, it got worse, with it going on to my chest and ultimately confining me to bed. I was always hoping I would get over it without the need for a doctor but that was not to be. You see, since becoming Hannah, even before as William, I had never registered with the doctor Jane had suggested. So, now we, or should I say, I had a crisis. Generally, I was not in any condition to fight anything that Jane might do, because when I awoke from a fitful sleep, the first person I saw was a strange woman standing at my bedside.
"Hello Hannah," she said, "I'm Doctor Helen Small and I'm here because Jane is really worried about you."
I was startled and began to get agitated, but the doctor just said, "It's alright, calm down, I know all about you, and your secret is safe with me."
"I'm sorry doctor."
"Call me Helen, please."
She asked me to pull down the bed covers and lift up my nightdress so that she could listen to my chest. I still had my breast forms stuck on and I was also wearing a soft bra and panties, so my modesty, if you could call it that, was not compromised. The doctor was able to do the necessary tests. She diagnosed a chest infection and prescribed a course of antibiotics which she said should clear up the problem.
"Thank you," I said in a small voice.
"That's alright, but once you're better, I am going to come and see you again."
"Why?"
"Because you cannot go on the way you are."
"What do you mean?"
"Because Jane told me about you and I would like to help and I should say, I was also John’s doctor."
“Oh, I see.”
I looked at Jane, who was also in the room, all was now clear.
Jane said, "Sorry, but we really needed to move things along."
"Look, don't blame Jane," said Helen. "I've known Jane for many years, after all I am her doctor and was John’s as well as I have already said. It was only because she was really worried about your health, she called me in."
"Is this true Jane?" I asked.
"Yes," she replied.
"Then I am sorry."
After Helen had left and Jane had returned from the pharmacy with my prescription, I felt strong enough for Jane and I have to have a little talk about the future. Really, I had been putting things off, but now Helen wanted to get involved, this seemed like a good moment to find out what each of us wanted. I started by asking Jane,
"Do you want me to take things further?"
And I got a typical woman's response. She answered my question with another question.
"Do you want to take things further?" said Jane.
Jane obviously wanted me to make the decision on my own and being in my weakened state with my illness, I was in no mind to stretch out the discussion any longer than necessary. So, I responded very hesitantly with a ‘yes’.
"Good," she replied.
Really, this was the reaction I was hoping for.
Once the decision was made, Jane admitted, for the first time she wanted me to go for a full sex change. I think this was what she wanted for John as well. I knew, right from the start, that this was the way I wanted to go but I suppose the reason I put things off was that I was scared. Now she had admitted her preference, a great sense of relief came over me. This was something I had been bottling up inside me for weeks and months. You see, I simply could not risk or afford to lose Jane because I loved her so much.
So, the final decision was made and yes, this was certainly what I wanted and it turned out to be what Jane wanted as well.
My chest infection soon cleared up after the course of antibiotics and I was back to my old self again.
The front door bell rang, Jane answered, it was Doctor Helen.
“Come in Helen,” Jane said, “Come through to the lounge.”
"Hello Hannah," Helen said, "And how are you feeling now?"
"It's nice to see you Helen, and I'm feeling much better, thank you."
"Good, well I'm here, because as I said the last time, I wanted to see you again. Now first, and I don't want you to take this the wrong way, I've been speaking to Jane and she told me your decision and with your permission, I want to get the wheels in motion."
This time, I didn't scowl at Jane as I had the time before, but just smiled and said,
"By all means, please carry on."
Helen went on to describe all the regulations that would have to be followed, the specialists, the surgeons, the costs involved and the places where the procedures could be carried out. I would have to have a psychiatric assessment done to see if I was suitable for the full transition from male to female. I knew I was suitable for that full transition; I didn't need a psychiatrist to tell me that. But these are the rules. I would have to live full time as a female for at least a year. Well, that was one test, I had already started.
The one thing, Helen could do to get me started on my road to being a real woman was to give me a prescription to start on my course of female hormones. Before giving me that prescription, she said she needed to examine me. I was asked to take off my blouse but I could leave my bra on while she listened to my chest. A few other tests were done including taking my blood pressure. I put my blouse back on. Having been satisfied with her examination, she wrote out my prescription and saw I was visibly shaking as she handed it to me.
"Are you all right?" she said.
"Yes, it's just this piece of paper you've just handed me feels like the greatest gift ever."
"Oh, you'll get over it fairly quickly when your chest starts to hurt as your breasts begin to bud."
"Right at his minute, I couldn't care less."
Helen gave me some leaflets explaining what I was likely to expect as my body changed with the hormones, information on surgeons who did Sexual Reassignment Surgery (SRS) and more details on the costs involved. She also said she would make the necessary arrangements for the appointments with the appropriate specialists. So now I was on my way, at last.
After Helen left, Jane said, “I want to pay for your changes.”
“Why?”
“Because I love you, well Hannah is the one I love, and want to be with her.”
“Thank you, and I think you know I’ve fallen totally in love with you as well, perhaps even more than I was with Maria. But, can you afford to pay for my changes, it’s going to be expensive?”
“John, I mean Johanna left me well provided for.”
“Look, I want this as much as you and I have some money as well. How about we go 50:50 if that is all right with you?”
“50:50 it is then.”

Chapter 6 - Starting on the Road

I knew it was going to take several months before any results of the hormones would begin to show, but I could not swallow that first doze quick enough. It just felt so good, so right. I felt that changes would now happen and this gave me a strange feeling of relief.
I think Jane was stricter about my medication than I was. She always made sure that my medication was there, at the right time, and she made sure I took it. There was no way I was going to miss taking it anyway, so Jane need not have worried.

Although I was told that the hormones might retard my beard growth, they would not stop the growth all together, so I embarked on a course of electrolysis. To say it was unpleasant would be an understatement, but a woman has to do what a woman has to do. Who said beauty was going to be pain free, and cheap for that matter? This treatment was done in a private salon out with the town, where my anonymity would not be compromised.

This was now my regime, hormones, electrolysis and doctors' appointments. Helen was of course correct that as my breasts began to grow, they would indeed be painful. But yet again, this was a cross I was only too willing to bear. As well as my breasts, my body began to change shape in other ways. Muscle mass gave way to more fat in certain areas. For instance, my hips became bigger and rounder. Although I never allowed any hair on my body, I always made sure any that did grow were swiftly removed, and this re- growth was now much thinner as a result of the hormones.

I was now living as a woman, happy and contented. I felt totally at ease going out and mixing with others because I looked like a woman and now sounded like a woman. Training my voice was difficult to start with, but eventually it became second nature and now I sound like a woman albeit with a slightly lower register. I would say, my feminization treatments were proving to be successful, even beyond my wildest expectations.

Socially, I began to mix more with some of the local women. Jane always had a circle of female friends before Hannah came along, but with me, Hannah, now able to pass as a woman, even at close scrutiny, I, now, became integrated into this circle. As far as they were concerned, I was female and always had been.

With my female style and look now established, I now faced a problem, a problem I never expected, and that was the unwanted attention of some men, predominately those in their fifties and sixties. It looked like I was proving to be attractive to that age group.
It happened one evening, when Jane and I were attending a social function at the local town hall. To be honest, I was not feeling a hundred percent, I think it being a reaction to my medication. So, I told Jane I was slipping outside for a breath of fresh air. Before I knew it, I was joined by a man who I had seen in the hall, a man I did not know or for that matter, did not wish to know. He approached me and unfortunately, with my back to the wall, he faced me and placed his hands, flat on the wall, either side of me, I was trapped.
He said, “Well, who have we got here? You’re a pretty thing.”
“Do, I know you?”
“I don’t know. Would you like to get to know me?”
“No, I don’t think so.”
“Don’t be like that. How about a kiss?”
“Pardon, no, get lost.”
“Don’t be silly, you know you want to.”
“I came out here for a breath of fresh air because I felt unwell, not to lure you out.”
“That’s what they all say. I can read the signs.”
“Well, you’ve got it all wrong this time.”
My appearance as a woman was after all a created image at this point. My breasts were false and I still had my male genitalia. It would only take a quick grope under my skirt, by him, to find out I was not what he thought I was.
It seemed this man would not take no for an answer, so there was only one thing I could do, reluctant as I was to do it because the idea disgusted me. I clamped my hand over his genitals, he thinking for a moment that I had fallen for his charms. He soon realised that was not the case, because instead of caressing his ‘package’, I tightened my grip, until he was feeling the pain. I still had the grip of a man. He tried to pull my hand away, but with his pain and my strong grip, there was no way he would succeed. With my other hand I lifted his chin and said,
“Look sunshine, when I say no, I mean no and if you try anything like that again, I will wrench that pathetic little package between your legs off, understand?”
“Yes, yes. Your hurting me. Please let me go.”
I released my grip, not before giving a final twist to cause extra pain, pushed him back whereupon he fell backwards on to the ground, allowing me to make my escape.
I heard him mutter, “Bloody lesbian.”
He never came near me again.

Chapter 7 - The ‘Ultimate’ Test

What was the Ultimate Test, you may ask?
Well, although Maria and I lived much of our married life here in this town before moving because of my job, also living in this town was my mother-in-law, that being Maria’s mother. Maria’s father had passed away many years before and although Maria was now gone as well, her mother was very much still alive. Let me state my attitude to her, instead of being regarded as an in-law, I prefer she be regarded as an outlaw.

As I have been transitioning towards full Hannah status, as I have already mentioned, I have trained my voice to be more female if you like and, mixing with other women around the town with never a problem of being ‘read’. Inevitably there would come a time when I would encounter my said mother-in-law, Bella. When Maria and I lived here in the past, we kept these encounters down to an absolute minimum.

Jane and I had been invited to a function, one we could not get out of, one which we would have loved to get out of, one that Bella would be attending. This would be the ultimate test, if Bella didn’t recognize me, then success. That, of course, still did not fill me with the greatest confidence.

It was into a suit of armour, at least some of my good strong foundation wear, I needed as much protection as possible, or so I felt. As well as the ‘suit of armour’, I was going to put my make-up and cosmetic skills to the test to create, if you like, the ultimate disguise.

“Hello Bella,” Jane said.

“Oh, it’s you Jane, I haven’t seen you in ages, almost as if you were trying to avoid me.”

“Of course not,” lied Jane.

“Who’s this then?” Bella looking at me with disdain.

“Oh, this is Hannah, my new friend and companion. She’s a widow like me.”

“Hannah is it; you look familiar. Have we met?”

“No, definitely not. I certainly would have remembered,” I also lied.

“You seem so certain and I’m sure I’ve seen you somewhere before.”

“You must be mistaken.”

“I know, you look a bit like that wretch of a son-in-law, William who married my now dear departed daughter, Maria.”

“Gulp.”

“You’re not his sister, are you? I never forget a face. It’ll come to me.”

“I don’t have a sis… brother,” I was beginning to panic, before Jane stepped in.

“Hannah is an only child. Anyway, I’ve heard that William has gone abroad to live,” Jane said.

“Where?” snarled Bella, always looking for more information so she could always be one up on her so-called friends.

“No idea,” said Jane, in a rather dismissive tone.

“So, why has he not told me where he has gone?”

“Maybe he thought you wouldn’t care where he went, because he has a new lady friend and I think he wanted to get as far away from you as possible.”

“So, who is this woman?”

“I don’t know much about her, like her surname, but I do know her Christian name is Jane, just like me,” lied Jane, with conviction.

“Oh Jane, you devious cow. If only Bella knew the truth,” I thought to myself.

“You know that Maria was going to look after me before that William Alexander turned her head against me. It was probably him that caused her death”

At this point I was fizzing with rage and if Jane hadn’t stepped in, I think I would have walloped Bella. Not very ladylike you may say, but she just made my ‘blood boil’.

Jane having got me away from the ‘witch’ that is my mother-in-law, I said to her, “I would have loved to give her a slap, and do you think she’s rumbled me?”

“As for giving her a slap, I think I would tend to agree with you, but you have to hold back with people like that and no, she hasn’t rumbled you. She’s bluffing because although she sees that resemblance, that’s as far as it will go because she will never believe in a change of gender. She will never believe you are, or were, William. In her eyes, women are women and men are men. There is nothing in between. That’s it.
As far as her saying ‘my dear departed daughter’, you and I both know, she treated Maria like shit and it was only when you married her, Maria escaped her clutches. That’s why she hates William.”

“I know all that.”

“Anyway, William has gone abroad to live with someone named Jane,” Jane said with a broad beaming smile.

“So he has,” I replied, with a big smile on my face.

Chapter 8 – Making Things Legal

But what about us?

Well Jane and I decided to marry with Jane actually proposing to me. Marriage can now be done legally, whether it be a man to a woman, a man to a man or a woman to a woman. I suppose we sort of fall into two of these categories. Obviously, we wouldn’t marry here in the town as this would cause no end of complications and would probably be the source of endless gossip. So, arrangements were made, for a very small private ceremony, the venue a registry office in Aberdeen and as far as witnesses were concerned, Jane arranged with Helen Small, our doctor, to be one of the witnesses and Helen said she would provide another witness who was a friend, a very discrete friend, name of Linda.

The diet I had been on prior to our wedding had worked wonders and along with good, strong, foundation garments, I looked like a woman with a slim build and a good figure. This didn’t go un-noticed by Helen Small who said to me discretely,

“Hannah, you look beautiful. You know if you weren’t with Jane, I think I would be the one pursuing you.”

“Helen, I didn’t know you were like that.”

“Well, actually, I am more like you than you may realise. You see in a former life, as it were, I was Henry, but am now Helen and have been fully Helen for the past five years. It was the best decision I could have made. That is why I am only too happy to help people like you and the late Johanna. I do know what it can feel like being stuck in the wrong gender. So, I am really happy for both you and Jane, especially Jane who was really low when she lost Johanna. I’m so glad she’s found happiness again and I was only joking about pursuing you. You see Linda is my life partner. She is a genetic female, just like Jane.”

“Thank-you Helen for confiding in me. I’m really happy to be among like-minded people and as for marrying Jane, I couldn’t be happier and hope I can make her happy as well.”

My outfit for the wedding ceremony was a straight, knee length ivory coloured dress with matching jacket. Underneath, as I have said already, I was wearing good strong foundation garments with a six-strap suspender belt. My stockings, fully fashioned, nude with seams.

The wedding ceremony went without a hitch. Afterwards, we returned to the hotel where we were all staying, had a few drinks to toast the occasion, then change for the evening ahead. The four of us adjourned to a rather nice, but expensive French restaurant to a table for four which had been booked earlier. So, it was French cuisine at its best, nice wine and champagne to further toast the occasion.

On a trivial matter, I can now truthfully wear my wedding and engagement rings.

Back at the hotel, Jane and I now alone in our room, nay suite, Jane went into the bedroom and asked me to stay where I was in the sitting room. She called me through and there lying on the bed was a white wedding dress, not the one I wore at the ceremony. This was the type that might be worn by a young woman for her romantic white wedding. Also, there was a pair of my ‘special’ panties in white lace, the ones with an opening at the rear. Jane asked me to now put it all on. I didn’t need much persuading, although I needed Jane’s help to get my dress fastened. Jane said she wanted me to wear this dress so that she could de-flower her virgin bride, as it were.
I was hardly a virgin bride.

All I said to that was, “Kinky.”

It didn’t finish there, Jane asking me once again to go into the sitting room now that I was fully adorned, and await her while she changed. I was thinking she was maybe about to change into a similar dress, but no. When she appeared, she was wearing a man’s tuxedo, with men’s shoes and socks and her hair slicked down. What I didn’t know just at that moment was, she was also wearing men’s boxer shorts in which there was a flesh coloured double ended dildo. So, with me dressed the way I was, and Jane dressed the way she was, all I could say was,

“Double kinky.”

We both knew sex was on the cards, but before we embarked on our sexual gymnastics, Jane asked me if we would take a personal set of vows, just the two of us, vows to each other. So, there we were, Jane in her tuxedo, not exactly looking male, but a representation of male and me in a beautiful romantic white wedding gown, looking like a blushing bride, facing each other with my right hand in Jane’s left and my left hand in Jane’s right.

We pledged ourselves to each other, promising to love and cherish each other and to have sex at every available opportunity.
We embraced and kissed each other passionately.

What happened next was not exactly romantic as I was led to the bed, made to lie down and my shoes were removed.
Next, my hands were handcuffed to the bedhead.
Jane removed her jacket, shoes and trousers, the dildo she was wearing popped out of her boxer shorts. It looked just like a man’s erect penis – yummy.
She opened a tube of lubricating gel and liberally spread it over my, soon to be penetrated by, ‘invader’.
Jane came on top of me spreading my legs in the process.
She hooked her arms under my legs lifting them clear and once my skirts were pushed out of the way, my ‘entrance’ was now exposed as that ‘invader’ of Jane’s came nearer.
All I could say, and I don’t really know why I said it, was,

“Master, please fuck me hard.”

Finding the spot, Jane pushed hard,
I was entered. Jane was entered, because, of course, she was wearing a double ended dildo.
I had no option, after all I was handcuffed to the bed.
It was absolutely divine as I was no longer in control.
I had submitted completely to my partner.

We had very little sleep that night. I didn’t even get a chance to put on my new nightdress I had bought especially for the occasion. We ended up just in our underwear, Jane in her boxer shorts and a very tight vest, just for a bit of support, as she put it. As for me, I was still was wearing my white basque along with my white stockings and ‘special’ panties I had put on when I changed into my wedding dress. My basque was supporting my budding breasts, along with a bit extra to enhance them.

We both enjoyed our breakfast later that morning.

Chapter 9 - Getting to The End of the Road

Jane and I made plans for my eventual SRS and decided that I would have it done abroad, in Bangkok in fact. Because my breasts were not going to be as big as I (I really mean we) would have liked, it was decided that I would have them enlarged by implants to about a D cup at the same time. All this was done with the approval of Helen who in fact made some of the arrangements on my behalf. When it came time for my surgeries, when final approval was given, both Jane and I would travel to Bangkok. For her it would be a holiday, for me it would the culmination of a dream come true.

When I was, at last, given the approval that my SRS could go ahead, the hospital in Bangkok was contacted to set up a suitable date for my surgeries. When the dates were confirmed, it was on to the Internet to make the necessary travel arrangements. Our social engagements were put on hold while we were away. My excuse was that I had to go into hospital for an urgent operation for women’s problems, which of course was partially true.

Jane and I were able to spend a few days sightseeing in Bangkok before my operation was due. This was between the tests I had to go through at the hospital before my surgery. I just couldn’t appreciate the sights and sounds of the places we were visiting, to be honest, I was too preoccupied. When we attended the hospital, we met the medical team and the procedures were explained to both of us. This included the aftercare and how long full recovery would take. Further medical checks and tests were done to ensure I was fit enough for the operation to take place. I was declared fit.

So, there I was, on a hospital trolley, in the ante-room next to the operating theatre. I already had been given my pre-med and now had to wait for the anaesthetic to be administered. I was nervous and apprehensive even with the pre-med. It did go through my mind whether I was doing the right thing but that thought was soon dismissed. I knew I was doing the right thing. I was not going to back out now having come this far along the road to womanhood and I wasn't going back to being a man. I would never want to go back. I even told the surgeon, if I should die on the operating table, I want him to complete the operation anyway so that I can be buried and be remembered as a woman.

The anaesthetist entered the room, exchanged the usual pleasantries and told me exactly what she was about to do in rather broken English. As the anaesthetic was being injected into the back of my hand, I was asked to count from ten backwards.

"Ten, nine, eight, seven..."

Staring in the full-length mirror, the reflection coming back was of a woman wearing only a negligee over her naked body, her dark hair touching her shoulders.
She had nice shaped full breasts and a nice womanly figure. A wisp of hair between her legs showed the way to her vagina. Slowly she ran her hands over her body, tracing the shape of her curves. She stared into the mirror.

Another woman appeared next to her, again wearing only a negligee, and said,

"Come back to bed, Hannah dear. You've all the time in the world to admire your new body."

My recovery was long and sometimes very painful. I had to dilate my new vagina according to the schedule I was given.

For the first three months, it was three times a day with the smallest dilator.
For the next three months, it was once a day with the next biggest size.
The next three months, it was every other day with the next biggest size eventually progressing to the largest provided.

By that time, this process was becoming almost pleasurable with me fantasising I was being penetrated by a penis and not a plastic cylinder with a tapered end. I even personalised my dilators by giving them names. Since I used to be named William, I decided my dilators should now inherit that name, or variants of it.

So, the smallest was named, ‘Wee Willie Winkie’.
The next sized one was named, ‘Little Willie’.
The next was given the name, ‘Big Bill’.
Lastly the biggest was named, ‘William the Conqueror’.

At one of my follow up appointments with Doctor Helen, she asked me which dilator I was currently using. Without thinking I said, “Big Bill.”

“Big Bill?” queried Helen.

“Sorry, pardon, what I meant was second biggest,” I said.

“So, have you given your dilators names?”

“Yes.”

“Come on Hannah, pray tell what they are?”

“Well, the smallest is named, ‘Wee Willie Winkie’, the next sized one is named, ‘Little Willie’,
the next is given the name, ‘Big Bill’ and lastly the biggest I’ve named, ‘William the Conqueror’.”

“Oh, that is delightful, especially William the Conqueror. But I hope these are not regrets for your previous life, because I notice they are all named as variants of William.”

“Not in the slightest, being Hannah is my greatest delight. I named them purely as a tribute to the ‘late’ William.”

“I just wish I had thought of naming my dilators when I was transitioning. One further thing, I sometimes hold discussion groups for transsexuals to allow them to voice their fears and concerns. May I use how you have personalised your dilators to lighten the mood of what are sometimes very serious debates?”

“Of course, Helen, feel free.”

After it was considered my ‘new equipment’ had healed sufficiently, it was time to try it out, after all there was no point in going this far, not to. So, come the day and come the hour, the bedroom, our boudoir was discretely lit with perfumed candles, just as before. I was dressed in my long white night dress, soft white lacy bra over my real, albeit enhanced, breasts and white full cut nylon panties with lace inserts, again Jane saying she wanted me to look virginal.

How many women get to lose their virginity twice?

Jane was dressed in a similar nightdress but in black and the same double ended dildo she wore for my de-flowering at our wedding. So, one end was already inside Jane and the other end was soon to be inside me.

I was taken by the hand and led to our bed and before sitting me down, she reached under my nightdress and slowly pulled my panties down. I stepped out of them then sat on the bed. I changed my position to lying on my back and Jane came on top of me spreading my legs. She pushed up the skirt of my nightdress to expose my new vagina and lowered her head to gently lick and wow, it was like an electric shock. She carried on like this for a few more minutes, with me letting out little moans of ecstasy, before resurfacing saying,
“Ready to lose your virginity, again?”
“Yes, yes, I’ve never been more ready. Please take me!”
Jane, lifting her nightdress to expose this double ended ‘weapon’ of hers which to all the world looked like a man’s erect penis. After lubricating the said ‘weapon’, she obliged by very gently pushing slow but sure, and entered me. These was no pain as I was fully entered.
This was divine, this was ecstasy, this was bliss, so different from anal penetration.
I was no longer a virgin, for the second time as a woman, the third time if you include my previous life as a man, if that makes any sense.
I came, we both came, I orgasmed a number of times, presumably female orgasms. As a man I hadn’t realised what I had missed. I just wished I had taken this route years ago. Jane orgasmed with me, we were both in heaven and in love.
So, our sex games carried on as they did before, actually more intense, and taking into consideration my new plumbing, some different positions. I never wore a strap-on dildo ever again, it was always Jane and always a double ended type. In essence I became the female partner and Jane the male and she always entered me.
There was still plenty of costume play with me spending more and more time as a schoolgirl, who was well and truly fucked during every session with Jane often playing a school master. That was one of the ways she liked to use her dominant streak over me.
We agreed that as we were getting older, we should make the most of our time we have left. I suppose when we get too old, we can always write our memoirs and shock the town.
But in the meantime,
I love being Hannah, the little girl.
I love being Lolita Hannah.
I especially love being Hannah, the schoolgirl.
I just love being Hannah.
I AM HANNAH

The End

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Welcome

Thank you for writing this story.

Jill

Angela Rasch (Jill M I)

A very enjoyable story

It reads like an autobiography especially as the author is Hannah, and the heroine of the story is also Hannah. Definitely a 'happy ever after' story with just a hint of drama when Hannah had to fend off an unwanted man.
Welcome to BC; hope you post more stories.

Kudos on your first posted story!

It's easy to hit "Preview" but can be daunting to hit "Save" - especially for the first time. :-)

Thank you for sharing. It was a very heartfelt read.

Thanks for adding your voice to the community. I look forward to seeing more from you.

K@

It is always nice

Monique S's picture

to read a story with chracters of a more mature age.

Too many stories here are about teens or coming off age, even though I am under the impression, that a lot of writers here are not in that age group.

While I can understand feeling sad about what one thinks one missed, fantasising about that lost time fills a present, that has nothing to do with that time and might lead to missed opportunities. I personally would not like to go back to that age, not after knowing what my life can be like now. And if I went back with my current knowledge and experience I'd probably become a radical anarchist. :-)

Like the story, well done.
Monique.

Monique S