Tom is now started on his reluctant journey to become a woman. He has a year to meet the terms of the wager or find a different way to save his wife and his life. The changes are starting and his happy old alpha male existence starting to go.

Chapter 7

Week two was underway, more hair treatment and no shaving. Sam suggested that I should think about getting a gaff and get used to tucking.

We contacted Jackie and she agreed to start with us in three weeks time. Because of the crash diet, I was now permanently hungry. I was just about 5ft 8inches wringing wet and weighed a bit over twelve stone. There were no love handles but there was a bit of surface flab. My target was to get down below eleven stone, hopefully ten and a half, if I could.

An hour a day was spent doing yoga and my reading matter was women’s magazines. Somehow, I had to try to catch up on twenty seven years of women’s knowledge. When we were out walking, or watching television, Sam would get me to analyse women’s make up, dress and hair styles. She had me commenting on what worked and what didn’t. The variety of make up that women wore came as a surprise. The subtle differences in colour, texture and shape of clothes and the effect they had on the look of a woman, had been an area of total ignorance. The differences between what worked for women of each age, was an eye opener. I had so much to learn.

Sam had me start thinking about what would be a good look for me. She also made me think about hair styles. Although my hair was long for a man, it was short for a woman. Sam made an appointment for me at the stylist and between us and the stylist we came up with an urchin cut that was kickass but feminine. The stylist was bursting to know why a butch guy with a broken nose wanted a feminine hairdo.

We did our first shopping trip for clothes. God was that embarrassing. It was bad enough walking around with a corset on. It was obvious to the sales assistants in the shops. The first steps were not too bad. Sam measured me for a bra and persuaded me to look for more knickers. We went to Marks and Spencer and visited the lingerie department. Sam wanted me to choose the style of panties that I wanted but my mind was totally blank. In the end I chose a selection of plain white cotton pants in various styles. Sam picked out a few A cup bras to match. She also put some satin and silk undies in the basket, despite my protests.

The next call was to get some feminine jeans. They just did not fit me right. With the corset they fitted my waist but were loose round my bum and tight round my legs. Sam predicted that they would fit better as time went on. We then looked at skirts, blouses, camisoles and jumpers. I refused to try them on in the shop and did my best to avoid any decisions and choices. The one thing that I could not avoid trying on was a waterproof jacket. It was tight in the shoulders and arms and loose around the chest. Despite my protest Sam said that it would fit me in time. We even bought tights and stockings and then went on to a shoe shop where I bought some girly trainers and a pair of ballet flats.

My most painful part of the week was not only with the electrolysis but with the waxing of my arms and legs. It was painful at the time but the feeling afterwards was so strange. My skin felt much more sensitive and I became very aware of the rough touch of clothes on my skin.

Sam loved my smoothness and lack of a scratchy beard when we made love. Boy did we make love.

The voice coach was good. She showed me that it was less about trying to talk in falsetto. The four main things were talking from the head and not the chest, getting more lilt and song into my speech, how I phrased, and the words that I used. When I got home, Sam was surprised at how female I could sound after only one session.

That evening we were going to attend our first support group meeting. Sam said that I would need to look as if I was in transition. My hair style was now feminine and I borrowed a pair of Sam’s moonstone studs for my ears. I agreed for Sam to put some light make up on me, weird. I put on my one silky cream blouse a camisole and a pair of women’s jeans as my first time dressed in female clothes. Sam also made me wear satin panties for the first time. I felt vulnerable and stupid in my outfit. If I had not had the corset on, there is no way that I could have got the waist band of my jeans to close. The seat was still a baggy and the panties felt tight. The end result was an androgynous looking male. No one looking at me in the light would mistake me as female, especially with the broken nose.

I was consciously playing a part. I did not feel, in the slightest, feminine. I was still me, mucking about.

The meeting took place in the local LGBT centre. What a motley crew. There were some couples there, much older than us. The transwomen were very varied in their look. Almost all were taller and bulkier than their partners. One was over six feet tall but elegant. Others went from looking like a docker in drag to a middle aged housewife who had put on too much weight. Amongst the unfortunates, there were a few younger ones who looked quite feminine and a couple who looked very attractive. It was clear that there were more singles than couples. One of the group, who had completed SRS some years before, gave a talk. She was smart elegant and very female. After the talk we mingled and chatted. There were so many sad tales of rejection and isolation. Some tales were of those who had taken their own lives because of the misery and rejection that they had met on their journey. There were also a very few joyous tales from those that had found love and contentment along the way.

At the end of the evening we said our farewells and that we would meet again next month I had been nervous that I would have to explain myself to the group and make up lies to a group of people who deserved the truth. There was no problem, acceptance was unquestioning.

We were both very sad after the meeting. The bravery shown by the members of the group was humbling. The sadness was because of how much many of them had had to leave behind them and how much hurt they had had to inflict on others including wives and children.

At the end of the week I got a letter asking me to attend the clinic of the endocrinologist for an initial check.

The gaffs arrived and Sam suggested that I start getting used to tucking. She also suggested that I start wearing female underwear fulltime. Everything seemed to be rushing at me. I wanted to leave it a little longer before I went that far. Sam had her way and I underwent the discomfort of the gaff. My balls were pushed back into me, very uncomfortable, and my old man tucked back. The only good thing was that my panties now fitted snugly. I was aware of the discomfort of the gaff all day and it was such a relief to take it off at night. I thoroughly enjoyed having a good rummage until things felt back to normal.

By the end of week two, I was becoming far more aware of things feminine. I was starting to get more knowledgeable about clothing and makeup. I got some strange looks when I unconsciously practiced my female voice when I was out. A lovely smile and a wink were a gift from an obviously gay male. He even looked me in the eye and tilted his head as if to ask me if I was interested. That was the first time to my knowledge that I had ever appeared on someone’s Gaydar. My posture was very upright and we had got the waist down another inch to 26 inches. The corset was not at the front of my mind, until I had to bend or twist.

Chapter 8

Week three saw another visit for electrolysis, more yoga, more dieting and more voice practice. At the same time we had been tendering for a couple of new contracts. We were both going flat out. I had lost four pounds in two weeks and my face was looking much smoother. My dress and makeup knowledge was growing. We went shopping again and I actually picked out a few soft sweaters and camisoles that complemented each other.

We purchased a basic makeup set for me and Sam and I practiced some simple make up in the evenings. By the end of the week I was wearing camisoles and soft sweaters rather than shirts. That weekend we had been invited to a party. I reverted to masculine wear and Sam wore a very sexy outfit. We had a wonderful night with our friends. The only problem was Doug. He was cold and distant and I felt that had it not been for patient confidentiality, he would have outed me there and then.

When I went to the clinic, I gave what seemed to be copious amounts of blood. I was measured, weighed, scanned and x rayed. My body was manipulated and probed endlessly. Hair and semen samples were taken and by the end I felt exhausted both mentally and emotionally. It was going to take a week for the samples to be checked and get the results. Going private had speeded things up massively. Had I gone through the NHS it would have taken so much longer.

The third week in many ways saw us settling into a routine. I was working at home wearing androgynous outfits. I was selecting my own outfits from my small stash of clothes and I actually tried on a pair of the silk underwear that Sam had bought. They felt slinky and made me think of sex every time I moved. I was hooked on them if nothing else. I was practicing my female voice as much as possible and forgot when talking to one of our clients. The client thought we had taken on a new member of staff. I was asked if Tom was available, so I put the phone down, picked it up and answered in my man’s voice.

We had not been to see my mum and dad since before we started. Dad was fine and the same as always, apart from making pointed comments about my ear studs. Mum kept looking at me in a thoughtful way.

“Tom, have you been losing weight?”

“Tom, that is an unusual hairstyle for you.”

“Tom, when did you start wearing ear studs?”

“Tom, your nails are looking a bit long, is there anything we ought to be talking about?”

Three weeks in and she had twigged something was happening. I didn’t come clean then, but I knew it would not be long before she would need to know.

Into week four and the routine continued. I was starting to become proficient at simple make up, my speech was confidently female and my knowledge of fashion was growing. More visits for electrolysis, more dieting, more yoga and more hormones. Towards the end of the week I had a quiet moment reflecting on what had happened so far. I looked in the mirror and was very aware of the small amount of make up round my eyes. I also thought about the surgery that I would be having the following week. Suddenly it all became too much and I started sobbing. I could not stop. I never cried and now I was a soggy wailing mess. Sam heard and came to me. We clung together and she stroked my hair and gently rocked me. I felt like a four year old who had been told that Christmas was cancelled. I had never felt emotional in this way before. I had never sobbed before.

“Welcome to the world of women Tom. Hormones 1, Tom 0.”

It was the first time I had been aware of the effect that the hormones were having on me. I just wanted to curl up and be comforted. Even then it had still not hit home. I was playing a part. It was an exercise. It was not real at a fundamental, life changing level.

Week five was due to start and first I would be meeting with the endocrinologist and then, at the end of the week I would be having surgery on my face. Come the weekend, people would know something was happening. We decided that I had to tell my parents. Sunday lunch was the chosen time. My mother was like a crack detective, ready for the killer interview.

“Now Thomas, you have obviously been hiding something and it is time to spill the beans. Are you ill? Is Sam pregnant? Is your company in difficulties? Have you been letting yourself and Sam down and got involved with another woman?”

We sat down and went through the whole sorry tale.

“Why don’t you go to the police? What Justin is doing can’t be legal.”

“I’m afraid it is mum, we have had it checked out every way.”

“But you can not do it Thomas. What you are setting out to do is cheat and lie to some poor unsuspecting man. You are aiming to trick some poor soul enough to fall in love with you and propose marriage. Then you are going to drop the poor man and break his heart. I have brought you up to be more caring than that.”

“Mum, I have no option. We need to buy time to find a way out. I hope it won’t come to getting some poor man to fall in love with me.”

“If you and Sam want to go through with the feminization, then that is entirely up to you, but I do not condone cheating others.”

It surprised me that she had not baulked at the hormones and surgery. It was only the moral issue that she stuck at. Dad was predictably mad at the situation. Once we reassured him that we were still planning to provide him with grandchildren he calmed down for a short while. He was soon making plans as to how he was going to arrange Justin’s death. Even Mum thought that was a better solution than conning some poor soul.

It took a lot of persuading dad that killing Justin may be justifiable, but was a non runner. We would be the obvious suspects, even if we could make it look like an accident. We told mum and dad that we still had 47 weeks to find a way out.

After establishing that we were trapped for now, mum was full of questions, wanting to know what I was going to do, how I was going to do it and what the residual effects would be. It was late when we finished talking and went home.

On the Monday, Jackie started with us. Her delight at becoming part of the team, was infectious. For the first time in weeks I felt happy and positive. Jackie had done some freelance work for Justin's company in the past and had hated it. She thought that Justin's work was sloppy and of poor quality. He cut corners everywhere, but he seemed to invest large amounts in procuring contracts and entertaining the buyers. Jackie had heard rumours that the software installation on the project behind the wager was behind schedule and not going well.

Justin was a very capable software designer, but lazy and with little pride in his work. He had always been wealthier than me. The reason being, that his parents had been killed in an accident when he was at university. The compensation cheque, the insurance money and his inheritance had left him very comfortably off. Two years later his grandmother's brother died in Australia and left him at least another fifteen million pounds. Justin mixed with some pretty iffy people but he had the bucks to pay his way. His net worth was well over twenty million pounds to our knowledge. The income from his company was pocket money, his investments elsewhere kept him in luxury. Jackie suspected that the software company may be more of a front to launder money from his other activities.

When we told Jackie about Justin's link with the Thai brothel and the disappearing young tourists, she was not surprised.

Our discussions started an idea of how we could get out from under Justin. Finding enough dirt on Justin could enable us to get him arrested and put where he could do no harm. Jackie knew a fair bit about his internet links, servers and local computer systems. With that knowledge we could try to get into his system and find some incriminating evidence. We could also dig into his contacts and his other businesses.

I felt a lot more cheerful now that we had the seeds of an idea of how we were going to fight back. The only problem was that none of us were capable of more than very simple hacking.

Chapter 9

There were four big events in week five. The first was unsettling and made me very nervous. My nipples had started to get puffy, sensitive and painful. It was another wake up to what I was doing to myself. The pain I could stand but the constant rubbing as I moved was driving me mad. Sam suggested that I start wearing the training bras that we had bought. It seemed ridiculous but I went ahead and did what I was told. They were a little tight but with full adjustment we could make them comfortable. I could no longer wear shirts without the straps showing. I started wearing baggy sweaters all the time when I went out and a simple camisole top when at home.

The bras did their work. It might have felt strange but the irritation was gone. It was interesting when my nipples were exposed, they tended to become rigid. The other thing was that my areolas had started to expand a little and darken. Sam and I had another visit to Marks and Spencer. This time I was a bit more adventurous in my choice of colour, styles and materials. I thought that I may as well enjoy the sensation of wearing women’s underwear.

The second event was my visit to the endocrinologist. For the visit I wore my ladies jeans, panties, bra, camisole and cashmere sweater. I also wore discrete make up, my best ear studs and a bangle round my wrist. I was definitely on the female side of androgyny. My beard was not showing, my skin had started to soften and I had lost half a stone. My muscle definition was just starting to soften. All that said, with my broken nose, masculine face and muscular build, I looked like a very butch woman. My mannerisms and behaviour were still normal male.

"Well Thomas, may I call you Thomas?"

"Tom will be fine."

"Well Tom it would seem that you have been somewhat foolhardy. Your samples showed very low levels of testosterone for a male and levels of female hormones that would have been high, even for a pregnant woman. You have been self medicating."

"Guilty as charged."

"Before we go any further I must emphasise how dangerous and foolhardy it is to self medicate. I do not know how long you have been doing it, but you are very lucky. All the other tests show that, so far, you have not damaged your liver or your heart or in fact any other organ. Whatever decisions we make today, you must promise to follow medical advice and guidance."

"I was desperate. I felt that I had no other option than to self medicate."

The doctor then quized me as to what I had taken, in what quantities and for how long. A thorough examination followed. He took it in his stride that I was wearing female clothes, it seemed that it was what was expected.

"At the moment your sperm is still active and numerous. The longer you take hormones the more your fertility will decline. You could be effectively infertile in four to six months. Have you saved some sperm for future use?"

"Yes, we did that a couple of weeks ago."

"Your breasts are the very early stages of budding. I see you have started wearing a bra. How do you feel about this growth?"

"Happy as a sand girl, I can't wait for them to develop."

"Breast development in MtoF transitions often disappoints. You may end up with cone shaped breasts, uneven development and you may not get beyond Tanner stage two. Are you intending to have breast augmentation?"

"Yes, in about five months time."

"Hm, that may be a bit too soon. It would be better to see how your breasts develop before augmentation. At the very least, make sure that your implants can be changed or altered. Breast growth can continue for years in some cases. What does your wife think of what you are doing?"

"She is very supportive. She knows exactly why I am doing this and has promised to support me all the way. Whatever the outcome for me, we intend to have at least two children."

"What about your sexual orientation?"

"I love my wife and have no intention of being with anyone else, however much I change."

"Have you ever had any sexual relations with a male?

“No”

“How far do you want to go? Do you want an orchiectomy, full SRS?"

"I don't know yet, but I do know that I must be able to live as a woman."

"Do you still have heterosexual intercourse with your wife?"

"Yes"

"Have you had any problems with erectile function?"

"No."

"You do realise that if you continue down this track, you will eventually become impotent, you will become chemically castrated, your testicles and your penis will reduce in size?"

"Yes"

"And you are content for this to happen?"

"Yes"

In giving the answers I expected my nose to grow. There was no way that I wanted to travel too far down the transition route. I wanted to keep my cock and balls in all their glory. I wanted to stay as a virile manly man. I wanted to go no further than I absolutely had to. The sooner we could find a way out of the mess we were in, the better. I knew that I was consciously running towards something that I dreaded.

We talked on for another half hour. Before we parted, he gave me injections in both hips, some pills to take and made me an appointment to see a psychiatrist in one weeks time. He made me promise to bin all the illicit drugs that I had. He finished by saying that he wanted to see me in two weeks time and further hormone treatment would be dependent on the psychiatrist's report.'

Sam wanted a blow by blow account of my first session with the quack and was not at all sympathetic about the ache in my but from the injections. That night when we made love, it was the first time that Sam had made a thing of playing with my sensitive nipples. It was such a wild feeling that I came far too quickly and my orgasm was intense. I could get to like having women’s nipples.

The following day was cosmetic surgery time. I arrived early at the clinic and after a further examination, I was prepped for surgery. The surgeon had decided to use a general anaesthetic and I did not come round until much later that evening. My whole head ached. It was so bad, that it was difficult to locate the seat of the pain. I was sick in a pan and only vaguely acknowledged Sam before a sedative sent me back to sleep. When I woke in the morning, I felt rough. I had bandages everywhere round my head. The surgeon told me that he was extremely pleased with the outcome and sent me home with some industrial strength painkillers. I was to return in a week to have all the dressings removed.

When I looked in a mirror I was reminded of the invisible man film. All I could see looking out at me were two black eyes. I looked as though I had gone ten rounds with the heavy weight champion. I just hoped that the changes would be reversible if and when we got Justin off our backs.

Chapter 10

That weekend we worked on ideas of how to get inside knowledge of Justin’s operation. Jackie had decided that she wanted to be part of the “get Justin” team. The first target was to trawl through all the public information that we could get and then back that up by hacking into his systems.

The biggest problem that we had, was a lack of hacking knowledge. Jackie gave us a solution when she told us about her partner Tim. He was a compulsive hacker and he was very good at it.

It was clear that, with our increasing workload and the amount of time I was taking away from the business, that we could do with extra hands. Jackie agreed to talk with Tim and see if he would join us. Tim was a brilliant computer wiz, but he did not have the focus or desire to set up his own company. We could afford to take on an extra member of staff and it would give me more head space and time to get on with my transition.

We were now into week six. Sam noticed that my muscle tone was becoming less defined. My shoulders, arms and neck were looking slimmer. My bum was no longer buns of steel and had softened a bit. My puffy nipples continued to ache. My visits for electrolysis were on hold while my face healed and I was now wearing my training bra as a matter of course. When I looked in the mirror I could see the bandages on my face and from the waist up my clothing was quite feminine. It was a constant reminder of what I was doing to myself. My sleep patterns were now very disturbed and I spent my waking hours worrying about my direction of travel. Sam felt helpless. She could sense my discomfort but could do little practical to make me feel better.

One thing that I noticed was that it was getting easier and less painful to put the gaff on. I would also go a whole day without feeling the need for a rummage.

I still moved and acted like the man I was. Apart from modifying my voice my behaviour was unchanged. The underwear would make me stop and think now and again and the corset was difficult to forget. I practiced the make up and read women’s magazines, but I was still me. The only change that I had found pleasant was the softness of the camisole tops and the silkiness of the panties.

Tim came in to see us on the Monday and said that he would be delighted to join the team. He was excited to have an excuse to hack away without being nagged by Jackie. In the short run, he had some outstanding work to complete, but he was going to join us for two days a week to start with.

In our house we had a large studio. The previous owner had been a renowned potter and this had been her workshop. The studio had power and heating and we had installed state of the art computers and internet connections. This was where we worked. It was a large area that we had designed to be our ideal work space. Our comfort was provided for by the comfy chairs and sofas. Our entertainment included sound systems, a dart board and a table tennis table. The inner programmer was catered for in a well equipped galley kitchen. The walls were covered in white boards where we mapped out our ideas.

I started finding as much as I could about Justin’s companies. Initially, I had thought that Justin’s software company was his only registered company. Not so, it was a subsidiary of a bigger company and he appeared to have directorships of several other companies. The next thing was to map the companies, what they owned, what they had returned as accounts, who the directors were and what data I could get from companies house.

The first thing that struck me, was the list of people who kept recurring as directors. The next step was to google both the directors and the companies. It was clear that several were shells and some were holding companies in tax havens. The directors were an interesting crowd. Two were straight forward, they were Justin’s accountant and his lawyer. The remainder were a mixed bunch. There were several names that were asian and some that looked eastern European.

The research kept me busy until my meeting with the psychiatrist. I had decided to look as feminine as I could for our meeting. I wore my gaff to give me a smooth line in the crutch and wore my best embroidered stretchy jeans, they were a much better fit around my hips and waist now. I could not wear the full corset with the jeans, so I wore a cinch around my waist. I wore my training bra, a camisole and one of my newly acquired soft polo neck jumpers. The neck line covered the bandage on my throat.

I went with Sam for another shopping trip and purchased a pair of jeans boots with a one and a half inch heel and a fitted three quarter length jacket. I wore the boots away from the shop despite the strange looks I had received from the sales assistant. I was just able to fit into the top end sizes of the normal female shoe sizes. I put on subtle but effective make up by myself. It was becoming a habit to put a little make up on each day. It was weird standing next to Sam at night cleaning our makeup off and moisturizing.

Had it not been for my face being covered in dressings and the bruising now starting to turn yellow, I would have looked like an unremarkable butch female.

I had been practicing my female mannerisms, voice and movement. It was becoming possible for me to get into character some of the time. Mostly I would forget and revert to my normal behaviour.

The psychiatrist was a good looking youngish woman with a very direct manner. I was very glad that I had been very thorough in my research and that I had worked out what my back story was. I was so into my story that my gender dysphoria was starting to feel real as I described it. I was so into my story that at one stage I was overcome by a feeling of helplessness and burst into tears. This was getting scary. What was real and what was a performance? At the end of the session, the psychiatrist confirmed an interim diagnosis of gender dysphoria. We arranged to have monthly monitoring sessions. She struck me as a very nice supportive person.

When I got back to base, Tim asked for us all to get together.

“Sam, Tom, you know that you suggested that I have a trawl through the recent systems that you have designed to familiarize myself with your methodology. Well, do you ever access your files and make modifications when you are off site?”

“Only from our tablets and occasionally from the big laptop.”

“Are you sure that you have never accessed the system from any other computers?”

“Yes.”

“I thought so. I think you have been hacked. I found traces that your files have been accessed by at least one other outsider. Whoever it is, they have covered their tracks well.”

“Shit, I bet that was Justin. I wondered how he was so knowledgeable about our work. Can we do anything about it?”

“I can try and trace who has hacked, but the first priority is to increase you protection. I will get started straight away.”

It was becoming clearer by the day that Justin was not only a shit, but was probably into a greater variety of illegal operations than we had originally thought.

At the end of the week I went to have my dressings removed. The results were startling and un nerving. Sam’s immediate comment was that I looked like my seventeen year old self only more female. If you discounted the residual swelling and the discoloration of the bruising, there was an innocent young face looking out. I could not stop studying my face in the mirror. Gone were the broken nose and the strong jaw line. The face was softer, the eyes now looked bigger and for some reason the lips looked fuller. I was looking at a face that could even be called pretty. It was so strange. It was still me but definitely not the old me. Sam could not stop inspecting my face.

It was not possible to judge any change in my forehead because it was still a little swollen. My jaw line was noticeably different. It was much less strong. It looked as though it had much less width. If I looked at it as male it looked young and immature. It looked all wrong. It was not me as a younger man, it was a female version of me. The nose was more of a difference. It had first been broken back when I was sixteen and had suffered further damage since then. The nose that I looked at now, was one that I had never seen on this face before. It was not me. I could recognize myself, but it was a very unsettling and alien version of myself. Apart from the bruising and swelling, I looked just like the surgeon had showed me on his computer. It had not really sunk in that it was how I was going to end up. I was no longer me, I had a female looking face, strong, but female.

When we made love that night, Sam kept closing her eyes. When we cuddled afterwards she told me that it had felt a bit strange. When she looked into my eyes, she kept seeing a woman and it kept disconnecting her from what we were doing. It also felt like she was being unfaithful to Tom, making love to this different person. When she closed her eyes it was still me and it felt right.

It worried me that after only six weeks, Sam was starting to feel that I was different. I knew that I looked different but I did not feel different. I was still that good old bloke Tom inside.

Chapter 11

Into week seven and our lives were changing more significantly and faster than we had anticipated. Sam had confided in her friend Sally about what was happening and why. I had also confided in my old friend Don. Both were sympathetic and offered any help that they could. We knew that we could not tell the rest of our friends and acquaintances or else Justin would soon get wind of it and call in the wager.

It was clear that with my facial surgery, the loss of my beard and the softening in my facial features from the hormones, that something was afoot. What we had decided was that we would tell people that I had a hormonal condition that was affecting me physically and mentally and that I would be undergoing changes that Sam and I would have to live with. One or two friends looked at the new me and shied away. Most were curious, because I looked so different, and asked question after question. It was difficult to come up with answers, to the barrage of questions, that made any sense.

Sam and I talked it through and decided that it would be easier to avoid our old haunts and seek out new places to go. We could drop out of our old circle until we could get out from under Justin. We would keep in touch with Sally and Don. We also had Tim and Jackie in our inner circle. I had met up with Rose, my contact from the transgender chat line. Rose was around forty years old. She was what one might call a handsome woman rather than being pretty. She stood a little taller than me and was dressed immaculately in a skirt, blouse and jacket. She wore conservative heels and her hair, make up and jewelry spoke of a successful and confident businesswoman.

When Sam met her they struck up an immediate friendship. Rose was warm and wise. She had married young and was had been the father of two children. At the time she had married she had been struggling with her gender issues. Her life became too problematic when she was in her late twenties and she came out to her wife. She had qualified as an accountant and was already a junior partner in an accountancy firm. She decided that she had to become the woman that she had resisted all her life. The accountancy firm supported her and so did her wife to start with. Rose’s transition started and over a two year period, she took hormones and lived as a woman. She had undertaken a small amount of cosmetic surgery but nothing major at first.

Her wife found that she could no longer live with her after she had undergone the full sexual reassignment. The separation was amicable and Rose still had a lot of contact with her two girls, who were now both at university. Rose’s wife had remarried ten years ago. Rose, herself, had no permanent partner but she had a couple of very good male friends. She said that they were friends with benefits and, for her, it was the perfect arrangement. She liked living on her own. She had a lot of good friends and enjoyed music, theatre and the arts. She was happy, contented and successful in her career.

It was good to meet someone who was so together. She had already been a font of information and advice. She did, however, make it very clear that the road that I was on would certainly be rocky.

We had our first indication of things to come when I had a disturbing phone call from an erstwhile rugby team mate. He phoned me up to say that he had heard that I was turning into a disgusting, queer ladyboy and that it was in my interests to stay away from the rugby club. He hinted that there could be violence if I didn’t. Two days later another old friend hit on Sam for a date saying that now that I had gone queer he could show Sam what a real man was like. We were only seven weeks in and it was all kicking off.

I had my first follow up visit to the endocrinologist. After a full examination and a testing of blood and urine we sat down for a chat.

“Well Tom, you seem to be a very lucky person. Your testosterone levels have reduced right down. Your body seems to be taking to female hormones as if you were born a woman. I think that you will be lucky that your development of secondary female characteristics will be both rapid and full. You are a rare person in my experience.”

I’m not sure that I was very pleased with his congratulations. He gave me follow up shots and arranged for me to see him in four weeks time.

I had been wearing the gaff and the corset for six weeks now and in my best ladies jeans, I already looked convincingly female. I may not have had a bust, but with ear studs, a female face and haircut and my gaff and corset, I was addressed as madam more often in shops. I habitually used my female voice now, but my behaviour and mannerisms were still noticeably male. I was self conscious about the image I presented. I think a lot of people suspected that I was, either, a guy in drag, or a very butch female. If I got angry or agitated I forgot my female voice and became very alpha male. I had the look but not the behaviour.

At our transgender support group meeting I was just treated as one of the gang. Both Sam and I found the meeting sad in so many ways. The people who were transitioning but still looked very male appeared to us heroic but sad. We had both come away from the meeting feeling depressed despite the courage and optimism of some of the group members. We decided not to go again.

Now that my face was healing I restarted my electrolysis. It was a lot less painful now and any regrowth was much finer now.

We had three new enquiries about potential contracts and with our normal maintenance work, all four of us were going flat out. We had no time for any research into Justin’s affairs. My progress into being able to pass as a woman was ahead of the target plan that we had drawn up in every way except my mannerisms and behaviour. I don’t know whether I was more pleased or more worried. I had now lost over ten pounds in weight and was starting to look slim for a man, but chunky for a woman. I had lost strength but the aerobics and yoga had made me much more flexible.

At the weekend we went out with Tim and Jackie for a meal and then onto a club. I had dressed as androgynously as I could and tried very hard to act in a female way. I was called miss or madam most of the time. I was getting upset and wanted to call it a day but the others said that if I was going to continue with the plan, I would have to get used to it. I suppose that I must have looked like a flat chested woman, who did not dress attractively and had fairly masculine mannerisms. I did not get hit on by any men but Sam did, much to her amusement and my annoyance. It was clear that I was agitated when men approached her and more than one man referred to me as a jealous dyke. Some just referred to me as a tranny. It was not a pleasant experience. I longed to be able to get back to being good old masculine me.

Into week eight and we were still busy with presenting our proposals for three new customers. We were going flat out. I was painfully aware of the tenderness in my nipples and wore a bra as a matter of course now. I was finding it impossible to get into my old jeans and chinos now. My waist was much slimmer but my bum and hips seem to have expanded. I had bought some loose sweats that I wore around the house and the studio. I had also bought a few more pairs of slacks and jeans that fitted my newly developing shape.

Our love life was as wonderful and active as ever, but Sam had got into the habit of closing her eyes when we made love. I already knew why and I found it troubling. My nipples were now very sensitive and I loved the feeling when Sam played with them and when she licked and kissed and sucked on them. We would have lovely cuddly times when we kissed and played with each others nipples. Sam liked to keep those times separate to when we made love. After we had made love one time she told me that I smelt different now. It was almost like making love to a different person.

This whole experience was strange. In some ways it drew us closer together, in other ways it pushed us apart. Sam and I talked much more freely about what we were feeling and thinking. Sam was more open about her wants and her fears. She was also much more confiding about her emotions. I found that I was happy to talk much more about my feelings. The only draw back was the feeling that my bodily changes were unsettling her. She was very supportive, though, continuously coaching me about my mannerisms. I could get the female me working for chunks of time before I forgot and reverted to Tom. It took too much concentration.

Chapter 12

Tim had taken time out to both strengthen our defences against hacking and to see if he could find a way into Justin’s system. I had got as much information as I could from a company search of Justin’s company. It surprised us that the turnover recorded for his company was many times what we expected. Our company turnover was now up to just over two million and growing fast. Justin’s company was showing a turnover in excess of twenty million. I knew that we had beaten Justin to most of the local contracts so I could not see how he could post such a large turnover. Tim undertook to try and see if he could hack into either the accountants or Justin’s systems.

During the week we had two pleasant surprises. One of the rugby crowd, John got in touch and suggested that we meet for a drink. I wasn’t sure how to deal with his suggestion but agreed to meet him. With my changed face and changing body, I decided to wear clothes that were female or at best androgynous, even when I went out. I wore female clothes at work as a matter of course. I had not tried wearing skirts or dresses, it was always trousers or jeans. The softness of the tops, however, and the slinky snugness of the panties were a pleasure. I had started to check how I looked every time I passed a mirror. I was already looking slightly more girl than boy.

When we met John was all smiles and gave the same old man hug as normal. I suspect that in doing so he could feel my bra strap. He was unphased.

“Hi Tom, I hope you don’t mind me getting in touch but I have heard a bundle of rumours about you.”

I was wary but I decided to let him continue.

“I can see now that the rumours were at least partially true. I will come straight out with what I was going to say and you can either tell me to bugger off or to stay. I believe that you are undertaking either a partial or full transition from male to female. I want you to know that I had a cousin with whom I was very close, he or she suffered severe gender dysphoria and started to transition. I supported where I could but she met with such aggression and opposition from family friends and colleagues that in the end she could not cope and committed suicide. I knew that I should have done more to help. I want you to know that, if that is what is happening, then I am in your corner. I hope I haven’t made an awful mistake.”

I was moved by his offer of support and to my severe embarrassment, I nearly burst into tears. After the comments from others at the rugby club, this was so nice. It took me a few moments to gather myself. I then told John an edited version of what was happening. Kind as he had been, we already had too many people knowing the full story.

During the same week one of Sam’s friends also said to her that if I was transitioning she supported the two of us. We had not lost all contact with the outside world.

Towards the end of the week we got the good news that we had been successful with the smallest of the three bids for new work. Our reputation was growing and we would probably need to take on more staff if the growth continued.

Sam and I continued our lessons in feminine behaviour, make up and fashion. I was now getting to the stage that I could recognize and describe colours. I could tell the difference between styles and types of clothing and I was becoming competent at make up. My nipples and areolas had continued to grow. They were still very sensitive and painful. Sam reckoned that there was a small amount of swelling behind the nipple. I was glad of my training bra. I was continuing with the electrolysis and I was getting less and less repeat growth. My face had softened and with the swelling and bruising going, I now had a face that looked young and very female. Whenever I caught a view of myself in a mirror or a shop window, I did not recognize myself. My mannerisms were becoming a little more unconsciously female. Far fewer people clocked me as male. It only really happened when I lost concentration. I noticed that both Sam and Jackie were becoming more gossipy with me. They were unconsciously starting to treat me as a woman.

The strangest time of the day was both morning and evening. When I got up in the morning I no longer had to shave but I brushed my teeth and put on some light makeup. The hand hat I could see had painted nails. It looked as though it belonged to someone else. The face that I saw in the mirror was not me. It felt wrong. In the evening I saw that same face in the mirror again.

During the day, I definitely did not feel feminine in any way. I was very consciously playing a part. There was so much going on that I was able to play the part without having to stop and think too deeply about it.

Tim had some limited success with his hacking. He managed to get into Justin’s system but could not crack the areas that were encrypted. What he did find however was a more detailed copy of Justin’s accounts and access to some of Justin’s emails. The accounts were not very detailed but they did show what parts of the world the turnover came from. There was significant income from Thailand, USA, Jamaica and France. There was no indication as to what the turnover was based on. From Jackie and Tim’s experience working as freelancers for Justin, it was not feasible that these were software contracts. The turnover credited to the UK was far higher than was realistic.

We thought that we already knew the probable source of the Thai money. The income from the brothel, bar and trafficking, probably accounted for that. It was clear to us that Justin was using the systems development company to launder his nefarious income. We needed to be able to dig further and try to build a case that we could take to the police.