Chapter 1

“Shit, shit, shit, Tom, how the hell did we let ourselves get into this situation?”

“Greed and overconfidence, love, greed and overconfidence, we only have ourselves to blame.”

“Yes, but we knew that little shit Justin was not to be trusted. Sooner or later he was going to catch us out.”

Justin had originally been my closest friend, right from primary school days. We had always been hugely competitive and I generally had the upper hand. We had indulged in dares and bets right from when we were nine or ten. We would race each other on foot, on bikes, in the pool and in boats. Competition was everything.

The loser would have to pay a forfeit and the forfeits escalated over the years. At first it was things like kissing the school bully (very painful, I lost that one) or stealing girls knickers and wearing them to school, shouting out a rude word in class. The forfeits were always getting us into trouble and giving us a reputation. It was fun at the start.

At the grammar school the challenges escalated. They ended up with us both having criminal records. Mine was as a result of ending up having to walk into our local police station, naked and ask the time. I was fourteen years old. I could have been done for indecent exposure but ended up with a formal caution for wasting police time. Justin ended up with a conviction for breaking and entering. The forfeit was to get in to the sacristy at the local church and liberate a bottle of communion wine. The dozy git chose to drink a bottle and a half of the wine and pass out. He was found by the verger. If he had not been so foul mouthed and aggressive, when he came round, he would probably have got away with it. At the age of fourteen he had a conviction for breaking and entering.

Our wagers carried on through university and later, when we each went independent as software designers. The wagers escalated and Julian got more underhand and sneakier with each wager. One major falling out was in the first year after university. Justin reneged on a £500 bet saying that the terms of the bet were different than we had originally agreed.

As a result we started to specify the terms of the wager and the forfeit in writing. We then got a lawyer friend to turn the wager into an enforceable contract. It was no problem because I won most of the time. Every time I won, Justin would come back to me with another wager. I was reluctant to continue because the wagers kept escalating. Justin just kept badgering me saying that it was only fair to give him a chance to gain back some of his losses. I had to be very careful every time I accepted a wager. Justin had become extremely devious. Fortunately I understood him well enough to see the traps that he had set for me.

Justin had started to get badly out of control when we were at university. He persuaded me into a bet that in the long run turned out wonderfully for me. There was a very attractive girl called Samantha, in the second year with us. She was very shy around guys but very bright and as good as I was at computer sciences. The bet was to go on a date with her and return with an article of her clothing.

I thoroughly enjoyed chatting to her and fell for her straight away. I knew she was shy and I did not want to spoil my long term prospects by rushing things. Justin, the devious bastard, came in apparently grief stricken that his mother had been diagnosed with terminal cancer and only had weeks to live. He went straight to Sam and broke down in tears in front of her. Sam, being the lovely person that she is, started to console him. From that point he played her like a violin. He kept escalating the grief and needed much care and attention. He eventually got her to his room and fed her a drink with a date rape drug in it. When she was out of it he stripped her and took photos. He kept her slip when he reclothed her. When she came round again, Justin told her that she had passed out and that he was just about to call an ambulance when she came round.

When I found out what Justin had done I paid my debt and then hit him as hard as I could. He had a beautiful shiner and I had a swollen hand. I was the winner in the long run. Sam was now my partner, my wife, my lover and my best friend.

The stupid bet that we had lost was one that we knew for definite that we would win. I should have known that something underhand was taking place. Justin had pestered us into a series of escalating wagers, each of which he had lost. The previous one had been a competition for a contract. Not only did we win the contract but we won £20,000 from Justin.

Justin had pestered and pestered to have another wager. I had told him that it had got totally out of hand and that we were never going to have another wager. Justin went on and on about the unfairness of ending after he had gone through a long losing streak. He claimed that one last wager was only fair. His suggestion surprised us. We were both bidding for an NHS project. The project would be the biggest we had ever gone for.

We had done more groundwork and research on this project than ever before. We knew that our bid was very competitive for price. We had discussed our bid at length with the end users who were delighted with our proposals. The finance people were pleased with our financial proposals and their IT department thought we were great. All it needed was for the procurement committee, or more importantly the committee chief, to sign on the dotted line. It was as close to a done deal as possible.

Justin’s wager was his house against ours. We had a lovely large house with a secluded garden and a large studio which we used as our work space. We had bought the house a year ago, off the back of our profitable and thriving business. We had had five years of steady growth and profitability and the bank loved us. The house was worth nearly a million pounds, the value had fallen slightly over the last year because of the recession. The house was mortgaged to the bank for a bit over £900k. We thought that we would only be wagering the £50-100k worth of the house that we actually owned. A huge bet, but we had over £50k in the bank, and could raise the balance by selling cars and borrowing a bit more money.

What fools we were. First we had not even considered that we could lose the bet. Secondly, we had stupidly misread the bet. The bet was for the full, unencumbered value of the house, not the balance. We owed Justin the full value of the house. Justin’s lawyers had moved fast to sequester our company as security. In order to meet the debt, Justin could strip us of our only asset of sufficient value. Justin effectively owned us.

Our company owned all our intellectual property and the income to come from the systems that we had designed. We were both contracted to the company for all our future developments for the next five years. We had become his slaves overnight. He owned us lock stock and barrel. We consulted our lawyers to see if there was a way out. We looked at the possibility of selling our company or our intellectual property. The lawyers confirmed that with Justin’s seizure of the company, he had blocked our ability to liquidate it as an asset. They only confirmed what idiots we had been. We would be slaves for five years and at the end of that time we would be penniless and starting again from scratch.

It would hurt like hell but we could do it.

We steeled ourselves to accept defeat when we had a message that Justin wanted to make us an offer. When we met Justin he was attended by his lawyer and two large, ugly men. It was just as well for him as I think I would have beaten him to a pulp otherwise.

He said that he wanted to offer double or quits. If we lost then we would have to hand over the business and remain working for him on our existing contracts for ten years rather than five. If we accepted the wager, he would release our company and other assets back into our hands for the duration of the wager.

The terms of the wager were typical of Justin. He had developed into a very twisted and vicious person.

“Right my lovely friends, the broad terms of the wager are as follows. You will have to get divorced and you will have one year to find a man and get engaged to be married. The wedding has to be already booked before the year is up. The man must be heterosexual, healthy, under 45, a British citizen, worth over £250k net and know nothing about the wager. The wager includes having to have spent at least three nights in the same bed with the man before the year is up.”

“There is no way I am letting Sam go through with that.”

He had a wicked grin that split his face.

“Who said anything about Sam. It’s you that will have to meet the terms of the wager.”

“What? You must be joking. I am a man remember.”

“Well you may be for now, but not for long.”

Justin was laughing when he said that the man had to believe that I was a woman. He told us that we had two weeks to decide.

Chapter 2

I was as angry as hell. I started listing down our options.

1. murder Justin (Satisfying but probably not practical)
2. work out the five years and start again
3 .accept the wager
4. run away (Would not be a long term solution)
5. declare ourselves bankrupt (Would not get us out from under)
6 find something on Justin to put him in jail
7 find a loop hole.

That left us four options. The last two were speculative. That left giving in and being slaves to Justin for five years, or accepting the ridiculous wager.

I was still raging away, saying that I would take on the wager just to spite him, when Sam stopped me.

“Tom, don’t be so bloody stupid, there is no way that you would want to stop being a man. Just think before you start contemplating being a total idiot. Even if it was a possible starter, just think what the wager would mean for us, I need to say what it would mean to me. I think the idea of divorcing is not a problem because we could remarry. What is more fundamental is what it means in terms of three things, my relationship with you, my sexual needs and my values.

I love you and the you I love is the one I see before me. We trust each other in every way and believe in each other. If you are going to con a man into proposing marriage you will have to change in so many ways.

Firstly you will have to prepared to lie and cheat an unsuspecting person. The Tom I know could not do that. In order for you to con the man you would have to be a very convincing woman. In order to do that you would have to change massively and I do not know how I would feel about the person you changed into.

Secondly, when we first got together I was naive sexually. You woke me up to the joys of being a full blooded heterosexual woman. I love sex with a man, with you. If you wore women’s clothes and started to become female, I do not know how I would react, but I know I am not a lesbian.”

Sam could see that I was wound up and not thinking straight. She was very quiet and looked very sad. That night we went to a cold bed, not talking. When we woke in the morning we hugged and had wonderful, slow, making up, sex. When we finally sat down for breakfast Sam sat deep in thought.

“Tom, I think there is no way that you should ever even contemplate taking up Justin’s wager. But, and it is a huge but, I am prepared to help you see what you would be like as a woman. I hope that it will convince you that it is a bloody stupid idea. We can then grit our teeth and survive five years of hell with Justin. It is the easier, safer option.”

We spent the morning preparing. First we went to Marks to get a bra and panties in my size and got some hold up stockings. We searched the charity shops for clothes in my size that would make a sensible outfit. It had us both laughing like naughty children picking out inappropriate and outrageous options. In the end we had a selection of stuff in my size that went together. We even found a pair of shoes, in reasonable condition, that were my size and that would go with the outfit.

When we got home Sam systematically removed all my body hair using a depilating cream. It took ages and left me feeling burnt and raw. The applications of a soothing cream felt wonderful and restored me to a feeling of ease. The hairless legs looked so different, but it was the arms that shocked me most. Suddenly they were not mine. Removing the hair from pits and cracks did not seem as strange as having hairless arms.

Sam then washed and conditioned my hair which was long for a guy, almost shoulder length, with her own special shampoos. The result was that my hair was more full and shiny than usual. Next Sam wound my hair, tightly, over hot rollers. It was uncomfortable but bearable. My nails were the next task. They were filed to some sort of shape and then both toe and finger nails were given coats of deep red polish.

We then started to get me dressed. Sam squeezed and manipulated my balls till they, rather painfully slipped into my body cavity. With that done she pulled my dick back between my legs and taped it down. It was uncomfortable, but bearable. She then pulled the panties up my legs. They were tight and gripped my junk into hiding. When I looked down it looked very female.

Next came the stockings. They felt wonderful and silky and erotic on my legs. I could feel my todger trying to stir within its restraints. If stockings felt that good, I could get used to them. Next the bra, Sam helped me fix it on and then stuffed the two cups with seed filled stocking socks that had been tied off in the rough shape of a bust. When Sam put them in the cups of the bra, I could feel my balance shift. They felt heavy on my chest, dragging me forward.

“Jesus, Sam, you did not have to make them this big.”

“God, what a wimp you are. That bra is only a B cup. Mine are C. you are a fair bit bigger and much heavier muscled than me. I should have given you a D cup.”

Next came a thigh length slip and then a very fine long stretchy grey woolen dress. It was long sleeved, with a high neck and came down to mid calf. Sam then put a deep red wide belt around my waist and pulled it in so tight it felt as though my lower ribs might crack. Sam then started on the make up. First the foundation, then she spent ages on the eyes. There was so much blending and shaping going on that we were a full twenty minutes just on that. All this time I had not been allowed to see myself. The rollers were removed and Sam brushed out my hair. Sam found a deep red choker with a small cameo on it and put it round my neck, to cover my Adam’s apple. She finished me off with a couple of bracelets and a ladies watch.

I then mounted the open toed red shoes and felt as though I was balancing on a tightrope. My feet, calves and shins protested. Sam led me to the full length mirror for my first sight of the female me.

“What do you think?”

Standing looking back at me from the mirror was a bloke with a broken nose, make up, a dodgy hairdo, muscles, bow legs and a frock standing as if he was waiting to tackle a second row forward. It was not a pretty sight. Both Sam and I burst out laughing and could not stop. Tears were running down our faces we were helpless. When we finally stopped laughing Sam suggested we analyse what we were looking at.

“First thing is to stand up straight with your head up and shoulders back, yes chin up, that’s better. Chest out and legs straight, stand with your legs together and one heel into the instep of the other. Good. Spread your weight across the whole of your foot. Now that is better. From the waist down you do not look bad. You have nice legs and ankles. Your legs are a bit too well muscled. Your feet are not too big. Your hips look too slim and your bum too firm. Looks a bit like Jess Ennis’s so I suppose that might pass. The top half is a different. Your eyes are lovely. Green eyes and auburn hair are a great combination. Your jaw is too strong and your neck too broad but the overall shape of the face is not bad. Your hands are not overly large and your fingers are slim and well shaped. Your torso has far too much muscle and definition and you have no waist to talk about. There is no chance, looking as you do, that you could convince anyone that you were an attractive woman.
I like you though, come here.”

What followed was some of the most wonderful kinky sex that we have ever had. Sam slowly stripped me down to stockings and bra and released my massively straining dick. It was weird, but nice, kissing when we were both wearing lipstick. The feeling of the stockings on my legs was very sensual. Sam must have thought so too because she kept rubbing herself against them. We got so into each other, that we spent a long time licking and sucking each other in a sixty nine. That was a very rare event for us. We eventually lay back in each others arms, totally exhausted and slept like babies.

When I awoke in the morning there was make up all over the pillow and when I looked in the bathroom mirror my face looked a total mess. A yawning and stretching Sam came up behind me giving me make up cleaner and moisturizing cream.

“Sam, just humour me for a moment and give me an assessment of what I would need to do in order to convince people I was an attractive woman.”

“You really want me to do that?”

“OK, top down. You would need to grow your hair, nurture it and get a woman’s style. Get your ears pierced. Eyebrows need shaping and possibly a shave of your brow ridge. A nose job is needed to straighten and reduce your nose. Cheek bones are OK. Beard needs removing. You need a reduction of your jaw line. Eyes are great and lips OK. Neck needs thinning. Adams apple needs shaving. Muscle mass needs a lot of reducing and softening. You would need to lose at least a stone possibly two. Your nipples and auriolas would need to grow. You would need at least B cup breasts. You would need to find a waist and grow hips. From the hips down you are fine apart from being too hairy and too well muscled.

That is the easy part. You are a natural alpha male, dominant and very competitive. You would need to change your behaviour, mannerisms and speech from very male to female. You would need to change your personality to lose all that lovely maleness and start to think and act as a woman. I have left the hardest thing of all to last, you would have to see men as attractive.”

“Wow, why do you make it sound so easy?”

“I’m just telling you how it is.”

“I reckon it would be possible for me to act female without actually changing personality. I could probably keep up a pretense for a few months.”

Sam gave me a look that made it abundantly clear that she thought I was talking bullshit.

“Tom, trust me on this, it is not a runner.”

“Sam, we have thirteen days before we have to submit. We should at least research the possibility. I can’t just give in without checking every last option.”

“OK, but it is a fools errand. I will help you research but you must know that I am 100% opposed to you trying to take on this wager.”

“Thank you Sam, I love you.”

Chapter 3

I decided to approach it in the same way that we would any project. I would identify key target points which had to be reached before other things could happen and then work out the critical path to those points. After a lot of discussion I decided that the target points would be.
1. get fundamentals sorted. Nose, jaw line, removal of beard and male pattern body hair, growth of nipples, loss of weight, softening of muscles, development of a waist and female body shape, brow alteration, breast implants
2. create the illusion of an attractive woman in dress and behaviour.
3. find and woo a qualifying male getting them to the point of a proposal of marriage.

The last part was the determining factor. How long, realistically, would it take to get through this stage? If we took it slow it would be at least six months. The shorter the time span, the hotter the romance would need to be. The hotter the romance, the more sexually attractive and active I would need to be. Whilst it may be possible to get a proposal of marriage after a brief courtship, without having first having sex, it would be extremely unlikely. Couples tended to move in together before marriage and celibacy prior to a marriage proposal would be rare. There was a need to allow at least six months for a more sedate courtship and a more conservative approach.

If that were the case, I would need to be passably female and able to have some lower level sexual interplay within the next six months. That would require that I was presentably female within six months. I would need to be able to look and act like a woman.

After a couple of days heavy research on the internet we came up with a list of actions that would be required.
1. get registered with a GP as transgendered. (week1)
2. get a referral to a specialist and a psychologist. (week 1)
3. get hormone cream to develop nipples and areolas. (week 1)
4. get hormones off the net until doctors prescribe (week 1)
5. contact a plastic surgeon about nose, jaw, brow ridge and Adam’s apple surgery. (week 1)
6. start diet and new exercise routine (week 1)
7. purchase corsets to start waist training (week 1)
8. start education on mannerisms and clothing (week1)
9. start electrolysis on hair, especially beard. (week 1)
10. start divorce proceedings (week 1)
11. start voice training (week 2)
12. probable first appointment with specialist and psychologist (week 5)
13. researching websites and dating options by Sam (week 4)
14. purchase first clothing and dressing at home as a woman (week 5)
15. undertake first surgery (week 6)
16. probable first hormone prescription. (week 6)
17. first visit to hair stylist and manicurist (week 9)
18. start correspondence with possible targets (week 10)
19. first outing as a woman (week 12)
20. first trial date (week 14)
21. first snog (week 16)
22. breast implants, these have to be left as late as possible to allow nipples and areolas to grow first(week 18)
23. first date after implants (week 21)
24. selection of target men (week 22)
25. first dates with targets (week 26)

All of those dates were, probably, excessively optimistic. Any delay, or slowness in development, and the whole timetable was unworkable.

During all that time we would have to keep our business going. That was not a major problem because Sam usually did all the customer contact. There would be the massive upset to our family and friends. I would not be able to explain why I was suddenly turning into a woman and dating men. I suspected that they would all be appalled by my behaviour. It amused me to think of how the rugby club would react to their first team scrum half dressing in skirts and dating men.

When we saw it all down on paper it really hit home what an impossible task it would be. It also hit me forcibly, what the wager would mean to Sam. She would be trapped inside a nightmare turning her husband into a woman and helping him get dates with men.

The residual situation, if we won the wager would be a damaged relationship between Sam and me. It would mean the loss of friends, the possible alienation of family. I would be able to remove the implants and when I stopped the hormones my body shape would return to something more male. I would probably become sterile and may lose the ability to get an erection. I would probably need testosterone supplements the rest of my life and I would have had to have some level of sexual relations with at least three or four men. I would have led at least one man to fall in love with me and left him feeling stupid, angry and broken hearted. My beard would have gone and I would always look feminine.

And the plus side would be? Not a lot, I would understand something of the woman’s lot and we would have our company, our home and a financially good future. We would not have to suffer any more Justin.

When we finished our analysis it was clear that it was a non starter. We would just have to grin and bear it.

The ridiculous thing was that, even after going through all that research and discussion, it had not registered with me, at any meaningful level, that I was actually contemplating giving up being who I was and actually becoming female. I was seeing it as a problem solving exercise and not as a fundamental change in both me and us.

Why I had taken the possibility of the wager in any way seriously, I do not know. There was a huge gap between what I had been thinking and reality. The more I thought about it, the more I realized that it was a total non starter. Chapter 4

We had five days left when Justin dropped the next bombshell. He outlined his plans for the next five years. I was to go straight to Thailand where my new home would be situated. I would work and live there. I would be located in the brothel of a notorious local madam. Justin was the joint owner of the brothel and ladyboy bar. I would be on very low income and would have no access to funds. My work would be whatever the madam wanted me to do and that was unlikely to be systems design.

Sam was to work with Justin and travel everywhere with him. He said that it would be fun because Sam would always have to share rooms with him. We both knew that Justin had been prepared to use date rape drugs in the past, so there was no doubt he would use them in the future.

As a Thailand employee, I would not be entitled to holidays and both of us would be required to surrender our passports to Justin for the five years.

Justin had got his lawyers to look over our contracts and established that we had both signed to give at least 5 years notice of termination. We had both agreed that the owners of the company would determine all our travel and accommodation arrangements. We had both agreed that the owners would specify what we worked on, where and how much we would be paid. We had been mucking around when we wrote our contracts. We wrote the contracts as the owners, but we were the owners no more. We were just the employees. The worst clause in the contract said that in the event of a breach of contract, the person in breach would agree to any penalty imposed by the owners. We had thought that very amusing when we wrote it.

Justin’s lawyers had established that because we had entered into the contract voluntarily and had worked to that contract without complaint for five years, then the contract was sound.

The first thing we did was to check up on the brothel in Thailand. It took a while to find anything but we eventually found a newspaper report of a joint raid involving UK and the national Thai police, the local police were in the madam’s pocket. There had been many cases of young male tourists disappearing whilst on holiday in Thailand. There had been a tip off that at least four young europeans had been working as ladyboy prostitutes in this bar and brothel. When the raid took place the police found three young people who were indeed working as prostitutes. All went by girls names and could not remember their real names. They found difficulty remembering any English. DNA tests showed that they were three of the missing young men. All three were very spaced out and under the influence of drugs. All three kept offering sex to the police. All three looked like females with significant bust and hip development. All three had no testicles and now had a rudimentary vagina. All three were HIV positive. They all still possessed the remains of a penis. None could remember how they had got to be where they were. All three were rescued but no one was prosecuted. The madam claimed that each one had approached her willingly looking for work as a hostess.

On their return to the UK all went through drug rehabilitation. One was by now in the advanced stages of AIDS and was very seriously ill. A second committed suicide when he realized what had been done to him. The third was in a secure mental hospital. The others had just disappeared some time before the raid. The police believed that the madam procured and supplied young European males, having converted them to work as ladyboys. The UK police believed that the Madam and her team drugged young men, then kept them under the influence of powerful addictive drugs. They further believed that the young men were kept in secure lock ups whilst they were treated with high hormone levels, surgically modified and brain washed into working as whores. The young men never stood a chance. They were unable to prove anything and the madam was left to carry on her trade.

Would I be able to avoid the same fate if I was isolated and under their control, thousands of miles from home.

“That looks scary. It looks as though Justin has worked out a way to completely ruin you and then make you disappear into a world worse than hell. It is just typical of the twisted bastard. When did he become such a vindictive shite. He was always bad but not this bad. What can we do to protect you Tom?”

“It’s not just me at risk, my love. Once he has got me out of the way, he can ask you to do whatever he wants and if you refuse, you will be in breach of contract and he can make you carry out any forfeit that his evil bloody mind comes up with.

“We are shafted in every possible sense of the word. He has us trapped.”

“Our only way out is going to be to buy time by taking up the wager. We will still have our freedom for a year and we will still have all our resources under our control. We can use the time to find some way to get out from under the evil bastard.”

“Don’t be stupid, that means you starting the process of transitioning into a woman and you know that is neither realistic or in any way acceptable.”

“Yes I know, but at least it would be under our control. I would not end up as some drug controlled freak, selling my body for pennies to all comers before I finally die of drugs, aids or just go mad and top myself.”

“We still have some time. Let’s go through it all with our lawyers and see if they can find a way out. I’m sure that Justin can’t possibly force you to go to Thailand. It can’t be legal. At the very least, they might be able to come up with some challenge that could put things on hold for a while.”

Next morning we spent hours with our lawyers going over every possible loophole. They were very apologetic and sympathetic but the final answer was that we had been idiots to enter a wager without being extremely clear about the terms. We had been even bigger idiots to play silly buggers and write ourselves into the contracts we were now stuck with. Our options were now starkly clear. I could put myself in Justin’s hands in Thailand, take on the wager, or run.

I had thought that if the worst came to the worst we could just say to Justin that we refused to meet the terms of the contract. I assumed that the result would be a civil court case for breach of contract where Justin would get damages equal to everything we owned and considerably more. We could then file for bankruptcy and be out from under as soon as the bankruptcy was discharged. Our lawyers reminded us that we were not currently in control of our company and, to make matters worse both Sam and my parents had acted as guarantors to the initial £400,000 bank loan that we had taken out to start the business. We had never paid it off. It had not seemed important when we had started making money.

If we went bankrupt as a result of breach of contract, both sets of parents would be met with crippling debt, neither sets of parents were well off. Sam’s mum was a widow and not in good health. We paid her a wage from the firm just to keep her afloat. My parents still had a smallish mortgage. Default on the bet would certainly lead to ruin for, not only us but, our families too. We worked it out that if we just broke the contract and went bust and the guarantees were called in, we could start again. Our parents, however, would have lost their homes and it would take a good while to get enough money to repay them. Sam’s mum would suffer most, but there was a chance that we could get out from under without everyone loosing everything long term. It was a slim chance but there was a very dim glimmer of light at the end of the tunnel. We needed to talk to our parents and see if survival for them was possible.

Chapter 5

We went to bed that night happier than we had for a few days. We now knew that there was a possible way out and that I would not have to go through with this ridiculous idea of feminizing myself.

In the morning we rose feeling much more positive. The way ahead was going to be hard, but our stupidity had got us into the mess. We were young and had marketable skills and contacts and a good reputation.

We were out of milk so Sam popped down to the shops to get some for our breakfast. Half an hour later and she had not returned. I thought that she must have met up with a friend and got chatting. Another hour passed and io was now starting to get worried. I walked down to the shops to see if I could find her. No sign could be found. I went into our convenience store and asked if she had been in for the milk. Mary in the shop said that she had been in and bought milk well over an hour ago. She added that she thought she had seen her outside the shop talking to two large men. She had been serving a customer and when she looked back again Sam was gone.

I was now starting to get worried. I called round all of Sam’s friends that I could think of and none had heard from her. I contacted the local hospitals, just in case. After another couple of hours had passed I contacted her parents and they had not heard from her.

By now five hours had passed and still no sign. I had covered the whole area looking for her. Her phone was switched off and everything was going to voice mail. I tried to see if the phone company would trace where she was but they dismissed me out of hand. After six hours I went on line to the bank to see if she had accessed any accounts or used her credit cards, nothing. I was getting desperate and went to the police to report a missing person. When they knew that she had only been missing for less than seven hours, they said that they were not interested and for me to come back if she had not returned within twenty four hours.

This was such a ridiculous situation. I knew that Sam would not just wander off, especially with the situation we were currently in. she may have taken an hour or two out to reflect on the situation and think through what our future looked like, but I was sure that she would not just wander off for this length of time. Maybe I had underestimated the pressure that this situation had put on her. Maybe she had just decided to walk away from it all, but it just did not feel like something Sam would do. I sat and worried about whether Sam had just cracked under the pressure and walked out.

In the end I was sure that something had prevented Sam’s return and that she would not be staying away voluntarily. It was then that a chilling thought hit me. What if Justin were behind this disappearance? I immediately got on the phone to Justin.

“Hello Justin, do you know where Sam is?”

“I was waiting for you to call, what took you so long? I want to see you at my place now, no police and be on your own.”

When I got to Justin’s place, I was met at the door by a large thug, who frisked me to check if I was wearing any recording device or bug. He relieved me of my phone and told me to strip. I needed to get to Justin so I complied with his order. Eventually, I was ushered into Justin’s presence where he was joined by the goon who had met me at the door. Another large thug was present, who pushed me into a chair in front of Justin and secured my arms to the chair with cable ties.

“It is so nice of you to come to see me, Tom. Please excuse the precautions, but I needed to make sure that there were no recordings of our conversation. I did think of getting my friends here to give you an internal examination just in case, but I thought that might be a little excessive. Now I suspect that you would like to know where Sam is. Well, at this moment she is out of the country in a house where friends of mine keep young ladies and make them service customers. At the moment she is safe and unharmed, but that could change anytime. We keep the ladies under lock and key and feed them drugs to keep them under control. The ladies are usually good for two or three years before they become too unattractive.

Now a little bird told me that you were thinking of welshing on our little wager. What I have done today is a demonstration of what I am capable of. I will return Sam to you unharmed, within the next twenty four hours. If, however, I ever get a whiff that you are thinking of backing out of the wager Sam will be taken back to the brothel. Do not think of going to the police or Sam will disappear to a short but unhappy whore’s life. The people that I know, are capable of kidnapping people off the street, even if they employ bodyguards. Now be a good little boy, or is that going to be little girl, and go back home. If I am happy that you are going to play by my rules, then you will see Sam safe at home. Oh, by the way, just in case you thought that I was bluffing, you can see Sam on this video.”

With that, Justin turned a screen toward me and I could see a very scared Sam, sitting chained to a bed naked. The room was bare except for the bed a toilet and a shower.

“At the moment, she has not been made to pay for her fare, but I could ask my friends to change that. My colleague will give you back your things and see you to the door. Goodbye Tom, so nice to see you again.”

The two thugs cut my restraints free, lifted me up, thrust my clothes in my arms and pushed me out of the door. Once outside I quickly dressed and made my way home. The situation was hopeless, if I went to the police, there was no link to Justin and Sam had not been missing twelve hours yet. I knew that Justin was evil enough to carry out his threat. I just had to wait it out.

That was a cold and scary night. I could not sleep and I could not stop thinking about how terrified Sam must be feeling. Morning came and the day dragged on, I tried working but ended up just staring at the wall and then pacing around. I tried Sam’s phone several times but there was no answer. Evening came and I was out of my mind with worry. Finally my phone rang. It was Sam.

“Sam, thank God. Where are you?”

All I could hear for a while was racking sobs at the other end of the phone. Eventually Sam was able to talk and tell me that she had woken up in a bus shelter in Acton, not very far from home. I told her to stay where she was and got to her as quickly as I could by car. When I got there she was huddled in the shelter sobbing. I held her in my arms for a long while before she was able to stand and walk to the car. We did not talk on the way home, she was dirty and disheveled and I had to drive with one hand because she would not let go of the other one.

When we got home I carried her from the car and took her up to our room. I ran her a bath and gently undressed her and then washed her. It was some time before she started to talk. Her first few attempts were ended by her sobbing and then just needing to be cuddled. Eventually she felt able to talk.

“I am sorry Tom, I did not see it coming. I could not stop them when I came out of the shop, this large foreign guy asked me directions to somewhere, I can’t remember where, and as I turned to answer him I felt someone behind me and then a prick in my kneck. It just went black after that. The next thing I remember is waking up naked on a bed. I was shocked and confused and when I realized that I had a shackle round my ankle and that I was chained to the bed I started to panic. I screamed and shouted for help and a large ugly man with a pock marked face came into the room. He spoke first in a language that I could not understand, but when I asked him where I was he answered in very broken english that I was in his whorehouse and if I did not keep quiet he would give me a beating. He said that he was looking after me for a friend of his and it was being decided whether I was to be put to work or not. With that he left. I was left on my own for hours, then the same man came and left a bowl of soup, some bread and water. I was too scared to eat but I needed the water. I was there for hours and hours until the same man came in and told me that I was a lucky girl and that I was going home. He injected something into my neck and the next thing I knew was waking up in that bus shelter. Tom it was so horrible in that place, I could hear other girls crying and sometimes screaming with pain. I tried talking to them but I could not understand their language. It sounded eastern European. I was so scared. It was Justin wasn’t it?

“Yes love. He, somehow found out that we were thinking of backing out of the wager and just letting him sue us for damages. There is no way I am going to put you at risk. The only solution is for us to accept the wager.”

“Can’t we go to the police?”

“And tell them what? We have no proof that anything happened. The bastard has got us.”

I put Sam to bed and sat and thought long and hard. There had to be a way out, but I could not think of it. The following morning Sam seemed fragile but much better than the night before. I was proud of the strength that Sam had, but there was no way that I would let her be in danger. I would do whatever it took to keep her safe.

I told Sam, when she woke up, that her safety was more important than anything else in my life. I had decided that I would protect her. She was the most important thing in my life and if it meant humiliation and being shunned by everyone, if it meant sacrificing my masculinity and risking losing her love, I would still go ahead with the wager. I was sorry but my mind was made up. It was clear that Sam had also thought long and hard after her ordeal.

“Tom, I know that we are stuck with the wager. I know that, however much we fight it, it will affect our marriage and our relationship. I hate the idea of what you will have to do, but, we will have to do this together. I will help you, every inch of the way.”

“Thank you. We just have to hope that we can find a way out before I become too feminine.”

Having made our decision we now knew the clock was ticking. We still had thirty six hours before we told Justin that we were taking on the wager. We decided that we would take a week away from work, other than dealing with correspondence and any emergencies from our clients. I decided that this Saturday I would play rugby and then after the match, tell the club that I would be unavailable for the rest of the season. I phoned the surgery and made an appointment to see my friend Doug. He was not only my GP but also a team mate in the rugby club and a friend of long standing.

Sam and I searched the net for a reliable source of estrogen breast cream, testosterone blockers and female hormone pills. We found a supplier in Canada that checked out fairly well. Transgender chat rooms were quite useful and I registered on a couple just to get tips and information. I then started mugging up on the process of getting onto a transition programme. I spent hours reading through people’s accounts of their transition. I was most interested in finding out what had convinced these individuals to go through all the agony and trauma of becoming a woman. The stories made hard reading in many cases, but I was going to have to convince Doug and many others that I was serious about transitioning. I had to convince them that I had a burning, overwhelming need to become a woman.

Sam researched cosmetic surgeons and found one that was fairly close to home and seemed to have a good reputation. She made me an appointment to see them the following week. She also booked an appointment to see about starting beard and excess hair removal.

Neither of us wanted to face Justin to give him the pleasure of seeing me agree to become a convincing woman. We did not want to see him gloat. We went to see his lawyers and signed all the paperwork that initiated the wager. From that moment we got back control of our company, our home and our lives. My first act was to contact the bank and arrange for the removal of the loan guarantees that our parents had taken out for us. Whatever else happened now, they would be safe

We had a quiet weekend, I played rugby and had one of the best games of my life. Sam cheered my efforts lustily from the touchline. We had a few pints in the clubhouse and I announced that due to a new project, I was unavailable for the remainder of the season. I had to deflect a barrage of questions from my mates and was made to promise that Sam and I would come to the end of season dinner. The thought went through my mind that I probably would not be welcome at the club by then.

This was my last day as a totally un-modified male and we enjoyed it to the full.

Sunday was spent planning and bouts of urgent sex. We almost felt we were facing Armageddon and we needed the comfort of our intimacy.

Chapter 6

We had spent hours on the net chatting with people who were undergoing or who had undergone transition. As a result we had got advice as to which organization in our area was best for facial hair removal and dealing with men transitioning. I phoned first thing Monday morning and managed to get an initial consultation for that afternoon.

The rest of the morning was spent on research. It was much more complex than I had thought. The overwhelming advice was to get to know people who had already gone down the road, befriend them and get their advice and guidance.

We found out that there was a support group for transsexuals and their partners locally. The woman was so kind and supportive on the phone and she invited us to the next meeting, which was a week on Wednesday.

That afternoon I attended the clinic for a consultation. It appeared that I was lucky because I had a slow growing and fairly sparse beard. The suggestion was that, if I had a high pain threshold they could do an initial lazer clearing of my beard over a week and then continue with frequent electrolysis treatments interspersed with more lazer treatment. I found out that my skin and beard type meant that I was lucky and that the process should be speedy and without too many side effects. The clinic were skeptical about my target of six months to totally remove my beard. The faster I wanted to go, the more pain and the greater the risk of unwanted side effects. The whole process was going to be very expensive. I was shocked when we were talking in thousands of pounds over the six months and many hours of treatment. The clinic advised me that if it was my intention to pass as a woman, then I should get further hair removal on other parts of my body.

I made an appointment for later in the week and while, I was there, I got my ears pierced and two little gold studs inserted. I was now on my way.

Sam enrolled me in a yoga class with the objective of becoming much more supple. My diet had also started. Sam also instructed me how to take care of my hair to make it more lustrous and healthy. Moisturising was now to be part of my daily ritual. Sam showed me how to take care of my toe and finger nails and I started to shape them and cover them with a clear varnish.

The next day I went to see Doug.

"Hi Tom, great to see you. Great game on Saturday, that was the best I have ever seen you play. Anyway what can I do for you?"

"This is going to be very difficult for me Doug, so please bear with me and listen to me all the way through."

"Shit Tom, you haven't been playing away and caught some STD, have you?"

"Doug, be serious. Listen to me. The up and the down of it is that I can't maintain the lie of being a man anymore and I must start transitioning to become the woman that I really am."

"Stop pissing about Tom, why are you really here?"

"Doug, I am desperately serious about this. I can't face life like this any more, I can't pretend to be a man any more. I need your help and I need your referral to see the right specialists."

"Tom it's not April 1st, stop kidding me."

"Doug, I need your help."

"But Tom, I have known you for years. I have played rugby with you, seen you take on forwards twice your size. I have seen your aggression. I see how close and loving you are with Sam. I have never seen any glimpse of femininity about you"

"I have kept it well hidden. Sam knows about me and accepts and supports me. She accepts that I can no longer pretend. You must help me."

"I can see that you have had your ears pierced but no other signs. Do you cross dress."

"Yes, Sam has helped me with getting women's clothes and helped me with my make up. She has helped me research what I need to do."

From that point Doug started to act like a doctor rather than a rugby mate. He asked many questions about what steps I had taken so far, when I had come out to Sam and whether I had taken any hormones. It was fortunate that he had the experience of dealing with two other transgendered patients, so he knew what to do next. He said that if I wanted to go national health, I would have about a two year wait to see a gender specialist. If I wanted to go private, he could arrange a quick meeting with a gender specialist. I would get a letter within the next two weeks for an appointment.

Doug and I usually parted with a man hug. This time he held back and did not even shake my hand on parting. Doug had always been a close mate and we had shared many escapades. When we parted he was distant and professional. I had my first glimpse of how my life was going to be, the price that I would have to pay and the friends that I would lose.

When I got home I told Sam about my experience and my sorrow at the probable loss of a friend. The implications of what I was doing were starting to sink in at a different level than before. I was realising what an outcast I was going to become. I knew that it was not going to be very long before friends started to find out. Sooner or later I was going to have to start looking more feminine and wearing more feminine clothes. I had six months at most to turn myself into a convincing looking woman.

Our research continued on the net and the following morning the hormone breast cream arrived. We rubbed the cream in straight away. Small steps would lead to big consequences. Later that morning I had my first laser treatment. It was agony. I had asked to do as much and as fast as possible. My face was red and felt raw. I was due for my next session on Saturday morning. Whilst they were at it, they removed the odd hairs growing round my nipples.

The cooling cream that Sam gave me made things a little better. When talking in the transgender chat room later, I expressed my surprise at how hard the hair removal was. Several sympathetic responses came my way and I had a lengthy chat with a transwoman called Rose, who was well down the road of transition. It was amazing the volume and value of the advice Rose could give me. It seemed that the chat rooms would be a very valuable source of support.

The following morning the hormones and blockers arrived and I took my first doses. Sam suggested that I start to get used to more feminine clothes. That was an immediate challenge because I did not have any. We went out and bought a couple of camisole tops and I wore one of them with a soft cashmere jumper that I owned. Sam insisted that I should start wearing panties instead of my normal underwear. We bought some and they were quite pleasant to wear except that there was no space for my meat and two veg.

That afternoon I had my first appointment with the cosmetic surgeons. They were unquestioning about my motives. Discussion about my broken nose was straight forward. There was not even a raised eyebrow when I asked that the nose be trimmed and made shorter and more feminine. When the surgeon understood what my objective was, he showed me examples of where feminisation of a male jaw line had been completed. The pictures that he had taken of my face had been turned them into a 3d model on the screen. He showed me what he could do with my jaw line, chin, nose and brow. It was amazing, the face on the screen morphed from a typical male into a female face that was not unattractive. The face was still recognisably me or me if I had been a girl.

The surgeon said that all the work, including an Adam's apple shave, could be completed in one sitting. A three week wait was all I had before the deadly dead was done. Healing time would be three to four weeks before the bruising and swelling went away. What did surprise me was the quote for the work , it was an eye watering amount. After stunning me with the cost, the surgeon went on to raise the issue of waist and hips. Being a genetic male my fat receptors were on my stomach rather than my hips and bum. My rib cage and hips were a different shape to a woman. He suggested that in order to get a convincing waist, he could widen my hips by cutting the bone and adding two grafts of bone. The recovery time was long as this was major surgery. An additional option was the trimming of my ribs and the removal of the bottom rib. The recovery time was not as long as the hip operation but still quite major.

He also suggested the transfer of fat and fat receptors from my stomach and love handles, to my hips and bum.

I confirmed the cosmetic surgery but ruled out the pelvis reconstruction. The rib trim was something that I had to think about and the fat relocation left me bemused.

"Sam, I booked the facial surgery, for next month. It is going to be more expensive than I thought."

"We are ok, the company is making good money and we have reserves. If we stick with what we are doing, new contracts will come in. Money is not the problem. We can find whatever money we need."

"The surgeon suggested pelvis reconstruction but that seems too serious. The other thing that he suggested was trimming my ribs to establish a female waist."

"I think we might be able to get some result with the use of corsets. Shall we try that first to see how much of a result we can achieve? I have found a place that specialises in corsets. Let's go there now."

The corset place seemed quite old fashioned. We were told that to get the best results, I should have a pair of corsets custom made. In the meantime I could use a couple of, off the peg corsets. The assistants first showed us how to put the corset on. She then showed Sam how to string the corset tighter. The process was extremely uncomfortable. My normal waist was a generous 30", possibly 32” when I let myself go. After a great deal of straining my waist was down to 27". My ribs felt as though they were being crushed and I could only breathe with the top part of my lungs. We were advised that if we wanted to reduce my waist size, then I would need to wear the corset at least sixteen hours a day and ideally overnight as well.

The corset was hell and I had to take it off to sleep. In the morning it was back on for my next visit for laser treatment. That afternoon was not pleasant. The discomfort of the corset and the pain of the laser treatment left me feeling sorry for myself. I had a moan in one of the transgender chat rooms and received some sympathetic responses. One of the useful things that I got from my chat session was the name of a voice coach who could help ne with creating a female voice.

At the end of week one Sam and I had a review of progress to date.

“Ok Tom how do you feel now we have started?”

“Scared, uncomfortable and worried. It is starting to hit home how much this is going to change me, us, our social life and even our relationship with our families. It is almost like a full time job changing myself into something I really don’t want to be. I feel that I am working hard to do something I don’t want. It is painful and is taking up all of my time and thinking capacity. It is overwhelming me. I feel as if I am running up a railway track, towards an oncoming train.”

“It is clear that your head space has been filled with making the changes happen. I feel helpless that there is so little I can do to help you other than research and love.”

“Don’t ever stop with the love, whatever happens. I need your love if I am to stand any chance of surviving this.”

“That is a given. One thing that we will have to think about is getting more permanent help with the business. At the moment I do all the work with the client and the initial systems research. You do most of the systems design and code bashing. We have used Tim and Jackie as freelancers to help in the past. We are going to have to take at least one of them on full time, probably Jackie. Our workload and customer base is expanding and your time for work will be reduced for a while.”

“If Jackie is willing to work full time we can make space for her in the studio so that we can work together. If we bring Jackie in, we will have to tell her what I am doing and why.”

“Agreed, I will talk to her tomorrow. There is one other thing that I have been looking up and that is preserving your sperm. There is a real danger that the hormone regime will make you infertile. I want our babies. Whatever happens to us, I want our babies and I would like to have our first one soon. I think that it would be wise to leave getting pregnant for at least six months and there is a risk that your fertility may be too reduced by then. We should deposit a sufficient amount of sperm for me to have at least two children. We should sort out the storage as soon as possible.”

“Wow, that is blunt, but you are right. We both want a family, whatever happens, and with the business going well, we would be able to support a family.”

Sam suggested that I needed to get to know someone who was much further down the road of transition and get their advice and help. She could help me as a big sister would help with things like dress, make up, mannerism and body language, but I would need someone who knew the practical problems.

At an intellectual level I was starting to understand what all this process would mean. I could understand the implications of each part of the process as a separate thing. What I was entirely failing to do was to get a gut understanding of the whole of what I was going to do to myself. I was in denial about the true destination of this journey.