Chapter 1

“You’ve got to know when to fold, know when to hold, know when to walk away, know when to run.”

They might not have been the exact words of the song, but they were running on repeat in my mind. I wasn’t in a good place, right now, and I think it was all of my own doing, although I didn’t know why.

I had a good job, earned decent money, lived in a reasonable apartment, and had just the one vice. That was my love of playing poker. I had learned how to play in university and had made enough money to avoid having to get a part-time job. I was born at the beginning of the new century, into a modestly middle-class family. My father was a doctor, and my mother was a teacher’s aide. I was the youngest of four, an unlikely surprise at their age, and my being somewhat of a runt could have been blamed on their aging bodies.

It meant that I was in my teens as they both retired, so was left to my own devices most of the time. They called me ‘Surp’ at home, short for surprise, or maybe surplus, but had christened me Jackson, my father liking the works of Jackson Pollock, the painter.

They sold up as soon as I was out of the house and moved to some place in Spain. They sent me postcards for a while, and then they dried up. They didn’t attend my graduation ceremony, and I had totally lost contact with my sisters.

I had done well at school, especially in maths, and had gone to university to study statistics. It was the maths and probabilities that attracted me to poker when I was taken to a Friday night game by a couple of my fellow students. They came to regret introducing me to the game as I generally took money off them. I had a good memory for number series, so could guestimate the likely hands of my playing partners. I never cheated, and even allowed my opponents to win smaller pots by discarding my hand.

I was head-hunted straight out of university, slotting into a seat at a stock broking firm in the City. It was interesting, for a few years, but then became a little predictable. That was what I was there for, after all. I spiced up my life with the poker games that were played on the Friday evening, sometimes going until sun-up on Saturday.

The company that I worked for was privately owned. The owner had a title and a place in the House of Lords. He had several properties around the country, along with a model wife and four children that I knew of. His three sons worked in the company, while his daughter was a well-known socialite. My apartment was part of my package, a peppercorn rental in one of his buildings. It was walking distance to the office, and I used Uber for anything else.

My social life wasn’t restricted to the poker games, although long sessions would mess up Saturdays. I was a film fanatic, especially the old ‘musicals’. I had a small collection, and often spent Sundays at various markets, looking for good DVDs to expand that collection. I had spent time with girls, usually at social events after work, but was keeping single, as the idea of being responsible was not part of my mindset. I supposed that I would settle down, one day, but that day had not happened yet, as I had not met the girl who made me feel that it was the right time.

It was late in March when I arrived at our usual venue for the poker games. It was the home of one of the sons of the company owner. He was a good guy to know and had a big house with plenty of room for his family, as well as a big garage with a rumpus room above it. The games night usually started with two or three tables, many leaving to go home before midnight.

On that particular evening, I sat with a few of my friends from the company, with the son on another table. As the evening wore on, I gained a little, with my opponents declaring that there was something they had to do. I watched the other games until there was a vacant seat. In the early hours, we were down to one table of six players. A few regulars, the house owner, me, and a guy who was obviously a friend of the host. After a few hands, the regulars made their farewells and left, leaving the three of us. We agreed on one more hand before calling it a night.

I had a good hand, and the bets rose, until the host threw his hand in and said goodnight, just leaving me and the stranger. No matter what I bet, the more he raised, and my instinct was that there was no way he could beat me, from my estimates of the cards. The guy had brought his girlfriend with him, and she had spent the evening talking with the other women until they had left. The guy looked at me.

“My girl will get us a drink each, so one can toast the winner. Then, I will call for a show, as it’s time for me to leave.”

I nodded, and the girl poured out two shots, going to give him his. She was bringing me mine as we showed our cards. I looked at his winning hand and just said, “Impossible”

His cards included two that really shouldn’t have been there. He smiled.

“That’s what I hoped you would say.”

At that moment, the glass was put in front of me, and I felt something prick my neck. After that, things went black.

Which brings me to where I am, now. I thought that I was likely in a van, stretched out on a mattress, by the smell. I was on my front, my ankles lightly constricted, and my hands behind my back. When I felt around, I realised that I was in handcuffs, but the ones you use for playful sex, with a fur cover to limit any marks. I had something in my mouth, and there was a bag over my head. That’s when the words of the song started in my brain, in an attempt to calm my panic.

When I had calmed my breathing, I listened as the vehicle drove on. There was very little traffic noise, not unusual in most places after midnight, but unusual in the City. I stayed still for a while, and then tested the handcuffs to see if I could release myself. That’s when a hand pulled the bag up from my neck and I felt the prick once more, plunging me back into darkness.

The next time I woke up, I was stretched out on a big settee. I groaned and sat up, suddenly realising that I was naked, except for a towelling dressing gown. I heard a movement from behind me and the guy I had been playing with walked into my line of sight.

“There’s water in the glass on the table, Jackson. Put your knees together, you’re flashing your tackle to the world. I’ll go and tell your host that you’re awake. Don’t even think of leaving the room.”

He left me alone in the room and I took a drink from the glass. It was like nectar after what I had been through. I looked around. The room screamed money. Even to my untrained eye, the furnishings had to be expensive. The ornaments and the pictures, if they were real, would have allowed me to live until I reached pension age.

The door opened and my boss’s daughter walked in, sitting on a chair opposite me, as I clenched my knees so that I didn’t flash.

“Good morning, Jackson. I’m glad you could grace us with your presence.”

“Did I have a choice?”

“You do have a point. The thing is that I’m going to offer you a job, but it will change your life for ever.”

“You could have just made the offer without abducting me.”

“I agree, but that would have made you privy to facts that we don’t want made public. Silvester tells me that you are a very good poker player.”

“At least I don’t cheat. I don’t know how he did it, but there were two cards in his hand that shouldn’t have been there.”

“You’re right! And that’s why you were brought here. Silvester has been trained by the best card players around in cheating. He is my head of security at the casino I own. He would not have brought you here if you had just accepted his winning hand as just that. You said one of the magic words that proved that you’re the one I need.”

“What about my job with your father, I can’t just jump ship. I have a contract.”

“My father knows about my problem and is good with you helping us out. As far as the office goes, there’ll be a new person at your desk, and anyone asking will be told that you have been relocated to somewhere else.”

“What if I don’t want to help you? Will I be out of a job?”

“If you refuse to help, Jackson, you will cease to exist.”

I sat there, stunned. Did I just hear he tell me that I would be killed if I didn’t agree to whatever she was offering?

“You would have me killed?”

“Not exactly. If you agree to help, you will undergo certain changes, then do the job that you have been brought to do, then will be paid well and given the choice of career paths. If you don’t agree, you will undergo the same changes and then shipped to a place where you will be sold. One way you have wealth and a new life, the other way and you will suffer a short, but horrible, existence.”

“Not much of a choice, as far as I can see.”

“It’s not meant to be. Will you agree, or will I call Silvester to come and restrain you, again. If you don’t agree, that’s a situation that you’ll come to take as usual.”

“Can you tell me what the job is, first. Is it something that I can do?”

“The job is in my casino. It will need you to be as good as you usually are with counting cards and estimating the hands of other players. We have a problem with some gamblers who have been trained as well as Silvester, and we can’t pin them down, even with overhead cameras. With you signalling the hand that is wrong, we can go through the footage to see how they do it. They are very, very, good.”

“So, why all this rigmarole to abduct me?”

“Have you ever been in a casino, Jackson? The croupiers in the best places are all women. My casino is known as ‘Bunnies’ and all the waitresses are in playboy bunny costumes. The croupiers are all well-dressed models. That’s the changes we want to make with you. You have the brain to do the job, and already have the body to make it possible. When we let you work in the casino, you’ll walk, talk, and act like a proper lady, and be good enough to get into modelling if you wanted to.”

“If I don’t agree?”

“Then we turn you into a woman, as before, but just leave you good enough to be a sex slave and sell you to an overseas trader. Agree, and you’ll be looked upon as attractive and kissable, keeping your life savings and a good wage. Otherwise, you just never get heard of again.”

“What’s to stop me just going along with it and then making a run for it?”

“Good question. Part of the cosmetic surgery will include breast implants. Within those will be enough explosive to kill you, with a receiver and a button battery with a year or so life. By the time the battery runs out, you will be so happy with your new life that you won’t be a problem.”

I sat for a moment, looking at the beautiful woman with such an evil brain. Or was it just business to her? I thought it through, with my lack of future thinking coming to haunt me. If I agreed, I would become a female, to all intents, and she had promised me that I would look the part. One way, I would still be the controller of my actions, the other was almost too bad to contemplate.

“Are you certain that I’ll pass as a woman?”

“With the treatment you’ll get, there’ll be no question.”

“What about my apartment?”

“Being cleaned out as we speak. Everything of yours will go into storage, and you will get access when we have completed the job. I will warn you that the job may take a while to complete, as it can only operate when the customers are in. Some don’t turn up for months. It may be some years before we know that we’ve caught them all, with you working at what you like best, playing cards and making money, even if it is for the house. I pay my girls well, and you’ll get a bonus for each one you flag. As front-of-house, you even get a clothing allowance.”

I took another sip of water, turning the pros and cons over in my mind. Whatever I said, I was going to be operated on to turn me into a woman. I thought about that. Did it fill me with disgust? Did it fill me with dread? When I realised that I wasn’t that stressed about it, I knew why I had been so reticent about going steady and getting married. I knew I wasn’t gay, but also knew that taking a woman to bed wasn’t front of mind as it was with others I worked with. I looked her in the eyes.

“I’ll do it, on condition that I’m told about every step as we move forward. None of this knocking me out anymore.”

“Good! Silvester will take you to your room. Tomorrow, you will be taken to a private clinic. The procedure starts with a lot of tests and some injections. The operations start in about a month. In that time, you will spend your time getting used to female clothing and getting lessons in how to act. Your voice will be female, but you will need to know how to talk to other women as if you were born to it.”

She stood and went to the door, opening it to let Silvester in.

“Jackson is on the payroll, Silvester. Treat him with kid gloves from now on.”

She left us and Silvester came over to me.

“Come along, Jack, you have a room to get some proper sleep in. A tray will be brought to you with a meal, seeing that you probably haven’t eaten for twenty-four hours. It’s Sunday morning, so we’ll get you a breakfast.”

He took my arm and guided me through the house and upstairs to a bedroom.

“There’s an ensuite bathroom, and some PJs on the bed. They’re a bit softer than you’re used to, but we want you to start the changes early. There’ll be a meal brought up in thirty minutes, enough time for you to have a shower. The door will be locked, and the window has been secured shut. Sorry about that, but we aren’t taking any chances.”

I went into the bathroom and had a pee, then had a shower, shaving my stubble under the water. Dried, I put the PJs on, and he was right. They were women’s and satin, feeling cool and slippery on my skin. I had just put the dressing gown on when there was a knock on the door and Silvester brought in a tray, leaving it on a table. He left me and I tucked in.

When I had cleared the plates, I started to feel weary. It had been a stressful time, but I wondered if some of the meal had contained a sedative. I took the gown off and got into a very comfortable bed, drifting off to sleep.

I woke and went to the toilet, with the sun shining through the window. I didn’t feel that I had slept twenty-four hours, so it must still be Sunday afternoon. The tray had gone. I sat in bed and noticed a book on the bedside table. It was a copy of ‘How to be a woman’, by Caitlin Moran. It was something that I would never have considered opening, but I fluffed up the pillows and started reading.

It was an entertaining read, and I learned a lot about a teenage girl and her moving to womanhood. It wasn’t for transgender, so much, but I thought that it was the start of my reading for the foreseeable future. I was over halfway through when there was a knock on the door and Silvester brought in a tray.

“Your Sunday dinner, Jaquie. It also has something to help you sleep. We will move you in the morning, after breakfast. It will give you time to finish the book. Bon Appetit.”

He was gone before I could think of anything to say. I ate the meal and then laid in bed to finish the book. The sedative must have been a lot weaker, as I had time to put the book down, go to the toilet, brush my teeth and get back into the bed. Before I went to sleep, I realised that my book reading had opened my eyes to what a girl thinks, and it was vaguely pleasant.

I was awake early, showered and shaved, and was wearing a clean gown when the breakfast was brought in.

“Good morning, Jaquie Doe. When you’ve finished this, clean your teeth and be wearing just the gown. I’ll come for you in an hour. You will be taken from here in an ambulance, on a stretcher.”

I ate the breakfast, went to the bathroom and brushed my teeth. I just had the gown on when he came back and took my arm, leading me back down the stairs and out towards the back of the house to a boot room. There, a guy in scrubs waited with a stretcher on wheels. I was helped up on to it and was then strapped in. Silvester then put a hood on me, and I felt myself being wheeled outside and into an ambulance.

The trip included a lot of countryside, as I could hear birds and smell odd odours. We arrived at the clinic and must have gone into a large garage, as the sound became echoed. It was odd how your senses can utilise the ones that still have access to the world. The hood was removed and the guy with the scrubs unloaded me, pushing the stretcher into a reception area.

A doctor, from the stethoscope, looked down at me, a clipboard in his hand.

“Jacquline Doe? In for a complete sex change as a private patient?”

“Yes.”

“Right. You will be taken up to your room. The rest of the day will be tests and measurements. For the next few weeks there will be some training, as well as some minor surgeries. We start you on hormones as soon as we get the blood results, so we know what dose to give.” I was wheeled to the room, where I was released from the straps and allowed to sit on the bed. It didn’t take long before I gave blood, and urine, with an attractive nurse called Pauline, who said that she would be my day nurse.

After that, I had my first hospital food, which wasn’t that bad, then taken to another room. There, I had to stand, naked, on a revolving platform as I was measured by light beams. The operator told me that it was to show the surgeons where to take fat from me, and where they could put it back to enhance my general shape.

Redressed in the gown, I was then taken to the training room, where a severe woman instructed me in walking, having to walk a line and altering my posture for a couple of hours. Back in the room, I was given tea, as well as my first hormone injections. The evening was spent in bed, watching a chick flick, and wearing a nightie.
That was the start of the first weeks there. Over the first week, I was taken to a room where they used electrolysis to remove all my body hair, and then what little facial hair I had, including some of my eyebrows and a lot of nasal and ear hairs. I spent my days wearing an assortment of shift dresses and shoes that I was told were ballet flats. The walking exercises now included me doing them with a book on my head, so I didn’t look down as I walked the line. My evenings were a succession of chick flicks and how-to films on make-up and hair care. My own hair, already longish, was growing quickly as my body absorbed the injections I had been given.

The second week started with me on the operating table, undergoing liposuction. It ended with me back on the table to be given my new breasts. When I was able to stand, I was surprised by the weight of them, but thought that it could be from the explosives that I had been told they contained.

It was after this operation that I was introduced to bra wearing, and all the different types that I could choose from. My dresses now reflected the bra choice, and my footwear was slowly being changed to more fashionable styles. The third week had me speechless after a small alteration to my vocal chords, followed by a number of cosmetic changes to my facial features. The fourth week started with me having some of my own fats added to my hips and bum and ended with me back in the theatre for the big one.

By this time, I was so steeped in hormones and training that it didn’t matter to me that I was about to lose the ‘outer’ and get an ‘inner’. I was living as they decreed that I would live. I was becoming Jaquie, and every time I looked in a mirror. It was Jaquie that looked back. I had absorbed the lessons and now walked and talked as a woman. I could sit, stand, make small talk, and could now understand why women were so open to each other. I could admit things to Pauline that I would have never admitted in my dreams.

After the big operation, I was confined to bed for a few days. After that, I was wheeled about in a chair, with places to put the bags that were fed from tubes coming out of my body. It was another week before the tubes were removed and I was allowed to have a shower. That was the most fantastic feeling that I had ever had, especially when I rubbed a certain part of me with the flannel. It was a sudden feeling that made me gasp. I was also feeling odd when I washed my new breasts. Now, I had three places that made me tingle from just a touch.

I was in the clinic for another three weeks, with further training in feminine hygiene and the care and attention of my new part. Now I could wear anything, the skirts got shorter, the tops were more revealing, the underwear was skimpier, until I reached my limit of modesty. I had built a good wardrobe of clothing that worked for me, as well as having advanced training in make-up until I could do it almost in my sleep and look good. It was in the last week that I was taken to an in-house salon and given a new hairdo and some studs in my ears. Then, a photographer came in and I had to pose for him, with many changes and different faces.

The following Monday, Silvester came to collect me, and I moved to the next part of my new life. Instead of being restrained and unable to see where I was going, he, and I, sat in the back of a Bentley, with a chauffeur driving, and my luggage in the back. I was taken to a large country house in South London. As we drove through the imposing gates, he squeezed my arm.

“Welcome to your home for a while, Jacquie. You have a month of more training and then you start working for a living.”

Marianne Gregory © 2024