And now for something completely different!

Chapter 1

I suppose that was inevitable that I would end up in prison. I had hoped that I could get away to somewhere safe before the brown stuff hit the fan. No, my greed held me back for too long and here I was, in court, with the judge about to read out my sentence.

“Delmore Edward Strauss, you have been found guilty of fraud, theft, trading under a false name and misuse of Government Property, namely two public buildings which you sold to unsuspecting citizens of another country. It may be that the other country might ask for your extradition, once your time with us has been completed, and I, for one, would be happy to see the back of you. I sentence you to ten years jail, with a parole allowable after seven years, should you last so long. Take him away.”

I didn’t have to wonder about that last remark. South African jails are the toughest in the world, often overcrowded by a factor of three and above. They were out of the hands of the authorities, who simply did their best to keep every prisoner in. Most of the prisons were run by various gangs from inside, with any leaders still organising his gang from his cell.

I suppose that I should have expected the worst, seeing that it was a fellow judge who had bought an ‘exquisite holiday home, next to golden sands’ from me. I had a system. I would find about four likely holiday properties which had the owners away, advertise them in an up-market magazine (without the addresses, of course) and sell them at prices so good, the buyers couldn’t believe their luck. With the system, I would visit the house and try the door with a soft key, then go and make one that worked. That way I could take my clients to inspect the property. I took all the deposits, promised settlement in three weeks, and then moved to a different city every six to eight weeks.

The two public buildings had been a gift from the government. I mean to say, if you build a police station that looked like an unmarked office block, you should expect someone to sell it. I even took my customer in for a walk around, telling him that the tenant wanted to keep a lot of the areas locked, for security. The second one was a long shot, a new, and unfinished, building with a nice picture on the fence showing the artists impression of the finished job. That one was sold ‘off the plan’ to an Asian investor.

I had made a lot of money, enough to retire on, but the excitement of the chase was my undoing. I had tried to sell the police station a second time, not realising that they had installed modern face-recognition cameras, my face on file from a description of the first buyer. It took several weeks to bring me to trial, but, once there, the process went like lightning. I had come to court, with my lawyer and a small suitcase, fully expecting to be found guilty.

I was taken from the dock, handcuffed, and led down to the holding cell. No-one bothered me until the door opened and a couple of court attendants came in and gave me a beating. I expect that they were friends of the judge. I was on the floor, feeling worse for wear, when a couple of prison officers came in, gave me a couple of kicks, for luck, and hauled me out of the cell and up to a loading dock where a prison van waited. I was pushed into a small cell, along with my suitcase, and left to wait until they had finished loading.

We went north out of Pretoria, my latest centre of operation. When we arrived at our destination, I had peed myself, unable to do much else with my hands manacled behind me. I wasn’t alone as we were herded into the reception room, via a washing area where we were hosed down with something that smelt like disinfectant. One by one, we were taken into another room, uncuffed and told to strip. Our wet clothes were put into a bag, which was attached to whatever bags we had brought, The guard told us that these will be kept for when we came out. That was a laugh for a start!

We were then issued prison orange, rather fetching, if you ask me. All of us, from the van, were taken to a reasonable sized cell, with just enough bunks for us all. As he locked us in, the guard laughed and told us that we were lucky that we were here first but to expect to fend off new arrivals as they joined us. Before the time for food arrived, there were three times as many in the cell. I had just given up and lay on the floor, rather than fighting for my place. I wasn’t feeling the best from the earlier beating, anyway.

The feeding was survival of the strongest, and I was still fitter than most of those around me, so didn’t take part in the skirmishes. Instead, I listened to the talk, finding out that I was housed in the Matatshe Prison, just north of Pretoria, and, from the consensus of my companions, not a bad place, as prisons go. Two days later, after some of the others had been hauled off, they came for me. It was good to breathe fresher air, as the two buckets in the cell were so rank, it was difficult to breathe.

I was taken to a holding area, where my sack of soiled clothes and my suitcase was put by my side. There was even a latrine area where I, with a guard to watch, was able to take the crap I had held in and was threatening to make me explode. Then three of us were taken out to the loading area and each given a small cell in a prison van. This one, at least, had small, barred, windows so we could see where we were going.

That trip was relentless. The guards swapped the driving, stopped for breaks without worrying about us. When one guy shouted, they waited until we were somewhere away from everywhere, then pulled him out and knocked him around a bit. After travelling the rest of the day, and all through the night, we arrived at an area which I recognised. I had set up an office, here, a long time ago. We were in Tokia, some way north of Cape Town City.

That’s when my heart almost stopped and what little in my stomach threatened to make its way to the outer world. If we were in Tokia, we were on the way to Pollsmoor Prison, the most feared in the country, not because of the guards, but because it was run by the gangs, and they had stopped reporting on how many had been carried from that institution in body bags. No wonder the judge had said “should you last so long”.

My lifespan, in this place, as a white, Afrikaner, short and slim, could be given in weeks, if not days. I allowed myself to look out of the van window and take it all in as if it was my last view of the world. Here, I would be beaten as a daily ritual, raped as a matter of normal activity, starved, and left to die, just another that couldn’t take the life that was normal for most of the inmates. The keys that were set into the heels of the shoes in my case would not be any good for me now. My nest-eggs would go uncollected.

The sun was coming up as we pulled into the main doors of the Medium Prison B. We stopped at another set of doors and the main doors were closed before the ones in front opened. The van then drove around to a set of gates to a wire compound, where we went through another double gate and into the compound. There, we were let out of the van and our baggage was put on a sack truck. The guard told us that they would be waiting for us when our sentence finished, smiling broadly as he said it.

We then went inside a building and ordered to strip. Then we were sent into separate shower cubicles, without doors so that one guard could watch. There, I had the best shower that I had enjoyed for days, with plenty of suds from the industrial strength soap. We were given new, orange, coveralls, and a pair of slipper-like shoes. We were registered on a big ledger and separated, the other two being led away. The guard who filled in the ledger grinned at me and tut-tutted.

“Who’s a lucky boy, eh? Take him to the games room, I believe there’s a trusty there who will show him his future.”

I was led through numerous doors, that were unlocked and then locked behind us. We reached a room where an older guy, dressed in the prison orange, waited for us. The guard just nodded to him and turned around to return back to where we had come from.

“Bit of a surprise, eh?” said the trusty. “This is where we run the place. Follow me.”

I followed him through an unlocked door, out into the daylight and into a fenced area with benches along one edge. He told me to sit on a bench. He stayed standing.

“I hope that you have a strong constitution and a sense of humour, young lad, because you’re going to need it. I’m to leave you here. Through that door over there, you will see two guys who will come and ask you one simple question. If you give the right answer, you get the chance of a lifetime. If you give the wrong answer, your life ends here and now. You’ll recognise the guys, their names are Pluto and Bluto, here in Medium B. They look a bit like Oliver and Hardy on steroids. Whatever happens, I’ll be a long way from here, in the company of guards. Good luck, young fellow. I don’t know why you were chosen, but, looking at you, I think that I might have a good guess.”

He went back inside, and I heard the sound of a bolt pushed home. I sat there for about twenty minutes, savouring the sun on my face and the breeze making my hair blow around my ears. I had been surprised that no-one had taken shears or clippers to it once I was incarcerated. I had my eyes closed when I heard a clang and looked up to see two monsters walking across the yard to come and stand in front of me. I could understand the description, I guessed that Pluto was the short, white, one, while Bluto was a massive native, maybe Zulu. They were both adorned with gang tatts. As they got closer, I realised that the shorter one was still a good six inches taller than me. He spoke as they stopped in front of me.

“Delmore, for some reason our boss has taken a shine to you. He has been following your case in the news. He has told us to ask you if you will give yourself to him for the duration of your sentence. Will you do that?”

There was only one way to go, so I nodded and said “Yes, I will.”

“Good,” growled Bluto, “We’ve already reached our quota of bodies for the week. The guards get upset if we have too many. Come with us.”

I felt like a child, between the two of them, as we went out of the door that they had come through, and into the maze that was the prison. It was a typical prison, set out in squares with yards in the middle. The noise was deafening, and the smell made me want to puke. We went right to the end of the corridor, where the air was much better, and the sound had diminished a bit.

Right at the far end of the row, there was a gang member standing guard over the last three cells. One thing that I had noted, on the way, was that all the cell doors were open, and the prisoners had free reign. My attendants stopped and ushered me on. The guy grinned, showing a mouthful of blackened teeth.

“Come along, Delia, the boss has been waiting for you. Don’t be shy, he doesn’t bite, unless he likes you.”

I walked to the last cell door, as he had indicated, thinking, Delia? I’ve just got here, and I’m already classed as a bitch?

The cell was quite large, obviously originally designed for four prisoners, or more. Sitting at a small desk was a large native, with only a couple of tatts. He was in his fifties, if I took a guess, but still fit. He gestured to a metal chair that was in front of the desk. I sat, and waited, as he looked at me with soulless eyes. I had seen those eyes in the paper. I was looking at Dirk Hender, one of the deadliest gang leaders in the country.

“Delmore,” he said, at last. “I was interested in you when I found out that you had tried to sell a Police Station, not just once, but twice. That marked you as being a man who took chances but was arrogant enough to think you could get away with it. I saw that the police could only stick a couple of charges on you, although I would guess that you had been in the business a lot longer. That shows that you can be careful, staying below the radar.”

I sat there, just listening, as he paused, tapping a pencil on a piece of paper.

“I have a need for a person like you, someone who can oversee my activities and co-ordinate the flow of information that comes into the prison. Can you do that for me?”

“I believe that I can, given a few days to find my feet. This is the first time I’ve been into a place like this, there’s a lot I have to learn.”

“More than you would think. Part of the job is to be my wyfie. You have all the looks that make you perfect, in fact, I think I like you already. However, I don’t class myself as gay, so our fun will have to wait until you look the part. I arranged you to be brought to me from the court. I’m sorry that the judges’ friends knocked you around a bit, it wasn’t something I could say ‘no’ to. You do have to negotiate, sometimes. For the first few weeks, you will stay in the cell next door, I think you will find it comfortable. You will be taken to the library. There, you will be shown how the inmates send and receive messages in books. New books that come in will have messages that the guards have read, but not understood. Old books are sent to a charity that we run, and they also contain messages. You will not be able to understand the messages as you have yet to gain my trust. We do, however, have seven years for you to achieve that.”

He smiled, for the first time.

“Welcome to my world, Delia, my sweet wyfie. If you thought that you were breaking the law before, becoming my right-hand girl will put you into another class altogether. Now, go next door. You’ll meet my current wyfie there. She is called Cloe and has been good to me for the last eight years. She will show you the ropes until she is to be discharged in just over three weeks.”

He looked down at the papers as I rose and left the cell. My mind was in a whirl, me, as right-hand girl to Dirk Hender, in more ways than one. My world had been turned on its head and thoroughly shaken. This was something that I had never contemplated, it was just too bizarre. I had expected to be raped and killed, not to be made love to and put into a sphere of total criminality. I was just a fraudster, not a murderer.

As I left the cell, I noticed that the corridor that ran at right angles, had a grill with a gate, so the access to our end of this row was just the way I came. As my gaze looked beyond the gate, a giant of a native, every part that I could see covered in tatts, gave me a grin. I realised that another gang leader may be that close.

I went to the next cell and walked in. It was a little smaller than the other one, possibly originally build to house three inmates. Waiting for me was a redhead, which was accentuated by her prison orange, altered to become a dress. She smiled and came to me and gave me a hug.

“Welcome to your new home, Delia. While I’m still here I’ll try to turn you into the next, and hopefully last, wyfie to Dirk. You will be the fourth wyfie; the first was Amy, and she was sent here just a month after Dirk got sentenced to twenty-five years without parole. She was let out after her five years. She had trained up the second, Bella, who was here for her five years. She trained me and I’ve been here nearly eight years. If you reach your release date, it will be within a few weeks of Dirk getting out as well.”

I looked around the cell, what little there was to see. Beside the latrine, there was a small metal desk and two metal chairs, a small cupboard, as well as a double bunk along the outside wall, with the upper one just below the barred window slit. I looked back at her and took in the obvious female shape, breasts, hips, narrow waist, bare legs, and arms.

“I know you think it’s crazy, but you don’t have to get to look like me straight away. We just have to get you looking, and acting, feminine enough for Dirk to pretend that you’re a woman who likes to have his dick in her arse. The consequences of not enjoying it are fatal. If you displease him, he will give you to the four soldiers next door, for that night. It is a very long night, I can tell you, from experience, but they do not damage the goods, so they don’t knock you around. You’ve already met Bluto and Pluto, there is one sleeping who is called Spike, and the one out in the corridor is Bull. He and Spike take twelve-hour shifts guarding these three cells. I hope that you have a good memory because there’s a lot to take in.”

“I do have an excellent memory, thank you, Cloe. I wouldn’t have been any good at my profession if I hadn’t. The double bunk, do you often have visitors?”

“No, but I keep it there so I can look out the window and see the glow of the outside world. Just on the other side of the wall is the Steenberg Village, where normal people shop.”

“I remember that from the times I worked in the city, I remember getting things in the Woolworths, there.”

“Right, we’re on the extreme corner of the prison. The part that you were brought through is set aside for the lower-level gang members, there are two other sections, each with their own leaders. There are three gangs here, we’re called the twenty-sixers, and we organise the gambling and smuggling. The twenty-seveners are on the other side of the yard, with their leader just around the corner. They are the enforcers, and you don’t want to upset any of them. The twenty-eights are the general soldiers, in the next block. We get an hour in the yards, each day, but we don’t allow exercise. That time is strictly when we find out what else is going on inside this place, and to make plans with other leaders. It’s also when punishment is given out.”

“Sounds like you’ve got it sewn up.”

“You’d better believe it. The guards allow us a lot of leeway because the alternative can be catastrophic. This place was built to house four and a half thousand, at a pinch. At last count, we were over seven thousand and it doesn’t take much to explode. Most of the guys in here have nothing to lose. They don’t have any chance of a job outside. A lot of them will kill another inmate, on request, just to get an extension of their sentence, so tread lightly.”

“What about you, looking the way you are?”

“That’s easy. Only a leader has the power to arrange these changes, so most of the prison population will steer clear, maybe giving you a whistle or a leer, but never if you have one of our enforcers nearby. There are several, like us, in the place, as well as a lot more wyfies who don’t have the advantage of looking good. They’re the smaller ones who get reamed, whether they like it or not.”

“That’s what I expected my fate to be. I suppose that being a wyfie to one guy is an improvement.”

“It certainly is. Now, we have to get you started. I have a new outfit for you, and you need to get some food into you so that you can start your pills. I saved you a bit of breakfast.”

I was sat on one of the chairs and presented with a bowl that looked like gruel but tasted like bacon. When I had finished it, she gave me two containers of pills.

“One is the testosterone blockers, the other I hormones. Take three of each, twice a day, for a week and we’ll see how you do on them. As the good doctors say, ‘You may have odd feelings and mood swings as they act,’ but don’t worry, you’re unlikely to die. Now, let’s get you looking the part.”

I took off the orange jump suit, then she attacked me with a small electric razor, plugged into a socket next to the desk. She took her time, going over some areas more than once, until I was smooth. She then handed me a pair of female panties and told me to make sure I tucked my dick between my legs when I pulled them up. Then it was a white, cotton, bra, complete with filling, to give me breasts. Finally, I pulled up the new orange dress, buttoning it up to a point where she told me to stop.

“Good thing we all wear these slippers, you don’t have to learn to walk in heels. But you do have to learn to walk as if you’re wearing heels. Short steps, one foot in front of the other, no striding, even if you’re in a hurry. Now, let’s see what we can do with the lashes and hair.”

She then began to pluck my lashes, the brushed my hair out to look a bit less slept in.

“I notice that you have the razor and tweezers, surely these aren’t allowed.”

“The razor is allowed, because we can’t have a blade of any kind, and the guards don’t want anyone growing beards, as it can make it difficult to identify someone. What they haven’t twigged is that the foil of an electric, if split, makes an excellent weapon. The tweezers are kept in a safe place, we always get advance notice of a search.”

She pulled out a tube of lipstick and told me to pucker. When she was happy, she grinned.

“Now, let’s see if you pass muster.”

I wasn’t sure of this, but she took me by the hand and pulled me out into the corridor.

“Hey, Bull, what do you think of our new wyfie?”

Bull looked startled and then broke into that black-toothed grin.

“Hell, Delia, I hope you get into some trouble so I can get a piece one night.”

As he looked me over, I could see his jump suit tenting. I gulped, then thanked him in my nicest voice. At that, Cloe laughed and pulled me back into the cell.

“Dammit girl, here five minutes and you get Bull aroused. I don’t think it’s going to take the full three weeks.”

Back in the cell, she showed me the two drawers set under the lower bunk. I was given the right-hand one, for now. It already contained a couple of cotton nighties, some bra and pant sets and a small box with cosmetics, as well a box of the pill containers. It wasn’t much, I know, but a lot more than I had arrived with. There was a bit of polished tin on the desk, and she got me to try to make myself up, wiping it off if she wasn’t happy. Then, she had me walking back and forth in the cell, until she thought that I could do it properly.

“Right, Delia. This is the first test. We are going to get our enforcers to escort us to the admin block, where we spend the afternoon in the library. We get lunch with the guards there. You’ll get to know them all, by name, before the first year is over. Remember, we don’t rush anything, one is because it gets the authorities jumpy, and the other is that you have seven years to endure. Rushing about isn’t going to make that pass any quicker.”

I hoped that her faith in me wasn’t misplaced as we went next door to find Bluto and Pluto.

Marianne Gregory © 2023