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Big Chicago

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Big Chicago… Samayel


This is what it comes down to. Hands clenched around steel bars, teeth gritted quietly, eyes closed while another pumps into my body. It isn’t an act of desire…it’s a matter of claiming property. It’s stress relief in a pressure cooker for humans. It’s silence broken by the small, wet sounds of a greased hole being used roughly and quickly and the terse grunts of the unsophisticated bastard behind me taking his pleasure. This is hell. This is where bad people go for good reasons. By that definition, I must be a bad person. I must deserve this somehow…someway. This is a federal penitentiary, where the worst dwell among the worst. This is my life, but it wasn‘t always like this. I came from heaven where the angels sip champagne and worry over brand names. It was a long way to fall.

My family was Old South nobility, back when things like that still mattered. After the Civil War they lost everything and moved north looking for a new start. My great-grandfather was a shrewd investor, and so was my grandfather. As for my father, by the time he took the helm of the family and controlled the fortune that had been left to him, he could have lit his cigars with thousand dollar bills and still never exhausted the interest on our accounts. Naturally, this being Chicago, he went for politics.

Father was the kind of man who made other people feel like they worked for him…even if they were nominally supposed to be the one in charge. The city aldermen of Chicago are a viper’s nest of movers and shakers and money makers, but without the need for obvious graft, my father quickly became untouchable. It was never about money…it was all about power and influence. In truth, now that I can look back, life really doesn’t deviate much from that in prison. It’s cruder and even more brutal, but it works the same as anywhere else.

I have come to realize that, no matter how much I adored her as a child, my mother is a self indulgent lush interested only in her own comforts. She is the ultimate trophy wife, and never complained because she really couldn’t have cared less. Her husband is rich, she has everything she wants, so nothing really matters. She’s little more than a glorified blonde lapdog to my father, but that’s neither here nor there. I know these things because I take after her in many ways.

Ours was the kind of family born into isolated luxury. Gated mansion and servants at beck and call. Cars and chauffeurs, stables and horses, gardens and parties that took weeks to plan. I am the product of private academies and tutors and piano lessons. I can speak French and Italian and Spanish and write or compose in them just as well as in English. It rather makes the irony of surviving based solely on my ability to sate an engorged cock somewhat more embittering, don’t you think?

Among the upper class, being beautiful is a way of life. It is the norm. People wonder why the spectacularly wealthy always possess the glow of good health and look younger than they are. There is a reason for things being that way. It’s called money. Doctors, nutritionists, dentists, plastic surgeons, personal coaches and an endless array of professionals who can help you change anything you don’t like about yourself. All it takes is money.

Only when one is poor or of the lowest class is being beautiful a crime or a curse. You become vulnerable to those who hate you for being what they can never be. Even if all you have to call your own is the image of beauty and success…the fantasy of what it must be like to be as fabulous as the rock stars or famous actors, there are a hundred bitter souls who would take pleasure from stripping even that from you…just because they can. Those kind of people tend to wind up here.

This is where beauty is a curse. It damns you to servitude or suffering, slavery or death. If you aren’t strong enough to take, you become the taken. This is where I fit in. There shouldn’t be any shame in being beautiful, but here, in this forsaken place, I wish I’d been born disfigured, or obscenely hairy, or morbidly obese. Anything but willow slender and smooth as a girl. Here, the way I look makes me a commodity. The only virtue in it is that, being exceptionally pretty, it was inevitable that whoever was strongest would claim me as their own, jealously guarding what they took to be their property.

I could have wound up like Nott. He could have been handsome enough, if he hadn’t tried to fight back. He got busted for dope just like I did, but he wasn’t a faggot with the good sense to bend over and just try to get the job over with. Once the dentist removed the shattered bits and pulled out the roots, he was left with nothing but back molars in his mouth. They don’t hire plastic surgeons in prison. The reason his left eye looks like it droops is because the bones near his temple were smashed beyond easy repair. He’s the kind of prison bitch that gets given away to anyone that needs him at the moment. As for me, I belong to Flint.

That brings us back to the fucking miserable bastard behind me, sweating and grunting, pushing hard just to be mean, making it worse than it has to be just because that’s what he likes. Flint held the dubious distinction of being both strong and smart, even if he is a crude and miserable piece of shit. He was arrested for committing serial rape throughout the greater Midwest, from Michigan to Montana, and for robbery, arson, weapon possession and for the famous interstate flight he attempted just before they caught him. Flint doesn’t fear death…or pain…or anything else for that matter. He exists only to control or to hurt others, and he made himself right at home here. He blinded the first person that picked a fight with him, and hospitalized several of the others that tried to join in. It didn’t take long before he assumed a position of leadership in this shithole.

I assumed a position here too. The cell I was placed in on my first night was famous here. ‘The Bitch Tank’ was a cell reserved for frail or small new arrivals who might need additional time to blend into population. I was pathetically grateful for it at the time, because I was eighteen and scared to death, sentenced to seven years for transporting drugs across state lines. Did you know an airport is technically federal land? It doesn’t matter what state you’re in or from, possession of narcotics is a federal crime, when the intent to transport them across state lines is established. Thus, a first time offender get a stiff sentence to a federal prison instead of a county lock-up. The cruel irony of the Bitch Tank is that it immediately marks you. Everyone knows who the new arrivals are and what they look like, and being in that cell for a week guarantees that you’ll be private property or every man’s toy within minutes of your release into the general population.

It was an hour after breakfast when Flint showed up with his goons at his side. I put on a brave face and pulled off the act of a lifetime. The siren…the seductress…every platinum blonde bombshell I’d ever seen in the movies guided my instincts. I vamped him the best I could, demanded that he be first, and gave the most ferocious, mind-shattering blowjob I’d ever given. I still had to do the others, but by then the hook was in, and from the corner of an eye I saw him watching while others enjoyed my talents. Jealousy and greed saved my life. As soon as his sidekicks were finished, instead of the gang rape they’d expected, Flint called me his own and had me moved to his cell. Power players can pull that kind of favor easily, even if they are prisoners, and I was Flint’s personal toy before the day was out. For the most part, he hates to share. Good for me. Yay.

A lot of people wouldn’t believe the amount of power a prisoner can have behind bars. Flint has control over others, and influence with other leaders in here. His cooperation can make things easier for the warden and the guards, so Flint gets what Flint wants…within reason. It also means that, as long as I play my part and don’t ask for too much, I can get what I want. I only have a couple months left to go. I don’t want much, but there are things I need that are useful.

The prison doctor gives away lubricant. Nothing good, just the cheapest brand of greasy petroleum jelly. The stuff that lingers and leaves you feeling like the cheap, dirty whore you are. Not because they approve, or care, or want me to enjoy the experience. It’s about economics. It’s less expensive to give away the stuff than it is to stitch up the torn asses of every queen in the prison every month. Aside from that, I need very little, and I ask for very little. Flint likes that.

Flint doesn’t like boys. He likes women, or rather he hates women enough to assault them, but he prefers to have sex with them…especially against their will. In fact, he hates fags and holds me in contempt, but what else is there here? To make it a little easier for him to enjoy himself, he got cosmetics for me. Eyeliner and eyeshadow, lipstick and nail polish. When I got here, I had the standard prison haircut and a cheap uniform like everyone else. It’s been ’customized’ since then. My slacks were cut so short that they look like something Daisy Duke would wear, and my hair has been allowed to grow since I got here. It hasn’t been cut since that first day, and it’s well past my shoulders now, bound in a pony tail with a rubber band. Not a very long one, but enough that, given my natural features, I look like a white trash prom queen. Being more than a little femme helps too. No one here really looks forward to fucking a man. They make do when they’re too horny to care, but the illusion on my part makes them less violent about it. I make a fantasy come true for a few minutes, and I get to keep my pretty face intact. Flint mauled the last person who bruised my face. Not for love’s sake of course, but because someone hurt something of his without his permission. Yes…that’s horrible. I know.

None of this means that Flint doesn’t hurt me. When we have time and privacy I live out his private fantasies. Mock-rape. Or real rape when you acknowledge that I would rather be anywhere but here and my other choice is being hospitalized regularly or used by dozens of junkies and killers. Nott was HIV positive before he was here for a year. That could have been me, and if I’m not careful, it could still be me. Thoughts like that make Flint’s fist in my hair seem like a small price to pay. Pretending to be terrified, acting like a surprised victim until he comes, these are easy things to do. The bruises fade, the soreness goes away, and the cycle starts all over again.

If I play it carefully enough, I might just leave here with only one scar. The one where a modified piece of wire was heated to white-hot and pressed into my lower back, just above my ass. The wire was shaped like the letter ‘F’. Flint’s brand, marking me as his, just to remind me in case I forgot. It only happened because I’d gotten just saucy enough to act demanding about something, and I’d picked the wrong day. He decided to make a big show of reminding me whose grace I lived by, and I didn’t forget again.

A little about how it came to this. There are very few ‘guilty’ people in prison. So many people who were ‘misunderstood’, ‘framed’, or just wrongly imprisoned. Honestly, there are problems with the criminal justice system, but the odds of ninety percent of prisoners being innocent are pretty fucking slim. At least Flint is proud of his crimes, and even if he belongs here, his honesty is occasionally refreshing. I could say I was framed. I could say the judge was unfair, or that my state appointed lawyer was a moron and misrepresented me, and those things might be true…mostly, but at the end of the day, I was caught in an airport with a bag full of cocaine in my luggage. And not just a little for personal use. Lots of it. I did what I was told. I kept my mouth shut and waited for Blaise to send a lawyer and bail me out. No one came.

I was eighteen, and I was stupid, and I thought I was in love, or at least thought that I was wanted and valued. How I wish I’d had just a little of my current cynicism. Blaise took my ass off the streets, made me the well-dressed trophy on his arm, gave me nightclubs and all the drugs I could use. He was gorgeous in the fine, cruel way that men with power can be. He was Italian, and loved that I could speak the language of his parents. He was Mafioso, and I knew it, but I didn’t care. He had wonderfully curly dark hair, the kind that made me think of foreign fashion models. The best of European genetics, and charm for days. He also had one of the most perfect penises ever attached to a man…at least in my opinion. Let me reiterate…I was a teenaged whore in a very big city, alone, and with very few prospects. I was stupid because I chose to be that way. Life was shit, and then there was Blaise, and I was living the life I’d left behind. Back among the angels, sipping drinks I wasn’t old enough to be holding, but with enough money no one asked questions.

In retrospect, I might have had a clue about the nature of our relationship, but I chose not to push it. Blaise had a lot to prove, because he was technically a low level pusher and errand boy and still had to earn his way into a better position with his ’family’. Seventeen is pretty young for a person with responsibilities, but Blaise was smooth talking and calm when others panicked. I admired that. How many other boys my age could afford to put me up in a nice apartment and take me shopping whenever I felt like it. Instead of street trash hooker-wear, he put me in outfits that made me look like a goddess. With him, I didn’t mind the clothes hitting the floor when the lights went out. He was good in bed, or at least my attraction to him was so great that I honestly didn’t care about anything but having him inside of me as often as I could get him excited, and he got excited a lot.

That kind of infatuation makes everything seem like a good idea. When he said he needed me to do a little favor for him, I did it without question. Shit…I was proud to be of use to him in more than one way. Not that I wasn’t enthusiastic about the way I was useful, but my ego was pretty battered before we met, and the way he made me feel needed was better than any drug you could imagine. So I did it.

I know enough now to know that someone tipped the security off before I got there. I was only barely eighteen, traveling alone in clothes that were worth more than the staff there made in a year. I suspect that Blaise sent me because he’d known he was about to be set up. I can’t even guess at the politics that might have caused that, and back then I was careful to ignore his ’business’, but the end result was the same. Blaise wouldn’t come anywhere near a courthouse or do anything that involved him with me at that point. So was I framed? Sort of.

Law enforcement goes a big rubbery one when it comes to drugs. They love them. Not the way club kids do…at least not always, but they universally owe their budgets and careers to drugs. If it wasn’t for people trying to party or just forget, the cops would be forced to concentrate on either serious criminals or traffic infractions. Drugs provide a steady stream of busts that are often uncomplicated, and move thousands of people through a system that employs clerks and lawyers on a scale that no Wall Street firm ever could. Drugs are bread and butter, and if they vanished like people wished, the system would collapse overnight. Like blood-gorged ticks on the back of a dog, law enforcement survives on the flesh and blood of junkies and fools.

‘Tough on crime’ is the watchword these days. Judges, even the ones who aren’t elected, are political creatures. They have to watch what they do and what they say, always thinking of where their career will be in a few years. A judge who shows mercy will sit a local bench for decades, but a judge who plays hardball and sends the criminals away is a hero. Of course, this philosophy doesn’t leave a lot of wiggle room for a basically harmless person who did something astonishingly stupid. It happens more than you’d think. I was charged with everything they could tack on, and the court appointed lawyer who defended me made it sound like he was doing me a huge favor when they dropped a few charges and pressed on with only the most serious.

I’ve realized since then that the court appointed lawyers see their client for a few weeks or months at most, but they work every day with the judges and prosecutors. It’s an unspoken deal between the two sides that, when a generic defendant is charged, the prosecutor will start by firing off stacks of charges, scaring the shit out of the defense lawyer’s client. Then the defense lawyer ‘saves you’ by getting some of the charges dropped or reduced, but not enough to actually get you free. They do just enough to make you feel lucky that you’re not going to prison for as long as you might have. I reacted just like so many others do. I was too stunned and scared to be cognizant of much, rotting away in the city jail for weeks, almost starved for something to change. I agreed to plead guilty to the remaining charges and hope for mercy. That makes me laugh sometimes. Not happy laughter…bitter, angry laughter.

I got seven years. The judge does this for a living. He can’t be innocent after years of sending people to jail. He knew exactly where he was sending a skinny, ignorant kid. When they read the sentence, they might as well have included ‘…the court sentences you, the defendant, to seven years anal intercourse with vicious felons, with the possibility of your death or permanent injury at their hands, and furthermore, the court finds this highly amusing, and hopes that you will scream a lot while they take turns fucking you.’

Seven years. I’ll be twenty-five just before I get out. it’s so close, but it raises new questions. Seven years keeping your ass greased for convenience doesn’t prepare you for much of anything. What could be worse than this? The answer is this: the unknown. The only practical skills I have are getting men off and looking good while I do it. The only thing waiting for me outside is a new chance to hook until I get killed or arrested. I’m still pretty, for now, but it won’t last forever, and the next guy will probably be just like Blaise. I’m a felon. It’s like a permanent tattoo that says ’don’t employ me’. There is no future after prison, or at least no future that doesn’t genuinely suck.

Some people come back here again and again. They need this place because they don’t fit in anywhere else. I have two months to go, but the question is where will I go in two months?

I won’t be going home to family. I’m dead to them, and it was that way before I even got here. It was traumatic enough for my father that he’d spawned a flaming faggot, but that his child preferred to dress like a girl was just icing on the cake. I thought they’d still be vacationing in the Hamptons. I was seventeen and I loved to get out of the house and take the BMW into Boystown, the gay district in Chicago, and just cruise for cute guys who knew where a party was being held. Even if you can’t get into clubs, being pretty and young will get you all kinds of places. I got into them all.

I came home at six in the morning, a little stoned and still walking a little funny from the two hotties that took turns trying to fuck my brains out for most of the night while sharing their coke, which always made me completely insatiable. I would have called it a good night, until I walked in the door, still dressed as a girl, and met my father. Thirty minutes later I was in a taxi with a split lip and a hundred dollar bill, most of which paid for the ride back to downtown. It didn’t take long before I was completely broke, and my father had disowned me and refused to answer any calls from me.

It’s amazing how many people adore you when you’re rich and pretty, and equally amazing how quickly they have contempt for you when you’re not rich anymore. With only pretty on my side, people had only one use for me, but that was enough to survive on. It wasn’t all bad. I got into clubs and got a fake ID. I knew people who would supply drugs to party with before we ‘played’, and genuinely pretty queens are in demand, which guaranteed me a certain steady income once I got used to it.

I got used to this too. I suppose I was lucky to be experienced before I came here. I took it like the pro I was, and I’m still here. I’ve seen more than a dozen others get sick or hurt. I’ve even known a couple who died. Nott only wishes he died. He’s been on suicide watch a dozen times or more, and in my opinion, anyone with a shred of mercy would let the poor bastard die. The world was happy to throw him away, but it’s stunning how hard they try to keep him alive and prolong his suffering. Nothing he did was so terrible that it merited what he’s lived through. Then again, it’s hard to feel pity when I’m holding onto metal bars, making the right noises, sounding like it hurts and I’m scared, trying to make sure Flint comes soon and enjoys it enough to not kick my ass. Two more months. Where do you go…after hell?