Prison Survival Guide

Everyone had returned to the court room after it was announced that the jury had reached their verdict. Sitting next to my public defender hearing the murmurs of the crowd behind me, no way could I turn around to see the look of my mother's eyes, I could feel my stomach churn. 23 years old, still a virgin, hadn't even gotten a kiss and I could be going to jail for the rest of my life, never to experience those parts of life or at the very least be greatly delayed. Closing my eyes thinking back on how I got here.

It all started when my dad brought home a computer. My family didn't have much, I was confused when he brought it home since I usually got second hand clothing from thrift stores or things my mom made, I would later learn that my parents were in crazy amounts of debts and the computer was just one more thing on top of that pile. My dad believed that computers were going to be a big part of the future and for once he was right.

I was obsessed with the computer, spending every spare moment not at school on it. Spending all my time on the internet which was just starting to pop off in a big way. Dial up was still the norm and it had its challenges but I was amazed at how I could live chat with someone on the other side of the world. My first job delivering flyers had every cent I earned put towards upgrading the internals of the computer. I learned everything I could about them. I devoured every bit of information I could about it. At the age of 14, I would discover something that would change the course of my life, like a fork in the road of life, I had found hacking.

Various forms of the techniques basic to the skill had existed for a long time but computers had kicked it into over gear. Gone was the silly phone jacking. A new era had arrived right as I was coming to age. I loved every aspect of it, part psychology, part code breaking and part technical skill. I honed my skills at every moment I could, getting more and more daring with each passing hack.

I didn't bother going to college, what more could they teach me that I didn't already know. I found a job right out of high school working cyber security. It was funny to work on the other side of it, setting up ways to stop people like me. I probably could have been someone but I had no ambition and no interest in becoming the next Mark Zuckerberg.

My hacks were mostly mixed, all illegal, some more morally questionable than others but even though illegal I did some things that made me proud, exposing several pedophiles was the highlight. Contacting the FBI, giving them all the information, I had managed to collect and then waiting to see the piece of shit arrested. I was sent into a spiral of depression a few times after they didn't act on what I had sent them.

It was during one of these downward spirals that it happened. I came across a posting on the dark web, offering a big pay out for a difficult job. I sent in my reply with a bit of my resume. My handle was well known online, so I could have probably gotten by with just that but I always liked to prove what I could do. By the end of the week, I had hacked in and stolen classified information only to hand it right back to the FBI. I was set up, or at least that was the way I felt. They did these sting operations often enough that I should have noticed the signs but between my depression and wanting the big pay day to finally get out of my parents' house, I had just pressed on.

I will never forget the day the cops came. Light rain drizzling down, the cool summer breeze, the sun hidden away by the clouds, the smell of wet asphalt, the sound of the cuffs clinking together, tears rolling down my mom's face, the look of disappointment on my father's, the lights of the squad car breaking through the grey dim sky, the force of being pushed into the back seat and then that all too familiar sound heard at beginning of every Law & Order episode, the jail doors closing.

I had managed to make bail with what money I had saved up, hoping to buy an apartment. The one thing they don't tell you is how long it can take for a trial date to arrive. I had basically an entire year before it would start. They let me out on the condition that I would not be allowed any access to electronic devices. I had no passport to surrender, was the furthest thing from a fight risk and a nonviolent offender of the law.

In that year I had decided that I would get in shape, I had nothing else to do, besides reading books, trying to prepare myself for what was to come. I was never in great shape, my life spent sitting at a computer, my meals small, usually ate at my desk, had kept me skinny with the slightest hint of a belly starting to form. I hadn't had a real hair cut since I was 14 years old. My brown hair constantly kept up in a pony tail that finished around my shoulder blades. If it got too long, I would just take a pair of scissors and trim it myself. It never looked good per se but it was what I liked.

The year of working out did not pan out how I had hoped. I wanted to put on a bunch of muscle and look like one of the dudes on the front of bodybuilding magazines. Nice thought, too bad I had no idea what I was doing and was not eating near enough calories to achieve any kind of muscle mass. So, I just ended up getting toned and even developing a bit of an ass, even if that ass did look like it belonged to a fit girl... at least I could run now... not that I would have far to run trapped inside the prison walls.

The judge commanded "All Rise" breaking me out of my memories, I stood up, my legs shaking under me. Deliberation had taken 14 hours. A good sign for me, it likely indicated a hung jury or even an acquittal. Maybe my lawyer's strategy of saying the state had entrapped me was going to work.

"Has the jury reached a verdict?" the judge questioned in a powerful voice.

The chairman of the jury stood, "We have your honor." You could hear a pin drop. The room was completely silent. My heart sunk in my chest as the next words left her mouth, "We the jury find the defendant guilty on all charges."

I felt my legs collapse under my weight, catching myself on the table and slumping into my chair. I could hear my mom crying from behind me. My dad trying to comfort her. I still couldn't look them in the eyes and face them. My lawyer patted me on the shoulder, "I'm sorry, it was always going to be a long shot. I'm just hope that your happy we took the shot instead of cutting a deal."

The judge spoke up, "Sentencing will take place tomorrow. You will be remanded to jail until that time." The judge looked at me. "Bailiff, please cuff Mr. Anderson." With that I was back behind bars. I had only spent a week here before my bail hearing and I would be here again for less than 24 hours before sentencing and transport to prison.

Back in the court room the next day, was a much quieter, somber experience. My lawyer argued as to why I should be given a light sentence. The judge locked eyes on me, "Thomas... Throughout this trail you've refused to admit any wrong doing or even acknowledge that you committed a crime. Now that you've been charged, do you still feel the same way?"

"Well, your honor, the way I see it is that the jury must have been barely unanimous, so it wasn't even clear to all of them that I was guilty, why should I admit guilt?"

"That's what I thought your response would be... Mr. Anderson, I sentence you to the state Department of Corrections on each of the indictments. I am sentencing you to a term of 15 years, the term shall be no less than 5 years when you shall receive the opportunity at parole. I hope you take this time to reflect on what you have done. This is the sentence of the court and you are remanded to the state Department of Corrections. And officers may carry forth on the imposition."

With that my hands were cuffed once again, driven back to the jail where a bus was waiting, escorted on to the bus to barely see a few faces before being sat down. I figured I would be going to a white-collar prison but given what I had just seen, I was sorely mistaken. We arrived at the prison, strip searched, forced to squat and cough. I along with one other new inmate turned in our belongings, turns out the other guys were just being transferred, and then us two were handed an orange shirt and pants, along with boxers, socks and slip shoes. I was confused by only getting one set and then being told by the guard that no one had their own clothes was something I was not expecting.

I was walked into my new home for the next 5-15 years, cell block C. I was told it was mostly nonviolent offenders but there were still some rough customers in here due to overcrowding. I was escorted to my cell; the doors open with a hulking menace of a man. Dark skin, 6' 5", at least 250 lbs, probably in his mid 30s, a surprisingly well trimmed short beard that complimented his bald head, covered in tattoos on his entire body, at least from what I could see from him wearing no shirt, 6 pack abs incredibly muscular all over, my eyes soaking in his body for some reason my stopping at his crotch. Even behind the pants I could tell that he had a massive cock that would make my 3" cock look like an overgrown clit. He spoke up his voice loudly booming, "Oh, you brought me a pretty one! What did I do to deserve this?"

"Someone must like you, Johnson." The guard laughed as he left the cell.

He stuck out his massive hand in a friendly way and I shook it, my hand looking small and dainty compared to his. "The name is Andre, nice to meet you."

"My name is Thomas." I replied looking up at the man. He was nearly a foot taller than me.

"Well Thomas, welcome to prison. I'm a lifer, so I will be able to show you the ropes around here... and if you want, offer you some protection, in exchange for something..." his words trailed off leaving me too think about what he could mean "It will be better than those Aryan fucks, plus they would likely make you cut your beautiful hair." He said playfully, gently tugging at my pony tail, winking at the end of his statement. I could guess what he meant but the thought of having to try to service this man made me more nervous than I had ever been in my life... even now being inside a literal prison cell.

"Ummm... Lifer? What did you do to get stuck in here for your entire lifetime." I questioned.

"Listen kid, first word of advice, don't ask someone what they are in for, at least until you know them decently. You're just lucky I'm such a nice guy... I grew up in a rough neighborhood, was in and out of juvee, a few short stints on drug charges in this very prison... and then I killed my dad. He was beating on my mom again, real bad this time and I ended up pummeling my old man to death. It wasn't intentional but I was filled with so much rage watching her get beat up along with me and my younger brother. If I wasn't such a fuck up before that I would have probably gotten a much shorter sentence."

I could see tears in his eyes recalling the story. It was odd to see such a mountain of a man crying, I instinctively reached up and wiped the tears away from his eyes the way my mom had done for me so many times as a child. "Fuck... I'm sorry Andre. I shouldn't have asked."

"No, you shouldn't but now you know my story, what about yours? How did such a pretty little white boi end up in a place like this."

I relayed to him my entire story, probably over sharing to someone I had just met but given what he had told me, I felt I owed it to him. "Well, that's how I got here."

"Ain't that a bitch. I'm surprised they threw the book at you after your first offense."

"Well, stealing classified information and then not admitting guilt, did not make the judge happy... I should have known something was up, it was difficult to get into the server but it should have been harder."

"You're clearly smart when it comes to some things boi but you've got a lot to learn about street smarts and just general life knowledge. If you had just admitted guilt and begged on your knees, I'm sure the judge would have let you off with a slap on the wrists."

"My lawyer thought we could get the entire case thrown out for entrapment." I frowned.

Andre laughed hard, "Seriously? Public defender?

"How did you know?"

"Those public defenders have such a massive case load that they don't have the time to put into such a case. Hell I'm surprised he even suggested it."

"He did his best." I shot back.

Andre smiled, "I know kid. I'm not ragging on him, it's the entire justice system but I guess I shouldn't expect a young white boi to know that." There was a palpable anger in his voice, not directed at me but rather at the system itself.

"Yeah... You're probably right about that."

Andre showed me around the cell block; showers, weight room, library, cafeteria, the hallway to the yard and a hallway to where he said some guys worked. We had finished our tour when the guard who had brought me in came back.

"Thomas, the Warden would like to see you. You're not in trouble, he just likes to meet new inmates on their first day and assign you work detail."

He escorted me to the Warden's office. It was a big fancy office, very out of place with the rest of the prison. I sat down. He was an older man, I would guess in his 60s, grey hair, chubby and average height. Not what I expected to see from all the movies and shows.

"My name is Warden Mason, I run this prison, there is nothing that goes on here that I don't know about. If you stay out of trouble, you and I will have no issues. Understand?" He spoke in a deep southern drawl even. I nodded as he continued along, "Now for work detail, do you have any skills outside of computers?"

"No, Sir... Other than computers and delivering flyers, I've never had another job." I replied with my head down in a little shame that I hadn't picked up more life skills.

"What about cooking or even just doing veggie prep?"

"You know the soup Nazi from Seinfeld?" He nodded "Well that was basically my dad. He did nothing else around the house but when it came to meal time, he and only he would do anything food related. I would help my mom with the dishes and that's about it."

"Well, we don't have anyone in the kitchen that only washes dishes, it's very communal... I would make you my personal assistant but you aren't even allowed to send an email. So full access to a computer isn't happening. I'm sure with your skills you could shut this entire prison down... Show me your hands." I stuck my hands out confused and he took them in his hands looking at them. "Ah, perfect! Exactly what I expected. Small, dainty and soft. Not a single callous on these hands." I pulled my hands back, sticking them in my pockets, shamefully, as he continued to speak. "How much do you know about prison labor?"

"Nothing to be honest. None of the books I read mentioned it." I replied trying to figure out the smirk on his face.

"Well Thomas, you might be surprised to hear that one of the ways these prisons make money, to help pay for your guy's basics, is that corporations and the state hire you guys to make things. License plates are highly common but here, we also make things for Victoria Secret. It's usually a woman's job, sowing, but I think you will be well suited to it. Plus, you will be able to earn a little bit of money for phone calls and commissary items."

"And if I don't want to do that kind of job?"

"Son, your only other option I'm giving you is going to be back breaking labor. Digging ditches and the like. This is a pretty sweet gig I'm offering you."

"Okay..." I meant to add something else but nothing else came to mind.

"Well Thomas, I think it's time you get back to your cell. I will inform the guards of your work detail. One will lead you over there tomorrow, after that it will be up to you to find your way."

I stood up and walked out the door, the guard leading me back to my cell, Andre was busy playing cards with a group of other black men at the tables outside of my cell. I walked over to him and sat next to him, not really wanting to be around anyone else. I only felt safe around him. He smiled widely at that. Andre slipped his hand off the table on to my thigh, his big strong hand made me feel so small. I could feel my cock twitch. My sexuality was something that I had never given much thought to. I had watched a lot of porn as a lot of single men did and I always choose scenes with guys with big cocks and always came when the cock was visible. At some point I had discovered trans porn and the fact of a girl having a dick did a lot for me... towards the end it was all I watched. I always thought that I would love to meet a trans girl but maybe it was jealousy and I wanted to be them not be with them.

Then a memory from my childhood popped back into my head, clear as day, staying home from school "sick" watching day time television, the all too common episodes of a trans woman revealing herself to someone she had a crush on or an ex lover. The episodes were always hard to watch the woman getting rude sounds from the crowd, the way her love interest would inevitably end up rejecting her and the way that would hurt me at such a deep level only being a preteen not understanding why.

I sat for a time with the thought until there was a loud yell from the guards yelled "Lock up in 10." Andre looked over to me, "Time to go back to our cell." We walked back in, shutting the door behind us, the lock clicking automatically. I climbed into the bed, if you could call it that, the mattress was barely 3" thick.

My stomach churned as I sat on the bed, locked in a 8x10 cell. The grime from the room, the one pillow, the steel combination toilet sink, confronted the fact that this was all Real now. I'd be forced to leave my home and family, been sent to prison and now I was here. It was done, my life here was now real, not theoretical. The previous thought that I would get through this with no issues was replaced by that realization, marred by an anxious kind of horror at the things I'd never do now.

I hadn't really thought about that before I'd left. But now realizing that I'd never get to see the world. I'd likely never see my mother's heartfelt face again-

I started to cry. It surprised me a little. For days now emotions had felt stunted, buried under the very immediate concerns of survival and the unknown. But as soon as I had a minute to breathe everything I hadn't been able to let myself feel flowed out of my, eyes first. I tried to fight it. But then Andre came over, wrapping his strong arms around me and the tears started to pour down.

So, I leaned in. I sobbed and sobbed and sobbed, shook and shuddered with a pain more profound than any I'd known before.

"It's alright." Andre reassured me in the kind of voice that I remembered my dad using when our dog was sick. "You will get through this and I will be here for you."

I stopped crying, wiping the tears away from eyes, looking up at Andre into his kind eyes.

"How about something a bit lighter, what did you get for work detail." Andre questioned.

"Ummm... well it's embarrassing."

"Out with it! I don't care" he grunted.

"Making panties, bras and lingerie, I guess."

"Oh, you're on Victoria Secret duty! Sweet gig. Usually, only girls get that. I think only one other guy in my time here has gotten it. You should steal a pair of panties to wear for me. They gotta be better than these itchy ass boxers." He said with a hard laugh. "I noticed that you didn't move my hand from your leg when I put it on it."

"Yeah... well... you make me feel safe and right now in here that's about all I can ask for. I'd prefer to get out of here alive." I smiled gently.

"Well Thomas... it feels weird calling you Thomas by the way, you don't look like a Thomas... you're much more of a Tabitha. You cool with that?" he said giving my thigh a gentle squeeze.