My First Train

Reader discretion is adviced, this story contain graphic content depicting violence and rape which may not be suitable to all readers. This is a fictional story and do not portray real events or real persons.

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It was one of those situations from back in the day. I caught an 18-month jail bid for something I didn’t do all because I was with someone who did everything under the sun and then some. While my felonious cousin Taree treated his time like it was just another vacation stint, I was scared shitless. This was my first time being in trouble with the law. I didn’t know the difference between jail and prison, and I was having a really difficult time erasing every rape scene I ever watched from the memory bank.

Even though I was livid with my cousin for getting me locked up with him, he did come through. It took me a couple of weeks for me to get what the hell he was talking about when he said he got us “sovereign immunity in gen(eral) pop(ulation).” It about another four months for me to calm down and enjoy it. It short, it meant he secured the highest protection any two civilians (non-gang affiliated) could receive. That meant I didn’t have to worry about anybody hemming us up or shaking us down, and in exchange we acted as the middleman for everybody involved in our new little ecosystem. This mostly consisted of being brokers for the DO’s (Detention Officers) and inmates for the things they wanted from the outside. Think of those stories you heard in the news of how inmates are found with cell phones, weed, and other illegal contraband in their cells. Well, it ain’t like DO’s go around taking special orders from every inmate of means or inmates can walk up to them to put in request. That’s where we come in.

Of course, I didn’t have juice like that much less understood the innumerable logistics to be able to bring in that stuff. My job was to operate as Taree’s assistant making deliveries and pickups. Some days I didn’t even do that. Sometimes I just made small talk with some of the DOs that got hard just talking to an inmate. I was surprised that with so few worries hanging over my head it left a considerable amount of time on my hands. I guess it wouldn’t be lockup if I didn’t hit the weights. But since I wasn’t lifting for protection or to obtain a “girl,” it was nothing more than for aesthetics that didn’t go unnoticed by some of the bitches hungry for a man.

Before I became a jail inmate, I was just your average, cookie-cutter black fat nerd on my way to college. It was by no means the best school in the world, but for a kid whose folks never finished high school I thought I was doing pretty good. And had I got shipped off to prison, I would have been on my way to earning my degree. With the time I had, I wouldn’t have gotten it there, but I could’ve transferred some of my credits. In part, I’m glad I didn’t. If I had, I probably wouldn’t have known that I could test out of some of my classes, thanks to one of my fellow inmates.

As another way to burn the time, I made good use of the library, which consisted of a small collection of donated books. It was after I made mentioned to the inmate librarian that I read through all of them, including the Bible and the Qur’an, I piqued his interest.

At first, I thought dude was putting on. Gangs have gang conversations with other gang bangers, and those that aren’t into that life try to mimic it just to fit in while the obvious outliers scramble for a connection that wasn’t likely to get them jammed up in the long run.

I was quickly relieved of that thought process when I was put on that most of the men in there couldn’t read or write whatsoever. And that gave me an idea.

Whenever I wasn’t in the groove with Taree, I created a side hustle reading letters for inmates and writing back for them in kind.

The first year sailed by so smoothly I was banking that the next few months would be just as kind. Then, there was a change in the plan. Taree got his charges dropped on a technicality, and with time served on another charge, I was left there alone. My public defender still thought my charges were outrageous for a first-time offender, so she was hopeful she could get me out of there sooner rather than later. But I spent just enough time with convicts to know I wasn’t getting out overnight.

An even harder truth was now that my cousin was gone, I had nothing to offer the inmates as far as getting things in and out of jail. I knew enough of the game to know what he was doing, but I didn’t have those kinds of relationships with his connections like that. As I felt my stock quickly plummet, I read and wrote more letters than I could handle until one day I was called out of my little hole to run an errand.

At first, I thought this was it. That some dude or dudes were about to turn me out considering that in the year or so I’d been in jail, nobody could recall if I used my dick or my ass. I was mildly relieved when I was asked to stand guard in various places throughout the jail.

I did what I was told. I was smart enough not to ask any questions.

Then I quickly saw guys left battered and bruised through gang fights and gangbangs for not paying off a debt or being a newbie with no protection. And while it was something I took no pleasure in doing, the realist in me was greatly relieved it was better them than me.

I started to sense a change in the wind when a couple of dudes came around trying to bait me, putting their hands on my shoulders, telling me how good I looked, and sniffing extra hard complimenting me on my clean scent.  Of course, I’d been locked up long enough not to let that go so easily, toeing the delicate balance of standing up for myself without getting stitched up either. I did this by reminding them about their folks back home, those folks I wrote handwritten letters to and stuff. And those that didn’t have people like that, I quickly put them onto some pop ‘n’ fresh that just came through there and I thought needed a man. Especially those young bucks that were bad enough to be tried and jailed as adults, but young and tender enough not to know what was coming at them.

I was running out of options with three months to go on my sentence when I saw Montay licking his chops at my rounded ass. Even though dude just arrived there, he was just like Taree, a seasoned vet to the game wanting to pick up where he left off. While any piece of ass might’ve done it for him, I became his target when he found out who my cousin was. Apparently, the handsome but evil-looking devil had beef with my cousin on the outside and thought making me his bitch was going to fuck up my cousin.

I was spared from Montay thanks to my boy Jamal and his strong-arm play cousin T-Bone. Jamal was one of those rarities that came with some sense and an avid reader. We could go back and forth for hours on different philosophies and felt like we’d solved world peace and hunger.

Even though I was locked up with him, he was such a breath of fresh air that I felt it was a damn shame he got locked up. I could really see him changing some shit. Jamal could’ve done just that too since he was going to school on a track scholarship. He got kicked out of school after he got caught with weed. And after a series of events that plopped him right back in his old neighborhood, he got caught slinging dope. His sentence wasn’t long either, but it remained a toss-up if he was going to serve all his time in jail or if it was a layover for prison.

Jamal was just protective of me. He said I was the only one that kept him sane through the juvenile ignorance of other inmates. But the truth was, he trusted me stuff he didn’t want his gang to know about. Particularly, about his boyfriend in protective custody he would sneak off to see. I can’t speak for the prison world, but in jail, while it was cool to have a bitch, it wasn’t so cool to be flowers and candy with one like that. In which he was with this boy named Ricky.

And while Jamal was this sexy, slim, light-skinned dude I should’ve been into, I found myself eyeing his play cousin.

T-Bone was a huge, dark-skinned man that stood about six-six or so and weighed somewhere north of three hundred. He was thick, in a muscle way without being close to diesel cut. He might not have been much to my liking on the outside, but then and there, on the inside, my thoughts ran wild about him.

Jail proved to be the strangest place to be sweet on a dude whose head looked like an inflated Milk Dud and dumb as an ox. But still, he was cute as a button in a he-man sort of way.

There was little doubt in my mind he was sweet on me, too, as he bought me a ton of expensive stuff from the commissary just for being his boy.

I guess I probably should’ve started out this shit by saying I had my fair share of playing the side dude on the outside. I might’ve been a fat nerd, but I was a fat nerd that knew how to hook up some shit that got me more than a kiss on the cheek. I also drove my dick through wall cutouts whenever I felt a booty drought looming. It could’ve been a grab bag of girls and guys. Of course, I really didn’t stick around to investigate further given that the result was the same. I did however use that same bravado to fuck a couple of guys that had a lot of negative things to say about big guys like me, only for them to track me down later looking for Round Two.  And when I caught the eye of some ballers around the block, I wasn’t above getting dug out by a nice hefty dick. Simply put, I was no virgin.

 So if I had to get my back blown out by some dude to make my final months go by smoother, I was definitely looking over at T-Bone than I was at Montay. Because if I knew if T-Bone claimed me, I was out to be just his. He wasn’t out to share my ass with the whole population for some obscure vendetta.

As least that was my thought before I caught a glimpse of him in the shower.

For such a big guy, he was packing an equally impressive dick.  No lie. This thing was about a footlong and thick. I’m talking about donkey swing-a-ling-a-ling dick, which meant I had to steer clear of dude if I ever wanted to walk away with a closed hole. Like I said, I was no virgin. But I wasn’t a power bottom that could take on a Mac Truck, either.

It was one thing if he tried to take it. There was nothing I could do except try to get away from him as fast as I could and sign up for protective custody. It was another if I gave in and gave it up to him with the pending threat of having to wear a diaper for the rest of my life!

There I was in the home stretch. About a good three weeks from getting out when Montay started turning up the heat on his advances. I think he got word from one of his DO bitches I was ready to clock out. He knew it was crunch time if he wanted to ride my ass. Jamal knew this. With his influence tried to get me in with some of the other dudes that weren’t interested in sexual favors while T-Bone was trying to figure out why I was putting some distance between us as he openly wondered if he could catch up with me on the outside.

Four days away from being released, and I was just leaving somebody’s house when something told me to switch up my routine. Instead of taking the direct route back to my cell, I took the scenic route. And on that scenic route I found Ricky in the corner crying as Jamal wailed on Montay.

It was on the day before my last day I learned that Montay found out about Ricky and forced him to give him head, swallow his nutt, and doused him with a boatload of piss.

At that moment, though, Jamal was wailing on Montay. The next thing I know I’m running in like the cavalry pulling Jamal off Montay, reminding him of the trouble he was in if he got caught. While I was getting Jamal to calm down, he kept screaming at me that Montay needed to pay for what he’d done. Then somebody, I don’t know who (as I noticed that four men piled into the cell including T-Bone) that it had been a long time since they had some ass.

It probably was a good second later before two of the four other dudes wrestled Montay face down into the cot and had his pants already off.

As strange as it might sound for somebody that’d spent more than a year and a half in jail up to that point, that I may’ve known the screams of somebody getting took and the aftereffects it left behind, that was my first time seeing the act live and in color. And if I’d blinked, I would’ve missed it all, too.

One of the guys that wrestled him to the bed was already squirting the globs of the creamy Vaseline into Montay’s crack before anything else could be said, aiming the tip of his dick right into place.

He straddled Montay like a bitch and rode him out like that in kind. I don’t mean his just ran up in the boy. I mean he dug him out with no mercy! To the point that after all the shit he put me through, the fear he’d instilled in me, I was feeling sorry for his poor ass.

This went on for ten minutes. Montay was screaming and hollering in the bed and his ass was popping like firecrackers, mumbling that his ass felt like it was on fire and that the man raping him was going to pay. The man fucking him laughed it off, fucking him even harder. Just ramming into the cot like Montay was just a fuck toy. Then as the man fucking him asked what his punk ass was going to do about it, the man busted his opened even wider, roared against the cries, and flooded him with his creamy deposits.

“Don’t say I don’t take care of my boy,” the man jumped to his feet as he egged his boy to take his place.

“Feels like butter, baby,” the other dude groaned, sinking his dick into that stretched out hole. The way he did it made me feel like I was missing out on the best feeling in the world. It must’ve been because Montay responded that way after a few minutes, throwing his ass back, meeting the man stroke for stroke.

I thought it was just me, but I knew it had to have been something to it because it looked like the piss-soaked Ricky was taking notes.

The man fucked Montay for about ten minutes as well as well before the third guy went and stayed inside of Montay for fifteen minutes more, claiming he couldn’t get his groove with the punk being so slick with loads. After he came, they egged T-Bone to get some, too.

I think he would’ve been riding that ass first if I hadn’t been there.

Like I said before, T-Bone was sweet on me.

“You’re going to go right after me, right?” T-Bone asked.

T-Bone looked at me like if I agreed this would make this alright and us bonded in this happenstance thing.

I nodded, remembering it was better Montay than me taking that ridiculous amount of man-meat.

I watched in horror as T-Bone pushed his mighty python up that battered hole.

Just from the sidelines, the way that diamond-cutter sliced through Montay’s poor hole and the indescribable searing pain that he let out had my own hole nearly lose its grip.

T-Bone fucked him for a long time, surely twice as long as his predecessor. Sometimes it was the rape it was, and other times he was so into it, the passion of a tryst, he nearly forgot I was there. Even more surprising was the way Montay was taking it. You would’ve thought he was the trampy slut that was used to taking a line of big black guys on the regular.

When orgasm was imminent, T-Bone’s body did like Popeye’s arm after the cartoon character guzzled down the can of spinach. His face tensed up and expanded, like a steam engine about to blow. That expansion left T-Bone’s face and I can assume shot through his body, and his cock soon erupted as he came and stuttered and came some more. And even when his face relaxed, as if he was done with Montay, he yanked out his cock and he was still shooting uncontrollably like a broken fire hydrant. If I wasn’t there to bear witness to it, I’d almost say it was a gimmick. Nah, that was for real!

I dove in right after him. The cum running out of the wide-open burrow as I tried to leave my own mark. Since there was no grip or no friction, the best I could do was pound the open airiness fast and hard hoping to get off in the cummy mess. I guess it was enough for Montay because he was begging for it. I swore up and down he was like a bitch in heat for real. Slowly but surely, I started to feel his slimy, trembling hole come in around me. I got in the zone. That shit was feeling good, real good. I was bucking like I was getting some for the very first time. Then, out of nowhere, I exploded up his asshole like a torpedo, pushing more cum further up in his guts.

I barely recuperated when Jamal knocked me over, getting his revenge. Of course, Jamal fucked Montay making sure he put the screws to him. Jamal grabbed Montay by the back of his neck like animals do, and Montay let everyone in the cell know he was in excruciating paint.

I would like to say that it ended there. That we left things even, but there seemed to be a line formed out the cell by the time the initial party had left. It was dispersed by the Dos by the time we made our way back to our cells at the other end of the block.

I never saw Montay or Jamal again after that. I just happened to run into Ricky and T-Bone at the same Wal-Mart two weeks apart. Ricky was on one end of the store with his girl and their two kids. He tried to make as little eye contact with me as possible. I could’ve been insulted, but I understood. In fact, it left me more curious than anything, about how many times guys that come out rewrite the history that happened inside. Ricky was in protective custody, a secret bitch, and got throat raped and pissed on during his stint. Montay was a seasoned vet. Not sure if he chalked up his violation up to the game, but I can’t see him broadcasting about what happened to him behind bars, either.

As for T-Bone, he got with some size queen that obviously used him for sex in exchange for a decent place to stay. He still happened to be sweet on me, even generously paying for my items at the store. In exchange, he wanted me to use the number he slipped to me in checkout. He said he wanted to catch up, but the bulge in his pants said a whole lot more!