(Edit added on 10/25)
I can't believe I'm actually going to try and make a short series from this. And I can't believe I have to go to such lengths to get people to see the secret at the end of this.
(End of edit)
I promised myself I'd never do this. But I might as well do this one to test the waters with my audience to see who would want to read another one after this. The only description of you I need to give is that your coat is brown and yer mane is jet black. And you have an orange prison jumpsuit. Why? Because you're in prison.

None of the source materials belong to me.

Enjoy I know I probably won't

You were lying on your bed in your cell, alone just the way you liked it. Every time the warden tried to throw another pony in there with you they would later be found dead with multiple stab wounds. He's not smart enough to realize he should stop giving you combs. Anyway you were lying there when the warden threw a new inmate in there with you. The mare was just lying there, unconscious.

(Y/N): Wow. He really picked this cell? Sure, she'd be raped in any of the others but I'm probably going to get sick of 'er in a day or two and shank them.

You laid your head on the slab again and closed your eyes.

(Y/N): Only time will tell.

When you opened your eyes you felt your own shiv being put to your throat. Looking at the now very conscious unicorn mare you caught on that she was the one threatening you.

(Y/N): You're more forward than my other cellmates, usually they wait a week before trying to kill me.

????: Where am I.

(Y/N): Put the comb down so we can talk like civilized ponies.

She glared at you and reluctantly lowered the shiv.

(Y/N): You're in a prison run by an undead behemoth who will beat you into a gooey pulp that'll be mixed into Thursday's stew if you're caught trying to escape.

????: Why am I here?

(Y/N): Ask the warden. Can I have my shiv back?

????: Why should I give it to you?

(Y/N): Because I can tell you want to get out of here as soon as possible and I can help. Also, if one of the guards catches you you'll be tied to a rotating post for three days.

She gave you a look of distrust until realizing you weren't lying to her and dropping the comb at your hooves. You hastily hid the makeshift weapon as one of the guards walked past. When he was out of earshot you continued your conversation.

????: You can help me get out?

(Y/N): I've been planning an escape for two months and I've almost got everything worked out.

Before you could continue you were interrupted by a new voice above you yelling, presumably at one of the guards, from the voice alone you guessed it was a he and one with a thick southern accent at that.

????: LET ME OUT OF HERE I DIDN'T DO NUTHIN'!

Following that one you heard another voice unfamiliar to you, another male but his voice leaned towards a military background.

????: WHEN I GET OUT OF HERE I'M GOING TO RIP YOUR HEAD OFF AND PISS DOWN THE STUMP!!

All the color in your cellmate's face drained after hearing them.

(Y/N): I assume you know who those voices belong to?

????: They're my friends.

(Y/N): Friends? Really? You, a mare, managed to befriend two bucks in the wasteland? (looks at her rear)

????: (notices) What do you think you're looking at?

(Y/N): Looking for blood I'm having a hard time believing that they're with you out of the goodness of their hearts.

????: I don't see what you're talking about.

(Y/N): Sweet Celestia you are stupid! I'm talking about the four letter word that starts with "R" and ends in a monkey! But seeing as there's no dried blood, nor any discoloration hinting at there being any blood, I'm suspecting that you three are slavers.

????: We're nothing like Red Eye. And for the record there's five of us.

(Y/N): Okay. I'm starting to believe the 'goodness of their hearts angle.'

????: Can you get them out too?

(Y/N): Depends on how many there are. If all five of them are here then one of you will have to stay behind.

????: Why one of us?

(Y/N): Because this is my plan cuntmuffin. I'm the only one that can get any number of you out. As I was saying, if you want in on my plan I'm gonna need a few things in return.

????: (sighs, frustrated) What?

(Y/N): One, If you and your friends want in on this then you're all going to keep your mouths shut. If you rat me out to the warden then I'm taking all of you down with me. Two, you're going to give me the names of every pony who's in on this and then you're going to tell them the first condition. Got it?

????: I agree to the first one not the second.

(Y/N): Listen here missy, you don't have a choice. It's either all or nothing.

She hesitated, looked out the window of the cell, and looked back at you with a glare.

????: (growls) Fine.

(Y/N): Glad we could do business. Names now, starting with yours.

????: Littlepip.

(Y/N): Littlepip? You grew up in one of those bunkers didn't you.

Littlepip: How do you know?

(Y/N): Because it doesn't make sense for a mare with a Pip-buck on her ass to be out in the wasteland where those are next to nonexistent. If you have one of those then you should hold on to it for dear life.

Littlepip: Maybe you should tell that to one of my friends.

(Y/N): What's the name of old Tex?

Littlepip: I'm going to take a shot in the dark and say you're talking about Calamity.

(Y/N): And the other one I heard screaming up there?

Littlepip: His name is Bob.

(Y/N): Okay, you're fucking with me. What's his real name?

Littlepip: I'm telling you the truth. I don't lie, that's not the kind of pony I am.

(Y/N): Okay. Who are the last two?

Littlepip: Well. There's one of Bob's marefriends, Velvet Remedy. The last is my buckfriend Alex, and yes his name is really Alex.

(Y/N): Alright. We find them and relay the plan tomorrow.

Littlepip: What do we do until then?

(Y/N): It's 9:30 so the lights are going to go out and the warden is going to start his rounds. Which means we make like good prisoners and sleep.

Littlepip: What choices do I have in that area?

(Y/N): Well, you could either sleep on your "bed" and hope to get a good night's sleep despite the cold.

Littlepip: Or?

You rolled over on your back and looked at her out of the corner of your eye.

(Y/N): You could share the bed with me.

Her face twisted with an expression of shock and partial disgust.

Littlepip: I'll take my chances with the weather.

She climbed onto the filthy mattress and rolled over facing the wall.

(Y/N): Suit yourself.

You followed suit and rolled over to go to sleep under the flimsy sheet.  Only a couple minutes later you felt something nudging you.

(Y/N): I'm not doing anything other than sleeping, leave me alone.

You were nudged again, angry you turned over expecting to see a very stabable guard but instead it was a shivering Littlepip.

(Y/N): (sighs) Come on, get in.

She hesitantly lifted the sheet and laid next to you.

(Y/N): Don't you try anything.

Littlepip: Still not who I am.

(Y/N): Whatever. Shut up and go to sleep.

You turned over and closed your eyes actually falling asleep this time.

[The next day]

You had woken up to a very awkward scene with Littlepip's legs wrapped around you, and as tempted as you were to steal the device clamped on to her foreleg you went against that and pushed her off instead.

(Y/N): Rise and shine fresh meat. You don't want to be asleep during roll call.

She shook herself awake and seemed to be disappointed by her current situation.

Littlepip: So much for hoping it was all a bad dream.

(Y/N): Join the club. Now wake up before they beat both our asses.

She stood next to you at the door along with all the other prisoners. The warden stood at the door of his office, overlooking the cell blocks as he spoke through the loudspeaker.

Brutus: All prisoners sound off.

You all obeyed knowing what would happen if you didn't. The warden's head turned to one of the cells on the row above you.

Brutus: I said sound off!

Then the buck in the cell above you made a mistake.

Calamity: You can go f*ck yourself!

The other inmates whispered among themselves as the warden glared at him.

Brutus: Take him to the post!

The post is the punishment for any infraction here since most of the solitary cells are either filled with radiation or some kind of mutative sludge. You could hear the guards beating him as he tried to resist.

(Y/N): Poor sod.

Littlepip: What's the post?

(Y/N): Exactly what it sounds like. They tie you to a rotating post and beat you while the other inmates watch. The infraction dictates how long you're tied to the post, and mouthing off to the warden is an offense second only to escape attempts. He'll be out there for at least two days. He better hope the warden doesn't decide to join in.

Littlepip: Why?

(Y/N): Because the warden's voice matches the rest of him. You'll see.

She nervously gulped and shuffled closer to you.

(Y/N): Go with whatever placebo makes you feel safest, because I'm not going to stand up to the warden. One of the guards, yes. But the warden? You'd have better luck doing your own colonoscopy... with a straw.

[Timeskip]

At lunch the guards went to town on every side of poor Calamity and you happened to read the lips of one which told you he was gonna be there for another day.

Littlepip: How long is he going to be there?

(Y/N): At least another day. So we can't discuss the plan until his punishment ends.

You turned back to your meal and resumed eating.  Later, during one of the free periods of the day, you were having a conversation with Finn, the prison's resident scroungy, as you were trying to buy some extra soap off him one of the guards, a unicorn, made an announcement that went through the entire prison.

Guard: Warden on deck!

You were confused, he never came out from his office during a free period. You were afraid that somepony had found out about your plan and spilled the beans. Everypony trembled, hearing his heavy footsteps. The warden marched to the post to make an announcement and an example. It was then that Littlepip saw the warden, and her jaw dropped.

Littlepip: THAT THING IS THE WARDEN?

(Y/N): Yep. Why the hell do you think we're scared of him? He's the size of a shitting house!

Littlepip: What happened to turn him into that?

(Y/N): We don't need to know. You might want to look away.

She didn't listen to you and kept looking at him in shock. You sighed and covered her eyes as the warden began beating the Pegasus black and blue.

Brutus: Let this MONGREL be an example of what will happen if ANY of you challenge my authority!

You removed your hoof from her eyes and led her away.

(Y/N): If you really care about him then you'll look away.

Littlepip: Why? Why would he do that?

(Y/N): Violence is the only language these convicts understand.

[Timeskip two days]

In the cafeteria you were finally able to tell the others about the plan since Calamity had healed from the warden's beating.

Bob: What did you need to tell us that was so important it needed to happen now?

Littlepip: This buck here tells me that he has an escape plan.

Bob:😶 That's a very good reason.

Velvet Remedy: We don't need to escape. The warden said we'll just be held here for another 5 days.

Bob: Velvet, why the fuck would we trust him? You saw what he did to Calamity!

(Y/N): Yeah, funny thing about that. My sentence was supposed to end in five days, four months ago! That bastard of a warden is going to keep extending your sentence until you die.

Bob: Wouldn't put it past that thing. So what's your plan?

(Y/N): I took one of the spoons from the cafeteria and I've been digging a tunnel in my cell and it will get us outside.

Calamity: That's all fine and dandy for you 'an her. You share a cell.

(Y/N): I'm sorry cowbuck do you want to get out or do you want the shit beat out of you again?

Calamity: ...

(Y/N): Thought so. Now, at 9:30 the guard begins his rounds at my cell block. I'm going to get him in there and stab him with the shank I made.  I take his keys and let you out of your cells then we need to get through the hole before somepony notices the guards' disappearance and out into the yard. Out there we get to the walls by the north tower, avoiding the spotlights, and crawl through the hole I covered up with a bush. If this goes off without a hitch then we'll be running free before the alarm goes off. And I'm going to tell you the same thing I told her, You all keep your mouths shut about this plan.  If I find out that any of you went flapping your lips to one of the guards then I'm taking you all down with me. We clear?

Bob: Crystal?

Littlepip: Have any of you seen Alex?

Bob: He got thrown in solitary after killing one of the guards.

(Y/N): Hate to break it to ya, but he's probably dead by now. Those cells have all sorts of deadly shit in them. If he didn't die from radiation poisoning then he got horribly mutated by the sludge in there.

Bob: Well, he is an Alicorn so radiation and Taint aren't really problems for him.

(Y/N): Then he's probably gotten out by now.

Littlepip: Why hasn't he come back for us then?

(Y/N): My guess is that he probably doesn't give half a fried shit about the rest of you. We enact the plan one day from now.

You got up and dragged Littlepip with you. The guards wouldn't be happy if your cellmate wasn't with you. That night she fell asleep spooning you again.

[Timeskip]

Your plan was almost ready, you were out in the yard with Littlepip tending to the little garden the warden let you keep by the north tower.

Littlepip: Why are we the only ones out here?

(Y/N): Because I'm a model prisoner when I'm not stabbing my cellmates to death for peace and quiet. The warden lets me have some luxuries.

You smiled as you tended to your little rosebush, one of the few precious things in your life. As you were doing this one of the other prisoners ran towards you with the intent to break your neck.

Littlepip: Shouldn't we be running?

(Y/N): (sniffs flower) No, it will handle itself. (humming as the vengeful pony runs towards him)

Littlepip was holding onto you for safety as the maniac got closer. But when he got within 5 yards of the tower half of his head vanished and the rest of his body fell limply.

(Y/N): Thanks Stanley!

Stanley: No problem (Y/N).

Littlepip: (loosens grip around you) What?

(Y/N): The towers have snipers, I'm the only one they have orders not to shoot.  And since my garden is here I occasionally talked with the guard stationed here.  And that is Stanley. We're sort of friends. we talk at lunch when nopony is watching.

You finished with your garden and went back to your cell. At lunch that day you found Stanley and talked to him.

Stanley: Hey there.

(Y/N): Stanley, I need you to do me a favor.

Stanley: I wish I could, but I'm not in any position to ask the warden for anything.

(Y/N): No, Stanley. I need you to get somepony else to cover for you tomorrow night. You don't want to be here.

Stanley: Why?

(Y/N): Stanley, just do that for me. You're my friend. Okay?

Stanley: O-okay, I'll get Block to cover for me.

(Y/N): Thank you.

You began to walk back to your cell to go to bed.

Stanley: Are you planning something?

(Y/N): Stanley, just do that for me. Take a break, you deserve it after all you've done for me.

You went back to your cell to be spooned in your sleep by Littlepip again.

[Timeskip don't worry this is the last one]

It was 9:28 and you were waiting for the guard to come by. Littlepip would provide a distraction and you would kill him. She was curled up on the floor waiting for her cue. When the guard, an old buck, came by you waved around for his attention, hiding the shank in your mane.

(Y/N): Hey guard there's something wrong with my cellmate, she needs help.

Guard: This better be the real deal.

He unlocked the cell and looked the mare over before you stabbed him in the neck and tore it open, gushing blood. You took the keys and went to the open door of your cell.

(Y/N): Get through the hole and wait for us out there. Stay out of the tower spotlights if you want to keep your head.

You quietly got up to the two cells and opened them as fast as you could.

(Y/N): (whispering) Go, go, go.

Bob: (carrying a sleeping Velvet Remedy) What about you?

(Y/N): I'll catch up with you. I just need to grab something.

They went down to your cell to crawl through the hole while you snuck into the warden's office to steal something from his 'private collection'. You ran as quietly as you could back to your cell and crawled through the tiny hole. You squeezed through the hole and found them pressed against the prison building.

Bob: Let's go Jailbird!

(Y/N): North tower, come on!

The five of you bolted towards the wall and as you reached the bush you planted to conceal the hole and you made sure they made it through first, but it was then that you heard something that made your blood run cold.

Brutus: WEAAAASELLLLL!

(Y/N): Shit.

Littlepip: Aren't you coming?

Heroic ending

(Y/N): (sighs) No, get going. Get as far away from this place as you can.

You took out the Python you had stolen from his office.

(Y/N): I'll slow him down as long as I can.

Littlepip: Please, one friend already abandoned me. I don't want to lose another.

She had tears in her eyes as she pleaded with you. You took her face in your hooves and kissed the mare, leaving her eyes wide open. In her shock you shoved her through the hole and faced the warden, accepting your fate as his light shined on you.

Brutus: YOUR NUMBER'S UP 101A!!!

(Y/N): YEAH! WELL COME AND GET ME!

You shot him twice, pissing him off and prompting you to run. He chased you all around the prison yard, you taking another eight shots at him before throwing the useless gun away. After what felt like a full minute of running you ran into a dead end and were struck with his baton, leaving you wheezing from what felt like several broken ribs.

Brutus: You thought you could run from me Weasel?

(Y/N): No, but you'll never see those four ponies again. (coughs up blood) They already got over the wall by the time you found me, and they're long gone by now. (chuckles) I win warden, I win.

He yelled in rage and beat you until you stopped breathing. But as he did it you laughed happy you had helped them escape.

Real ending

You shoved her through with you following close behind. On the other side of the wall you were jumping around with joy.

(Y/N): I DID IT! MY PLAN ACTUALLY WORKED!

Bob: Wait, you didn't expect it to work?

(Y/N): Admittedly, not with the added escapees. But does that matter now? WE'RE OUT!

You followed them for a few minutes with a smile on your face when you met a suspicious horse in a duster and riot gear. Littlepip ran to him and wrapped her arms around his neck.

(Y/N): So this is Alex?

Littlepip: Yeah.

(Y/N): So, before we go our separate ways is there anything you'd like to say to me?

Littlepip: Yeah, you kinda need a shower.

(Y/N): Anything other than that?

Bob: Nothing comes to mind.

Littlepip: No.

Calamity: No.

Those words pierced through your heart like an ice pick.

(Y/N): (he he he he) You mean that, after what just happened, you have nothing you'd like to say to me?

You stood dangerously close to the Alicorn, chuckling softly as you looked Littlepip in the eye.

(Y/N): I thought we were friends in some small way. I really did.

Your head moved close to where you had hidden the stolen magnum, laughing like a mad scientist.

(Y/N): And now you're telling me that after everything I just did for all of you YOU HAVE NOTHING TO SAY?! NO 'THANK YOU FOR HELPING ME ESCAPE FROM A MAXIMUM SECURITY PRISON'?! YOU KNOW WHAT I HAVE TO SAY TO THAT?

You quickly drew the gun and fired a bullet into Alex's temple at point blank. Before you could turn the gun on the others you were thrown to the ground. The last thing you saw was an M1911 with "Mustang" etched into the slide.

{The end}

There you go. That's the end, or is it?. I don't know, you tell me if you want this to become a series.

Yes

or no?

{extended ending}

Stanley solemnly went to the warden's office and knocked on the door.

Brutus: I told all of you not to bother me.

Stanley: I'm sorry to interrupt sir, but we've found (Y/N). He's dead, gunshot wound between the eyes.

Brutus: (growls softly) Bury him in his beloved flower garden.

Stanley: Yes sir.

Stanley left the office, his head hanging low after the death of his friend. He went to your cell that had yet to be filled and looked into the mirror.

Stanley: I should have stopped you. I should have realized it when you told me to take the night shift off.

He turned around to go back to his post.

Stanley: I'm a terrible friend.

{The end}

{For real this time}

Thanks to AlexGasai243 for letting me use his OC at the end there.

{Nekorbnu si elcyc eht}