(On Hold) Male reader prisone...

By underboundsans34

152K 2.1K 1.3K

As the title suggests, you're the only Male prisoner transferred to a female prison. I'm aware of this concep... More

chapter 2: meddling kids
chapter 3: guard captain
chapter 4: quest for cake
chapter 5: contraband
chapter 6: neighborly
chapter 7: power fantasy
chapter 8: fringe benifits
chapter 9: most dangerous woman in the world
chapter 10: the fight of your life

Chapter 1: The transfer

30.4K 334 550
By underboundsans34

You start out in this county jail. You are under watch but they escort you to a giant truck where women in full cuffs on their arms and ankles, while they shimmy themselves into the trailer in the back there's like 20 or so women all in the back.
You go in last and climb in easily.

Prisoner: damn girl! What estrogen are you taking to get that kinda muscle?

They probably assume that you're a trans man with everything changed down to body hair, little do they know that you do still have a dick.
The truck is more or less a toxic waste dump, some of the older prisoners have already passed themselves from being woken up in the middle of the night. They ain't gonna hold in that piss when it causes physical pain, can't say you blame em.
It stinks a lot, the cuffs around the ankles are so tight that it rubs on their ankles making them bleed as the teen girls in there, probably about 16 or 17 years old. These girls are rowdy don't give a single fuck, and they won't shut the hell up. Along the ride they keep asking you why you aren't cuffed, you ignore them until one of the kids grabs you, you grab their arm and twist it.

Prisoner: OW OW OW OW!!!

Y/n: don't ever touch me without my say so

You let go and she scooches over.
You keep sitting and waiting for the incredibly long truck ride, so many thought are running through people's head. As for why you aren't cuffed, don't worry, we will get to that, just like we will get to why you're being taken to an all female prison.
For now though you feel the urge to pee, you don't have cuffs so you just stand up and walk to the back where the door is, the trailer bounces with every slight bump but you've had worse.
You take out your dick and start pissing and NOW the whole trailer is dead silent. The teens have stopped screaming and people have stopped crying and regretting their life choices and the only sound is the trickle of piss hitting the door of the trailer.
One you're done you put your dick away and sit back down. All eyes are on you and you know it, but you're used to it.
It would be more uncomfortable holding it in then letting everyone know you're a dude about to go into a female prison. You're not a small guy either, you're 6 feet and 4 inches tall weighing in at 245 pounds of muscle, you've been to male prisons and you've worked out a lot, what else are you gonna do in the hole besides push ups, also push ups and sit ups was how you counted seconds and minutes.
But now, every girl is fixated on you.
Eventually one of them spoke up.

Prisoner: how? And why? Not only are you not cuffed, but you're a full on guy?

Y/n: we're going to prison
Why and how I'm here is the least of all of you're concerns.

You eventually get there and it's still night time, these women guards come out yelling at everyone to move, you take your time and move at the same pace as everyone else.

Riot guard: WHAT THE ACTUAL FUCK?! WHY IS THIS MOTHERFUCKIN BITCH NOT CHAINED UP?! GET ON THE GOD DAMNED GROUND!!

Another guard hops out the truck and tells her to chill the fuck out.

Angelina: Orders from up top, no chains, no shooting him, just escort and process

Her name was Angelina, or ange as you call her. She was sent as basically you're personal explain the situation person to all the staff. Also these are the only guards that have guns.

Riot guard: WHAT THE FUCK ARE YOU TALKING ABOUT?!

Ange takes the guard and they have a short talk along to explain everything.

Riot guard: ugh...what a headache, fine

She pushes everyone forward and you keep pace as you're all shuffled and stripped down.
They get to you though...

Guard: What the actual fuck?! This prisoner has a dick???

Riot guard: YES! KEEP PROCESSING!
SPREAD THOSE FUCKING CHEEKS YOU SLUTS!!!

You just stand there as she literally looks up to tell at you.

Y/n: you spread em, since you want it so bad

She looks like she about to blow a fuse, she almost shoots you but ange stops her and they have a short spat before the riot guard reluctantly agrees to do your search more personally.

R. Guard: fucking christ...why the fuck do I have to do this fucking bullshit

She puts on some gloves and searches you then she looks at your dick.

R. Guard: fucking cock probably isn't even real...

She grabs hold of it and squeezes it a bit, not really hard but she sort of rubs.

Y/n: woah...what are doing back there?

R. Guard: SHUT.........UP.....mmm....

She gets closer and you feel her breathe as she starts licking and sucking on your balls.

R. Guard: mmhf~...mm

Y/n: ooohhhkay...that's uhhh an interesting way of search...IIING

Guard: the fuck shannon?

Shannon: I needed to see if they're real...they are

She licks her lips and sends you to a room to watch the most outdated VHS tape of all time telling you how the whole prison works the rules and all that.
During the video you're told not to talk but a girl touches you and you  squeeze her hand hard making her Yelp and stop.
After the video you go out to the walk and it's bright outside now, you squint your eyes and adjust to see that everyone in front of you and behind you in their prison black and whites. Yeah, it's that kind of prison, you've had prison orange and prison blues but the stereotype black and white stripes, that's a new one. You walk outside to this long chain link fence with lady prisoners closing in on both sides. You flinch and play the, timid but not to timid act and look at everyone's shoes. Believe it or not shoes are really important, ef people are wearing sneakers or flip flops, then everything is fine, wearing boots means these guys are dangerous.
But the gals here are more difficult, high heels could mean anything to you and there are still flip flops but everyone has different designs, also high heels are really short and flat, stilettos must be considered weapons, and they're right.

Prisoner: ooo~ hey girl~ I'm getting myself a piece of that~

Prisoner 2: a tall tran glass of water here~ mmm...MMM! tasty!~

Prisoner 3: you have big muscles~ can I touch?~

This prisoner you can tell what she's like. She's probably just messing with you so you turn smug and shoot a kiss at the red haired flirt.

Y/n: 😘
Heh heh

Her eyes widen, you knew this would catch her off guard as she stands there frozen, she then realizes what just happened. She tried to mess with you but she got messed with.
She starts to pout because of how she let herself show weakness.

Her outfit had a hat on probably a custom job. You might think that a hat would be easy to hide things in, to which I say.
They check under their boobs and their armpits. What makes you think they won't search the hat?

You finally get to the final part. A room full of beds, just beds on beds on beds just everywhere.
Some girls aren't doing very good, there is one girl that you can't help but go to and try to comfort.

Small girl: I'm...I'm sorry p-please...don't

Y/n: shhh...its ok, what your name?

Tomoko: t..t...tomoko... 

Y/n: stick with me for now, look...it can be scary and you won't know what to do
But just remember, trust no one.

Tomoko: can...I trust you?

Y/n: no, but right now you don't have much of a choice
I'm y/n, btw

Tomoko: o...oh...o...ok...

You hold her hand and she looks up at you.

Tomoko: why...why do this? Why pr..protect...me?

Y/n: because you were the only one in the truck that was quiet and didn't annoy the shit out of me

Tomoko: i... i... thanks...

Y/n: don't thank me for long, you're gonna be in YTP

Tomoko: YouTube poop?

Y/n: surprised you know about those and no
Youth Treatment Program
It's where they gather up anyone from 8-18 and put them in the junior division

Tomoko: s-so... I won't get to see you??

Y/n: probably not...how long are you in here?

Tomoko: um ...3...years...

Y/n: I'm gonna be here a lot longer

Tomoko: h-how long?

Y/n: officially, Life. Unofficially, I won't stay in here forever, I'll bust out at some point but maybe not for a long while

Tomoko: o-oh...what...what did you do?

Y/n: I murdered 386 cops

Tomoko: WHA?!

Y/n: yeah...it's complicated

Tomoko: why aren't you on death row?

Y/n: trade secret 😏

Tomoko: i...you...

Y/n: I'm not gonna hurt you, if I wanted you hurt, you would be hurt
Just be careful and stick to kids your age, it won't be easy but you can survive
Whatever you do, don't go near the smaller kids. Trust me, bad idea.

Tomoko: o...ok

She hugs you and you escort her to a place to piss, you help her relax by standing guard and she breathes managing to do so after you cover her ears and let her hear only your voice.

Y/n: I'm not watching you...no one is watching you
And you shouldn't care

She relaxes and finishes into some girls piss pot and you leave before whoever it is gets pissed, like literally...or un-literally you know what I mean.

You head back and start sleeping as her hand goes to to the bulge in your pants and she blushes red.

Y/n: don't do that

Tomoko: s-sorry .\\\.

She snuggles with you as she can finally sleep. Other girls get jealous as you sleep with her, not sleep sleep, which wouldn't be allowed but you lay next to her until the next day.

A/n: first part of the story! I wanted to put my own spin on it, I do wish I could have a cliff hang-

(Wardens office)

Ange: warden, it's a pleasure

A/n: oh...nevermind not done quite yet

Warden: cut the crap, I want to know why you thought it was a good idea to bring a big MALE IN MY PRISON

Ange: lady meiko...I'm sorry but we ran out of options

Meiko: what do you mean, ran out of options?

Ange: it's...he's been in 14 prisons...escaped them all
Medium security, max security, supermax, even escaped off of an island, we even designed a specific prison deep underground JUST to hold him. He still got out

Meiko: IF I believe that, how is that possible?

Ange: we...don't know how its possible
But what we do know...y/n can escape any prison, even if it should be impossible
Cuffs? Doesn't work...gas? Even passed out or comatose, he just gets up and somehow walks out. tranquilizer? Still didn't work, he ended up outside, still paralyzed.

Meiko: so how do WE contain him?

Ange: we...made a deal, despite everything he honors a deal when it's made
We've never had a male prisoner in a womans prison so I offer him to be in an all female prison and he in turn doesn't escape

Meiko: typical, his horniness was his downfall

Ange: actually...I offered him a personal clean hooker and it didn't work...I don't think urges are what made him agree

Meiko: so what did?

Ange: maybe...he just wants to personally experience what would happen
It's more plausible than being horny as what's keeping him here.

Meiko: is it?

Ange: YES! weren't you listening??

Meiko: whatever, call him to my office tomorrow
I won't deal with this today

Ange: of course

She leaves and meiko looks through his file explaining more of exactly how he escaped all those times.

Meiko: there's no way, this can't be for real...

A/n: ok, real cliffhanger now? Alright
Now we're done for the first chapter, so now that I've got everything down
Next time
Chapter 2: meddling kids

Continue Reading

You'll Also Like

29.9K 3K 200
Have you ever loved a videogame so much that you wished you were somehow magically transported into it? Tough luck, this isn't your typical isekai st...
41.4K 3.6K 36
This is crazy... As fu***ng crazy as it gets. But I was sucked into a comic book... In to a world where I am an Omega... And I have an Alpha... And I...
7.1K 447 46
When all of the night guards have a crush on you, who will you choose?? (Scott isn't a love interest, sorry.) (Rated mature for strong language and s...
1.1K 94 32
‼️DISCONTINUED‼️ Before the summery, this is a Reader Insert book. Y/n will be used, as well as acronyms like (f/c) and (e/c). These are minimal, but...