Debs Vacation Becomes a Hellish Prison

Deb's Life Turns Upside Down

As I get ready for vacation I look in the mirror and brush my curly brown hair that surround my shoulders. Then finish with my makeup around my deep brown eyes. Looking down at my body knowing my tan/olive complexion is about to get even darker in the Caribbean sun. My 36d breasts, curves and relatively flat belly don't look too bad if I say so myself. I turn to look at my bubble butt and nod, okay that passes, but probably could lose 5 pounds. Not too bad for 35 years old.

Planning on enjoying my vacation under palm trees on a beach and just zoning out. I needed to get away from city life for a week. God I can't wait. Wearing very short jean shorts and a yellow crop top. Underneath a yellow bra and yellow bikini panties. Beige sandals. Yep I'm so ready for the beach.

Several hours later...
First on a tiny boat to some small island way off the Caribbean tourist island I was suppose to be vacationing on. Then transferred to an old beat passenger van. The furthest thoughts from my mind were ending up with a 3 month prison sentence here on an island that isn't even on the map. All for possession of a half ounce of weed which was for my own use. It's total bullshit. Arrested and trial on the same day as was the sentencing. It's a whirlwind and totally surreal.

My assigned attorney had explained that the only positive is that this prison is minimum security and also serves as a community service prison. So no uniforms, you wear your own clothes, which I have in my suitcase. Supposedly there is plenty of freedom to roam around. But work days are long as they expect us to earn our keep plus give back to the community for our crime. I'm guessing the reality is they need laborers under the guise of rehabilitation. Fuck I'm so mad at myself for being stupid enough to take weed with me.

As the bus pulls into the prison I see the standard barbed wire fences surrounding it as well as huge farms and grasslands. A couple of prisoners in the fields picking vegetables, but besides that not much to see until we drive up to the building itself. It's brick and very institutional. I suppose that what prisons are, but this is supposed to be minimum security and serving as community service. Doesn't quite give that feeling so far. But maybe it's better inside.

I feel my nervousness increase as the bus stops and the four of us get off the bus and are told to stand in line. Which we all do. We stand there for several minutes and then the door to the building opens.

A new day begins

It's hot. Way too hot. My dark coloured uniform soaks up the heat like a sponge, sticking to my large frame, and I am already sweating at 8:30 in the morning. The prison is relatively quiet for the moment, but it won’t be for long. Another busload of new inmates is due soon, and that is the one pleasant thought in my head now, because it means fresh meat is on the menu tonight.

I rub my head, feeling the damp sweat clinging to my greying hair cut short, military style. The warden insists that the guards always look professional, even if what we do here is not professional. Or legal. Despite this being classified as a minimum security facility for women, it is in fact far from it. The Snake Island Correctional Center (SICC) is really a private prison run by a criminal organization and headed by a brutally sadistic warden. It wasn’t always like this; when I first became a guard 20 years ago, it was a legitimate state-run women’s prison. But when it was sold to a private company nearly 6 years previously, it essentially became a private, maximum security brothel serving the needs of the warden and his circle of wealthy friends. It is filled with attractive female tourists from the region, often brought here on trumped-up charges to be used and abused by the guards, the warden and his friends, and sometimes even other inmates.

My sea blue eyes blink in the bright sun before I don my mirrored sunglasses and look to the west, where I see a dust cloud raised by the bus heading this way. I am one of the most senior guards on the island, and I can use that to my benefit, thanks to the warden. He knows that to facilitate the operations of the prison he needs assistance from us, and to keep us happy, he allows us a great deal of freedom in using inmates for our own enjoyment. That’s why I like to meet the new inmates and be part of their intake process – I get to choose an inmate to serve my needs, while of course ensuring she serves the warden’s purposes as well. These new inmates are in for a rude awakening once they are inside the razor-wire topped fences and meet me for the first time.

The Guard Approaches as I Nervously Stand There

As the four of us stand there waiting, it feels like forever. Nothing worse than the unknown. I mean now what? I suppose we are waiting for someone to direct us. But none of us move or step out of line. Seems we all want to be on our best behavior and not violate any rules or orders. We are told to stand here and we will. I guess we are all thinking alike, obey, do the time and then get the fuck out of here and never look back. Hopefully it's as my attorney said, minimum security and more or less doing community service stuff. Still it all scares me.

Feeling myself breaking into a sweat from the heat and humidity. But I suppose also from nerves as the wait continues. A long streak of sweat drips down the back of my yellow crop top and land at the waist of my jean shorts. Feeling sweat also collecting under my breasts. This as a bead of sweat drips from my forehead and down the side of my face.

Finally a guard approaches. Kind of a typical guard, maybe in his early 50's, a solid build, short hair with gray in it and of course the mirrored sunglasses so I can't see his eyes. He looks tough, mean and no nonsense. But I'm hoping that's just an act and maybe he's a nice guy. I know I have to try to be nice to the guards. I would assume being nice will make my life easier here. I'm generally good at that and people usually like me.

Of course I'm surprised there isn't a female guard, that would have made me more comfortable but I suppose a male guard is okay. I'm sure there are cameras all over so I don't have to worry about anything. I mean it's not like this is a nasty maximum security state prison. They probably wanna keep us busy to serve the community, yeah total bullshit, but it is what it is and I just have to get through this.

I watch as the guard walks up to us, feeling more nervous with each step he takes.

Welcoming the ladies

The four women stand there frozen, looking terrified as I approach. The one on the end catches my eye. She’s got dark curly hair, brown eyes, and a nice tan, very sexy – just the way I like them. Nice set of tits on her too, underneath her yellow crop top, and hot legs. There is something about her besides how she looks that I’m drawn to. Maybe a hint of defiance? She looks like she is trying not to show her fear. That makes me smile.

“Welcome ladies, to Snake Island Correctional Center. This is your new home. I am Captain Gibson, but you will call me, and any other man here, whether he is a guard or not, Sir.”

The women are paying rapt attention to me. They still look intimidated.

“You have been told that this is a minimum security facility,” I continued, walking around the prisoners as I talk. “On paper, it is. But in reality, it is something far different. There are varying levels of security throughout the facility, so some of it does resemble minimum security, where you may be free to walk around with very little supervision.” I stopped in front of one scared-looking blonde and moved closer to her. “Do not make the mistake of thinking that means you are not being watched, because you are, all of the time.”

“You will obey the directions of all correctional staff, without question, and without hesitation. Failure to do so can, and often will result in the offender receiving punishment. Failing to obey the rules of the facility will also result in punishment.”
Now I was by the dark-haired one I had been eyeing. I took off my sunglasses so she could look into my eyes. “Punishment here ladies, is not an enjoyable experience. We use a variety of different disciplinary methods, most of them painful, and all of them effective. All of you,” I said, leaning in closer towards my chosen inmate, “will learn this. You will learn to obey, to comply, and to please.”

The Rules: Obey, Comply, Please? Oh god.

As you speak I watch your every move. I stare straight ahead as you walk behind us and continue talking. I'm trying to appear strong. I know appearing weak is never good anywhere especially in a prison, so I've heard anyway. I know the guards will pick on the weak as will the inmates. So I will keep up my appearance of being strong the entire time here.

It seems you look at me more than the others, so I'm thinking that might be a good sign. Maybe you like me and if I get the chance to talk later I will do my best to make that happen. It has to be much more difficult to punish people you like.

When you explain about the punishment and how this prison is very different from what people on the outside believe I begin to get more nervous. Now thinking in my head that I will definitely follow every rule you have. It's the only way to prevent being punished.

You approach me and look into my eyes. As you take off your sunglasses I look into your blue eyes. I'm determined not to look away to show my strength. You are actually very handsome, but stern, tough, rugged and probably mean as shit. I just feel fear, hoping you don't sense that on me too much. Then you go into more detail about being punished and how the disciplinary methods are painful and effective. Each word frightening me more.

The final word in your last sentence scares me the most, 'we will learn to obey, comply and please'. Please? You can't mean sexually can you? Oh god. Please don't mean sexually.

I feel sweat dripping down my face and now my yellow crop top is sticking to me, as are my sweaty panties now plastered to my ass, luckily no one can see that. Knowing this is about to begin and I need to follow orders as much as possible. But the sexual implications scare me, I am not just submitting like some bimbo. I'm smart, strong and will fight even if it means being punished....I think I will anyway. I suppose I'll have to see the situation first. But hopefully that never comes up.

Debbie gets strip searched

Three more guards join me outside, one of which hands me a clipboard. I scan the paperwork, checking to ensure the faces match what’s in the file. The one I’ve taken a fancy to is Debbie. She doesn’t know it yet, but she and I are going to become very close over the course of her stay here.

“Debbie, you will come with me,” I say, handing the clipboard back to my subordinate who nods. “The rest of you will go with these guards,” I add, stepping beside Debbie and marching her towards the building where we do the intakes. She is keeping her head down and can barely bring herself to look at me. We enter the building, and I escort her to an open door on the right, telling her to enter. As soon as we are in the small room, I close the door and lock it.

At this point, new inmates are stripped and searched before proceeding further into the facility. This allows me to begin having fun with Debbie. “Remove your clothes and place everything on the table,” I bark. Startled, you hesitate. “Now!” I add, forcefully taking a step towards you, and you begin to undress, starting with your sandals. You are obviously reluctant to undress in front of me, as most women would be, but finally you remove your matching bra and panties, and stand there naked trying to cover yourself.

I point towards the back wall. “Stand against the wall, palms flat against it.” You move to comply, your back now to me. “Spread your legs. Spread them wider,” I say, moving behind you. I place my hands on your waist, and pull you back a couple of steps. I kick your legs out even wider, and now you are bent forward, hands on the wall, with your ass pushed out. Both your holes are now completely exposed to me, and I take a good look at your pussy. I see that your dark pubic hair is neatly trimmed. I like my inmates completely bare, so I make a note to get you shaved as soon as possible. Examining you like this is making me hard.

I take a few moments to go through the process of checking your body, starting with your arms and working down. I take the opportunity to feel your breasts, and give your stiff nipples a little tweak. I feel down your legs, and make you lift each foot so I can check underneath and in between your toes. I make you look at me so I can shine a light in your mouth, looking for anything that shouldn’t be there. That only leaves 2 more places on you to search, and I take a pair of disposable gloves from my pocket, slowly putting them on. “Relax now Debbie,” I say, letting the gloves snap into place, “and let me check your sweet little pussy for any signs of contraband.”

Total Humiliation as I'm Ordered to Strip and Spread

Seeing the other guard approach you with paperwork as you scan it and look at me. It seems you are looking at me more than the others and I'm unsure if that means you like me and intend to go easy on me or don't like me and intend to go hard on me.

When you single me out and tell me to go with you it confirms my thought that you did have your eye on me. Still totally unsure whether this is positive or negative.

Into the building and then a room as you sternly tell me to remove my clothes. Then yell 'Now'. I flinch as you do, kind of expecting a woman guard to do the strip search. Feeling awkward, very nervous and really frightened now.

I remove my sandals, then my top and jean shorts. Placing them on a table. Then I unclasp my yellow bra and remove it, placing it on top of my other clothes. Then a quick hesitation, I guess hoping you say I can stop, but there is silence. So I know I have no choice as I place my fingers in the waistband of my yellow panties and lower them. Then step out of them and out them and place them on top of my other clothes.

You order me to stand towards the back wall and I do as I place my palms against it. Then spread my legs some as ordered. As I stare at the wall as I feel total humiliation. Feeling like I have hit rock bottom, all for a half ounce of weed. Fuck.

But it only gets worse as you place your hands on my waist and pull me back further causing me to bend more. Then you kick my legs further apart. Knowing now you can see everything and most likely intend to do a search like I've seen in the movies. It's totally degrading and I know it's what prisons do, but I also know it's a way to mentally strip me of my pride. I now realize that you targeted me and don't intend to go easy on me. God I hope I'm wrong.

As you inspect my body my breathing is heavy as I'm nervous and shaking a bit. I just look down, feeling so humiliated I don't wanna look you in the eyes. I flinch as you tweak my nipples, not expecting that. Then feeling your hands trace down my legs. Then lifting each of my legs as you check my foot and toes, then the other. All I can think of is, hurry up and get this over with so I can get dressed again.

I look up at you as you order and you shine a light in my mouth. Then I see you putting on disposable gloves. I whimper, but don't say anything. I clearly remember the talk you gave us about being punished physically if we don't obey.

You tell me to relax, but that's impossible. Feeling my breathing increase more as I try to mentally brace for my cunt to be cruelly inspected. My eyes well up in tears as I think to myself, I can't cry, I have to pretend I'm strong, despite being naked, spread and about to have my cunt searched by a male prison guard. Oh god why me?

Debbie gets probed

I take my right hand and begin to inspect your cunt. I spread your soft lips apart and take a good look. I am surprised to see some wetness there. Apparently this is not completely unpleasant for you. I use my finger to stroke you a little, laughing as you squirm uncomfortably.

“Well, look at this,” I say, playing with you. “You’re enjoying this Debbie. What a juicy, little cunt you’ve got,” I murmur, taunting. I stick a couple of fingers inside you and probe around, placing my other hand on the small of your back to hold you in place. My probing continues as I tease you and enjoy your reactions.

“Oh yes, old Gibsy’s got himself a ripe one this time,” I say to myself, toying with your cunt. I thrust my fingers in and out of you slowly, fucking you. “I bet you’d like to cum, wouldn’t you, cunt?” I ask, my gloved thumb flicking across your swollen clit.

Before you can respond, I withdraw my hand, and move to whisper in your ear. “You’re very lucky to have found me,” I say, taking a handful of your hair and making you look at me. “I can be a very good person to know in this place,” I explain. “I can make your stay a little more bearable if you stay on my good side,” I add, pulling your head back to lick your neck. “But for cunts who cross me or fail to please, I can make their time here a living hell.”

I return to your upturned ass, and begin the rectal exam, inserting a finger deep into your ass. “Good thing I’ve got your juice on my finger, Debbie,” I say, probing around as you whimper with discomfort. “Hurts more when it’s completely dry.”

The Degrading Inspection

Feeling your gloved hands on my cunt as you supposedly inspect it for contraband. You touching my cunt lips as you fingers trace them up and down. Feeling my body react and begin to get wet. Oh god how can I be getting excited from this? This is total sexual abuse and yet I'm reacting sexually. Fuck what is wrong with me? Maybe it's my bodies self defense mechanism in case you rape me. All I know is I don't like reacting like this.

Your fingers begin to move up to my clit as you rub it some. I begin to react more and know my cunt is getting wetter. Fuck no. The last thing I need is for you to think I like this.

I try to keep my mouth closed and grit my teeth but a slight moan comes out, hating myself for letting that happen. This as you taunt me about enjoying this and then your fingers enter my cunt. I can feel your fingers moving around inside and it's just fucking humiliating. You taunt me more when you ask me if I'd like to cum, this as you flick my clit several times. I shake my head no, but it's obvious you know you have me very excited.

Feeling you pull your hand back as you whisper to me that I'm lucky I found you as you basically tell me that you will protect me as long as I cooperate. This as long as I don't cross you. So I'm thinking if I'm your personal sex slave then you will protect me from the other guards and other prisoners too. Not sure if you are the lone guard who's perverted or if it's widespread in this prison. But I do know that you said punishment will be severe if anyone crosses you so I have no choice but to obey. I suppose within reason anyway. Fuck, why did this have to happen to me? I nod my head in agreement, hoping this begins an end to this inspection.

But then I suddenly feel your gloved finger push into my asshole as I let out a grunt. Some pain but mostly from the surprise of you doing that. You mocking me about lucky my cunt was wet as your finger moves inside my ass. Your finger remains into my ass for while, twisting and turning as it hurts. Facing the wall I groan, my groan more from the degradation of it all rather than the pain.

Drugs in Debbie's shorts

Hearing you moan and groan during my inspection has made me hard, and I would like nothing more than to fuck you as you stand her with your ass stuck out. But I don’t have the time that I would like to take. My only consolation is that you will be mine for the duration of your time here, and I will be enjoying you in a number of ways very soon.

The rectal exam ended, I remove and discard my gloves, and put on a new pair to inspect your clothes on the table. You turn your head, trying to see what it is I’m doing, but I tell you to keep facing the wall. I search your bra and panties, bringing the sweat-soaked items up to my face to inhale the aroma of your sex. My cock twitches with the thought of having you.

As I begin a cursory examination of your jean shorts, I feel something. Deep inside a very small pocket on the right side of them is a small pill, wrapped in tinfoil. I know this wasn’t put there by you; it was Eddie, one of the guards down at the courthouse. He was always trying to stash stuff in the clothes of the convicted women being sent here, knowing that if we found the hidden drugs, the inmates would pay with longer sentences or some other form of punishment. If we didn’t find them, the Warden would find out we were getting sloppy with our searches, and we’d be in trouble.

“What is this hidden in your shorts, Debbie?” I asked, approaching you and holding the small tablet up. “That is a very serious no-no here, the Warden is very hard on inmates who try to smuggle drugs into the prison.” I can see by your wide, frightened eyes that you had no idea it was there. I sigh and pocket the drugs. “I’m afraid the Warden will have to hear about this,” I say, shaking my head. “Normally this means a 4 to 6 month addition to your sentence,” I explain, watching the panic begin to settle into you. “Of course, I do have some influence with him, and could try to get him to substitute some other form of punishment instead. Would you like me to do this for you, Debbie?”

Trying to Explain Morphing to Begging

As you pull your finger out of my asshole I breathe a sign of relief that is over with. I turn and see you go over to my clothes but you immediately order me to face the wall, which I quickly do.

I hear you ask me what's hidden in my shorts and at first I look at you puzzled, knowing I didn't have anything in my pockets and my phone and everything else I came with here was checked in at processing. I turn to see you holding up a pill. Then you proceed to lecture me on the seriousness of that and how it will add 4 to 6 more months to my sentence.

Knowing that you or someone planted that on me as I look at you while still remaining in the position of bent over with my hands against the wall. "Sir, that isn't mine. Someone put it there. I swear to god it isn't mine."

Then thinking this might be a game with the guards, getting me to be their sex slave or whatever gets them off in exchange for dropping or reducing some bullshit trumped up charges. But I suppose I have to play the game because there is no way I'm staying longer than 3 months here.

"Sir I understand, but I don't deserve any punishment. I know you know that, but I would appreciate it if try convince the warden to substitute for another form of punishment. But Sir, just between you and me, do you even have to tell the Warden? You know I don't deserve to be punished and I have cooperated with everything you wanted so far. Please go easy on me Sir. Give me one chance"

Knowing begging while I'm completed naked and bent over as I lean against the wall with my cunt and ass facing you is not the best position to be in. But what choices do I have? Feeling a tear drip down the side of my face as I add, "Please Sir, please I'm begging you."

Nothing is for free

I hear you protesting your innocence, and part of me is sympathetic to that. But the risk I would be taking by not telling the Warden would be considerable, and I am not about to do anything to jeopardize my position here, especially for a weepy piece of ass I’ve only just met. I look at you, watching the tears fill up in your dark eyes.

“I’m afraid I can’t risk my career by not informing the Warden,” I say, “not even for a juicy cunt like you. I will, however, do my best to get the Warden to show you leniency,” I continued, watching your face fall as you realize there is no escaping punishment for this. “That is all I can do,” I say, walking around to the other side of you.

“You may remove your hands from the wall inmate, and get dressed” I say, sounding business-like again. “In ten minutes, I will have to escort you to your cell before reporting this to the Warden.” I walk around a little, and you watch me carefully, wiping tears away as you put your clothes back on. You seem relieved to be dressed again, even if the outfit shows some skin.

“But this doesn’t come for free, Debbie,” I warn, walking towards you until we are face-to-face. “Nothing is for free in this place,” I say, slowly unzipping my pants. “In here, everything has a cost. Every choice, every decision, and it’s best you start learning that now.”

I place my hands on your shoulders and slowly force you to your knees in front of me. You look up, pleading with your eyes, while I show no emotion as I pull my hardening cock free from my pants. I stroke it a couple of times as you watch, almost mesmerized by it. “Now cunt,” I say, placing my hands firmly in your hair and letting the tip of my cock brush your face, “show me how badly you want me to help you get your sentence reduced with the Warden.”

Dressed But The Humiliation is Not Over

I listen as you mention risking your career if you don't report finding contraband in my jean shorts, then you go on to mock me adding 'not even for a juicy cunt like me'. Knowing I'm screwed and feeling like all hope is lost on becoming a model prisoner as I realize I'll be physically punished no matter what. I don't even believe you will try to get leniency for me, but I'm not about to come out and say that.

Finally you tell me to remove my hands from the wall and get dressed. Relieved this part is over, although I know more is coming later, but at least now I can go back to feeling like a human. I quickly grab my clothes, putting my yellow bra and bikini panties on and then my jean shorts and yellow crop top. I brush tears away and turn to face you.

You approach me again and let me know nothing is free here and how I have to start learning. Then you unzip your pants as your cock appears. My mind races as I try to figure out my options. Within a few seconds I realize my options are basically zero. I mean I can see you telling the Warden that I disobeyed you and for hasher punishment. Or you might just kick the shit out of me right here if I don't listen.

With your hands on my shoulders I feel pressure as I go with it and kneel. Then look up at you. Then demeaning me further as you call me 'cunt' and I feel the tip of your cock brush back and forth across my face. "Sir you know this isn't right, that I deserve better than this. But I do understand and will listen and obey. I wanna be out of here in 3 months so I'm trying Sir." Pissed that I have reduced myself to accepting this, but knowing the options are a severe beating and doing a lot more time in prison and god knows what else.

I open my mouth and begin sucking your cock. Feeling totally humiliated as I ride it up and down fairly rapidly. Not wanting to prolong this, hoping you just cum and end this quickly. Feeling your rock hard cock in my mouth as my head bobs up and down, now tasting your precum and knowing you will be cumming soon. Assuming you will be cumming in my mouth as I doubt you want me to pull off and put my hands around it. So as I ride your cock I prepare for a dose of cum to be shot in my mouth. I look up at you as you tense up as your cock throbs, knowing it's within seconds.

A reluctant cocksucker

You are reluctantly sucking my cock, having told me that you deserve better. I chuckle at this. “Cunts like you get exactly what they deserve,” I explain, feeling your mouth sliding up and down on me. You are no stranger to sucking cock, that is obvious to me, but you are businesslike in your approach, bobbing your head up and down rapidly so I can feel the tip on the back of your throat.

As you suck, I can feel my balls tighten, my orgasm getting closer. The sounds of you slurping and sucking my cock fill the small exam room, and I close my eyes, savouring every moment. A deep moan rises from my chest as your mouth works my cock, bringing me closer. I tell you to put your hands behind your back and hold them there. Another time I might have had time to cuff them instead, but this will do. My hands stay wrapped in your hair, and I just hang on to you while you do the work. I would fuck your face if I needed to, but right now I don’t. Another time I’ll give you that experience.

“I want you to look at me when I cum,” I say, pulling your head up. Nodding, you keep up your energetic sucking. With a groan, I start to cum, my cock jerking in your mouth. I can feel my hot cum shooting into your mouth, you looking up at me with your big, brown eyes. “Swallow it bitch, every last drop,” I say. I can feel your throat working as you obey and swallow it all.

I keep hold of your head, leaving my cock in your mouth, until I am satisfied that you have sucked me dry. I pull out and zip up, while you remain kneeling with just a trace of cum on your lips. I grab you by the hair, pulling your head up to look at me. “Not bad for your first time,” I say, “but a little rushed. I’ll let that go this time, seeing as I need to be somewhere else now. But try that again, and I will make you pay for it.”

I tell you to stand and place your hands behind your back. It is time for you to head off to your cell, while I go and have a chat with the Warden about your drug infraction. Taking my handcuffs off my duty belt, I cuff you quickly, then grab you by the arm and take you out of the room. Down the hallway, another guard is doing the same with one of the other inmates you arrived with. Another guard stands nearby watching, and I call to him. I hand you over and tell him to take you to Cell Block B and put you in your cell.

As he takes charge of you and heads down the hall, I smile and head off to speak to the Warden thinking that this day is off to a pretty good start.

Swallow It All and Then Locked in a Cell

Knowing you are close as you moan and your cock throbs in my mouth, hoping this ends soon. As I continue to ride your cock I hear you order me to put my hands behind my back and I quickly do. This as you grip my hair but thankfully don't control my head movements.

It's all so nasty, having just had my cunt and ass totally violated by your hands now I'm on my knees sucking your cock. At least I'm dressed, but still, this is totally demeaning. The silence besides my own sucking and slurping over his cock just make it all that much worse.

You order me to look at you as I suck you and I nod as my eyes look up. Knowing I have to look totally pathetic looking at you with your cock in my mouth. But I continue riding you, feeling your hard cock going back and forth in my mouth. My thick coating of saliva on your cock making it a bit easier.

Hearing you groan and feeling your cock throb more as you begin cumming. Your cock shooting thick cum into my mouth and down my throat. This as you order me to swallow it all. I continue to look at you while keeping my hands behind my back as ordered but also try to concentrate on swallowing without gagging or coughing. Knowing that would piss you off. I gulp hard and then a couple more times managing to get most of your cum down.

You finish cumming but leave your cock in my mouth and I know you want me to clean it. I do as I ride it up and down getting all the remaining cum off of it and swallowing that. Then you grab my hair and pull me off as you tell me I better not rush next time. I nod my head yes, feeling like a pathetic puppy dog.

I stand up and you cuff my wrists behind me, then you hold my arm and guide me down the hallway. I can see I'm not the only inmate being abused as I look into one of the rooms I'm passing. Fuck, this place is totally sick.

You transfer me to another guard and I'm fearful of being sexually abused again. He walks me further down the hall and then pushes me into Cell Block B. Relieved to be alone as I sit on the bed, which is totally uncomfortable. Hating myself for going on vacation alone and putting myself in this situation. The thoughts of the degrading things I just experienced cycle in my head. Then thoughts of what punishment the Warden is gonna inflict. All over bullshit. This place is mad and who knows if the Warden is even making the punishments. Fuck I hate myself for being trapped here. I sit there as tears stream down my face and unto my cropped top over my breasts.

A chat with the Warden

I do go to see the Warden, and we talk about Debbie and the drugs. He is around the same age as me, but native to these parts. We get along well, and over the years he has entrusted more responsibility to me in terms of dealing with overseeing other guards and managing the inmates. When I mention what I found in Debbie’s clothes, he doesn’t give it much thought.

“Forget charging her, some sort of public punishment should suffice. You know how we’ve dealt with this before. Handle it however you want, I trust your judgement.”

I nod and recall the various punishments meted out for smuggling drugs into the prison this past year. There were a couple of public whippings (for women who really had tried to smuggle contraband), many severe applications of the prison strap, sometimes in combination with field punishments. As a facility that cultivated and harvested food crops, field punishments took place outdoors in front of guards and inmates involved in food production. There were some cruel methods used – anything from being tied out naked in full sun until the skin burned, to being hitched to a plow and made to pull it while a guard drove them with a whip. Last year one of the guards staked a naked inmate out over a large anthill, applying a sweet attractant to key areas on her body to lure the little stinging creatures to her.

I didn’t stay long, but headed back to Cell Block B to find Debbie. She should be put to work doing something useful today, and I would need to check the assignment roster to see what was available. I’d have to give some thought to what punishment to give her too. I wasn’t going to see her whipped, but I figured 20 or 30 strokes with the big strap we used would be a useful lesson for her. Maybe some field punishment too. I’d consider that more later.

I consulted the roster and saw an opening for Debbie that would work out just fine. Each cell block held up to 30 prisoners, and right now there were 22 in Debbie’s block. She was inside number 11, sitting on the bed with the flimsy, ratty mattress. The small 10x10 cell also held a crude toilet and small sink, which even worked sometimes.

I rapped my baton on the bars, waking you from your stupor, and shouted for you to get up so you could get ready for your first work assignment. “Good news cunt,” I said, “you get to help scrub the toilets and showers. Strip, and get all your clothes off now, unless you want them to smell like shit when you’re done.”

Naked and About to Clean Toilets

It's all a nightmare as I sit on the lumpy mattress and sob. I look around at the tiny cell and the toilet in plain view. This is all so wrong, being put here and earlier being sexually abused and humiliated, I can't believe people would even do things like this to others. Especially when I know that you know I didn't try to smuggle that pill in.

My sorrow for myself is interrupted by you banging the bars with your baton. I jump and then stand up as ordered. When you first say 'good news' I'm hoping any punishment was waived, but instead you tell me I will be scrubbing toilets and showers. Okay I suppose that's better than being beaten. But when you say I need to get all my clothes off and do it naked. I know it's a way of demeaning me in front of all the other inmates. Kind of putting me on the bottom so they think they are better than me. God I hate you.

I first slip off my sandals, then remove my yellow crop top and jean shorts. Then my yellow bra and yellow panties. I place them on my bed. Then stand there naked, not saying a word. But I look at you directly in the eyes, although t isn't easy. But I have to appear strong. Knowing if I appear weak you will only abuse and demean me more.

A dirty job

I accompany you down the hall where we go through a locked gate, and into another hall that leads to the showers. When we arrive, there are already 2 other naked inmates starting to clean the floor. I take you over to the area where there are half a dozen toilets along one wall, all in various states of cleanliness. Which means some of them are practically covered in shit, because the plumbing in this place is old and toilets clog and back-up easily.

An old bucket with some rags and old brushes sits at one end, with some cleaning chemicals. “Time to get started, inmate,” I say, pointing to the bucket. “On your hands and knees, Debbie,” I add, gesturing to the other prisoners, “just like them.” Both of the others are on all fours, one scrubbing the floor with a brush, and the other using a rag.

You don’t look happy, but you get down on your hands and knees, and start wiping down the nearest toilet. One of the other prison guards comes over to talk to me.
“How’s it going, Gibsy?” he asks, smiling and watching your ass as you work on the toilet. “She working out for you?”

This is Carter. A dipshit, but he does what he’s told. Seems like you have a fan.
“Just got in this morning,” I say, “I’ll know better in a day or two. I think she’s a fast learner.”

Carter nods, watching you deal with the disgusting looking toilets. “If she doesn’t work out for you, just send her my way. I’ll fuck the shit out of her,” he said, laughing.

You must have been listening, because you had stopped cleaning and were just staring at us. I unclip a strap from my belt, about 18 inches long and 1 ½ inches wide with a black wooden handle. It’s not as bad as the big strap used for punishments, but it stings pretty good. We use it when inmates need a little encouragement.

I step behind you and swing the strap hard so it connects with a loud crack across your ass. “Get the fuck back to work!” I yell, giving you a second hard smack as you scramble to resume where you left off. “If those shitters don’t sparkle when you’re done, I’ll fuckin’ beat your ass raw!”

I tolerate Carter’s idiotic chit-chat for a few minutes, and then happily he fucks off to bother the other guard. You are moving down the line of toilets cleaning like no tomorrow, no doubt owing to the 2 angry red marks on your bare ass and my threat to beat you if I’m not pleased with the results. I lean against the wall, watching you work, and wonder what’s for lunch today.

Naked and On All Fours Scrubbing Toilets

Hating walking down the hallway completely naked. The only thing that makes it a bit better is I'm not the only naked woman. Seeing two other woman naked makes it like it's some kind of sick way of punishing us all. But I know it would be worse if everyone was dressed and I was the only one naked. So I suppose that at least is a positive, although a very small one.

You coldly tell me to get started as you call me 'inmate' and then tell me to get on my hands. I listen and get on my knees as I take the brush, rags and cleaning supplies. It's humiliating being naked and on my hands and knees, but I suppose that's the point. Treating me subhuman and stripping me of every ounce of dignity.

I see another guard come over and talk to you as you both look at me on all fours as I scrub the totally gross toilets and the floor around them. I hear some of the things that your both saying, one being how the other guard will fuck the shit out of me if I don't work out. I scrub harder in frustration thinking what a nightmare this is. Then I pause to hear more of what you two are saying but quickly get back to work when you unclip your thick belt and yell at me to get back to work or you will beat my ass raw. I quickly put my head down and scrub the toilets harder. Knowing not to pick my head up again.

Despite me putting my head down and working hard again I feel you strike my ass with your belt. My arms in front of me buckle and my face nearly touches the nasty bathroom floor. I straighten my arms back up only to feel a second vicious strike on my ass as my arms buckle again. My ass stinging badly as you lecture me about making all the toilets sparkle. I nod my head and keep it down as I scrub more. My ass cheeks burning, but I'm not about to complain.

The other guard leaves and you continue to watch me as I go down the long line of toilets and clean every one. Finally getting to the last and finishing. When I do I remain on all fours and keep my head down, then quietly say, "I believe I'm all done Sir." Feelings so low and disgusting and just wanting to take a shower and get clean and then put some clothes back on.

Finishing up

I inspect the toilets you’ve cleaned, and grunt in approval. “Not bad, inmate. Go help the others over there finish up,” I say, indicating the prisoners on the shower floor. The showers are communal, basically just several long rows of big showerheads that spray water down over the concrete floor. One of the prisoners, a blonde, must not have been doing a proper job, as a guard was using his strap to stripe her backside. She cried out in pain after a few blows, then got busy again with her scrub brush.

You join the women in the shower area, getting back on your hands and knees. Carter sees you, and hands you a toothbrush, indicating that you should start scrubbing with it. I walk over and see you scrubbing at a dark patch on the concrete, pausing every so often to dip the toothbrush in a soapy bucket. Carter is grinning and leans down to say something to you. I can’t hear what it is, but you blush deep red and put your head down, scrubbing furiously.

I really do enjoy watching you do this, naked and on your knees. Your entire body is on display, and seeing you work hard at something this demeaning, your tanned skin covered in sweat makes me think about wanting to fuck you. I stare at your sweet cunt and your puckered asshole and imagine ramming my cock into both as you crawl around on the floor. My cock throbs as I think about having some fun with you tonight.

When you finish, one of the other prisoners removes the buckets and brushes, while you and the remaining woman are allowed to clean yourselves up. Carter turns on one of the showers, and the blonde with the whipped ass goes and stands underneath it. I stop you on your way, and hand you a new, small bar of soap. “Soap is a luxury here,” I say, as you take it from me. “It has to be earned. You will earn this tonight.” You say nothing, but head back to the shower, and I stand back and watch you soap up your whole body and scrub yourself with your hands.

Cleaned Toilets and Showers But That Bar of Soap

Glad you approval of how I cleaned the toilets but then you tell me to help the other inmates clean the showers. Now on my hands and knees on the concrete shower floor, it really hurts my knees. I'm not about to complain as I scrub the corners with a toothbrush. It is totally surreal seeing the other naked women scrubbing the showers too. Thinking we were probably all framed and that this place is where the island gets free labor from us and the guards and whoever else get free sex too. Plus apparently they get off on beating and humiliating the shit out of us too. It's all so totally sick.

My attention is suddenly drawn to a blonde girl being whipped and yelled at, as her ass gets beaten and she screams out in pain. Then she scrubs diligently to avoid being beaten again.

The other guard Carter walks over to me and bends down as he whispers to me, saying he likes my ass and intends to stick his big cock into it unless I scrub harder. Of course I scrub harder, hating him for that threat.

I see you and Carter standing there staring at me and hear you mumbling to each other as I continue to scrub the fall with a toothbrush. We all finish and the buckets and brushes are taken away. My knees hurting and my arms tired, but knowing that is the least of my problems.

We are told to take showers, which is a relief, but you stop me and I take the bar of soap you hand me as you say it has to be earned. I think about throwing the bar of soap in your face, but decide to remain passive, at least for now as I turn the shower on and wash myself thoroughly with it. Dreading what you plan for me tonight, all for a supposed bar of soap. But I know that the reality is that you will do what you want with me no matter what and me rebelling will only make it worse.

Back to the cell

The guards and I watch as the three of you wash yourselves. I can see you touch your ass tenderly, where I left you a couple of nice welts. Not as bad as the blonde cunt though; she can barely bring herself to touch her reddened ass. I notice your stiff nipples, and I am amused. You notice me looking and turn away, blushing. I guess showering in front of me turns you on!

After your shower, you look around, but there is no towel to dry off. I tell you not to worry about that – with the heat you’ll be dry and back to sweating in no time. The other guards grab their prisoners and begin to walk them back to their cells. “Let’s go,” I say, pointing to the door. “And don’t forget your soap. You’ll need that.”

I escort you back to your cell and lock you in. You waste no time in getting dressed again. I grin at your modesty; you turn your back on me to slip on your panties and bra. It won’t be long, I think, before you put an end to such pretense. There is no modesty, and no dignity here for inmates.

It is almost lunch, and I explain that the guards who normally work in your cell block will see to you and the rest of the inmates. I have work to do this afternoon, setting up shift schedules, dealing with guards, complaints from locals – it never ends.

“Try to stay out of trouble this afternoon,” I say before I leave. “Be careful of other inmates,” I warn, “long-timers like to fuck with the new cunts like you.” I promise you before I leave that you and I will spend some quality time together later. “I’ll be back after chow tonight,” I say, as you sit in your cell, alone.

Back in My Cell, All Dressed But Crying

I grab the soap I used as you tell me to, then walk back to my cell with water all over my body, feeling myself leaving a trail of drips behind me. This as you promise that I'll be dry and sweating again soon enough.

I actually feel some security back inside my cell and I can't wait to put my clothes back on. Wishing I had more clothes to wear besides my yellow bra, panties, crop top, jean shorts and sandals. But it's certainly better than being naked. When I was first processed here they took the rest of my clothes and everything else I had on my vacation. Things like makeup, my handbag with cash and a bunch of other things in there, ID and credit cards. Then I think, oh fuck my magic wand was in my suitcase too. Shit, embarrassing. But I suppose that's the least of my problems.

As I put my clothes on I see you grinning at me, not sure what you're thinking but it's not a friendly grin.

You give me a warning about the long-time inmates and how they will take advantage of me if they can. Also that other guards will be watching over me this afternoon. Then of course your reminder of spending 'quality time' with you tonight, knowing that means you will most likely be raping me. Fuck I hate you so much.

You leave and I can't help but think about the long-time inmates and how they might fuck with me. I know I have to appear strong and try to avoid being at the bottom of the ladder here. I've seen enough movies to know other inmates can make someone's life a nightmare. It's all just another thing for me to stress about, between the guards and other inmates, this is pure hell. I sit on my bed and sob.

Running the prison

I stop to talk to a few of my subordinates on the way to my office, and ensure things are running smoothly. Not too many issues so far today. I have paperwork to do, so I spend a good amount of time working away on that. One of the guards brings me some lunch so I can keep working at my desk.

It is a relatively quiet afternoon, with only a few interruptions. Some of the scheduling I am responsible for concerns the comings and goings of inmates, as new prisoners are always arriving, and those that have served their sentences get released. Whenever possible I try to arrange for those to happen on the same day, so that we make better use of our transport capacity. Boring stuff, but prisons don’t run themselves.

By dinner time, I am finished and decide to head to my quarters that are located within the prison. The Warden, myself and a few other key personnel have quarters on site that we often use, which for me is convenient. I don’t really have any use for living in town and have everything I need here – including overnight visits from select inmates. The kitchen always prepares separate meals for managers and guards, and I have my delivered to my quarters. I will have a quick dinner, followed by a visit from Debbie.

About 7:00 I get a radio call telling me that a guard has been dispatched to fetch Debbie. Protocol for this requires him to put her in handcuffs and leg shackles, as he will have to bring her into an area of the prison that is less secure. Not that we have too much trouble with escape attempts – those that try are usually caught very quickly and face horrendous consequences upon their return to prison. But occasionally, someone tries, or seizes an opportunity to attack a guard that they have a grudge with. I don’t take any chances with any of these bitches.
Twenty minutes later the guard is at my door. I open it up to see Debbie cuffed and shackled, and once again trying to put on a brave face while I know inside she is nervous as hell.

Handcuffed and Shackled

Thankfully the afternoon is peaceful and no one bothers me. I lay down on my bed and sob from time to time. Between sobbing I'm thinking what I can do to make you go easier on me. After thinking about it I don't come up with anything besides trying to obey and be nice to you. Maybe I can smile at times to make you realize that I'm a woman not an animal.

I sit up in my bed and have to pee, just glad no one is around as I pull my jean shorts and panties down to my knees and pee. I wipe, flush and quickly pull them back up. Then sit on my bed again, waiting and worrying. Time crawling as thoughts of what will happen tonight with you cycle in my head.

Finally a guard approaches and he handcuffs and shackles me. It makes me feel like the prisoner I am, which I suppose I need to get into that mindset. I hobble down the hallway along side of him. Passing other prisoners in their cells and other guards walking by. I'm just glad I have my clothes on as last time I walked this hallway I was completely naked and it made me feel so pathetic.

The guard opens your door and there you are. I hobble in and stand there trying to appear strong. Then decide to at least say hi as I try to make you see me as something more than an object to humiliate, "Hello Sir." I smile just a bit, hoping you see a personality. Of course the reality is I hate you for how you treated me before but trying my best not to show it.