Debs Vacation Becomes a Hellish Prison

[Mkmydaze]

Hogtied and vibed

The guard removes the cuffs and shackles from you and closes the door. “Finally, we are alone,” I say, moving to stand behind you. “Raise your arms,” I command, watching as you do so. I lift your top off and throw it into the corner. “Keep them there,” I say, now undoing your bra, and setting it on the bed. I stand close to you, and you can feel my cock through my pants, pressing up against your ass. Reaching around, I undo your jean shorts and pull them down. “Off with the sandals,” I say, and you quickly kick them off your feet, then step out of your shorts. I throw the shorts over where your top is. I slowly pull your panties off, telling you to put your arms down at the same time. You stand there naked, as I put your panties on the bed with your bra, and now your sandals.

“As part of your punishment for having drugs hidden in your clothing when you arrived, I am taking these away,” I say, taking up the bra, panties, and sandals. “You’ll get them back if and when I decide,” I add, tossing them onto my desk nearby. “But that’s okay,” I continue, “I have something else for you to wear tonight.” I open a desk drawer and pull out four heavy leather cuffs. “Extend your arms,” I order, and you stick them out so I can buckle the thick cuffs onto your wrists. “Now sit on the bed, and stick your feet out over the edge,” I say. I grab your ankle and fasten it in a cuff, then quickly do the other ankle as well. The cuffs are strong but comfortable.

I stand back and look at you. “You look good in them cunt,” I say. “Lay face down on the bed.” Slowly, you do as I say, and watch as I take two lengths of rope with snap hooks on the ends and clip them to D rings on your wrist cuffs. I pull them tight, until your arms are stretched up and out toward the bedposts, then tie the ropes to the posts. I am about to do the same with your ankles when there is a knock at the door.

“Fuck,” I swear under my breath. “What is it?”, I say loudly, moving toward the door but not opening it.

“Sorry to bother you sir, but the Warden wants to see you,” the young guard reports timidly, sensing that I really don’t enjoy being bothered like this.

I sigh, wondering what the hell he wants that’s so urgent. “All right. Tell the Warden I’ll be there in 15 minutes,” I say, and the guard leaves to report back.

Now I turn my attention to you. I’ll have to leave you for a while. I have an idea, and release your wrists from the bedpost ropes. Instead, I pull them behind your back, and clip them together with a zip tie I had on my night table. Always lots of those around here. With another tie, I tie your ankles together, and then force your feet towards your ass. A third zip tie is used to link your ankles and wrists together, so that now you are lying on the bed, hogtied. I grab your panties and wad them up. “Open your mouth,” I say, then jam your panties inside when you do. “Keep these in your mouth until I get back. Finally, I take a vibrator, and jam it against your cunt, held in place by your thighs and ass. I turn it on low.

“This should keep you occupied until I return,” I say, giving your ass a good swat. I leave my office and lock the door. You are left alone with the vibrator until I return after half an hour. I turn the vibe off, noticing that it is covered in your juices. “Glad you had some fun,” I say, taking the panties out of your mouth. “Well Debbie, I’ve got good news and bad news,” I say, rolling you to your side so you can look at me. “First, the good news,” I say, giving your tits a good squeeze. “The Warden had some ideas about your punishment, and so it’s been decided what it’s going to be.” I pinch your nipples, making you gasp. “The bad news is, it’s a lot harsher than what I had originally planned. You, my juicy little plaything, are going to be in for a week of hell.”

 

[debbiev]

Dreading a Week of Hell

Laying there, feeling totally embarrassed as I'm naked and hogtied on your bed. Knowing this is probably gonna be the norm around here, between you and the Warden and I'm sure plenty of other guards that are perverted, I know I'm in for three months of constantly being stripped of my dignity. All for what, a small amount of weed. Fuck.

Just when I think you have humiliated me enough by being naked and hogtied, you shove my dirty panties in my mouth and order me to keep them there. Feeling like that is the ultimate stripping of my dignity. These are the same yellow panties I left home with and have worn them for two days, so not very pleasant. God this is so wrong.

But it gets worse as you shove a vibrator between my thighs and push it up against my cunt. I groan, more in the humiliation of it all than anything else. You turn on the vibrator at low speed and then leave your office as I hear the door lock. Seriously? You are gonna leave me like this until you get back?

As the vibrator hums I feel myself getting wetter. It excites me but on low speed not enough to put me over the edge, but just enough to keep me very excited. It's almost frustrating that I can't cum, but I suppose if I gushed all over the vibrator that would be worse. I wouldn't want you to see that, so I'm glad I can't cum on low speed. I hear my own moans of being edged mixed with moans of frustration as the vibrator relentlessly continues.

Finally I hear your office door unlock and you return. I look over at you and know that you can tell in my face that I'm near the edge. You pull out my panties from my mouth, which are now saturated with my saliva. Then you roll me onto my side. When you squeeze my nipples I grimace in pain.

I listen as you tell me the Warden supposedly told you that my punishment is gonna be a lot harsher than originally planned. When you describe it as a 'week of hell', I feel myself tense up as I realize obeying you and hoping that you go easier on me were useless. That you and/or the Warden, for whatever reason, just want to see me suffer. "Sir, you know I didn't so anything to deserve harsh punishment. Please speak to the Warden again or something. I swear I'll be a model prisoner, please give me a chance Sir. Please Sir, I beg you."

Knowing pleading probably won't help but figuring at this point I have nothing to lose.

 

[Mkmydaze]

Our fun evening begins

I just laugh, listening to you beg. “You’re just turning me on begging like that,” I say, flipping you back onto your stomach. I take my time undressing, looking at you squirm, naked and hogtied. “You’ve got a nice ass, Debbie,” I say, tossing clothes onto the floor. “Totally fuckable,” I say, kneeling on the bed with my cock in the air. I rub your ass, then give you a few good smacks with my hand. “Totally spankable, too,” I add, squeezing one of your red ass cheeks.

I kneel behind you and grab your ankles. “And you’ve got pretty feet too, cunt,” I say, rubbing the bottoms of your feet. “I bet you didn’t know old Gibsy’s got a thing for feet,” I say, lowering my mouth onto the toes of your left foot. I suck your toes together, and then each one individually. “Mmm, I do love a little shrimp for dinner,” I joke, then move to your other foot to give it the same treatment. “Do you like that cunt?” I ask, lowering your ankles and unclipping them. “I think I heard you moan while I was going down on your toes,” I chuckle. “I think you are a kinky bitch.”

I pull you by your ankles down the bed and spread your legs wide. Each ankle has a rope attached from the bottom posts. I put a pillow underneath your hip, raising your ass up off the bed. I climb on the bed between your legs, and start rubbing your dripping cunt. “You are so fucking wet! What a total slut you are Debbie.” I begin to rub the tip of my cock on your slippery cunt lips. “I’ve been waiting all day for this,” I say, and plunge my hard cock deep into you.

Slowly I fuck your wet cunt. You are so ready; it slides in like nothing. It feels good, and I move my upper body over yours, whispering in your ear as I fuck you. “Your boyfriend must fucking love this,” I say, thrusting my cock deeper and harder. “Does he like fucking your cunt like this?”, I ask, pulling your head back so I can look at your face. “Which do you like better Debbie,” I taunt, “him fucking your cunt, or fucking your ass? Come on, you can tell me.” I slow down a bit, not wanting either of us to cum just yet. You are still on edge from the vibe, and this bit of fucking has got you turned on again. “Not that it matters to me,” I say, pulling my cock out and slapping your ass again. “I’m having them both tonight, and anything else I want besides,” I explain, pulling your head back while I stick my fingers in your cunt. “I want you to beg me to cum.”

 

[debbiev]

Tied Like An Animal and Humiliatingly Fucked

When you laugh it's obvious that trying to be a model prisoner and begging for leniency is not working. Then you just make it worse show you when you tell me I'm turning you on by begging. Which instantly makes me stop begging. I watch you remove all of your clothes and then smack my ass a few times. It hurts but I keep my lips sealed, trying to be strong despite my ass stinging.

I'm surprised when you suck my toes and weirdly enough it tickles me but I resist laughing. The odd thing is I actually feel myself getting wet. Not sure if it's what you are doing with my toes or being hogtied like an animal. Although the vibrator under me is definitely adding to it. Maybe my body is just preparing to be raped and it's a self defensive mechanism to prevent injury.

You then suddenly pull me down the bed and unfasten my ankles and then spread my legs as you bind them to the bottom posts on the bed. This worse than being hogtied as I know my ass and cunt are totally exposed. I groan, knowing you are gonna rape me now. Oh god, why me, I didn't do anything and I've been good. You push a pillow under my hips as my ass is forced upwards towards you. Then feeling your finger rub my cunt, knowing you feel my wetness. But hearing you say it out loud like I'm some sort of worthless whore makes me feel more embarrassed.

I groan as I feel your cock pushing into me and then going deep. It's a groan of defeat, not that I had a chance, but feeling your cock in my cunt just makes me feel like I finally lost everything. The odd thing about it is that my feeling of defeat is coupled with it actually feeling good sexually. Fuck what is wrong with me?

My head juts back hard as you grip my hair and ask about my boyfriend and if he likes this. Then asking me if he likes my ass or cunt better. I don't answer, I just groan. I just know that with your cock in my cunt and the vibe buzzing on my clit I'm actually close to cumming. I try to resist cumming as it's the last thing I want you to see, but not sure I can. But when you suddenly pull out of my cunt I'm half relieved and half frustrated.

I take a few deep breaths, relieved you are no longer raping me, at least for now, but then I feel your fingers enter my cunt and I groan, knowing you are gonna keep tormenting me. As you finger fuck me you order me to beg you to let me cum. I hesitate a few seconds and then know I don't have a choice, I might as well just beg. Being tied like this, you could beat the shit out of me if I don't beg.

"Okay okay. Sir please let me cum, I wanna cum, please Sir." Feeling totally foolish hearing my own pathetic words asking you to make me cum. I put my head face down in the bed as my hair falls around my face. Glad my face is covered but wanting to just crawl under a rock and die.

 

[Mkmydaze]

A cunt gets to cum

You begged me to cum, and I decided to let you. I place the vibe on a higher setting, letting it buzz your throbbing clit while I stroke my cock that is still wet with your juices. “Now Debbie,” I say teasing your puckered little asshole with my fat cockhead, “I’m going to fuck that pretty ass of yours,” and I start slowly pushing my cock against your sphincter. I force it open slightly, but you are very tight. Grunting, I push in a little more, using my body weight while my hands hold your hips. “Damn, you are so tight cunt!” I exclaim, finally pushing the rest of the way into your ass.

It feels good with my cock buried deep inside you, held so tightly. I rock back and forth, letting my cock slide in and out, just a bit. Your wrists are still bound behind your back, and I grab your arms above the cuffs, holding onto them as I begin to fuck your ass harder. “Fuck yes, how’s that cunt?” I ask teasingly, slamming into your ass hard and hearing the slap of my flesh against yours. I keep pounding, forcing my cock deep into your ass, and I can feel myself getting close to cumming.

“You belong to me now,” I say, “and you will cum when I say you can.” I have a feeling that you are very close yourself. The buzzing on your clit must be driving you crazy after all this time. “Not yet, hold it,” I say, spanking your ass with my hand as I continue to thrust into you like an animal. I keep spanking and squeezing your red ass cheeks, ramming my cock home hard, until I feel my cock start to jerk. I let go of your arms and lay on top of you, snaking an arm around your throat, squeezing. “Cum now my pretty little cunt, cum for me” I whisper by your ear, continuing to pound your ass until I feel my cock start to jerk and shoot my hot cum deep into your ass. I hear you gasping for breath as you start cumming yourself, your whole body shaking with the force of your tortured orgasm.

I release my arm from around your neck and pull my cock out, moving to a cabinet to fix myself a drink. “Are you thirsty?” I ask, while pouring myself some whiskey. I pour some water into a shallow dish and set it in front of you on the bed. “Don’t fucking spill it,” I warn, brushing some sweaty hair away from your face. “I’m going to have a shower, be a good cunt while I’m gone and I’ll let you cum again.” I leave you tied to the bed like this while I walk towards my bathroom where I have my own stand-up shower. Unlike the showers the inmates use, it has good water pressure and hot water when I want it.

 

[debbiev]

Ass Raped, Bound and Laying in Cum

Hearing you say you intend 'to fuck that pretty ass if mine' makes me totally fearful. But my emotions are riding all over the place as the distraction of the vibrator relentlessly humming away on my clit is driving me crazy. The thought of being bound on my belly with my legs spread and about to be horribly ass raped with you just using the juices from my cunt is terrifying. Yet me being on the edge from the vibrator causes my mind to wobble from horror to pleasure. The fact that I had to beg you for the right to cum just makes it all so much more humiliating.

Feeling your hard cock against my asshole I feel myself tense up more. I mutter, "Please don't." Knowing it's a waste of my breath, yet also knowing I needed to say that out loud to justify to myself that I don't want to be fucked in my ass by you.

It's obvious nothing is going to stop you now and I feel your cock push harder against my asshole and then my asshole open as I grunt in pain. My cunt juices obviously not sufficient enough for lube. I groan and drool into the bed as my hair remains around my face, my asshole at first resisting your cock but then opening up as I grunt louder. Now grunting more from the feeling of total defeat then the pain.

Feeling your hand on my cuffs as you thrust inside my ass. I can feel every inch of you and it's totally degrading. Yet, I'm close to cumming with the relentless vibe under me. Fuck what is wrong with me?

The sound of you pounding my ass echoes throughout the room as you tell me not to cum. Knowing I have to listen otherwise more punishment, so I grit my teeth and try to resist cumming. This as you continue to fuck my ass. When you begin spanking me that only causes me to nearly go over the edge. You slapping my ass like you're riding an animal. I breath heavily into the bed as I try to hold on.

When you permit me to cum I instantly release. Hearing my own muffled moans into the bed as I feel a gush of cum from my cunt and my body convulses. This as I feel a huge dose of cum going into my ass. It going deep as you hand grips my throat. Feeling you continue to pump your cum deep into my body. The horrible thought that I was just ass raped hasn't sunk in yet as I just came so hard and my emotions are all over the place.

Finally I begin to come down as you offer me water. "Yes thank you." Thinking at least you're concerned enough about me to give me water. Maybe you realize I am a human after all.

But when you put a bowl of water in front of my face and tell me 'don't fucking spill it', then you go to your bathroom to take a shower I know nothing has changed. Leaving me naked and bound on my belly with my hands behind my back and my legs spread. I lay there, feeling your cum seeping from my ass, mixed with my own cum below me soaking the bed under me. Plus I'm soaked in my own sweat and I reek. I feel totally disgusting.

The additional degradation of having to drink out of a bowl like an animal just adds to the hopelessness of it all. I drink most of the water from the bowl. My nose and chin ending up soaked as well as parts of my hair that went into the bowl. I wait for you to come out of the shower, hoping you untie me and let me go back to my cell. But what you did to me cycles in my head and I feel like I just wanna crawl under a rock and die.

 

[Mkmydaze]

Blowjob encouragement

I take my time with my shower, knowing you won’t be going anywhere. Thinking about you lying on the bed with my cum leaking from your ass gets me hard again. So far you have been adapting to your new reality fairly well, but I can tell it has been a big shock. Not as big as what is coming tomorrow, though. Your punishment for the drug smuggling charge starts in the morning, and it will not be a fun day for you.

Upon my return, I see you have had some water, but some has spilled onto the sheets. Not to mention the dark, wet spots from your juices and body sweat. “Damn, you are a messy cunt,” I remark, taking away your bowl. “You don’t deserve to cum again tonight,” I say, “but I do. I undo your ankles from the posts, and clip them together, then bring your feet back down towards your ass to clip them to your wrists. You are hogtied again. I bodily drag you around so your head lies off the end of the bed, and you are looking up at me as I remove my towel to show you my erect cock again.

“You’re going to suck me again cunt, only this time do better,” I warn, finding myself a thin rattan cane. Without warning I whip the cane across the soles of your bare feet. “This will keep you on your toes,” I quip, laughing as the pain of the unexpected strike settles in. “Now open your mouth, and get to work,” I say, pushing forward until my cock slides past your lips. “Take your time, and make it feel good,” I say, “or you better get used to this,” I add, giving your soles another stroke with the cane. I stand there, letting you suck me, flexing the cane in my hands. I think my encouragement has worked, because this bjowjob feels different from your first.

 

[debbiev]

Hogtied and Forced To Give a Blow Job

I watch you return, dreading you walking back over to me but also glad because I hope you will release me from being tied like an animal. Laying there naked, my hair knotty, my body all sweaty and cum seeping from my ass and cunt. But there isn't a thing I can do besides obey. It's frustrating to be stripped of everything and be helpless. But I know I have to get through this and in three months I'll be free. At least I hope so.

Your first words mock me as I listen to you tell me 'I'm a messy cunt'. It just adds to the humiliation of it all. You release my ankles and I slowly put them together, my legs hurting from being spread so long, but it feels good to close them. But then I feel you tie my ankles together and pull my ankles up to my bound wrists behind me as you secure it and again I'm hogtied. I groan, as you pull me so my head is over the edge of the bed, knowing I'm gonna have to suck you again.

I watch as you remove your towel and I'm ordered to suck you. You threaten me to do better this time and before I can respond you cane the bottom of my feet. I yelp out in pain. Then immediately open my mouth and wrap it around your cock.
I listen to you tell me to take my time as you strike my soles again. I grunt in pain into your cock, drooling as I do. Now trying desperately to give you the best blow job ever, fearing more pain on my feet if I don't.

I ride your cock up and down, slowly at first so it prolongs the enjoyment for you.
Then a bit of teasing as I slow down more, then speed up a bit. My mouth now up at your tip as I lick it and then wrap my lips around your cock again and ride it back down. Then increasing my pace, my head bobbing up and down as I feel every inch of your cock and now taste your precum. It's not easy in this position but going by your reaction, I think I'm doing okay.

I do know one thing and that this has made my cunt moisten again. Why I'm not sure, maybe from being bound, maybe from sucking you or maybe even from the pain and humiliation of it all. I don't know, but I hate that my body reacts like that.

Speeding up more as I feel your cock throb in my mouth knowing you are close to cumming. I look up at you and hope that is okay. I continue riding your cock with my mouth and know you are about to flood my mouth with your cum.

 

[Mkmydaze]

Cumming on a horny cunt

You do a better job at slowing down this time. I watch your head bob with satisfaction, and feel your tongue work my cock. Your toes wiggle as you suck, and I can see thin red marks on your soles. Your ass rises up and down as well, and it is almost like you are trying to hump the bed. “You horny little cunt,” I mock, grabbing your hair and forcing my cock deeper. “You’re getting off on this.”

Before long, I am cumming again, and before I finish pumping out my load I pull back, letting my hot jizz splash onto your face and hair. “Just a little souvenir to take with you back to your bunk,” I say, wiping my dick off with the towel. I get changed back into my pants and radio to the guardroom to send someone to take you back to your cell. I sit beside you and undo your ankles from your wrists, then reach down to check your pussy. Sure enough, you are wet.

“Are you a dirty little sub slut?” I ask, teasing your cunt. “You like being tied and used,” I say, “even some pain seems to turn you on.” You don’t answer, but it feels like the truth. “In a way, that is good for you,” I say, “because tomorrow you start several days of punishment, and if you get any pleasure at all from it, be thankful because it will be hellish. Trust me, if I allow you a visit back here in the evening after a day outside, it will feel like a vacation.”

I remove the leather cuffs from your wrists and ankles and get you standing up. I use a set of handcuffs to lock your wrists behind your back, and leave you standing in the center of the room when the guard arrives and knocks at the door. “Enter,” I say to the guard, remembering I have confiscated your underwear and sandals. “Take her back to her cell like this,” I instruct, handing him what clothing you have left. “And let her sleep with the cuffs on, this dirty cunt will be fingering herself all night if you don’t.”

The guard grabs you by the arm and marches you naked out into the hall, my cum still visible on you. “Sweet dreams, Debbie,” I say as you leave, closing the door and going back to clean up the mess on my bed.

 

[debbiev]

The Naked, Sweaty, Cum Soaked Walk of Shame

You continue to mock me as I suck you and it only serves to make me feel even lower than I already do. The mocking is worse because some of what you say is true, I am wet and I hate that I am.

Feeling you grab my hair as you force your cock deeper in my mouth, this as you begin cumming. Feeling your cock throb and then fill my mouth with cum. Then you pull out as see a stream of cum land on my face and in my hair. This as you continue to degrade me saying that it's a souvenir to take back to my cell.

You leave me hogtied as I watch you clean your cock with a towel and then get dressed. Then then you undo the binds and I lower my aching legs. Suddenly I feel your finger push into my cunt, like it's an inspection. I flinch and tense up. Then announce that my cunt is soaked as you mock me again about how being tied and the pain must turn me on. The worst part about it is it could be true which makes me think there is must be something wrong with me.

I listen to you telling me about how my punishment is gonna be hell for the next few days and I begin to realize that I may not be released when my 3 month sentence is finished. I may end up dead or worse, a permanently tortured sex slave.

Standing up now, with the cuffs still securing my wrists behind my back as another guard enters. You ordering him to take me back naked and cuffed so I don't masturbate in my cell.

Walking out naked, sweaty and my wrists cuffed behind me with cum on my face and in my hair. Plus dried cum on my upper thighs. It's a walk of shame as other guards laugh as do other inmates. Then the guard announcing to the inmates that you cuffed me to prevent me from masturbating in my cell. It just humiliates me more. Them calling me whore, skank and a barrage of other nasty names. It appears that my reputation here has sunk to the bottom rung of the inmates.

Glad to be back in my cell as I lay on my side in bed. It's uncomfortable with my wrists bound behind me and also being naked, sweaty with dried cum all over me. The guards walk by and laugh. But at least no one is touching me or raping me. After laying there for an hour or so I get up to go to the bathroom. Weird being cuffed and sitting on the toilet in the middle of the cell. But worse not being able to wipe myself. Fuck. I lay back on my side in bed again and just sob as I mumble, "Why me?"

 

[Mkmydaze]

Punishment - Day 1

I am up early, getting things ready for you to begin your first day of punishment for having drugs on you when you arrived at prison. You can thank the Warden for insisting on this extending over 5 days. One of the higher-ups at the Ministry is visiting this week, and the Warden knows that this official enjoys observing the discipline dished out here on Snake Island. He isn’t expected until tomorrow or the day after, but the Warden asked for it to start today, just to make sure.

I arrive outside your cell at 5:30 am, and see you sleeping on your bunk, still naked and cuffed and curled up into a ball. “Wake up cunt, time to go,” I yell, rapping my baton on the bars and startling you awake. You walk over to the door, backing towards me until I can remove your handcuffs. You look like shit. No matter, you’ll look even worse after today. “Don’t even bother with your clothes,” I instruct, seeing you move towards your shorts and top. “They wouldn’t survive what we have planned, so you’ll be working naked today.”

Before long, we are outside, and you line up with other prisoners on their way to work in the fields. Many of them are naked like you, but a few wear ragged shorts. Most of them are doing this work as part of their normal day; only a few like you are being sent out for punishment. All of you are loaded into a truck and transported outside the fence to the fields where various crops are grown: bananas, coffee, tobacco and sweet potatoes are the key ones. Our prison is responsible for over 100 acres of land under cultivation, and there is always work to be done on our farm.

When the truck arrives, guards usher you all out, and get you sorted into group based on the tasks you have been assigned. Two other naked women stand with you, as your group is set up for punishment. A guard directs you and another brunette prisoner to a couple of plows sitting in the dirt, with leather traces out in front. The other inmate, a crying redhead, gets pulled over to an area where there are several wooden posts and devices set up to secure prisoners in. She seems like she’s been here before and can be heard pleading with the guards who force her into a pillory. She is bent forward with her head and wrists placed on the bottom part of the wooden device, and then they are locked in when the top part swings shut. Almost immediately her cries fill the air, as a guard standing to the rear holding a heavy, leather strap by its wooden handle begins laying strokes upon her pale ass. The strap is thick and full of holes, designed to inflict severe punishment upon an inmate. The woman wails with pain after every stroke.

“Over here,” I say, pushing you forward to one of the plows. “You are going to be a workhorse today Debbie,” I explain, “and you are going to be responsible for plowing 4 acres of this field today. If you do not meet your expected quota,” I add, “you will face additional punishment.” A couple of guards place you in front of the plow and secure a wooden yoke across your shoulders. Leather straps secure your neck and wrists to the yoke, which then has the leather straps from the plow attached to it. A thick belt is fastened around your waist, with additional straps that attach to the yoke from behind. I explain that a guard will walk behind the plow, steering it, and he holds a driving whip in his hand, which he will use to encourage you to work.

I chuckle, seeing the look on your face. “So my advice to you, cunt, is to work hard.”

 

[debbiev]

Pulling the Plow Like an Animal

The sound of your baton hitting the metal bars on my cell wakes me out of a sound sleep. After laying awake most of the night I think I finally dozed off an hour or two ago. It's not easy sleeping while my wrists are cuffed behind me and my mind repeatedly replaying what is happening to me here.

I stand and you undo my cuffs and I move my arms back to my sides, them aching as I do. You tell me I'll be working naked and I know that will just add to keeping me at the bottom of inmates. I don't say a word, knowing it's pointless. I just listen and follow your directions.

Loaded into a truck with other inmates and taken to a huge farm just outside the prison. I can see various crops and I suppose if picking crops and working on the farm is punishment then it's not too bad. We are divided up and two other naked women stand next to me. At least I'm not the only one naked, so that makes it slightly better.

Me and another woman stand by the plows and the sobbing redhead gets pulled to the wooden posts and locked into the pillory. Then the guard begins whipping her ass. I'm guessing she previously failed at her job, or maybe they don't like her constant sobbing. I try to remain strong and not show them that they are breaking me. But watching this is difficult, her cries of pain are hard to listen to. I suppose they are whipping her in front of us to show us they we better work hard out here, otherwise that will be us. I intend to do whatever is necessary to avoid that fate.

You yell over at me and I walk to behind the plow, figuring your gonna get a horse or oxen or whatever to pull it and I'll be guiding it. But instead you point to the front of it and I look at you puzzled. Then it clicks, oh no way, oh god no. I know the expression on my face is one of shock as I walk to the front of it and two other guards secure a wooden yoke to my shoulders. Then straps around my neck and wrists. Then they strap a thick belt around my waist.

Feeling stunned as you tell me I have to plow 4 acres today, otherwise I will face additional punishment. I look at you, feeling a tear streak down my face, "Sir, I will do the best I can, I swear I will." Hating that I cave to what you want instead of spitting on you. But I know protesting will only make me end up like that redhead and that is something I need to avoid at all costs.

The guard guiding the plow yells at me to move and cracks his whip on the ground. I quickly walk forward, but it's seriously difficult to pull. The plow is in the dirt and the equipment is heavy. But I pull, slowly making progress. My arms hurting but my thighs aching more as I lean forward and slowly pull the plow through the field. The hot sun just making it harder as sweat quickly beings to pour off me.

Not sure how much time has gone on, but I feel myself slowing down, despite trying to pull as hard as I can. I look up and I notice that I have plowed very little and realize that plowing 4 acres like this is impossible. But I have to show them that I have tried my hardest. Maybe they will then go easier on the punishment.

My eyes burn from my own sweat dripping off me, my hair feeling plastered to my back and my body reeking and drenched in sweat. At this point knowing I'll eventually collapse. But I keep pulling like an abused animal, but now slowing down more as my legs are getting close to giving out. I need a break and some water. I continue pulling but then also yell out, "I need water Sir." Hoping he has some mercy and lets me drink some.

 

[Mkmydaze]

Thirsty work

I watch you pulling the plow as best you can, knowing that you have been set an impossible task. Setting unrealistic targets for inmates is part of the psychological aspects of the punishment. An inmate will suffer more knowing that she cannot do what is being asked and will end up paying for it afterwards. I can see you tiring and signal to the guard to give you a water break.

I walk over to you after one of the inmates has been by to give you some water. You are kneeling, with the yoke resting heavily on your shoulders. “Very hot out today, isn’t it cunt?” I ask, standing above you. “See that redhead in the pillory?” I say, pointing to the woman who was beaten with the strap earlier. Now, 3 guards were lined up behind a fourth who was vigorously fucking the woman from behind. “She didn’t meet her plow quota yesterday,” I say, “so today she is making up for it by providing entertainment for the boys.”

In a few minutes, you are up and plowing again, straining hard against the traces. I whisper to the guard steering the plow, and he hands me the whip. “Come on cunt,” I yell, swinging the whip at your sweaty ass. I hear the satisfying sound of the leather as it slashes across your skin, and see you damn near jump. “You can go faster than that,” I add, watching you speed up. Eventually, you begin to tire again, and I give the backs of your bare thighs a couple of strokes with the whip, causing you to cry out. Once again, you increase your effort, trying to avoid the whip.

I wander around the fields for a while, checking on things. In one of the fields, a woman stands bound between two poles, her arms and legs spread wide, while some of the inmates on a break torment her. One is playing with her cunt, and another two are pinching and sucking her tits. A large woman stands behind her and spanks her with a flat, springy board. The bound woman is gagged, but she can be heard howling with every smack her ass receives.

Not far from there, another woman is tied face-up on a wooden bench, and her whole body has been covered in oil. She is gagged with her own panties, and she shakes her head frantically as several inmates take positions around her, looking to have some fun. One prisoner starts fucking her with her fingers, while one standing at the end of the bench starts tickling her feet. When two other women start tickling the bound prisoner’s armpits and ribs, the woman starts shrieking into her gag and begging them to stop. A group of guards stands nearby, laughing at her.

The morning is almost done, the sun is high, and I am getting thirsty just watching you pull that plow.

 

[debbiev]

The Inhuman Grueling Plowing Continues

My call for water is met by the guard authorizing another inmate to bring over a bottle. Lowering myself to my knees as the inmate holds the bottle to my lips. I guzzle nearly all the water in the bottle as the inmate then pulls the bottle away and leaves. Feeling like that helped prevent me from passing out. Then you walk over and mention how hot it is today. As if I don't know, knowing you are doing this to mock me. You go on to remind me about the severe beating the redhead got for not meeting her plowing quota. You also let me know that she will be gang raped by the guards, or as you put it, be the entertainment.

I look up at you and plead, figuring why not try one more time. I mean what do I have to lose. Hearing my own weak and out of breath voice, "Sir, I am doing the best I can, but plowing 4 acres like this is impossible. If I complete a quarter of an acre it will be a lot. You see me working hard out here, I am pushing and doing the best I can Sir. I haven't given up, I should get some leniency for that. I mean I tried and will continue to push. Look at me, I'm a mess, I'm exhausted and yet I will go on plowing as much as I can. I'm doing my best, please consider some leniency. I doubt that redhead plowed as much as I have. Please Sir, I beg you."

But instead you go behind the plow and take the whip from the guard, I quickly stand up and start to pull the plow, the plow at first moving slowly as I have to gather up momentum. But before I do I feel my ass severely struck by the whip as you call me 'Cunt'. Yelping out as I stumble, but saving myself from falling in the dirt. Then I try to get my momentum going again and do this time, knowing you are now controlling the whip and knowing I have to move fast to prevent being struck again.

After several minutes of me pulling the plow much faster I feel myself getting weaker, my legs aching as are my arms, back and neck. I try to continue but know I have slowed down some. Then the back of my thighs are struck two times as I scream out in pain, "Aghhh ughh..fuck", this as I fall to my knees. But I quickly stand back up and pull again. Grunting as I do, both from the burning pain on my ass and the back of my thighs and the grueling torture of having to continue to pull the plow.

Finally you give the whip back to the other guard and you leave. I suppose I should be grateful that the other guard hasn't whipped me once. I wish he was in charge of me instead of you. I continue pulling, but as I do I speak out, "Thank you for not whipping me Sir. It's good to know some guards here are decent. So just know I appreciate that so much." Hoping I can get him to like me and maybe convince you and the other guards to go easier on me. I need someone to protect me from this madness.

It has to be near noon and as I look over I see you off in the distance watching me and I wonder if you will consider some leniency for me putting such a huge effort out. I bet I have plowed more than most of the other women here. Exhaustion is setting in and sweat pouring from every part of my body. My hair is glued to my neck and back, my legs covered in dirt and still feeling the dried cum in my ass crack from you raping my ass yesterday. Fuck I hate you. Yet I continue on, my body leaning forward as I push, hearing my own heavy breathing as well as the scraping of the plow into the dirt behind me. Not sure how much more I can keep doing this, but I know I can't quit.

 

[Mkmydaze]

A touch of heat stroke

I watch you struggle to pull the plow all afternoon. You stop many times, then are encouraged by the guard who finally lays the whip across your ass. Some of the other inmates know you are being punished (only those being punished pull the plow) and hurl abuse at you. One inmate picking weeds as you pass by yells out, “Look at the dirty cow pulling that plow!” You turn and realize she is talking about you. The inmate laughs, and yells at the guard walking behind the plow. “Hey Ronny, maybe you should use that whip on her stinking cunt instead, maybe then you’d get her moving!” Guards and inmate alike laugh at the joke, and you continue to push on.

I’ve seen women endure this punishment enough times to know that you are in total misery. Deep red marks cover your back and shoulders where the leather traces bite into your skin. Angry welts on your ass and thighs show where the whip has been used on you. The bottoms of your bare feet are bruised and sore, little cuts on them from the small, sharp rocks you trample over amongst the dirt. Sweat pours off you every second under the brutal sun, and you are covered with dust and dirt. Several times you fall to your knees, unable to rise until the girl staggering around with the water cans comes by to let you drink. I am impressed that you are able to keep going; more than one inmate has suffered heat stroke from this treatment in the past and had to be taken to the infirmary unconscious.

After seven hours hooked to the plow under the merciless sun, you are completely spent, overwhelmed by exhaustion. I see you fall and run towards you. Ronny looks down at you and checks your vitals. “Looks ok. Probably some heat stroke,” he says to me, and signals for the water girl to come over again from the other field.

“Fuck, I can’t have her dying on me, she’s got 3 more days to go,” I say, checking your pulse and breathing myself. You are ok, but barely conscious. I give you a couple of sips of water from my own water bottle, and you take them weakly. I instruct Ronny to get a jeep over here to take you to the infirmary. “I want the doc to treat her as soon as she gets there,” I say, making my way towards another group of guards. “Williams will finish supervising things here,” I explain to Ronny who is getting set to do as I asked. “Let the doc know I’ll be by within the hour to check on her.”

 

[debbiev]

Physical and Mental Degradation to Collapse

As I continue to pull the plow, my hopes continues that they see how hard I'm working and they go a bit easier on my punishment this week. I know I had to do better than the redhead who got put in the pillory, beaten and gang raped. So hoping they see that. Despite how grueling this is, I'm trying my best to follow orders. I suppose trying to be a model prisoner for leniency.

The sun is still high in the sky as every second is brutal. My back burning in the sun as sweat continues to stream down my face and body. It burning my eyes as it drips in and I can taste the saltiness as it surrounds my lips. My feet totally cut up and sore, my arms and shoulders aching and my legs are getting wobbly now. Feeling like I'm gonna pass out so I stop but the whip viciously strikes my ass and gets me to move again. Step by step I continue on. The inmate bringing the water helps but if I take too long I'm again struck by the whip. Now knowing Ronnie the guard behind the plow is mercilessly just like the other guards around here.

It's bad enough having to reduce myself to this but it makes it worse when the long term inmates and guards that are close by laugh at me. I suppose the inmates being glad it's not them pulling the plow, but also it probably makes them feel superior to the new inmates. I hate that they call me a 'dirty cow', I suppose because my breasts are hanging down and bouncing as I'm pulling the plow all hunched over. It just makes me feel even lower. I also worry that being totally degraded and punished like this puts me at the bottom of the inmates pecking order. I then hear the inmates telling Ronnie to 'whip my stinking cunt to get me moving faster'. Thankfully he doesn't, instead he just laughs.

I continue on, step by step trying the best I can, but suddenly things around me go darker and I feel dizzy as everything gets fuzzy. I feel myself falling. Hearing voices around me as I feel water on my lips and in my mouth. I also hear your voice.

The next thing I know I'm inside on a bed. It's a well lit room and I'm figuring I collapsed in the field. My body from my feet to my shoulders are aching so badly as I grimace in pain. My head even hurts as does my back, ass and back of my thighs from being whipped. Right now just glad to be inside and resting. But the horror or what happened in the field today cycles over and over in my mind. Hoping the rest of my punishment isn't as bad, but knowing the insanity here, not hopeful.

 

[Mkmydaze]

Room service

I caught up with the doc in the infirmary, where I could see you sleeping in one of the beds, hooked up to an iv. “How is she doc,” I asked, pointing towards your unconscious form.

“Getting some fluids and electrolytes into her,” he said, “and we treated some minor cuts and abrasions. She’ll be fine.”

I learned that they were going to let you sleep a couple of hours, and then they were going to let you go. “Ok doc. Have her brought to my room when she’s done here,” I said, leaving him to his duties. It was not uncommon for inmates to suffer dehydration and heat stroke in this climate, particularly when the punishments involved physical exertion. I guess the surprise was that you lasted as long as you did.

Around 7:30 guards ushered you into my room. You weren’t cuffed this time, and they had let you put on your shorts and top. You walked gingerly into my room; the bottoms of your feet still sore from today’s activities. I gesture for you to sit on the bed as the guards leave us. “Glad to see you are still with us Debbie,” I say, taking a seat at my desk. “Hard first day, but you survived. You’ll need to stay strong to get through the next few days as well.”

While you sit, I bring a tray over to you with food on it. It is the food we get as guards, better quality than the slop fed to prisoners. “There’s some chicken with rice and vegetables, and a small bowl of mango and pineapple for dessert.” I give you a bottle of water with it, knowing you still have to replace fluids. I let you eat in peace, working on a report quietly, stealing glances at you as you devour the best meal you’ve had in several days.

Afterwards, I help you take off your shorts and top. Painfully, you raise your arms so I can take your dirty crop top from you. You seem so tired and sore, you don’t even raise a fuss about undressing in front of me. Your shorts come off next, and I look you over. I can still see some marks, bruises and welts, but mainly I still see a lot of dirt. “Take a shower and clean up,” I say, handing you a towel. I swear you almost smiled when I said that. Sensing that you might think I’m softening towards you, I grab your wrist and tell you that I didn’t bring you here to wine and dine you. “You’re still mine cunt,” I say, “and I want you clean.”

You head off into my bathroom, and I soon hear the sounds of the shower running. While you clean up, I take off my clothes and lay on the bed, naked. My cock starts springing to life thinking about you in that shower, soaping up your tits and cunt, running your hands all over yourself. I stroke my hardening cock and wait for you to finish.

 

[debbiev]

Naked, Clean and in Your Room

Waking up and seeing the IV in my arm as I begin to recall what happened. It all begins to cycle in my head. The aching over my entire body serves as a reminder of each horrible thing that occurred. My shoulders, arms and legs severely aching.
My back, ass and backs of my thighs stinging badly from being whipped when I didn't move the plow fast enough. To my feet cut and swollen from the stones and pebbles in the dirt. My body is covered in dirt, mud and dried sweat and I reek.

I know I did my best of the totally unreasonable assignment and I just hope you, the other guards and the Warden see that and now go easier on me. I know most other inmates that have done that assignment in the past couldn't have lasted as long as me. I have the drive and determination and I'm mentally strong, something most people don't have.

In the evening I'm taken to your room, wondering why I'm not taken back to my cell. Feeling nervous you are going to punish me more. It's odd I'm not cuffed so I suppose that is some consolation. Also they gave me my jean shorts to wear and my cropped top, both now dirty but at least it's clothes and it makes me feel human.

I walk into your room and you are actually polite to me. I'm a bit confused, I mean the things you did to me and the punishment I underwent today is your doing. I know you are a sadist and enjoy my misery. But now you seem different, so strange. I sit on the bed as you instruct. My hopes fade when you mention staying strong as I have to endure more punishment the rest of the week. The only good is I can finally eat real food and not the mush they serve in the prison cafeteria. I'm starving and I quickly eat my dinner. I do notice you glancing over at me, almost like you wanna tell me something.

You walk over and tell me that I can take a shower in your bathroom, which surprises me. Maybe you like me, maybe you will go easier. I doubt you normally let inmates take showers in your bathroom. You help me take my top off, my arms severely aching as I raise them. Then I stand up and undo my jean shorts, lowering them and stepping out of them. I see you look up and down at my filthy and bruised body. I highly doubt you are looking at me sexually, first I'm totally gross now and second you just seem caring towards me now.

You hand me a towel and I look at you and wonder if you've changed, maybe me working so hard plowing the field changed how you look at me. Maybe you will be on my side and protect me. I do see signs of that, but still unsure. When you grab my wrist and call me 'cunt' some hope fades, but still maybe there is that little bit of caring in you. I decide to play into it some, "Yes Sir, I understand. Thank you for dinner and letting me take a shower in your bathroom. I really appreciate that. Just know I'm trying my best for you." I half smile, hoping that helps you like me, or at least see me as a woman who shouldn't be treated like an animal.

Getting the dirt and sweat out of my hair and off my body feels so good. I look down and see dirt streaming off me and circling the drain. After a long shower I step out and dry myself. Then walk out naked as my top and shorts are still on your bed.

I turn into your room and see you lying in bed on your back, naked and your cock hard. I stop in my tracks, my hopes of you being kind now gone. "Oh, um...Sir, umm, I thought I was, well, what do I do now? I mean you know, do I go back to my cell? Or stay here, I do need more rest. But, um, well you tell me what I need to do." Hating that I appear confused and probably coming off like a ditz. But I'm certainly not gonna just get on my knees and suck your cock, well unless I'm ordered to, then I'll have no choice.

 

[Mkmydaze]

Deb's Pain Relief

You seem surprised to see me like this. I smile, and motion for you to come over. “For future reference cunt,” I say, wagging my cock at you, “when you are here and my cock is out, you job is to attend to it.” You seem to deflate, and slowly walk towards me. I spread my legs open, and point to the bed. “On your belly, get up nice and close. Start with your hand,” I command. You comply with my instructions, crawling on the bed until your face is close to my cock. I’ve already lubed it with the oil, so now you take it in your hand, and begin to stroke.

I lay back and enjoy the feel of your hand sliding up and down my cock. Before long, your little tongue darts out and licks the head which now shows some drops of precum. Your tongue licks up my shaft, and I moan, but I warn you to slow down. “I don’t want to cum yet,” I say, as you go back to just stroking slowly. “Make me cum too fast, and I’ll add to the marks you’ve got on your backside.” You swallow nervously, and nod, and your hand moves even slower on my cock.

After several minutes of slow stroking, I have had enough and tell you to stop. I get up and tell you to move further up the bed, staying on your belly. “I have a treat for you,” I announce, removing a small bowl of ice from my refrigerator. “This will make you feel better,” I say, taking a cube from the bowl, and I start using it to trace the cuts and marks on your feet. Slowly I rub the cube across your soles, listening to you react to the cold as it touches your skin. Once the ice has melted a little, I move down and lick the water from your aching soles, your pretty feet squirming underneath my tongue.

The ice travels up your calves, across bruises and scrapes, and traces the lines of the welts that cover the backs of your thighs. I kiss and lick my way up your legs, following where the cube has been. I tell you to spread your legs, and I lick the newly exposed flesh on your thighs, following a welt that curved around your tanned leg. When I get to the spot where your legs and ass meet, I pause, and get a fresh cube. Now the ice travels up your aching ass, finding every welt and bruise there, while I lick the moisture from your hot skin. You tremble every time my tongue traces a welt, the pain still fresh. Looking down, I see you are wet. I tease your cunt with the ice, your heat melting the ice like a blowtorch. Then I use my tongue there.

It’s only a tease, a few licks to get you hot and your hips moving. Then I play with your slick lips, tickling them with my fingers, until I find your clit. I stroke your swelling flesh, making you moan. Meanwhile I have moved on with the ice up your back, and across both shoulders. I cover your cuts and abrasions with more kisses, and lick the raised welts caused by the whip. You are moving too much, so I tell you to remain still, which you struggle to do. I am licking your neck and have a handful of your hair in my hand. I whisper to you that you did good today, you worked until you dropped, and you gained respect from me and others.

I move forward overtop of your prone body, and my cock seeks your hot opening like a missile. In one fluid thrust, I am deep in your cunt, and I rock back and forth, fucking you. The pleasure of my cock inside you mingles with the pain from your ass, as I now grab your cheeks and squeeze, fucking you hard. Teasing your clit had you close to cumming, and now the pounding finishes you off. It does not take long before you begin to shudder and groan, your cunt squeezing my cock like it had a mind of its own and triggering my own explosion. I can feel my cock pumping hot cum into you, while you continue cumming loudly, clawing the sheets with your hands and crying out as your orgasm tears through you and leaves you breathless.

 

[debbiev]

The Mind Blowing Fuck and My Long Shot Offer

I stand there totally disappointed as my hopes of you actually caring about me now gone. When you call me 'cunt' and tell me that my job is to attend to your cock I know nothing has changed. I also know that I need to obey completely as I don't wanna end up like that redhead locked in the pillory in the hot sun and being publicly gang raped all day.

I get on the bed, laying on my belly as ordered and put my hand around your hard cock. You obviously oiled up your cock when I was showering so my hand easily slides up and down it as I stroke it. Then as ordered I lean closer and begin licking your cock. My tongue tracing up and down your rock hard cock as it throbs in mid air. I pull my face back a bit and stroke your slippery cock more and then I wrap my mouth around the tip as I can feel it throb in my mouth. Soon tasting your precum. I try to prolong this for you as much as possible as you warn me that you will add to the welts on my ass if I make you cum too fast.

I slow my pace down, licking, stroking, sucking as I try to keep you near the edge and make you enjoy this. Suddenly you order me to stop and I do as I lift my head to look at you. I watch you stand up as I scoot further up on the bed as ordered. Seeing you come over with cubes of ice in a bowl as you claim it will make me feel better. Knowing what will make me feel better is being in my own cell alone. But also knowing I better not protest.

Still laying on my belly as you trace my cuts on my feet with an ice cube. My body tenses from the cold as you rub all over my feet. It's torture and yet I feel myself getting excited. Fuck what is wrong with me? I'm surprised when you lick the melting water off my soles. I feel like kicking you in the face, but I don't. The consequences of doing that would not be good.

You trace the cube up my legs and to my cut and bruised thighs. I grimace in pain and also from the cold. I spread my legs as you command and then feel you licking a vicious welt on the back of my thigh. It hurts and I can't help but think this is totally weird. I mean it's almost subservient of you to do that, but maybe in your own warped mind you actually adore me. Who the fuck knows. I just know my cunt is moistening despite the pain and the coldness of the ice cube.

With a new ice cube I feel you tracing it up to my upper thighs and to my ass. Feeling your tongue then licking the welts and bruises on my ass cheeks. I moan, both from the pain of my welts and the fact that you are getting me more excited. When the cube touches my cunt it makes me flinch and I rock my head a bit trying to get past the coldness, my cunt feeling like it's being frozen and starting to go numb. I can feel the ice cube melting quickly as you leave it on my cunt. The water seeping down to my clit and my pubes. Feeling the bed below me getting soaked too.

Surprised as I feel your tongue at my cunt and me instantly feeling like I'm getting closer to the edge. When you tongue my cunt and combine that with rapidly stroking my clit I almost go over the edge. I know you can tell I'm totally wet so no reason to hide that now. I moan and squirm but you tell me to keep still. I try but find it difficult to do as you relentlessly tongue my cunt and clit. Knowing I'm seconds away from cumming.

But then you pull up and put an ice cube on the welts across my back. I cringe in pain but remain on the edge of cumming. After tracing the welts on my back you grab my hair and grip it as you gently trace the ice on my sore shoulders, this as you kiss my neck like we are some kind of lovers. It's odd, but at this point I either wanna cum or wanna be released and go back to my cell. I'm confused and my emotions are all over the place. You confuse me more when you praise me on how hard I worked today and how I gained respect from you and others. How can you say that when you were the cause of me being tortured out in the field. I hate your fucking mind games but as much as I hate it, my cunt seems to be controlling me and god I'm so fucking close to cumming. God I need to cum now.

I watch you as you move over me and then quickly push your cock into my cunt. My cunt is seriously wet so it doesn't hurt, but I grunt from the speed and shock of how roughly you entered me. Feeling you thrust hard inside me, your cock pounding my cunt but it feels so fucking good. The welts on my ass cheeks hurting as you thrust into them but I don't care, I just need to cum.

A couple more hard thrusts and I feel myself gushing cum all over your cock. This as I hear you moan out in my ear as you release your cum deep inside my cunt. My own moans combine with yours as I feel my orgasm continue on, totally intense. Not sure if it's because this is all so fucked up or you are just that good. I just know it's mind blowing.

Finally my orgasm subsides as you remain on top of me. After a couple of minutes I feel your cock leave my cunt and I know there is a mess of our cum below me. I also know that you know I possibly just had the best orgasm of my life. Figuring I could maybe use this to change things between us.

As you roll over, I look at you and smile, figuring now is the perfect time to get you to look at me differently. "Sir, not to be crude, but that was the best fuck I've ever had. You are totally amazing. If you don't mind I would love to make this a habit between you and me, like me kinda being yours and only yours. I know I'm a lowly inmate but in the outside world I'm not. I really think we have something here. Like I wanna be with you and I don't mean just in prison. Like maybe after I get out too. If I'm beaten and raped by others then I won't be able to give you everything I have to make you happy. Please just consider what I say and I think I can make a different in your life. I swear to god I will try my best Sir. I mean you have seen my determination already, so you know I will do everything I possible can to make you a happy man, both sexually and otherwise. Please Sir give me that chance."

Hoping you buy this as being your mistress or whatever could save me from the punishment from the rest of the week and from being gang raped. If you truly like me and want me in one piece you will consider it. But if you still don't give a shit about me then what I said will just be a total waste of breath. It's my last try at getting you to like me and go easier on me.

 

[Mkmydaze]

Change of plans

After I finish cumming, I roll over and relax. Then I hear you saying some shit about wanting to be with me after you get out and making me happy. I chuckle, wondering what the hell you are thinking. “Listen cunt,” I say, grabbing your hair and bringing my face down close to yours. “You are mine in here, for as long as we are both here,” I explain. “But do not think that I can control whatever happens to you here on Snake Island.” I grab your cunt and squeeze until you gasp. “This does not belong to you anymore, but it doesn’t belong to me either. We just get the use of it sometimes,” I say, giving your cunt a slap. “So get used to the idea that whatever is going to happen to you from now on is beyond your control,” I say, getting up and grabbing my radio. While you ponder what I’ve said, the guard who brought you returns to take you back to your cell. “Tomorrow is Day 2,” I say on your way out, “so get some rest. You’ll need it.”

The next day it is raining. Much of the work outside cannot be done. The Warden calls me to his office first thing in the morning to tell me that the Superintendent is arriving sometime this morning. He was hoping to show him some discipline, but I explain what was planned for you has to be delayed because of rain. The Warden isn’t having it.

“Look, this fucker can seriously mess with how this place runs, not to mention our careers,” he said. “He gets off on seeing the inmates humiliated and punished, so let’s not disappoint him, okay?”

“Of course Sir, I’ll come up with something,” I say, walking away and trying to think furiously. You were supposed to be carrying the water cans today, but that isn’t happening. I find some guards who were supposed to be detailed to the fields today and tell them to come with me as I try to figure this out. I send two men to pick you up following breakfast, and the rest jump in my jeep as we head out in the rain to one of the farther fields. When we get there, I can see it is pretty wet. Inmates had been picking stones out of it a few days ago, and there was still a pile of them sitting at one end. Suddenly, an idea comes to me, and I smile.

I get on the radio and explain my plan to the Warden, who agrees with it. He will contact me when the Super arrives, and then he will drive him out to the field so he can observe what is going on. I walk out into the field a little way and see how my boots sink down into the muddy soil. The rain isn’t that hard, but it is continuous. A jeep arrives and parks beside mine, and two guards get out with you. They bring you over and I see you wearing your top and shorts, your bare feet squelching in the mud.

“Welcome to Day 2 of your punishment, cunt,” I say, standing in the rain with my hands on my hips. “Off with the clothes, and come here and kneel,” I say, pointing to a deep puddle in front of me.

 

[debbiev]

Naked, Wet and Kneeling in a Muddy Puddle

You squash my offer of friendship and plenty of sex even after I'm out of prison. Okay it was bullshit anyway, no way would I ever wanna know you outside of prison. But I figured it was worth a shot offering it. You make it really clear that my idea is totally rejected when you grab my hair and call me Cunt as you explain how you control me here and how day 2 of punishment is tomorrow.

Another guard shows up and takes me to my cell. When I get there I'm totally exhausted and just collapse on my lumpy bed. At first the day cycles in my head, how I had to pull the plow, naked, sweating and at times being whipped like an animal. The guards and inmates laughing at me and calling me nasty names as I pulled. Then collapsing and ending up in the infirmary. Then in your room only to be raped by you again. But it's over and I just have to hope tomorrow's punishment isn't as bad as today's.

Next Morning...
I wake up and go to the bathroom and then they call me for breakfast. Glad to be wearing my yellow crop top and jean shorts again, although they are pretty nasty as besides the times I've been naked, they are the only clothes I have worn for 3 days here. My bra and panties as well as my shoes have been taken from me, along with everything else. As soon as breakfast is over two guards guide me to a jeep and take me out to the fields. It's raining out and few inmates are out tending the crops today. I'm driven further out this time, like to the far end of the fields.

Then the jeep stops and I get out and see you. My bare feet sink into the mud as I walk over to you as told. You order me to remove my clothes and I do, pulling off my crop top and then unbuttoning my shorts and lowering them as I step out of them. Placing both on the least muddiest place I could find. Knowing you having me out here naked only serves to demean me more, kind of a way to make me feel lower than everyone else. Like I don't deserve to wear clothes. God I hate you so much.

As per your order, I take a few steps towards you and kneel in a puddle. Then I look up at you, trying to show you strength, but difficult to do being naked and kneeling in a puddle, my hair plastered to my face and neck as the rain pours onto me. But I'm not about to cry and scream like that redhead in the pillory. For my own sake I need to stay strong. I refuse to show that you are breaking me. But I also refuse to disobey, at least for now as I don't wanna end up like the redhead when she was gang raped for hours. That is the thing I have to avoid and the reason I will continue to do as they say what you want me to. Even if it's stripping me of my dignity. I just know I have to get through this.

 

[Mkmydaze]

Hauling rocks ...

After you kneel in in the puddle looking up at me with barely disguised hate, I explain what you need to do in this field that is quickly becoming more like a big mud pit. I start by pointing down to the end of the field where you see a big pile of rocks.

“That pile of rocks needs to be moved from there, to this end of the field,” I say, motioning to where a guard stands about 20 yards behind me. The field must be 250 to 300 yards long; a very long distance to carry rocks that range in size from a couple of pounds, to probably 10 or 12 pounds each. “You can carry the rocks to this end however you like,” I explain, “but when you return empty-handed, you have to crawl.”

I let this sink in for a few seconds, watching the expressions change on your face. “Not only must you crawl,” I go on, “but if any of the guards, including me step onto the field while you are crawling back, you must go up to him and beg to suck his cock. Failure to do so, will be punished.”

With a look I’d call pretty close to a glare, you get down on your hands and knees in the mud and begin crawling towards the end where the stones are. It is slow going, and the mud is deep in places, up past your wrists and getting all over your legs. Seeing you crawl in the mud like this amuses the guards watching on the side and at the rock pile, who laugh at your predicament. Some of them start making pig sounds, and call you a dirty sow, crawling in the mud.

Finally you reach the pile, and take a rock in each hand, and begin the long walk back to the other side. You seem to be in no hurry, walking slowly with the weight of the rocks pulling on your arms. When you reach the other end where I am standing with a guard I posted there, I tell you to pick up the pace. “You have an hour to move that pile over here,” I say, “and if all those rocks aren’t here when that hour is up, you’ll be very sorry.” I hold the strap I’ve used on you before in my hands, certain that you understand what that means.

Your return trip crawling back takes less time than before, and soon you are bringing more rocks back to start a new pile at the other end. I go off to speak to some of the guards watching and taunting you from the side, grabbing one and telling him that once you are crawling on the way back, he is to walk out into the middle of the mud field and wait for you to reach him.

“Sure Captain, but what do you want me to do out there?” he asks, confused.
I watch you struggling in the mud, slipping, and dropping your rocks. The mud is getting slicker and deeper as the rain continues. “You do what she asks,” I say, and wait for you to arrive at your cocksucking rendezvous.

 

[debbiev]

The Humiliatingly Cruel Muddy Task

Naked and kneeling in a mud puddle in front of you. I look up as the rain hits my face and you instruct me on my next insane punishment. As the words pour from your mouth my hatred of you just continues to increase. I'm not even sure these punishments are the Warden's ideas, maybe they are your ideas. But doesn't matter, either I do the best I can or I end up gang raped in the pillory like that Redhead was. Fuck I have to avoid that at all costs.

The punishment gets worse when you add that I have to suck any guards cock that stands in front of me when I crawl back to the rocks. You are totally sick, I have to figure out a way to escape before you end up killing me. But right now I have to obey since the penalty for not obeying is something I could never recover from.

I begin crawling in the mud towards the rocks, some areas deep in mud making it difficult to pull my hands and knees out for move forward. The rain pours down on my back and as my drenched and now stringy hair falls around my face and also sticks to my upper back. As I'm crawling closer to the rocks my right hand slips and I do a face plant in the mud. Mud now caked on my nose, cheek, chin and is caked in my hair. My right breast is also caked in mud. I quickly pull my face out and continue crawling. All to the heckles of the guards at the rock pile. Hating them calling me a dirty cow and oinking at me too. Them laughing and commenting as my breasts sway every time I move.

I reach the pile of rocks and take several. They are seriously heavy as I cup them in my arms and against my belly and breasts. I walk back, trying to avoid falling in the mud and trying not the drop any rocks. I put the rocks down as you yell at me to hurry and let me know how sorry I'll be if I don't complete this. I see the strap and quickly get on my knees and crawl the second time through the mud, this time trying to crawl faster, but it's being really difficult as I sometimes get stuck in the mud for a few seconds.

Taking another pile of rocks back and then crawling back again. But this time a guard is standing in my path. I hear the other guards taunting me, yelling out it's snack time for the filthy whore. Approaching the guard who actually looks like he doesn't want to be doing this. I kneel and look up at him, knowing I better follow your instructions, "Sir, may I suck your cock?" I hang my head down, hating hearing those words coming from my mouth, but knowing I have no choice.

 

[Mkmydaze]

... and sucking cocks

Rain continues to fall, making the field a miserable mud pit. On your knees in front of the young guard I sent out, I see him slowly take out his cock, which you hold in your hand and begin to suck. Given the time constraints I have placed on you, it seems you are wasting no time getting the kid to blow his load. Your head is bobbing up and down as you go to work on his cock, and very soon he is tensing up and shooting his cum into your mouth.

Moments later you resume your crawl back to the pile, which still has many rocks left to move. My radio squawks, and I hear the Warden’s voice looking for me.

“Gibson here Warden, go ahead,” I respond.

“Gibson, the Super has arrived. I’ll be driving him out for some observation in 30 minutes. Out.”

“Copy that. Gibson out.”

I go back to watching you from the sidelines. You slip and slide in the mud, carrying as many rocks back as you can. I see you crawl as fast as you can, but you are obviously tiring. At one point you slip face first into the deep mud, coming back out with the stuff all over the front of you, and your hair and face. Fortunately, the rain is falling hard enough that it helps wash it off.

The Warden and his guest arrive out at the field just as the hour I’ve given you is about to expire. Despite your best efforts, a good portion of the rock pile has yet to be moved, and its obvious to all of us that you will have to be punished for that. The Warden has told me the sort of thing the Super wants to witness, so I call a bunch of the guards together and explain what we’re going to do. Before you can crawl back to the rock pile a couple of the guards go out to get you and bring you back over to me.

I look over my shoulder and see the Superintendent in the Warden’s Hummer, looking out at us. He wants a show, so we’ll give him a show. “Inmate,” I say to you, standing there shivering in the cool rain, “you have failed to complete your task in the time allotted. You have earned punishment for this,” I explain, as guards begin tying short lengths of rope to your wrists and ankles. Once that is done, you are forced onto your belly in the mud, and then four guards holding the ropes move away from you, pulling the ropes tight, and lifting you off of the ground, with your arms and legs spread widely. I stand in front of you and pull out my stiffening cock. I don’t even have to say anything, you know what is expected. As I guide my cock into your mouth, I tell you to just keep your mouth open and let me do the work.

While I hold your head and fuck your mouth, another guard has come along beside you, and has begun to whip your ass with his slim, leather strap. With each stroke I feel you jerk and when you scream, I feel the vibrations all along my cock, yet barely as sound escapes your engaged lips. The guard uses the strap on you, whipping your ass and thighs with relish, while the rain washes your tears away and your screams are choked off by my cock.