Purty Prison Guard

WARNINGS: Contains transgender themes, Sci-Fi, explicit sex, mild violence, bad words, and strange ideas. It has only the strange things that dribble from my head. If you are not old enough, mature enough, open minded enough, and especially not smart enough to stop reading should you find yourself becoming offended viewing such a story, don't!

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-SECRET-

Personnel Record

********************

Job Title:Security Guard

Name:Buttman, Harold A.

Age:22

Disciplinary Action Record

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Employee's conduct is deserving of the most extreme punishment, within this institutions capabilities.

Description of Disciplinary action and reason for said action is as follows in the employee's own account:

-SECRET-

My name is Harold Buttman, sure go ahead and snicker, everybody does. Yes, I do go by the nickname, Harry. I've been teased about it my whole life so I'm used to it. It doesn't help that I'm only 5' 4" tall. I make up for it by being heavily muscled and meaner than a rattlesnake.

I'm a prison guard at the Purty Women's Correctional Center, and I love my job. Women all over the place, big ones, small ones, fat ones, and pretty ones, I love the women, and can't get enough sex, so in my position as a guard, and with all of these love starved babes around, I've been able to get enough sex to almost satisfy even me.

I trade cigarettes, drugs, and favors for sex, with the occasional blackmail for the unwilling ones for whom I set my cap.

I've got my little love nest set up in one of the locked electrical maintenance rooms. No one ever goes in there and I have the only key. My little operation is perfect. To top it off I they pay me to do it. That with the money I'm making selling merchandise to the prisoners outside of the parameters of my discerning tastes, I figure I'm making $100,000 a year. Life is good when you know how to work the angles.

Today I have a meet set up with this hot little blonde from C Block that I blackmailed into being my first of today's parade of sexual conquests. I caught her lezing her cellmate, which goes without saying, is strictly forbidden by the prison rules. So now, that bitch is all mine and I'm going to do my best to turn her into a heterosexual, or at least a bisexual.

********************

I met up with Callie outside her cell and had her follow me to my little love nest.

"You are looking lovely today Callie," I started, "I have been anxiously looking forward to this since yesterday." I told her as I opened the room with my key, and ushered her inside.

She was grinning ear to ear, acting as if she wanted me bad, "You look pleased Callie, as if you are hankering for a bit of man meat for yourself."

She quickly entered the room and started stripping.

Seeing this, I followed suit assuming that she was as enthusiastic as was I. My cock was rock hard and wanting this woman badly.

She smiled seductively and pushed me down on the airbed set up there, "Eager little thing aren't you honey?"

She made no effort to answer. She just took my hands and placed them on her lovely DD cup breasts that I had been drooling, over.

"Oh God, these feel... incredible!" I enthused.

She was sitting on my pelvis in just her panties and my cock was at attention between the cleft of her heart shaped butt cheeks, straining at the silky material of the pink panties, she wore.

"Mmmm," she moaned as I manipulated those intoxicating mammaries.

I closed my eyes concentrating on her wonderful breasts, and the next thing I knew there was a, "Click, click," sound as a pair of handcuffs were, clipped around my wrists.

'Wait a minute, she's an inmate, where did she get handcuff?' I thought as my eyes flew open and I felt a pair of manacles being, affixed to my ankles.

"What the Fuck...!" I exclaimed trying to dislodge Callie and force her to unlock my bindings, but the dozen women that surrounded me held me down to the mattress.

Then I saw the face of the Warden, Ms. Sterndackle, "You have been a very bad boy, Harry!"

She turned and addressed the women, "Do it, and then take him to his cell," she exclaimed with vehemence and disgust.

I felt the sharp poke of a syringe in my butt cheek and everything went black...

********************

I awoke in the warden's office in chains and shackles, forced into a kneeling position, with the Warden behind a big desk, wearing a black robe, in front of me.

"I see the accused is conscious again," Ms. Sterndackle announced, "The witnesses may come forward."

Prisoner after prisoner came to the desk in front of me and told the Warden about every incidence, every dalliance, and every indiscretion I perpetrated since coming to work at that Prison, and every time I opened my mouth to protest, I was, zapped with a stun gun.

After my third time though, the warden grew tired of it and had one of the female prison guards shove a cock gag down my throat and strap it in place.

"I trust there will be no further outburst now, Mr. Buttman," she admonished, though she looked amused at my predicament.

I had to struggle just to breathe and suppress my gag reflex so as not to vomit while my face was impaled on that disgustingly, realistic looking thing.

"Please proceed with your story, Helga," the warden continued.

Proceed they did, until every sexy babe in the prison and even one of the guards had testified against me.

Ms. Sterndackle called to the bailiff, "Bailiff, please run the video."

The monitor behind her showed my 'love nest' and a few of the dalliances I'd had in there over the last few days.

When it was over Ms. Sterndackle picked up a ledger and said, "I have here your business ledger, detailing your illegal activities in my prison and here," she picked up a passbook, "is the evidence of all the profit you have made off of the suffering you have caused, some three hundred, fifty four thousand dollars."

"Bailiff, un-cuff his right arm please," Ms. Sterndackle, ordered, which they promptly carried out.

She handed the passbook and a pen to the bailiff, "Now Mr. Buttman, if you know what's good for you, you will sign that withdrawal slip."

I hesitated. After all, it was $350,000 bucks.

The bailiff took her stun gun and fired it off into my balls, "Yaaaaaaaahhhhhhh!" I screamed

After twenty minutes of intense testicular agony, Ms. Sterndackle again stated, "Sign the slip, Mr. Buttman!"

This time I grabbed the pen and signed quickly, I didn't know if my testes could take another hit and still produce sperm.

"What you have done here Mr. Buttman is beyond reprehensible. You have frustrated the rehabilitation of my inmates. You have raped, stolen, and preyed upon the weaknesses of these women. God help me, I'm partly blame myself. I have failed in my duties and failed to protect my employees and prisoners. I failed in that I did not catch you until now."

"A diseased creature such as you must be made to pay, and I will not leave it up to the legal system outside of these walls to punish you. You will be punished here and in a way I deem appropriate compensation, that will rehabilitate you before you leave these walls," she struck her desk with a gavel.

"Bailiff, sedate the prisoner," Ms. Sterndackle ordered and I again felt my ass jabbed with a syringe.

********************

'What a fucking weird dream that was,' I thought as I swam my way back to consciousness. I opened my eyes and saw that I was in a Pink Cell.

I sat up quickly and felt a wispy feeling garment, shift around on my body. I looked down to see that I was wearing a pink baby doll nightie.

'Cute, real cute, wait till my lawyer gets hold of that warden,' I thought nastily, 'She'll rue the day she humiliated me like this!'

I peered around my environment, seeing a typical solitary confinement cell with a full bath. Except that this one was pink, I mean everything was pink, the sheets, blankets, false curtains, commode, shower, sink, floor, ceiling, everything.

There was a small dresser in this cell and a television. "Well at least I can watch some tube until Ms. Sterndackle comes to her senses," I said to myself.

I turned it on and the screen warmed up to Ms. Sterndackle's smiling face, "I see you are once again conscious and obviously bored. Welcome to Ms. Sterndackle's, Buttman channel, the only channel you have. This television is programmed with training videos," I tried to change the channel, but whatever channel I turned to there was the warden, saying the same thing, "you will be rewarded with a movie after watching three videos, but only after demonstrating that you learned what was taught in the videos. Yes, you are under video surveillance at all times. You might as well get comfy because you are not getting out of there for quite a while and not until you have been rehabilitated, which means you will have seen all the videos and learned what we want you too learn."

'Well let's see what educational video she wants me to learn. Anger management, or some lame sexual harassment awareness video...' I thought as the leader on the tape wound through the system.

______________________

"Hello," said a pretty woman standing in front of a nondescript background, "and welcome to Personal Hygiene for Girls. Before your teacher has to tell you, I will... Let's keep the giggling to a minimum, ladies."

The instructor walked to her left and stood in front of a drawing of a naked female, "This anatomically correct drawing, will be used to show the areas of your body and we will run films segments to better illustrate the techniques we will be instructing you in today."

"This series of 5 films will be presented one per day for the whole week."

"Your bodies are changing, starting to blossom into full womanhood, and you will need to know how to keep yourself healthy and beautiful."

"Today's lesson is washing your body. I know that most of you, have been taught by your mothers but we may have some girls in this class who do not have mothers in their lives. There is also the possibility that we might know something your mother doesn't or has neglected to teach you, so pay attention."

"Now I know that many of you may use antibacterial soap, we are not recommending the use of this since studies are showing that using this type of soap all of the time tends to breed antiseptic resistant bacteria."

"This is a washcloth, and though many of you have been taught to use them, some have not. The cloth holds the soap and provides a soft yet increased ability to remove the dead skin cells that your bodies are constantly shedding..."

I turned it off

**********

'Great I'm being, shown hygiene for little girls. I guess since this is a women's prison that's all they have on hand. Well at least they show half naked little girls and have a drawing of a naked girl on it,' I reasoned

"I better have a look around my cell before I zone out on the tube for too long," I muttered to myself, "and see if there is something else to wear in that dresser."

I made my way over to it and opened the drawers. They were all empty except for the bottom one, which had a half dozen baby dolls, which were also all pink. There were subtle differences in the lace and shapes of them but to me the all looked the same.

"You could at least give me something decent to wear," I yelled at the walls not expecting to get an answer.

You can imagine, my surprise when I heard, "You will be provided clothing when you earn it Mr. Buttman, not before." The warden's voice came seemingly from all around me.

Now that I knew she was listening, I was going to give her a piece of my mind, "You fucking bitch! You can't do this to me! This is illegal and you know it! You wait till my lawyers get done with you!" and then I got foul mouthed and nasty.

As I continued my tirade, I failed to notice a hissing noise emanating from the wall, as I lost consciousness and fell flat on my face.

********************

I could feel myself strapped down in bed as I awoke, but could see nothing, nor could I open my eyes. The only thing I knew is that I was, drugged and my face hurt terribly.

"Hello, is some one here?" I asked.

"You were very bad Harry and the warden had to gas you. The only trouble is when you fainted and hit your face on the floor. You broke your nose and shattered your brow but don't let it worry you, I'm a rather good plastic surgeon and I have repaired the damage beautifully. You will look a little different but that couldn't be helped," the lady doctors voice came to me sounding strangely familiar.

I felt a needle stick on the side of my butt.

"I'm going to have to do some more work on your jaw, so when you wake again, don't try to talk," she said, I felt her grab my wrist and check my pulse as blackness swept over me.

********************

I slipped in and out of consciousness a few times again but not for long enough to really remember anything until I came around to a brightness that caught my attention and the sound of someone calling my name...

"Harry... we need you to wake up now..." the female voice called.

"Mmmmf?" I answered.

"Good you're awake. Now don't try to talk. Doctor, the patient is conscious again," she called.

"Thank you nurse. Well Harry, it's time to take the last bandage off your eyes. Now things are going to be blurry at first, so if you are ready wiggle your right fingers," the doctor asked me, again with her familiar sounding voice.

I wiggled as asked, then felt gauze being unwrapped from my head and cotton balls removed from my eyelids.

"All right, you may open your eyes now Harry," the Doctor said.

I opened them and saw the rather lovely face of the Doctor, who was also my last intended victim, Callie.

"That is wonderful work doctor. Harry should be grateful we have such a talented plastic surgeon in our midst," the warden's voice praised Dr. Callie.

I could not see the warden but I saw the doctor move out of my limited view and listened intently. The only words I could hear was, "eye shadow," so I figured that it was just girl talk and allowed myself to fade into the drowsy state that the drugs kept me in.

Later the nurse came in and I discovered my wired shut jaw, when she fed me a milkshake through a straw. When I was finished, she took out some kind of cream and rubbed it into my face, wherever the skin was exposed.

"This will prevent scarring and help you heal quicker," the nurse said, then she jabbed me with another syringe, "That's just vitamins and stuff to keep you healthy since your jaw is wired and you cannot properly chew solid foods. I'm going to turn up your dosage on the morphine pump now so, nightie night."

********************

It was like that for, I don't know how long, then finally one day they wakened me, and the nurse removed the last of my bandages. I was, escorted to my cell and left there, my food, which I ate through a straw with liquid pain medicine and 'vitamins', brought to me at regular intervals and pushed through the slot in my door.

I became bored enough to watch the stupid hygiene tapes and finally was able to watch a movie ...'Miss Congeniality,' whoopee. I wasn't too bad though, better than learning how to shave my legs. That damned warden made me shave my legs and underarms, moisturize, and exfoliate before I could watch the movie.

I was so weak from the stay in the hospital I could hardly believe it. To top it off my appetite was gone. I was eating barely enough to keep a bird alive. I must have lost fifty pounds over... well to tell the truth, I have no idea how long. I have no clock, no window, and no idea how much time has past.

They finally unwired my jaw, and it feels so weird, like my jawbone is smaller and I can open my mouth farther. I suppose it is going to feel weird, until it is totally, healed. I wish they had put a mirror in here. I can't even see if Callie did a good job on my face, or if I look like Frankenstein's monster. At least she must have given me something to temporarily stop my beard from growing, I can't even feel the stubble.

Every so often, I have to back up to the door slot so that they can give me a shot of antibiotics to keep me from getting an infection. How long do you have to take these though? I'm sure I've had forty or more of them so far.

I keep yelling to have them let me out long enough so I can get some exorcise but there is no answer, the walls just stare back at me. I can't wait until that bitch of a warden has something to say to me. I'm going to give her a piece of my mind. This is just illegal and she is going to be in here, instead of me, as soon as I can manage an escape. My friends must be hunting for me by now, my sister at least. She calls me every weekend to 'check in' she should be looking for me and filing a missing persons report at least.

Well enough staring at my toes, I might as well watch the next installment of the young and hygienic, let's see what the next installment is today...

**********

"Hello," said the woman again, "and welcome back to Personal Hygiene for Girls. Today we start a more advanced topic, 'Hair Styling'. We will show you how to do some basic hairstyles and how to use the tools of hair care that the beauty salons do."

'I suppose that whacked out warden is expecting me to put my hair up in a ponytail,' I thought and quietly snickered to myself. 'Ouch, what in the hell is that prison laundry doing? The baby doll I was wearing was irritating my nipples. They are all swollen and puffy looking.'

**********

A few minutes after the video ended I heard the warden come over the intercom, "Harry, we are going to need a blood sample from you."

"Fuck you, bitch. You send someone in here to get it and I'll fight tooth and nail. This is illegal imprisonment. Pretty soon my sister and my friends will put enough heat on, that the cops are going to search this prison, find me, and that will be the end of you!" I screamed at the ceiling.

"First of all Harry, no one is looking for you. Listen to this recording your sister Simelda, made for you," she told me sounding smug.

"Harry, you pig... You low life scum bucket! You total waste of skin! I... I can't even think of you as... as my brother anymore! Don't ever call me! Don't talk to me! As far as I am concerned, I have no brother! I saw all of those women tell what you did to them. I saw how you sold drugs in the prison, and anything you could to make a buck off or... or...(sobbing wail) trade for sex! I hope you die!" then the tape, with my sister's voice on it, went silent.

"I don't think she is looking for you Harry. If she is, she probably has something sharp with her," Ms. Sterndackle said.

"You Cunt! You fucking..." I screamed at her, as the gas took me again.

********************

"Well Harry, you did it again," the nurse said, "You weren't even healed up from the last time so the doctor had to do more extensive surgery on your face, which is why you cannot see. You also managed to break your foot when you passed out, then unconsciously you tried to break your fall with your hand and broke that as well." She sounded as if she really cared about me so I held my tongue and was a good patient for her especially since they wired my jaw shut again.

"The doctor has you on a morphine pump, so if the pain starts to creep up on you, press the button that I am placing in your right hand, feel it? Now I am pinning it to the sheets right next to your hand, so it will always be there when you reach for it. Now I am taking your hand to the call button on the side railing of your bed. If the morphine pump isn't keeping up with the pain, press this button. I am sliding your hand down the railing to the bed controls. Feel them there under your hand. This button raises the head of the bed. This is for moving the foot, up and down. There you go. That should make you more comfortable."