All My Prison Pussy: A C.O.'s Tale

Chapter 1: Michelle

I worked as a prison guard, or a Corrections Officer, or a C.O., or a hack, in a women's prison for two years, but before that I worked in a men's Maximum Security prison.

In the men's facility I performed like a true professional. Having grown up in all the bad neighborhoods, all the worst inmate knew me or one of my brothers. Hell, two of my cousins resided in Maximum when I was hired, and a handful of inmates had been schoolmates, personal friends of mine or had dated one of my sisters. Even so, I remained professional and conducted myself accordingly, the perfect guard.

Sure, I spoke their language and could relate to the worst of the worst, but I never sunk to their level. I didn't abuse inmates like some of the cop wannabes and I didn't carry in drugs or contraband like some of the dirty maggots who were either intimidated or bribed into doing those things.

Then, when a post opened up in the women's division, I applied and was awarded that post on third shift.

Drugs, intimidation or bribery had never worked on me, but I had no idea that pussy would turn me into a dirty cop. Actually, it turned me into a filthy cop, and I fucking enjoyed every second of it.

I ended up with a harem of four sex slaves in that prison, and this is our story. 

There were over eight hundred women in that prison. Most of them so disgusting that you would sooner have sex with a goat than choose one of them to have sex with, but there were a few exceptions.

Don't get me wrong, very few of those women were attractive when they first arrived. Most were heroin junkies and prostitutes with missing teeth, bruises all over and their hair matted together with blood and dried sperm. These women stunk like cattle and crack dens.

Their mug shots looked like crime scene photos of corpses, and it always made me chuckle when I saw how half the women would smile for that photo simply due to being conditioned to smile for a picture.

They looked hideous, missing teeth, split and chapped lips, maybe a black eye, but smiling for the camera like it was a god-damned highschool year book photo.

Most of those ugly mugs remained ugly throughout their incarceration, but a tiny percentage of those girls made miraculous transformations. These few worn, battered and drug addicted street walkers, after being forced straight in prison, taking daily showers, healing up and eating regular meals, transformed into normal, healthy looking young women.

A few of them actually became living dolls, sexy, attractive and what most men would quickly categorize as a dish.

Sure, there were those women who came into prison looking great, but those were usually in the Intake wing and not general population long termers.

Housewives, business execs, teachers, students and all kinds of regular ladies spent a single weekend in prison, so the Intake wing had a constant influx of halfway decent females incarcerated in the short term, but the women who were convicts and were sentenced for a longer stay were usually disgusting, drug addicts, prostitutes, bag ladies and hosebags.

The women incarcerated for murder, a tiny percentage of the population, were the exceptions to that rule.

I am about to break a rule of writing. I am going to list the biographies of my four harem girls before I get into the stories of how we met, what we said to each other and how we ended up having sex together while they were in prison.

This list is not in any particular order. I guess I'll start with the two brunettes first.

Harem Girl #1 - Michelle Benton.

Michelle was a short (maybe five foot two inches), sassy, biker chic with long black hair, and a tattoo of a giant python that wrapped all around her body twice, from her lovely left ass cheek, over her shapely hip, across her slim waist, behind her supple back, under her toned arm and poised with an open mouth over her large right tit and as if it were about to bite off her large left one. She had big intelligent eyes and a sharp tongue. Michelle was in for murder. She had covered for her biker boyfriend and taken the wrap, not out of love or loyalty, but because she was scared shitless of the guy. Her biker boyfriend had strangled the victim to death right in front of her, and Michelle didn't want to be next. She was two years into a thirty year sentence, and she was only twenty- three years old.

Harem Girl #2 - Julie Ferreira

Julie was a slim, tall and sexy doll, with a movie starlet's face, long straight dark brown hair, and a killer smile. She had full lips and dimples. Her athletic, small breasted body had been toned from years of dance classes was exquisitely muscled with a tiny waist and long legs. She may not have had much up top, but her ass was to die for. Julie had been incarcerated for smuggling a hundred and fifty kilos of cocaine. She claimed she was forced to drive the shipment from Mexico to Boston by the Cartel under threat of rape and sexual slavery, but the Rhode Island Prosecutor hadn't believed her story. I didn't either, but it could have been true. Julie also claimed she had never done a drug in her life. That, from the looks of her well-toned body, appeared to be true. She was a year into a twenty year sentence and was only twenty-five years old.

Harem Girl # 3 - Diana Nichols

Diana, or Nicki, which she preferred to be called, was a small time thief who had gotten incarcerated for twelve years after being caught with over a hundred grand in stolen goods. Apparently, someone had invaded a woman's house and mutilated her with a knife to steal those goods. Nicki was busted trying to pawn a diamond necklace from that home invasion for fifty bucks. It was worth a small fortune, and she claimed she stole that necklace from a different house, which was probably true, but because of the severity of the crime and the value of the stolen item they threw the book at her.

Nicki was cute as a button, blonde, blue-eyed with a voluptuous body for only being five foot tall, but she wasn't very smart. Her hot little body made up for it. Out of my four girls, Nicki turned me on the most. She wasn't the prettiest, but there was something so sexy about her that it took my breath away just looking at her. She was only a year into her twelve year sentence and was only twenty years old, the youngest of the bunch.

Harem Girl # 4 - Tammy Stone

Tammy was the only girl in my harem who had been a prostitute and a junkie. If you looked at her mug shot when she arrived you would wonder how the hell anyone could ever be turned on by such a hag.

She was only twenty-two, but she looked as if she were in her late forties or early fifties in that photo. At least she wasn't smiling, but her sunken, hollow cheeks and compressed lips showed an obvious lack of teeth in her mouth.

That's right. Tammy came into prison without a single tooth in her head. She had also been emaciated, beaten, bruised, drug sick due to being addicted to heroin and an overall hot mess. I shit you not when I tell you that her transformation in prison from a used up old looking hag of a prostitute to a stunning, fresh faced beauty was miraculous to see.

Tammy Stone was one of the most beautiful girls in my harem. Her new dentures filled out her face. Her blonde curly locks grew full and long down her back. Her body filled out, giving her huge perky tits, a slim waist and a gorgeous, sexy and inviting ass. Tammy's STD tests all came back negative, and she thanked God every day that the police had gotten her off the streets before she had killed herself. She had been sentenced to sixteen years for murder, but swore it was in self defense. She said she had stabbed her pimp for trying to have sex with her and claimed she was still a virgin, which I, and everyone else, thought was laughable.

Tammy admitted she had been addicted to drugs and a prostitute since she was fifteen, but swore to God she had only ever used her mouth for sex, both professionally and personally. I came to believe Tammy's wild claim she had been a virgin, or at least that she thought she was still a virgin. That vagina of hers seemed way too fresh and tight for a sex worker, although I know a penis had been in there before due to her missing hymen.

My guess is that at some point, Tammy must have been raped when she was passed out on heroin and never even knew it. She was two years into her sixteen year sentence.

These four girls all lived in C wing, a dormitory that housed sixty inmates in 15 rooms with four beds to a room.

When I got assigned to C wing on third shift none of those four girls were in the same room. Eventually, I would start fucking all four girls, and then I would put them all in the same room.

What happened after that was the greatest sexual experience of my entire life. All four of these beautiful women began openly competing for the privilege of being the one I would impregnate. Some of those competitions were amazing.

Think of having four gorgeous women all lined up in a row on a bunk, with their pussies, asses or mouths waiting their turn to see which one can make you cum first, all so the winner can earn a single point. (The last point winner chose which hole they would all use and the first one who got to twenty-one points was the winner!) That contest went on every night for almost three months, and the competition was fierce.

Those are the memories I will think about as I draw my final breath. I wonder which competition I'll remember last.

One of them won that competition, but that comes later. First, let me start this story at the beginning.

After three months on C wing, getting to know each of the inmates, I began to grow very close to one of them in particular.

Michelle Benton worked as a porter, doing all the laundry for C wing on her own. This job sometimes kept her up and out of her assigned room long after lockdown.

On those nights when her job kept her up, we began sitting together and watching TV in the dayroom while she waited for the laundry to finish drying.

Quite accidentally, and to both our surprise, we hit it off and realized we were both strongly attracted to each other. I say it came as a surprise to both of us because Michelle, up to that point, hated any man in uniform and I had a general dislike for inmates, the females included.

Neither of us openly acknowledged our attraction, but it was clear after sitting and talking with her the first few times that we were enjoying each other's company a bit too much.

Neither of us had said anything even remotely flirtatious, but we had talked a lot about life and had laughed at each other's jokes. There was a genuine affection building and both of us knew it.

As we watched Johnny Carson, maybe our third time sitting alone together, Michelle began staring at me instead of the TV.

Without looking over at her, a lopsided smirk crept onto my face and I said, "What the hell you looking at?"

I felt her eyes boring into me. Out of the corner of my eye I saw her shrug. She said, "You look like you're in pretty good shape. You work out?"

"Tae Kwon Do," I said. "What's it to ya?"

She snickered. "So, you some kind of a... tough guy?"

"I'd qualify as more of a badass," I said, smirking more and nodding. "Sometimes."

"They say that's a sign of a guy trying to compensate for a small penis. Is that true?"

My smirk grew into a grin. "Not sure," I said, enjoying her question. "Small? Big? It's all so subjective. What's small to one person might be huge to another."

She scoffed, looked back toward the TV and said, "That sounds like something a guy with a small dick would say."

I snickered. "You want to see it?" I said. "Decide for yourself?"

She spun her head back. We stared at each other, both smiling. "You wouldn't dare," she said, a look of excitement in her eyes.

I laughed, and shook my head. "Nope, I wouldn't."

She frowned and turned away again, waving a hand at me. "Fucking cunt tease."

"Okay," I said, "I'll show you mine, but only if you can make him grow."

Michelle scowled and pulled her head back, blinking. "Excuse me?" she said, feigning being offended. Playfully, she twirled her hair with her fingers. "And how would you suggest I do that?"

I shrugged, "I don't know if you can, especially without touching it. That would be against the rules."

She huffed out a scoffing breath. "Hah! I could make that thing pop out all on its own if I wanted to."

"Then put your money where your mouth is," I said. "I mean, only if you want to."

"Hmmm," she said, looking like she had to think about it, her eyes peering thoughtfully at the ceiling. "Let's see? Haven't even sniffed a dick in over two years. I'm thinking... Hell, fucking yeah, I want to.

"Alright, Officer Badass," Michelle said, standing up. She turned to face me and grabbed the tie on the front of her terry cloth robe, looking like she was about to untie it and rip her robe wide open.

I held up my hand. "Wait!" I said, "Not out here." Looking past her down the long corridor toward the C wing door and then toward the window in the fire exit door, I frowned and shook my head. "No way. Too many ways to get caught with our hands in the cookie jar."

"Okay," she said, dropping her hands to her sides. "I need to check on the laundry anyway. Let's go in there and lock the door."

I followed Michelle into the laundry room, turned, shut and locked the door behind us, and turned back again.

The sight that greeted me, a completely naked biker chick, sporting both the most spectacular tattoo and the greatest tits I had ever seen up to that moment in my life, nearly popped my dick right out of my pants, just like she had bragged she could do.

"Wow!" I said, very much impressed.

"Is it hard yet?" She asked.

Clearing my throat, I shook my head.

Michelle frowned and looked over at the dryers. She walked up to one, put both hands on it, lifted one leg and rested it on the dryer next to the one she was holding onto. Arching her back, and looking at me over her shoulder, she placed a hand on her ass cheek and lifted it up, spreading her butt crack.

Biting her bottom lip, she growled in a low tone, "Watch what my asshole could do if you rammed your hard cock inside it. Watch it close, now."

She never had to say anything. I couldn't take my eyes off her small wrinkled button of an asshole or the luscious looking full-lipped pussy jutting out at me beneath it.

Her gorgeous butt hole began pulling in and then pushing out, moving into her and then puckering out again, over and over and over. "You like that, Harry?" she asked. "Imagine if you slid your cock into it? You can if you want to. Do you want to?"

My cock throbbed, feeling harder than it had ever been. I unbuckled my belt and pants, and unzipped my fly. "You did it, Michelle," I said, "It's hard... now you can decide for yourself."

Pushing down my pants and boxers, I displayed my erect penis for her inspection.

Her brown eyes widened, her mouth popped open, and she took in a loud gasp of air.

"HO-LEE-SHIT!" she cried. Smiling giddily, she spun, yanking her raised leg down from its perch and she charged, headlong, right at my cock.

All thoughts of teasing, pretense or decorum of any kind abandoned, Michelle jumped down onto her knees in front of me. Latching onto my thighs with two hands, she opened her mouth wide and took the entire length and girth of my eight inch cock into her glee-filled face and all the way into her throat.

Michelle's whole body heaved mightily, as she choked as hard as a person can choke. Yet she refused to pull away. Instead, she stayed on it, tears of pain and joy springing from her bulging eyes and flowing down her quivering red cheeks.

The huge, thick cock, which she had so quickly and forcefully stuffed down her own throat, continued to gag her.

"Hey! Hey!" I said, getting concerned and pushing her head back. "Take a fucking breath!"

She pulled her gullet off my cock with her mouth wide and gasped for air, loudly heaving in a long deep breath, and then succumbing to a fit of coughing and wheezing.

"Jesus!" I said, chuckling, "You're going to choke yourself to death on my fucking dick!"

"I don't... (ack-ugga) care!" she cried, still choking, coughing and wheezing. "I want it... (ahemmm) so fucking bad!" She swallowed a couple times, wiped tears off her face, took a deep breath and took my cock deep once again.

This time Michelle slowly worked it deep into her throat, and slowly back out again. She moaned so loudly as she worked at blowing me and savored every inch of my cock that I could feel the vibration of her moans in my balls.

Thus began the hungriest, most intense dick sucking I had ever experienced. 

She pulled her mouth off for a moment and said, "Cock-starved, Harry. That's what I am. Thank you. Thank you so fucking much."

She went back to sucking it, making yummy sounds, moaning in bliss, and doing a better and better job as she worked.

Michelle pulled her mouth off again. "You can do whatever you want to me. Make me do anything. I am so fucking grateful."

She went back to hungrily devouring my cock. I felt my orgasm stirring as she worked tirelessly at pleasing me with her mouth, tongue and throat.

Lifting her mouth off she spit on my dick, licked my balls voraciously and said, "Fuck me in my ass. Fill my womb up with your fucking baby batter. If you tell me to have it I'll fucking squeeze out your little brat. Anything you want, Harry."

Michelle stood up, turned around, bent over and backed her pussy right onto my cock. It slid into her, as she let out a long, loud groan.

"UNG!" she cried. "Ho-lee SHIT! That feels so fucking GOOD!" She began pumping her pussy back into me hard, and heaving in loud gasps with each pump. Her rough plunges onto my cock pushed me back into the door. "Anything!" she whined, "Anything you fucking want!"

All I could do was grab two giant handfuls of her big soft tits and hold on as she went wild fucking me.

Grabbing the door handle and my shirt, Michelle thrust her pussy back into me, burying my cock deep. She ground her ass cheeks into me and shrieked out in rapture, her teeth clenched and her whole body shaking, lurching and jerking. "YES! FUCK YES!" she screamed.

Then her body relaxed and she fought to catch her breath.

I slowly fucked her pussy, enjoying the silky wet feel of it relaxing around my dick. Pumping faster and faster, I approached my own orgasm. Michelle began helping me fuck her, and as I felt my orgasm beginning, I said, "I'm about to cum, Baby... Drink it!"

"ANYTHING!" she said, pulling her pussy off me and spinning down onto her knees. She opened her mouth, put out her tongue, positioning it just below the tip that was about to explode, and jerked my cock off with both hands.

I felt the delightfully powerful surge of a massive load shoot through me, and grunted loudly as I completely creamed her outstretched tongue. Ropes of cum as thick as my thumb landed in quick succession and splattered into the back of her gaping mouth.

Michelle urgently milked my cock with her hands and tilted her head back as I filled her gullet with a huge puddle of thick, gooey sperm.

My orgasm subsided after six or eight substantial blasts and Michelle continued collecting as many drops and dribbles as she could squeeze out of my spent penis.

Looking up into my eyes, she wagged her cum coated tongue, causing the lumps of sperm pooled up in her mouth to roll over each other. She closed her mouth and swallowed with a loud clicking gulp. Her brow wrinkled and she squinted, seemingly in reaction to swallowing so much thick sperm. Popping her empty mouth open, Michelle gasped in a quick breath and then pursed her lips and blew out the air, shaking her head. "Oof!" she said, "That was a huge ass load."