Time Well Served

Tagline: Three tales about incarceration.

Category: Dickgirl / Futanari

*

- Sammie -

My name is Samantha or Sammie, and I am currently serving a life sentence in prison. My crime? Masturbating to dickgirl art without paying the license fee. My caseworker said it was a very serious crime that defies several federal laws. So I was immediately taken away from my life in Texas and thrust into a prison guarded by gorgeous but firm kawaii futanari jail guards. Cute, slightly insane, little girls with the supreme might over a bunch of inmates.

I still have a lot of unresolved feelings on the matter. To say I've had a normal response to everything would be ludicrous. I am certain I will need a lot of time in therapy after I'm freed from prison. That being said... It's a life sentence so what am I talking about? No help for me now. Not now. Maybe never. Hopefully never; I had heard rumors how the petite little girls could thrust your yearn for freedom away with ease. Pff.

The first night was filled with ringing moans of desperate pleasure echoing against the concrete corridor outside my cell. From inside my small space, I could hear the whimpering moans of other girls from down the hall being given their orientation to life inside a futanari prison. I held back a moan while my hand crept beneath the hem of my blue prison panties. It sounded like there was a party happening somewhere and everywhere just beyond the four walls of my tiny holding space.

I could hear flesh pounding against flesh, the cute girlish giggles, hoots, grunts and hollerings from the guards mixed in between the sounds of bodies slamming together, and the scent of musky sex hung so thick in the air you'd be able to cut it with a knife. Even though we were sealed away from all the action I could still feel the vibrations coming down the halls and into our cells. The very floor beneath our bare feet seemed to hum with an orgasmic intensity that just increased with each passing second.

How much time passed I cannot tell you. Every passing second felt like another eternity until I started hearing the sounds of cum dumpsters being moved through the corridors. More than a few times I heard a feminine grunt in an effort to heft a girl's body in the air before a heavy THWAP sent shivers through me.

"Gee golly, you're all cum guzzlers, huh?" One kawaii futa was saying out there while lifting one of the girls up into her arms, her voice sultry yet amused as she seemed to chuckle to herself before slamming a door down the hall closed and putting her prisoner inside a storage cell, "You'll spend the night in the spunk bin, cum dumpster."

I knew the time was ticking for me as well... I was a thirty-one-year-old woman with big thighs and heaving breasts, there was no way these lustful girls wouldn't catch interest. But I knew they liked their prey to simmer in their cell the first period of their stay, especially when we're already sexually charged from the sounds echoing through the concrete corridors. The harrowing sounds of women getting the fucking of their life acted as a promise for the rest of us.

The guards let the sounds do most of the work. Leaving us to squirm on our bedding on the cold concrete floor listening to the echoes of wet bodies colliding together, girlish giggles turning into exasperated moans as the school-uniformed dickgirl guards emptied themselves of cum. And not a small amount of cum, but a lot of cum. At times the entire floor was coated with an inch of the stuff just from one evening's activity.

So time went by in my tiny little concrete cube with one barred window and the door shut behind me. An hour turned into two. Two hours turned into three. Three hours turned into a day. I spent every day with echoes of pleasure keeping me hot and wet with the scent of hot semen just out of reach of my grasp. The other prisoners were too lethargic to speak or say much of anything and our conditions were sub-par to the point that none of the prisoners had enough strength to stand up from the floor after that initial night, forced to slither and slide over the floor because the concrete was coated with sperm that hadn't been washed away from the first round.

So the following weeks were spent eating bland foods and having no company beyond the constant screams of female orgasms filling the hallways beyond the cells. I would hear the guards talk to each other as they went past my cell.

"Gosh darn it, I think I broke a hip doing that last slut," a giggly voice chimed to another.

"You sure broke something!" the other replied, causing both the guards to burst into fits of adorable laughter, "Hopefully it doesn't impede her productivity. We were ordered to fill the storage silos by today and you broke a prisoner, kyaha!"

"Well can you blame me!?" the guard shot back, "She kept gripping my cock so perfectly I thought I was going to lose my mind! How does she squeeze my shaft that tightly?"

The second guard went "oooh" in her throat for a moment, "I was with that one earlier today!"

But I never heard the end of it as the two trailed off in some unknown direction.

*

A whole month went by before my door slid open and one of the adorable kawaii futa ladies appeared at the cell door, smiling her warmest, friendly smile. I saw her first with bleary eyes, exhausted by a full day of literally nothing to do but exist within my cramped surroundings, the concrete walls not lending themselves to good moods. She looked like your average busty cute school girl... big tits, slim hips, long blue hair, and the characteristic lust in her dark purple eyes.

"Hey there, Sammie-chan!" she giggled and waved at me.

"What's... going on?" I asked nervously while picking myself up off the concrete bed.

"I'm here to do some educational training," the cute dickgirl replied, and with that she threw the door behind her shut and locked it so we were sealed alone together in the room, "My name is Sparkles and I'll be your educator for today. I'm going to teach you how to take proper care of a futanari dick. But first!"

I bolted out of bed just in time to see the small girl angle a firehose into my small cell. “You need to clean up! Remember to wash behind the air,” the girl cheered.

In a fraction of a second later I was flung against the concrete wall by the mighty stream. I couldn’t move an inch as my entire body was covered and held up by the sheer force. For several minutes Sparkles concentratedly showered my filthy limbs with cold water. Finally, I slunk to the floor as she let up.

I slowly stood up in my concrete room, dripping wet. Even the clothes she wore were tight-fitting uniforms with a sexy cut in the midriff so her impressive breasts were shoved forward in the air, the nipples visibly protruding the thin fabric. She took a step in, letting the door slam shut behind her as she eyed me lustfully.

"Hey cutie, you can make this a pleasant experience for the both of us if you behave," the girl said, slightly more menacing… though it was hard to focus on the menace part with how adorable she looked and how innocent and almost naive-like her voice was. “Get out of yer jammies, hey?”

The small girl called Sparkles came up to me, looking up into my eyes. She was half a foot shorter than me, but the power dynamic was oddly in her favor.

"I don't... really want to get it on with..." I tried in a low voice.

"Do you prefer the hard way?" Sparkles interrupted, sounding suddenly stern.

"What's the hard wa-...WHOA!" I said, interrupted in a gasp.

Before I could even register it, she dropped to her knees and ripped aside my white cotton panties, then darted her tongue across my pussy lips, ripping an audible gasp from me while she used both hands to grip my full ass cheeks.

Her lips planted a kiss upon the pussy lips, and she looked up at me with the most cheery expression, "Let's start lesson one, Sammie-san. You are a cum dumpster for your Futanari teachers. Your primary function is to maintain your health and make yourself available to take care of our semen needs. When we are tired from the day's activities, you should offer to comfort us and nurse us back to health. So when you come out to the center courtyard I want you to offer your warm embrace to the guards stationed there."

"Huh?! Wait... you're not actually-" I started.

Sparkles stood up, raising her fist with the first two knuckles presented as she smiled. Then she drove the bony protrusion of her knuckles straight against my tummy, and the wind came out of my lungs so quickly I was already reeling from the blow. Before I could recover, her knuckles slammed against me again and then a third time, slamming me to my back where I lay wheezing on the floor for a full minute.

"Okie dokie", Sparkles lifted me by my armpits with ease. "The hard way then," she giggled.

She got me to my feet only to immediately ram her knee into my stomach, knocking out the remaining wind and doubling me over. That's when she shoved me onto my bed, I landed on my stomach barely able to brace myself with my hands before I felt Sparkle's strong hand yank at my prisoner jumpsuit. Unable to fight back, it soon was ripped off of me and thrown aside while leaving me naked, her hands working over my soft tummy, full bosom, and wide hips before shoving a finger against the ass in a probing manner.

"Just kidding Sammie-chan" Sparkle's giggle had a derisive edge to it, "I will be very caring and gentle... the first time..."

As I gasped for breath her hand left me momentarily and there was the sound of a uniform getting ruffled and shuffled. When her hands returned to me they were slick with lubricant and a slippery finger slid between my cheeks to press against the tight virgin entrance.

"W...Wait!" I tried.

Sparkles leaned her lips over my ear, "Once a year the girls at the prison have a dickgirl baby boom, and my sister guards and I are given leave to get the horniest bitch on campus pregnant."

I grunted and resisted as much as I could, but soon Sparkles pushed past my resistance and my hole stretched around the first invading penetration.

"Good girl." Sparkles licked her tongue across the outer shell of my ear as her digit pressed and popped into my untouched orifice.

For some reason, it was hard to stay mad at Sparkles due to her upbeat manner. Even when she complimented me I felt myself flutter and my resistance fade away. All I knew for certain was that it would not end well to make an enemy out of the jail staff.

"Hnng... ahhh!!" I hissed at her, trying to stay calm in an effort to defuse any potential outburst on her part, "Please be gentle... I've never done this before..."

"Oh wow!" Sparkles leaned forward and licked my nose affectionately. I turned my head away bashfully, making her giggle, "You are such a sweetheart, Sammie-chan..."

Her fingers didn't waste time as they sought and found spots within my asshole that made my entire body sing. The knuckles bumped and pressed against something inside and caused my whole body to seize up while my breath came out in ragged gasps. The intensity of those knuckles as she worked and wormed her fingers inside me caused my thighs to clamp down tight upon her hand, preventing any further escape even if she wanted to pull her fingers free from my tightening hole, I didn't even know why but my own hands shot to her head, my fingers entangling through the silky strands of her blue hair. It was embarrassing but her fingers worked the tension out of my body as I let out a moan loud enough to reach far down the concrete corridors.

"Sammie, you need to turn over!" Sparkles encouraged, and I obliged immediately, laying on my back in an instant.

My vision was filled with Sparkle's cheery face as I felt her finger return to my ass. Sparkles turned for a second, hawked, and spat on my anal entrance, thus sliding her finger into me with ease. She immediately started to fingerblast my already prepped ass. It wasn't long before the stimulation brought forth an explosive release from the pressure inside me. I could feel the fluids splashing upon my thighs as a splash of nectar shot out from the center of my slit and squirted all over Sparkle's hand.

"Are you cumming already, Sammie-chan?" Sparkles asked in a low sultry voice, as sultry as her voice got that is.

My mind was dazed, and I felt utterly humiliated when confronted with the girlish glee sparkling in the guard's violet eyes as her finger pumped and spread me open even wider. Her grin widened even more as her fingers wiggled and stretched my butt apart.

My heart thudded in my chest, and I felt it rising from my loins.

"It feels... It feels good. My butt!" I wailed, clamping down on the pumping digit while throwing my head side to side. I must have looked like a deranged person losing control as I kept gasping.

"Such a horny cum dumpster." She punctuated the insult with a wicked gleam in her eyes.

My tongue flopped from my lips while my hips undulated to try to get the finger deeper into me. In my heart I did not see any malice in her words, nor any acknowledgment of my offense. In fact, the idea that I would be bred was becoming an exciting proposition, though I knew it was supposed to be bad. It felt so very good I nearly forgot I was being punished! The bratty tone she had added to her taunt sounded almost sisterly, rather than menacing or demeaning.

I had never given thought to what it would be like to be in heat. As her knuckle slid into me and caused every muscle in my abdomen to seize and uncoil I screamed louder.

"Fuck me!" I exclaimed as I came again.

Sparkles took it as encouragement, however, immediately throwing herself onto me, her whole face disappearing into my cleavage as her cock disappeared between my thighs, into my folds, and deep in me. I screamed out in agony and pleasure from the sudden intrusion of the nine-inch cock stabbing through me. I thrashed for a moment and soon it was followed by an orgasm. It came on so intensely that I howled so loud it hurt my own ears.

Her cock slid in all the way, meeting no real resistance and finding my cervix with no difficulty. I clamped my pussy around the girl, milking her for the precious substance all the cells inside me wanted. A piece of me still screamed that none of this was right, yet in a heartbeat, I went from scared little bitch to slutty cum receptacle for a ditzy kawaii dickgirl.

"Mmmm Sammie," Sparkles whined as her cock began thrusting like a jackhammer within me, her hips smacking down onto mine, "Oh fuck you feel amazing on my dick!"

Her ass smacked and humped in and out, the flared tip of her massive rod spearing into me with every motion of her little frame and reaching as deeply inside of me as she could go. This kawaii little creature fucked me, impaled me, and drained her hot thick ball butter into my core without hesitation. Her large testicles pulsated as her jism pooled in my baby room, spurting thick ribbons of hot fertile spunk inside the mouth of my cervix.

"I'm going to do a lot of damage to your guts," Sparkles promised with a purr, pulling back until the cockhead popped from me, then her strong arms forced me to roll over.

"That was so intense," I muttered as her dick slid inside me once again, deeper than before.

"Aww, don't say things like that Sammie," Sparkles huffed while she continued to plunge that heavy shaft into my twat with increasing force, the flared crown spearing through my womb to nudge against the roof again. I could hear the little bottom-heavy creature giggling and moaning. "You're too cute!"

With a loud grunt, she smacked my ass with both her palms, followed by a hiss, "Unghhh!! Ahhhhhh...." She exhaled a groan through her clenched teeth, "Your ass is a gonna get it after."

Before I could say anything in response to her demeaning promise I felt the powerful deluge of her girl jism spray my walls, forcing me to cry out, "OH GOD!!!"

"I haven't even stopped cumming yet!" she squeaked. She pulled out her rod and hosed me down with so much thick goo it felt like I was getting a wet, sticky blanket draped across my entire body.

"Oopsie daisy," Sparkles giggled.

She then forced the remaining portion of her rod into my twitching depths. Her sack drew up tight to my flesh and she drew back an inch or two, and that's when I heard a distinct plopping sound of fluid hitting creating a puddle beneath us. She had made a mess of me, and my room was going to stink of sex. But the biggest indication was how it suddenly overfilled and flooded from my entrance.

*

- Jake -

By some crazy mistake, I had been placed in the wrong prison. This isn't the facility that the federal government set up to help those on death row find their place in society, like was indicated on my paperwork. This is some futa lesbian max-security prison. They must have made some kind of mistake during the transfer process from my federal court sentencing in Colorado to wherever it was these chicks were dumping me now.

Can’t lie, spending time in a womens facility was enticing if wasn’t for all those brony fucking kawaii girls. The fuck was up with that? Huh, a 6 foot 4, 230 lbs of athletic man who had no business milling about such small fragile things. I’d break them in half! Maybe I had to, knowing what they did to the prisoners down there.

To top off my shock and amazement, my very first night here the sound of intense sexual torture was making its way through the cold walls all around me. When I fell asleep the echoes of sobbing moans still rumbled around my eardrums, even while the air had long grown still. There is something disturbing when you wake up from a hard night's rest and find that sounds still echo from the hallways long after they should have faded. It made me fearful, and the feeling didn't abate when I awoke. It only increased in the following weeks as I endured the intense echo chamber of squeals, slaps, and girlish giggles. The faint aroma of sex never faded away, permeating the air with musk from a seemingly unending orgy.

As the days grew long and repetitive, I felt my senses heighten. I knew my situation was not good, yet nothing changed. I was stuck waiting until some resolution could be found. There was no way I could possibly be expected to stay here... I mean, it was better than death row, but only by a small measure of betterment. Not much of a recommendation in the end.

Every single day is a carbon copy of the last: a meal is dropped off three times a day, delivered by the adorable, buxom guard in her revealing skin tight schoolgirl uniform. As a man I couldn’t help but stare, causing the small girls to giggle, but there was no way I lusted for such abominations. Like I said, as a man. I had to watch breasts, and I had to watch asses, just part of being a warm blooded dude.

Then there are the squeaky boots patrolling just on the other side of my cell door. That was all I did, just laid and wondered what else to do as each day passed, knowing full well it was a carbon copy of the day before and would continue to be tomorrow. And that is what they would do to you: day in, day out, one month bled into two. At least when I was first here and heard the sounds of torturous copulation echoing along the corridor it made the time pass quicker as it shook the floor beneath me and sent a chill down my back. But now... well, now the novelty of it is gone. Now all that was left to occupy me were my thoughts and my hunger for a good warm shower.

Then things changed. On the first day of my third month, my door finally swung open. A pink-haired Futanari was standing in the door with the smuggest grin I had ever seen. She walked in wearing her policewoman attire consisting of a high school girl's uniform. A short skirt, thigh-high leggings, a white top that barely kept the buttons closed over her expansive boobs, and a cap on her head. Even though her size did not befit the position of a jailor, she still demanded obedience as soon as she entered my cell.

"Time to train you, slut", She said. I blinked, and she was behind me. I couldn't say a thing.

I was slammed into the concrete floor, knocked senseless by a fist from the little girl. "My, you're one beefy boy," she said. "We'll have fun breaking you. We prefer that all our prisoners--"

"There has been a mistake, bro," I croaked, interrupting her. "I am supposed to be at a male facility in Colorado!"

She grinned evilly. "Male, huh? That might prove a challenge when trying to knock you up!" the pink-haired futa girl giggled, patting my cheek.

"N-N-No-no-no-no... Knock me up?! No! There has been some mistake!" I stuttered in horror.

"Yes, no mistakes," the girl stated while bending over in front of me and sliding off her red thong and letting it hang down from her ankle, "but you have such a perky cute ass. Can't wait to rip that v-card out of ya! Come on!"

With no time for debate, the Futanari stepped toward me and then stomped down onto my face with her foot. That's all she did; she placed her shoe upon my forehead, placed her weight to press it down upon me, and my world started spinning, blurry with tears, and all I could feel was her toes flexing upon my face, massaging it while her gleeful, starlight blue eyes were locked upon me.

"N-Now let's... n-not be dr-dramatic..." I started to say with a dry tongue and a strained voice.

The little girl slipped a toe up and into my mouth with the cutest giggle and hum, "It's too late. I'm in heat right now. So I'll fuck the resistance right out of ya! Get on the mattress, cutie!"

She dragged her delicate, manicured foot up to my temple and pressed hard. The pressure upon my temple soon went away and I realized I should obey before she decided to plant another vicious kick upon me. This jail cell was built just as poorly as my last with no lighting above save the dim lamp outside my bars, yet even here I saw the wild look in the girl's eyes as she eagerly stroked the bulge in her skirt where her cock was. I rolled onto my back and looked at my assailant.

"Oh, you want to be on your back? Wonderful, then we can look each other in the eyes while you feel this mammoth beast slide deep inside you! Wonderfully romantic!" she giggled with a clap of her hands, "Now lay back and let us love your insides."

The little futa propped her foot up onto the side of the bed and yanked down the hem of her skirt, letting that monster bounce free into the cool air, but the girl paid it no mind. She crawled down onto the mattress, placing her knees between my thighs, forcing them apart with no effort at all.

"My name is Peppermint, by the way," she winked, leaning down on me, her erect, pulsating dick scraping across my belly.

My eyes were filled with her freckled little face, smiling blue eyes, and her glaring white teeth biting her bottom lip. I thought that a dickgirl couldn't possibly be desirable, yet I stared back in awe at her and how gorgeous she looked even with her oversized balls knocking against my rear. In all my life, I had never seen such a cute and enthralling female. Even if she was about to rape me.

"What's my name?" she asked calmly and collected, smiling at me.

"Peppermint?" I answered, trembling under her body.

"Oh! Aren't you adorable!?" she replied, cupping my cheek and planting a gentle kiss on my forehead.

"Uhh.. I-I'm Jake. My name's Jake" I muttered nervously as my eyes shifted to the huge girlpenis dangling between our stomachs. It had to be at least nine inches at least, was extremely fat, and it looked utterly revolting. How could I have thought she was cute when such a monstrous thing was dangling between her legs!?

Peppermint ran her fingers along my jawline, forcing my gaze upward, "Call me Pepper, cutie, or Daddy."

My hands, which I had kept to myself all this time, were hypnotically lifted to grab her, my fingers pressed to the little girl's buttcheeks and a deep, resounding moan escaped her lips. I didn't stop caressing her body for one moment and, just a second later, Peppermint crashed her lips against my own while one hand tore away my boxers.

Peppermint slid herself back and then yanked up my leg, lifting it across her shoulder, turning me sideways upon the mattress, her cock jabbing down at the entrance to my privates. "First time huh, Jake?" I had only a split second to reply before her hips snapped down and that giant tool plunged into my little, underused ass.

"AHHRRGGGGHHH!" I screamed, biting down, and clenching my eyes shut.

Peppermint wrapped an arm under my left thigh and pulled herself close, slamming her crotch into mine. It was a violent plunge and the entire time she kept the smile on her face and looked me deep into the eyes, her own shimmering with pure delight, while her shaft pumped in and out of me without relent.

"Yes! Take it, bitch," she whispered sweetly, "Take this entire cock up your pretty little boy-hole."

Every few pumps, I felt a spurting blast of precum. That, and the massive tool pounding into my gut was more than I could bear. When she released my leg to lower herself on top of me, I bit into her shoulder. Not hard, but just to ease the pressure, the intensity of it. And with each pump she made I felt my anal walls give a little more and accept the entry of this larger woman. I started whimpering, cooing, and shaking uncontrollably in her arms.

"That's a good bitch," she soothed while her heavy shaft thrust and moved against my inner walls, and she held me while it speared deeper inside.

The sensation was nauseating, and every stab came with an eruption of burning fluid into the depth of my bowels, causing them to convulse and ripple, and even squeeze back, taking the engorged muscle deep. She moved in ways that kept me whimpering and my legs tensed with the stinging force, then, gradually, her cock stopped stretching me and she began using my asshole to its full extent.

"Hoooolllllly crap," she gasped, looking down between our bodies. “GEE GOLLY!”

But Pepper was far from done. As my pain subsided, my whimpers of pain were swapped for grunts of pleasure and exhaustion.

"Huff, huff, HNNG..." I grunted and Pepper drove her lips forward to mingle her tongue with mine again, slapping the underside of my thigh, "Gods damn, what an ass, my gods, such a tight ass..."

Her cock never stopped working, punching through me, then she hit a nerve that made my cock start sputtering cum and she laughed.

"Now that's what I'm talking about!" she exclaimed, plowing into me with gusto and milking my penis in order to bring me to a fast, humiliating release, and once I did, she gave a chuckle. "That was one powerful little dud missile," she cackled, rolling her eyes in jest.

Her hips bucked back and her member came loose with a loud POP before she turned herself on the mattress, ending on her back and staring up into my eyes with an eager, lustful stare. Then her lips twitched and she wiggled her eyebrows, "I have a surprise for you."

"Wh-what is it?" I gasped, realizing in the back of my mind, I was responding like I was getting brainwashed. The more she had her dick inside me, the more my reservations were washing away.

Pepper leaned back on the concrete bed. A warm smile spread across her face, "You get to suck this thing next. Want a snack?"

What happened next was entirely out of instinct and the heat of the moment, I had never, not even once in my entire life, not even during an intense jerkoff session, considered sucking on another dude's penis before. Yet... that thing looked like a dream, large enough to really stretch out the cheeks of the jaw, long and slim, yet massive. And it wasn't another dude... it was Pepper, my cute little futa prison guard.

"Th-That's so big," I gasped.

"Come get that salami," she goaded, grabbing it and stroking it for my viewing pleasure. "You need your protein. You're gonna be taking some hardcore punishments, if I'm being perfectly honest."

I crawled along the concrete until I was face to face with her groin, her cock rising up into the air. Before me, I saw the heaviest-looking, fattest balls I had ever beheld hanging like ripe melons ready to be cut from a vine.

Peppermint glanced down at me, giggling, "Ever given a blowjob?"

Before I had even answered her, I felt her hand on my head and my lips gliding down the top of the shaft, slowly taking her meat pole into my virgin oral cavity and working my way down her shaft. It was the strangest taste I've ever had. It was delicious but weird. My tongue didn't know what to do so it tried to taste the fat nine-inch dong by twisting around the veiny appendage and lapping her delicious flavor. Her throbbing head met my uvula, making my throat constrict, and then her hot cum flooded out and straight down my throat.

"Fuck!" she shrieked, grabbing a fistful of my hair, "What the heck?"

"MhmmmMmfphhhgg," I tried speaking but only gagging and gurgling was the result as her cock flexed and spat its hot girl-spunk down my neck.

Peppermint threw her head back with a husky laugh, the whole prison rocking from the force of her hips shoving against me, trying to pound me face-first into her groin with her mighty girlcock. All I did was wrap my lips around the thickness, knowing my slurping around the shaft must have felt exquisite if the sounds she was making were any indication, and I began swirling my tongue along the flared, pulsating crown, sucking hard to extract the maximum flavor. I gulped for everything I was worth, trying to swallow the musky taste of her cum.

I realized soon I loved every second of it.

I worked that little cutie's dick into me, using both of my fists to make my hands into a dual vice. Up and down with my two palms, working the cockmeat in and out in a motion that I instinctively understood would make me slurp and gulp her batter down with a level of skill I'd never heard of, the heavy, potent balls bouncing off my chin and lips every time my head bobbed down to her crotch.

"You made me cum way too early!" the girl scolded in her cutesy voice, her groin pulsing under me while the shaft pumped semen straight into me, shooting thick wads of girl batter that could be nothing but the seed of her production.

"Uh, uh, sorry!" I panted.

It was strange how apologetic I was and how much I enjoyed my place under the domination of Peppermint, all at the same time. There was a mixture of conflicting emotions with her and I wasn't sure what to think as her girl cum coated my entire throat from one end to the other in a hot creamy film of tasty love.

Peppermint drew back and pulled me from her prick, my saliva streaming and creating a thick bridge between us. "Well, now that we got that out of our systems," she giggled, "let's fuck."

That was a promise as she threw herself over and atop me. Her dick immediately jammed deep inside of my rectum once again, sending a pang of extreme pain through me, though that pain subsided almost instantly and was followed by the sensation of Peppermint pumping her slick cock back and forth inside of me. My ass ached as it took that large cock for the first time, but it felt wonderful the further we went.

My breathing grew heavier as each new sensation rushed through me, every stab of her prick touching parts I've never reached with my own hands, her rod forced itself past any barriers that were in her way, and I felt the sticky wetness between my ass cheeks where my rectum was being opened and filled for the second time.

"Is that okay? Does it feel good?" she gasped out, slowing the momentum of her pumps, "Does it still hurt?"

"No," I cried, the heat burning in my eyes. Peppermint immediately caught the quivering in my lips and how I started to cry, so she stopped moving her hips completely.

"Did I just hurt you?! I'm sorry, honey!" she exclaimed.

"Y-Yes..." I replied through the haze of bliss, "B-B-But..."

The kawaii prison guard placed both her hands along my jaw and stared deeply into my eyes, "It's okay, babe. I'm right here, I got you!"

"O... Ok," I stuttered through the shock and warmth of having a beautiful girl whisper to me, caring. It brought a fresh bout of tears to my eyes and I didn't resist when she crashed her soft lips against mine for another soulful kiss.

When she slid her massive dong back into me I couldn't do anything except for cling to her like my life was ending. She had pulled out of my ass just to line the tip up and slip back inside me and she began rocking her hips gently, pumping me in a sweet, leisurely rhythm, slowly, steadily, and with perfect control. The way she touched me was careful and measured. This was Peppermint showing concern, showing me a degree of compassion. I appreciated the moment, the special treat of not being immediately fucked by the brute. I needed a little gentleness at this moment.

"Doing okay, babe?" she whispered in my ear, making me tremble.

She rubbed a palm against my scalp as her hips picked up their pace and the thrusts into my ass began to get more purposeful. This is what being with an assertive woman should be, the kind who controls your body, takes over, and doesn't allow for resistance... at least not too much resistance. I did, of course, squirm as she pushed the whole length into my anal cavity.

"It's going so deep," I murmured, still dazed and confused about this treatment.

"You like it?" Pepper asked cheerfully, a never wavering smile on her face.

"Y-Yes," I whimpered.

"Good, else I'd have to rape you," Pepper cheered. "Or do you want to be raped? Some girls love it but I'm usually just as happy with consensual sex. But if you want it rough, I'll give ya a good tumblin'."

I didn't really know which I wanted, either of them seemed quite dangerous. I didn't dare let my confusion or fear show in the face of Peppermint's resplendent cuteness. I knew she'd do either in a heartbeat if the urge struck her so the easiest route was to nod and take whatever I could.

"Good, now lets cum together. I have this new harness where I put you upside down I want to try. And I want to see what kind of sounds you make when I bring my pink flogger!" she said gleefully, forcing her penis deeper into my ass as if giving a preview of how rough this kawaii little girl actually gets.

"Alright," I sighed. "Please just let's try it a bit easier today. Let's have a break after and we'll see," I said, trying to be reasonable and to play along.

Peppermint drew a hand to stifle a laugh, "Oh don't be silly. After today you'll be well-trained and accepting my huge tool!" she added, demonstrating her point by giving my guts a healthy poking. "Well, let's get a move on, chop, chop, newbie, the day's young, let's break that ass in with a big warm load."

As Peppermint proceeded to twist and turn me in whichever position she desired, while emanating cute grunts in her struggles, the feelings that dominated me were a combination of emotions, such as nervousness, excitement, afraid, yet mostly intrigued as to what was to come, though a bit disturbed by it all the same.

"On all fours, Jake. Head low," Peppermint commanded, her dribbling cock slapping down atop my spine and sending a cold chill throughout my core.

I did as I was told as soon as the command was given. Once my shoulders were on the concrete her cockhead tickled my bottom and with an enthusiastic shout, her shaft pushed against my asshole, shoving its way deep inside. I felt myself clamp down hard, yet it didn't stop her and there was the sensation of pressure building deep within me as she stuffed her engorged organ into me, sliding past those tightly pressed butt muscles, sinking balls deep into my core.

Once fully entrenched within my hole, her pelvis came to rest against me. I could feel my asshole struggling around her invading appendage, my inner walls hugging her girth and being stretched wide. Slowly, deliberately, and without a word, Peppermint worked herself into a comfortable position. I heard her groan from the sensitivity in her buried cock as she shuffled in place, my insides massaging her erection, her heat beginning to pool inside.

The entire time I bit into the thin foam that was my bed, waiting for the inevitable hammering to come. When I finally felt the swell of her giant sack hit my taint and scrotum, I knew the end was upon me. Then, Peppermint shuffled again, positioning herself closer so that her dick pointed forward and down. I was left quivering beneath her, terrified, anxious, and wanting…

Her powerful hips slammed forward, the meaty, throbbing shaft plowing into the confines of my depths as my sphincter seized. At this new angle and position, it felt so good I couldn't even form words. There were only inarticulate squeaks and mewls that escaped my mouth as the muscles in my ass protested. Yet Peppermint relentlessly ground her crotch into me.

"Oh! Gosh dang, baby. You're so tight," Peppermint gleamed, her whole body shaking on top of my own. "Feeling good? Oh, oh! You're twitching! Your poor prostate! Hanging onto my dick for dear life," she gasped. "How is your little G-spot?"

Every fiber of me wanted to answer her question, tell her everything, and share the pleasure she gave me, but I was a moaning mess. Peppermint's strokes were picking up a beat as my moans were getting louder, the burn of my ass spreading warmth through me that I couldn't describe.

"Ah, ah, that is so good, little boy, you're doing so good! What a sweet young thing," she shrieked. "I can't believe it's still this tight in there, ah, wow...! Take that big cock, yeah. Nngh!" she added through clenched teeth.

Even though I had never penetrated that deep before and felt I might actually rip open, however, my anal sphincter and glutes were burning with friction and stretched further than ever before. But with it also came the waves of pleasure, hitting me from a mysterious depth inside myself I had never known was there.

"You feel it?" she grinned, "Your little sweet spot is being bashed by me, baby! Busted open by that bitch stick! Fuck! I have to stop or I'll break a leg with how intense it is, honey!"

There was a brief moment when her pace stopped. The sensation of her shaft scraping my tender insides ceased for a split second, then her pelvis smacked against me with all the force and fury of her rutting, burying the member so deep into me a wave of sensations surged through my gut.

"Hold still, babe, please," she pleaded, sounding alarmingly calm. Her balls slapped hard against my perineum. But then, "Fuck it, I can't hold back."

Pepper started immediately to thrust into me frantically again, possessed by the need to cum herself, though all I could do was keep still as her sweaty, smooth legs pressed hard into mine. Her tool hammered at a blistering pace, skewering my prostate and punching against my cervix, sending convulsions running down my core to squeeze the big piece of dick within me.

"G-gonna knock you u-up," she promised as she continued driving that piece of flesh in my rear. "Shit... s-so close... It's a b-bi... I mean I've mmmf uhhh" she exclaimed with a particularly sharp jostling. "I can feel it cumming!" she begged, her fingers digging deep into my sides.

As her entire body lurched, I could feel her twitch inside and then her load began blasting my insides, her giant member shooting a hot wad of potent seed deep into me that quickly spread across my insides. I could sense the fullness within my bowels increase, feeling her sperm pumping from that enormous dick all the way through my bowel. It didn't end and I could only lay there, limp in Peppermint's arms while I was ravaged, seed spurting in continuous streams.

Peppermint leaned her weight back on her feet, her cock slipping free, dragging against my wall, and making the torrent of seed splash and spatter in great spurts that struck my scrotum and upper thighs. When it finally dribbled to an end, a few residual drops stained my thighs and lower cheeks, dripping onto the floor. My asshole gaped and spasmed around the thick emptiness. I could feel a thick dribble of warm fluid drain out onto the floor below, too shocked and horrified to even speak. I had truly been infected by her DNA.

"Boy, now that was fucking epic!" the futa cheered, "Gee golly! And you survived my brutal pounding, great! I can't wait to make sure we spend some quality time again! Would you like that?"

"You're gonna be my... erh. My guard" I asked, swallowing hard in the wake of this realization.

"I'm your girlfriend, silly pie. Everyone gets one, honey," she replied, stroking my ass, "Though we don't mind sharing with our sisters, so sometimes you might get another girl in here to pound that cute ass of yours."

That was a very overwhelming sensation, all of it happening at once, knowing I'd just had anal sex, had lost my virginity, had been bred, and now I had a futanari girl who wanted to be my girlfriend and who wanted to share me around the prison. I was suddenly very, very afraid. And happy. How does that even work?

Peppermint took in my horror, and ran a single finger along her lip. "You'd like that wouldn't you, baby? If two sexy chicks fucked your tight little asshole? At the same time? Made your body submit to them and be our cum dump? Used up until your stomach bulges with our seed?" she taunted, a lust in her eyes.

A flush rose through my chest, cheeks.

Pepper pressed against my chest, crawling to bring our faces level, her big, blue eyes piercing into mine, "Don't worry, love. I will sleep in here tonight and protect you."

I felt her press a quick, almost innocent, kiss against my nose.

"But I don't sleep unless I'm reeeally tired, Jake, so you know what that means," she laughed, forcing my hand onto her hardening cock, the girl whispering, "You'll be bouncing up and down on this baby, over and over, and over, for as long as I like… all night..."

I swallowed hard at that. She couldn't have made that sound more appealing. She shot her mouth down on me, forcing her eager tongue into my mouth.

“You don’t need sleep, you need a good dick in your ass,” Pepper giggled cutely.

With my mind filled with her, I couldn't deny anything anymore, I realized it all: the assault and breeding, the way Pepper's body was so warm, and comforting, and most of all the way she worked her tongue to kiss me. She pulled away, a trickle of saliva dangling between us. The futa giggled when she saw my face and pinched my cheek lightly before planting another peck to the corner of my lips.

"I wanna see you bounce that ass," the pink-haired prison girl commanded.

I did. She didn't touch her rock-hard dick. I did. I jumped on top of her, straddled her waist, and grabbed that dick between my thighs, and aligned the thick shaft against my stretched ass. Then I sank down on top of her length and began bouncing myself up and down. I felt like such a dirty slut fucking myself on her, but I didn't care. It was only me, Pepper, and her big juicy cock, and no amount of societal humiliation would stop me from riding her.

"G-gee golly! That feels so good! Yeah! Slide that tight ass up and down," she said, smiling and panting through the words.

Five minutes later she had me on my back with my legs on her shoulders. The girl was grinding into my backdoor like a steamroller, I was bent double and crying my lungs out while her giant dick kept rubbing my prostate and causing me to orgasm without pause. After several more times, I didn't know what I preferred anymore; to be lying on top of Peppermint with my ass invaded and rutted into oblivion or lying below the pink-haired jailkeeper with her massive pole plunged through my anal depths.

Either way, at the end of that day I had become the kawaii guard's little plaything. I couldn't run from her anymore because she had me on a leash. But more importantly... I didn't want to run from her, and in no time the desire would completely overwhelm me.

*

- Steven -

I had heard about that poor guy who got transferred to the wrong prison. Jake. You would think they would fix their transfer systems, but no. I got mistakenly transferred into the wild, somewhat alluring prison we all had heard so much about. Not for everybody, but I had a dirty secret. I wanted to be here.

I can't explain it, but I had always been into femdom anyway so this was like the ultimate fantasy for me. Getting used and abused for the rest of my life. I stole some Futa NFTs and that landed me in prison for life, and with the shitty transfer policies I hoped destiny would land me shackled to a shitty bed frame while getting gang-raped by a pack of adorable, hung kawaii girls. And, to my elation, it happened.

The door slammed open. A group of beautiful little chicks surrounded me, three of them, and my dick already twitched at the sight. "Hello ladies," I teased, smirking from one to the other.

"This boy is way too dirty!" one of them exclaimed pointing a stern finger way above my head. "Rose, Blossom! Get the rope!"

"You got it, Daisy!" the girls called back. They sounded so stern, but their cute little voices made it just so adorable! I couldn't wait!

As the girls dragged me out of my cell, I took notice of each of them. Rose, Blossom, and their leader Daisy. All dressed the same, wearing cute, summery short-shorts, flattering tops, and stockings, a trio of really adorable little gals!

I was led by the three girls to a small chamber of six showers, as I was guessing me being dirty called for me to be scrubbed down. Once inside, the leader Daisy kicked off her shoes and went to take my rope and clothes off and shove me underneath a shower.

She forced me under the running water, her smile contagious and endearing. The hot shower was turned on, splashing me and then the girl threw some soaps and other liquids onto the floor next to the shower, announcing.

"There we go! You take the full minute to scrub all those bad stenches off you and out of your body! Come, come girls. You get into the shower too, let's help him wash."

Daisy nodded toward Rose and Blossom who, along with their leader, then started to undress, peeling their tight, smooth outfits from their bodies. I immediately took one of the bottled shampoos and lathered myself up, eager to drop the soap at a moment's notice. Rose and Blossom looked at me sternly, before discarding all their clothing.

Both were in immaculate shape. Big strutting breasts, strong thighs, and delicious abs were part of the whole package, as well as each of their soda-can wide cocks, long and raging. It was hard to fathom in real life how hung they were, and how endearing they looked compared to their angry-looking cocks.

Then it was Daisy, the brunette of the trio, as the two other was as sunstruck as the day was bright. As soon as her clothes dropped off she displayed her immense frame, fit, huge-breasted, and cock-heavy. I had never met a futa as massive as her, not even in the porn, so this would be an intense one.

I stood there with three naked, hung dickgirls just staring at me and licking their lips. I dropped the bottle of liquid soap I'd been scrubbing with and kneeled down to pick it up and as I stood back up my cock brushed against Daisy's bulky package, which was bigger and thicker than my thigh, making my penis twitch at the feel of her hardened length.

"Why did you drop that?! You need to be punished! What do you have to say for yourself?" Daisy insisted, her frown looking both angry and cute on her lovely features.

"Sorry ma'am! Please let me try again?" I pleaded, eager to get defiled.

"You're not taking this seriously! Dropping the soap is a serious crime around here! You need to be spanked! Are you ready to accept the consequences?!"

"Yes. Please. Hit me."

"Step forward, feet on either side of my cock, hold the railing."

I followed her instructions to a t, getting in place setting one foot each outside of Daisy's slender feet, grabbing the railing, and presenting her my ass. Daisy gripped her mammoth fuck-cudgel, slowly stroked her flesh log, then raised it high above me and thrust down, spanking my ass with its spongy, silken head.

"Do you like getting spanked by that huge tool?" she whispered huskily to me, a feeling I wouldn't have forgotten for as long as I'd be around.

"Fuck yeah," I groaned, gripping the rail hard.

"We better treat you some manners!" the cute prison guard directed, a naughty smirk on her lips.

She leaned in behind me, pressing her oversized member against my crack, sliding it up and down teasingly, and pressing in close, "Stay nice and still," she warned in a sing-song, soft voice, her breathing brushing warmly along my ear. "In order for the lesson to sink in deep enough."

"Yeah, thanks," I shivered, turning my head back to face her. Then my face was grabbed and I was forced away from the rail.

One moment I was breathing like any sane human, but the very next second Blossom's huge cock threatened to enter my throat. I clenched my eyes shut, just in time for Daisy to press her huge cock directly on my entrance, and by sheer force she entered me, splitting the tight ring of muscle guarding the inside of my bowels wide open.

"Oh fuck, oh fuck," I grunted, in absolute heaven and beyond the realm of pain.

I had wanted this my whole adult life, but nothing could prepare me for the real thing. Nothing. As her mighty trunk slipped in, and my hole clasped about her length, feeling every inch of her magnificent member spread my anus open, her strong hands dug deep into my butt cheeks.

I opened my eyes in a craze and could barely focus for long. With a giant throbbing cock blocking my vision as it stuck down and into my mouth, I was in a helpless heaven. If I got choked out by this huge thing, or if Daisy ruined me forever, so be it. They could do with me what they wanted. This was it, it was what I'd been praying for.

When Blossom started to grind against my face, her entire weight behind it, her giant meat log bulged from the sides of my cheeks, reaching right to my tons and causing me to gag. As I got spit-roasted on the two insanely huge dicks, Rose came up to the left of me and forced a hand onto her own cock. It must have been twice my own. She then grabbed the head and forced it into my fist and she used me to jerk herself off.

"Rose, did you remember to bring the handcuffs?" Daisy panted as she gave me the best forced entry one could wish for, followed by a frenzy of thrusts before disengaging from my rectum, pulling her large cockhead from within. I moaned.

I hadn't meant to, but the loss was monumental.

"Aaa-HUMF," Daisy exclaimed, kicking my legs under me, thus losing also Blossoms phallus from within.

I fell down, crashing my legs into a bent position and the moment the pain receded I gazed up. Rose was holding two sets of steel-wrapped handcuffs and Blossom put her finger on her lower lip.

"Ready to be our bitch, Steven? In training I mean?" the trio of kawaii chicks smiled wickedly.

I didn't hesitate for a moment, "Yes, please! Just... keep... punishing... me!"

"Drag this insubordinate bitch back to his cell and lock him to his bed," Daisy commanded, fists on her waist, a huge meat pole stuck into the air and almost reaching to my neck. "We'll run a train on him until he learns!"

"Ahh..." I grunted through clenched teeth as the weight was transferred to the left ankle and I was promptly towed across the hard floor, naked, aching, and still horny as hell.

"Wait!" Daisy commanded. "Let's kick his ass first!"

Immediately the small girls started sending delicious kicks into my ribs, my face, ass, and other places. I groaned in a mix of sheer bliss and pain, rolling over on the cold stone tiles. I just listened to their dainty grunts and ravishing angry hisses as they continued their assault, stomping on my stomach, slamming into my arms and face, and beating me black and blue. I never thought something could be so utterly divine as being raped by a gang of hung dick-girls and then beaten until I was barely able to stand up.

“So…. good…” I managed to groan from under my pain.

"This guy is fucking unbelievable," one of the girls groaned annoyedly, her puffed cheeks huffing with anger.

They had used me as a punching and kicking bag for 30 minutes at least before leaving me in a corner, nude and badly beaten up.

"I don't think he's learned a damn thing yet!" Blossom said defeatedly.

The three were so annoyed and angry with me and I couldn't wait to get dragged back to my cell and fucked for hours and hours until morning.

I wanted this. I wanted it to last for a long, long time. I dreamed about being the favorite bitch for the kawaii girls of this strange, hardworking prison. It was more of a dream come true than anything I could have hoped or wished for. And in no time did I feel that tug at my ankle as Rose and Blossom dragged me away from the shower and to my new, eternal home.

They carried me to a private cell and attached each handcuff to my wrists to either end of my iron bed-frame. "Don't move! You fucking maggot!" Blossom shouted, almost poking me in the eye and spitting at the ground.

"Ah... Will I get punished if I do?!" I asked.

Blossom held my eyes and nodded with a very stern face. I immediately started thrashing around, bucking and twisting until a sharp impact forced all the air out of my lungs as her heavy boot stamped down on my stomach. I ceased moving after that.

I lay there on my back, knowing what's to come, my ass flexing, longing for a harsh invasion. And it came, and when it came, it came with a vengeance. Rose took position between my locked thighs and rammed into my tight, abused, and incredibly horny anal depths. Blossom sat on my face, her bulbous glans pushing hard against my mouth and lips, sliding wetly against my nose, slapping my temples and forehead, smearing precum everywhere. She did everything in her power to force me into taking her engorged knob, while Rose plunged her prick as far up my ass as I had ever been and continued to ride my butt until Rose squealed, "Ngh, ngh, fuck! TAKE MY DICK, YOU DIRTY BITCH."

I felt Rose's engorged crown slam into me and it was over for the first time that night. Blossom ground her polehead into my temple, nose, cheeks, and smacking my chin and lower lip, forcing a sigh from me, which she took as an immediate invite for her cock to slip in through my parted mouth, then deep inside me, battering my throat.

Meanwhile, Daisy had found herself a nice, pink flogger, which she was tickling my stomach with.

"Maybe we can teach you something after all!" she threatened.

"Mmmgmfmmmfh," I mumbled with my mouth filled with Blossom's bloated dick, the meat filling my cheeks to their maximum and going through my jaw so far back my tonsils felt strained. It hurt so bad and was exactly what I had yearned for.

Daisy delivered a slow, delicious slap to my upper arm. The whip gently lashed the skin. A long, feathery swish, followed by an exquisite and explosive sting. It made me want to move away from the torture, but as I did the sweet pain from Blossom's stout, imposing cock massaged my insides along with Rose violating my innermost reaches in a relentless pattern.

Blossom erupted without warning inside my throat, spewing seed that I immediately gulped down. In the very next second, Rose unloaded her jism straight into my ass, her semen flowing deep into my belly in thick torrents. That feeling made Blossom pull her slimy shaft from my gullet to paint the rest of my face in the fluid she had deposited into the very pit of my stomach. Rose followed suit, hosing my body down with the remnants of her girlcum.

Once more I was discarded. When I regained consciousness both futas were standing in front of the door, with a simple smile.

"Maybe he is not worthless after all. I'll carry him to the shower again," Daisy said.

'Yes, more', my depraved brain thought. The three girls picked me up and half an hour later I was again tied down and ready to receive.

And boy, did those adorable girls deliver. They delivered round after round of rough sex, fucking the absolute shit out of me. A bunch of their kawaii sisters joined too, eager for their piece of my stretched-out asshole. Their plush bodies smacked against my beaten-up flesh while they continued pounding away, treating my battered butt and thighs as their fuck-hole.

I drifted in and out of consciousness and time became irrelevant. There was no darkness between the waves of orgasmic bliss, only constant flashes of euphoria and the deafening pleasure of feeling endless giant cocks destroying the inside of me. It went on and on and on, and I knew it'd never end. I'd spend the rest of my life like a prisoner, just a hole, getting gang-raped. There was no higher purpose to my life than this. I'd achieved it, finally, and they would continue to use me every day.

This is what I was destined for. To be the prison's number one cum-dump. For life.