By Brutal Beauty Bent

Chapter Three-1

Chapter Three

Prison Bitch

I’ve been scared out of my mind for months now. How do you compare varying states of terror? From being suddenly surrounded by screaming cops with guns to hearing the jury say guilty and the judge say life and the guards say this way to your next cell it’s all been a horrifying progression though ever-deeper levels of hell.

I certainly didn’t kill my next-door neighbor – though I’ve confessed to a sick obsession with her. Three years my senior, I grew up worshipfully ogling and eventually spying on her. She was just so hot! From climbing a tree to peek in her window at night, I eventually progressed to climbing a trellis when I knew her whole family was out so I could pop free a screen and sneak into beautifully stacked Madison’s bedroom.

All I wanted was a pair of her panties – and the chance to sniff her pillow and rig her computer camera so I could peep at her from her own desktop. I never dreamed leaving fingerprints and blood from scratching my hand would see me sentenced to life in prison at eighteen. I mean it defies common sense!

At five foot-four and one-thirty-five, I could never rape and strangle someone – much less a bigger, older woman I’d revered for years. That didn’t stop the prosecutor however. Whoever did kill her used roofies and my public defender was pathetic. So here I am, just about finished with the admissions process at the state prison I must henceforth call home.

I’m scared shitless yet again because I’m sitting here naked and shivering only minutes from joining my new cellblock. For the first time I’m going straight into general population. And like everybody else I’ll have walk in unclothed.

By some miracle I’ve escaped being raped so far. Surely that can’t last. Indeed I expect my reprieve to end at any moment. Still while I can I treasure the relief afforded by this interruption, this unexpected extra step in the usual procedure.

I have no idea why I’ve been brought from the admitting physical to this small interrogation chamber. Everyone else has been led away to their next designated cage. They’ve already met their no doubt predatory cellmates. In any case I’m beyond grateful for the delay.

Uncomfortable but uncomplaining, I shift my bare butt on the un-cushioned seat.

With my cuffed hands locked to the back of this simple metal chair, that’s all I can do. I certainly can’t kneel, lie down or stand up. A tauntingly more comfortable chair sits across the small table from me; a file folder with my name on the tab rests there in the center of a bright circle of light. Other than that harsh overhead lamp and my timid, skinny reflection in the wall-length mirror (no doubt concealing cameras and/or observers) the obviously soundproofed room is empty. But then a door in that mirror opens and that fact changes in a really big way.

The woman who emerges is enormous – and I don’t mean just the bosom beneath the badge.

She’s the largest guard I’ve ever seen and that includes the offensive line of our divisional champion high school football team. Her ash-blonde hair is secured in a tight bun and her brow well lined with responsibility. Her forty-something face would be attractive if it wasn’t so forbiddingly set; the gray of her gaze is pitilessly flinty. With only a scowl she takes the chair across from mine. Picking up my file she taps it against the tabletop and eyes me quietly. Finally she sets the folder back down without opening it.

“You didn’t do it.”

“Ma’am?”

I’m so surprised I forget to stay silent. She frowns thunderously down

“You’re a filthy little deviant. But you never killed that girl. Look at you. You couldn’t kill a kitten. Still, prosecutors got to become DAs, DAs got to become governor and so on up the ladder to the presidency. I’ve seen it over and over again. Got to rack up those convictions, justified or not. And nobody’s going to sympathize with anybody who breaks into a girl’s bedroom. Not even me, you f*****g slime.

‘So here you are, and what a rare treat too: a pretty-looking young white boy, long hair, clear complexion, barely out of high school and about the size of my fourteen year-old daughter. A convicted s*x offender, your defense at trial was that you’re really just an uncontrollable pervert. You are bloody chum going into a shark tank boy, you realize that right?”

“Absolutely, ma’am.”

“The only reason you haven’t been raped already is that I have an arrangement with some colleagues over at county, I knew you’d be coming this way and I paid them off to look after you for me. Now why would I go and do a thing like that?”

“Because you know I’m innocent?”

My unexpected savior snorts at this description.

“Partly, perhaps. You didn’t rape or kill anybody. But you still need to suffer for how you did violate that poor girl. Which brings us to my more selfish motivation for saving you.”

The look she gives me is unmistakable. A sinking in the pit of my stomach contrasts with a hideous stir of excitement just below that. Women in authority have always confounded and aroused me. I lower my gaze to see my stupid p***s begin twitching. This will be unstoppable.

“You want my innocence all to yourself. You want to oversee my punishment personally.”

“Exactly, delectable one. I will be your protector in here, tender virgin girly-boy that you are. But you will have to satisfy my appetites in return. And I mean eagerly and willingly at any time forever. You know how it goes with the alpha dog always getting the pick of the litter. You can be my little b***h – or everybody else’s on this cellblock. Take your choice.”

“Where do I sign?” My voice cracks like that of a pubescent. “You can really keep all the other rapists away from me?”

“Of course I can. Ask anyone here. I’m Officer Barnes. I run this f*****g block.”

“I’m delighted to meet you Officer. I’d shake your hand or even kiss your feet if I wasn’t handcuffed to this chair.”

“Well, in that case you’d better prepare to suck my cock.”

Before I’m even sure I heard this, Officer Barnes stands and unzips her pants. Reaching into those baggy institutional khakis she pulls out a big rubber dildo that she must wear strapped on underneath. Seeing my jaw drop even as my own virgin tidbit raises its shameless head she laughs with a kind of grim affection.

“I don’t carry lube with me boy. You want to go to the infirmary after losing your cherry?”

I shake my head emphatically and start licking my lips. By the time that huge woman is perched on the edge of the table in front of me (oh she towers like a mountain!) my own little wienie is stiffer than that big fleshy rubber one.

Having to do this for any man much less some scum-ball convict would have me retching myself to death. This is my savior however, a feminine benefactor I’m prepared to worship as an erotic goddess forever if it spares me the fate-worse-than-death I’ve been expecting. I’ll play the sissy as enthusiastically as she asks me.

“You’re outrageously erect down there. You really are eagerly willing, aren’t you?”

“Only for you, my owner. Please let me belong to you for the rest of my despicable life.”

“Prove to me that I should, b***h. Show me now why I shouldn’t just toss you to the gangs like insignificant garbage!”

I’ve never done what she wants of course, or had it done to me. But I’ve seen as much pornography as anybody. With my lips all wetted well I don’t hesitate to plummet onto that up-jutting erection.

Its realistically contoured head fills my mouth up superbly. Immediately I suck it, not like a living lollipop but like the giant-size lifesaver that it is. Savoring the taste not of crotch-hot latex but absolute female authority, I slurp and slather and swirl my oral organs-orifice all over that two-by-three inch ovoid. Drooling down the vein-wrapped shaft, I slavishly establish how ecstatic I am just to get to lovingly suckle. Before my owner can become impatient however I quickly go to work on urgently servicing her.

Seeking to add expertise to my mad enthusiasm, I lip-grip and knob-bob feverishly. I take as much thick shaft as I can in rhythmic sycophancy. Damn, I love the way my stuffed mouth is curved into a perfectly stretched circle! I even gag myself deliberately trying to take more organ than I comfortably can. When two huge hands palm my skull and force me to take it all, comfort be damned, I approve even as I’m wracked by automatically rejecting retching. Clearly deep-throat acceptance and endurance is going to be as essential a skill for me to master as it would be for a triple-x movie starlet.

What’s also obvious is that I’m going to need considerably more training.

I’m continuously trying to turn myself inside out throughout the many messy minutes that Officer Barnes spends grinningly force-f*****g my helpless face. By the time the saliva so over-spilling my lips that it’s coated my chin and throat runs all the way down to wet my own silly little stiffy, she decides I’ve lubed her sufficiently to f**k my far more satisfying other entrance. Only as she pushes me back, pulls sloppily out and rears upright does Officer Barnes let me know how much worse is in store for my squeamish gorge.

“You’d better school your system in submission quick, b***h. Slaves serve as their owner’s toilets in here too. It’s the second-best way to demonstrate total domination over your sub-human personal property. This is of course the best way.”

Her d**k still dripping with a viscous sleeve of spit, Officer Barnes is saying this as she unlinks my cuffed wrists from the fitting on the back of my chair.

She lifts me up as effortlessly as if I was the daughter of whom she spoke. Then dropping her khakis to her ankles she sits down in my place.

Again Officer Barnes handles me almost maternally as she pulls me onto her lap. Only instead of settling me crosswise I come down astride and facing away from her. And as I do she guides that big slippery prick up into my suddenly agonizingly compromised opening.

“Ah! Ah! Oh! I’m sorry but – ouch!”

“Go ahead and squeal, little piggy. No one can hear you but me. And I just love the sound of a b***h-boy sissy losing his virginity!”

“Oh, goddess, it hurts!”

“Good!”

So I let go of dignity and sob unabashedly at the agony coming up my ass. In history class we studied Vlad the Impaler, the Romanian prince who spawned the Dracula legend.

His preferred method of dispatch can be deduced from his identifier. And that’s what I feel like now: a condemned criminal being lowered onto the pointed execution stake. After skewering up through my guts I’ll be left to linger like this all day…

Not so fast – or should I say not so slow.

Once she’s got me securely spiked atop the first few inches of her, Officer Barnes begins bouncing me vigorously up and down.

Once again as easily as a momma dandling her babe she soon has me pogoing woefully on her up-jabbing erection. This longitudinal rhythm drives it so rapidly ever deeper up into me that she might as well be using a sledgehammer on that imagined gallows-stake. Immediately I begin shrieking through my already constant sobs.

Seeing my shrimpy-slim nakedness bobbing so comically in that one-way mirror, tears sheeting down my flushed, crumpled face as I bawl like that fussy babe, wondering how many might be watching and laughing at all this flames me ever hotter with unbearable humiliation. Then I begin slapping down fully atop my owner’s big lap at last. Officer Barnes has my bottom spiked completely and the excruciation of my first rape grows astronomically ever worse.

With my hands still cuffed my wimpy little body is reduced to a toy in this giantess’ grasp. The pain and shame and hideously stuffing-stabbing sensation of that invasion are all so horrible that I can only weep harder yet at the recognition of the scale of the challenge now before me.

If I can’t learn to love this, I will have to live with far, far worse. And while the female domination is exquisite, and that rag-doll manhandling of my naked helplessness secretly exciting, the rest is all a horrible nightmare. How will I ever feign eager willingness for this?

Officer Barnes seems to sense my distress.

Pulling me back against her hugeness so she can rub my n*****s, bounce me more brutally yet and speak right into my ear, she croons with soothing approval.

“Don’t worry, b***h-boy. It’s okay to hate it for the first few years.

“This is poor dead Madison’s payback, remember? Nobody knows who killed her, but you certainly betrayed her. It wouldn’t be a real punishment if you enjoyed it too much. Then I’d have to begin whipping and b***h-slapping you around before and after and through using you that much sooner. If this big p***s is too much for you to take, then just imagine your gorgeous neighbor has caught you spying on her and has turned herself into me in revenge.

“You’ve got a whole life sentence to come to terms with both your guilt and your emerging femininity, my permanent new sissy. For now though it’s enough that I’ve eradicated your cherry and you’re finally suffering so wonderfully! And look: some teeny part of you is enjoying your new s*x life a whole lot already!”

Without even withdrawing, keeping me pegged firmly onto her c**k-spike, Officer Barnes stands up. Lifting my little body by the d**k-stake I’m impaled upon, she exposes the shame of my own still rampant little erection to the mirror.

Oh God, she’s right, how could I still be so hard? After allowing me a roiling moment of reflection on that reflection, my gigantic mistress suddenly shoves me facedown over that table. Under that hot spot of incandescent light, with my official file scattering and printing backwards ink fingerprints across my t**s, she sets herself solidly and begins pounding into me properly.

Getting all her weight and strength behind it, and all her joy, lust and sadistic zeal for punishment, Officer Barnes butt-f***s me right back into shrieking delirium.

Dimly I can hear her exhorting me to come, to marry this kind of unmitigated agony-shame to s****l arousal forever. Despite suffering far worse than that initial impaling I can almost see how easily that could happen. But this is still my first pegging after all. I can’t really focus past anything but the constantly worsening trauma and the terrified awareness that I have a million more ordeals like this (or worse) to still get through.

Finally even my broken screams are drowned out and Officer Barnes is the one who is wildly coming.

Her feral grunt-shrieks sound like Serena Williams serving up an endless run of aces! And her rapidly slapping-and-stabbing hips-and-prick batters me so savagely against the table! Even though it’s bolted to the floor this hard metal surface shudders like my cuffed and pinned body, until at last my owner’s cataclysmic climax has peaked and passed.

When she pulls out after what seems like hours I can only wilt in sob-slobbery relief. But then with the snap of a rubber glove two fingers (each alone bigger than my still-erect prick) suddenly ram back up my ass.

What is this, another gratuitous body cavity search? Or something worse? Over my renewed gasp-sob-groans Officer Barnes confirms the latter.

“Hold still, bitch.”

She’s rubbing on the nubbin of my prostate in the most evocative way.

“We need to get rid of that stubborn little stiffy. And we really need a semen sample that we can plant in evidence in case someone someday manages to secure you a new trial. I’m not letting you go that easily. If you won’t spew before being locked up, we’ll have to get it from you the hard way. Though I must say, you’re really jeopardizing my protection already by not cooperating, boy.”

“I’m so sorry!”

And I’m so hard!

Oh, my little tadger feels as dense as a neutron star! Stuck to the last knuckle in my brown-if-not-black hole, Officer Barnes’ rubbing is doing something truly insidious to me. Compared to that excruciating p***s-pounding it’s less damaging yet even more unendurable. When other fingers rub my perineum, massaging the prostate from both inside and out, I’m suddenly certain I need to pee despite how painfully hard that rubbing now has me.

“Officer, I’m going to—”

“Shush, boy.” Her voice is as surprisingly gentle as those fully inserted fingers. And naturally my owner knows what she’s doing. Just as that need-to-pee feeling peaks it passes. And the fluid now dribbling thickly from my glans has the scent and consistency not of pee but seed!

Though I’m having no orgasmic spasms, my screaming steeliness and bloated sacs are inexplicably emptying themselves. Officer Barnes gloatingly explains as she massages me professionally on and that second hand now holds a plastic evidence container up to catch what’s being so methodically drained out of me.

“I hope you’re enjoying your first milking slave. Aside from providing the proof that will keep you in my power forever, this is the only way you can ever again hope to empty yourself.”

After capturing the last dribbles Officer Barnes withdraws her fingers and snaps a lid on that vial. The gloves come off, her pants come back up and her big c**k is tucked away.

Effortlessly I’m flipped over. Into one pocket goes the semen sample that damns me forever. And from the other pocket comes a clear silicone chastity device that is locked swiftly onto my finally flaccid c**k – doing likewise to my ejaculatory capacity.

“As long as you wear my p***s cage, everyone in this prison will recognize you as my property. None of them will harm you without my express consent.

“Of course you’ll have to go without erections or orgasms, but that’s a small price to pay to avoid homosexual rape. The other prisoners might despise you as my favorite, but they won’t dare to touch you. The only time you’ll have to worry about suffering an extended gay gang-banging is when you somehow disobey, displease or otherwise fail to completely fulfill me.

“So you see, you really should have ejaculated when I ordered you to.”

Officer Barnes is already turning to toward the door. “Someone will come and take you to your new cell. As I said, the other cons are going to revile you the whole way. They’re just jealous, and upset they can’t have you for themselves. Ignore them. And don’t give me any more reason for them to get their hopes up!”

With that my protector has gone, leaving me shivering naked and handcuffed once again.

Still badly terrified, I’m now abysmally sore and limitlessly appalled as well. But at least I’m no longer a semi-innocent virgin.