The Jailhouse Blues Ch. 02

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

(Greystone Prison operated a staggered-shift system, and ran a free, two-hourly, round-the-clock Greystone Prison - Brighton Bus Station bus service for its staff: the next two buses would depart from Greystone Prison at 20:15 and 22:15 - and those two services would return, departing Brighton Bus Station at 21:30 and 23:30).

Prison officer Billie Jo said, "Ma'am, could you ask Adele in the bar to put a couple of beers in an ice bucket for me and officer Bella Donna? We'll be in for them once we've returned prisoner Lightwood to his cell."

"Of course, BJ," said the Governor (Oh, it's 'BJ' now, is it? I thought - now that they were off-duty). "I'll let her know you'll be about ten minutes."

"Um... we might be a bit longer than that, ma'am. I want to have a... little chat with prisoner Lightwood."

"Ah... I see. Of course, BJ. I understand perfectly. Prisoner Lightwood sullied your good name. He impugned your fine reputation. Cast vile aspersions. Made egregious, groundless allegations. Assassinated your character. Of course, you must have a... little chat with prisoner Lightwood. I mean, where would we all be, if we let these things go unchecked?"

"My thoughts exactly, ma'am," agreed prison officer Billie Jo. "But we won't be long. And then we'll join you and the others in the bar for a cold one."

The angelic, too-lovely-for-words prison officer Victoria, piped up, "Ma'am, I don't drink. So if it's okay with you, I'll help Bel and BJ escort prisoner Lightwood back to his cell - in case he doesn't want to go quietly."

"Ma'am," said prison officer Billie Jo, admiration in her voice. "I've said it before, and I'll say it again: Vicky, here? She's a natural!"

* * *

"Well go up in the lift," said prison officer Bella Donna, slightly out of breath now as she and prison officers Billie Jo and Victoria escorted me across the open expanse of the Ground Floor.

They'd had a struggle on their hands in getting me up the basement steps, and, much to prison officers Bella Donna and Billie Jo's displeasure, a number of prison officers had had to be summoned from their barstools to assist them.

While they'd waited for prison officer Victoria to return with the extra helping hands, prison officers Bella Donna and Billie Jo had expressed to me in no uncertain terms their strongly-held sentiments as to why, from now on, my life wasn't going to be worth living.

Now, handcuffed again to prison officers Bella Donna and Billie Jo on either side of me, they cursed me bitterly as they continued to support the cumbersome weight of my sagging, walking-wounded body, while prison officer Victoria did her bit by putting her hand inside the back of my shorts and hauling me upright by the elasticated waistband.

As it happened, the lift was already at the Ground Floor. Prison officer Billie Jo pressed the Call button, and when the door opened she gave me a look that sent chills tingling unpleasantly down my spine. "Right, you... Get in there!"

When prison officers Bella Donna and Victoria moved to follow us into the lift, prison officer Billie Jo said, "Bel, could you and Vicky use the steps? I'd like a few moments on my own... with Grass-up, here."

"Heh heh heh... No problem, BJ," said prison officer Bella Donna, removing her handcuffs from my right wrist. "Me and Vicky will take the stairs. We'll wait for you outside the lift on Level One."

"Don't let anyone into the lift on Level One, Bel. And I'll disable it from being called to another Level. I won't be long. I just want a bit of privacy, while I have a... little chat with prisoner Lightwood."

With that, prison officer Billie Jo closed the lift's door on prison officers Bella Donna and Victoria's smiling, nodding faces.

When the lift's door had closed on us, prison officer Billie Jo stood in front of me and flexed her whippy cane... and then she stood her cane in the angle of the back left-hand corner of the lift. "I won't be needing that," she told me. She then removed her handcuffs from my left wrist, and tossed them over towards her cane in the corner. The shiny metal cuffs hit the lift's bare metal floor with a dull clang. "Or those," she said.

"Now... It's just you and me - Grass-up!" said prison officer Billie Jo, as she put her hand down the front of my shorts, going for my balls. "Time for our cosy little chat!"

She tried to grab hold of both testicles together. But, due to prison officer Bella Donna kicking them five times, while I'd been restrained to the Wheel of Chastisement, my balls were now too swollen to fit into prison officer Billie Jo's small hand.

So she settled for firmly grabbing hold of just one of them.

Immediately, wave upon wave of pain-filled nausea flooded through me as prison officer Billie Jo cruelly rekindled all of my terrible hurt, fanning the flames of agony anew to a new, unspeakably devastating dimension of testicular torment.

I started sagging to the lift's bare metal floor, no longer able to support myself as the modicum of residual strength I'd had now drained out of me like water from a collender. "Oh no, you don't - Grass-up!" snarled prison officer Billie Jo. "I said: stand up!" she snapped, as she gave me a 'little helping hand' to do just that.

The pain was indescribable.

Indescribable, as prison officer Billie Jo's 'little helping hand' took me straight to hell. She was literally hauling me upright, by one tortured, semi-tenderised testicle.

"So... grass me up to the Governor, will you, prisoner Lightwood?" snarled prison officer Billie Jo through gritted teeth, emphasising each of her words with a none too gentle squeeze of her 'little helping hand'.

The pain was terrible.

Terrible, as I moaned and groaned in wretched, abject misery.

"So... (squeeze) I'm corrupt, am I? (squeeze squeeze, squeeze squeeze). I'm no good, am I?" (squeeze squeeze squeeze, squeeze squeeze).

The agony was unbearable. "Please, Miss Billie Jo!" I cried beseechingly. "I'm sorry!"

With her remarkable capacity for astonishingly accurate, true-to-life imitation, prison officer Billie Jo sarcastically mimicked, "Please, (squeeze) Miss Billie Jo! (squeeze squeeze squeeze). I'm sorry!" (squeeze squeeze).

The anguish was intolerable. "Oh! Please, please, Miss Billie Jo! I beg you!" I wailed, in pure torment. "Please, please stop!"

And prison officer Billie Jo cruelly mimicked, "Oh! (squeeze). Please, please, Miss Billie Jo! (squeeze, squeeze, squeeze squeeze squeeze). I beg you! (squeeze squeeze squeeze). Please, please stop!" (squeeze, squeeze squeeze).

I was at the end of my tether - I just couldn't take any more. "Miss Billie Jo! I'm sorry! I'm so sorry! And it'll never happen again. I promise! Oh, please, Miss Billie Jo! Please! I'll do anything, Miss Billie Jo! Anything!" I desperately pleaded and promised.

And prison officer Billie Jo sadistically mimicked, "Miss Billie Jo! (squeeze squeeze squeeze). I'm sorry! (squeeze squeeze). I'm so sorry! (squeeze squeeze squeeze). And it'll never happen again. (squeeze squeeze squeeze squeeze squeeze). I promise! (squeeze squeeze). Oh, please, Miss Billie Jo! (squeeze, squeeze, squeeze squeeze squeeze). Please! (squeeze). I'll do anything, Miss Billie Jo! (squeeze squeeze squeeze, squeeze squeeze squeeze). Anything!" (squeeze).

So why didn't I keep my mouth shut? I asked myself. All I was doing, was playing straight into prison officer Billie Jo's hands - or rather, her 'little helping hand'.

When I didn't say anything further, prison officer Billie Jo grunted disappointedly, and with obvious reluctance she finally let go of my grossly swollen right testicle. "Huh! Not an ounce of guts in you. I was expecting more from you. But you are not much more of a challenge than your pathetic cellmate - snivelling little crybabies, the pair of you!"

As she watched me slumping slowly to the lift's bare metal floor; my tear-streaked face contorted in agony; my hands protectively cupping my ballooned and battered and badly-bruised balls; and my body crumpling and folding like some bargain basement store mannequin until finally I was laid out flat on my back, her face wore a highly-gratified expression.

The lift's bare metal floor was unpleasantly cold. I could feel the chill of it through the thin material of my prisoner's dark-grey uniform T-shirt, which was scant protection indeed. But what was far worse, were the raised ridges of the floor's grated surface, designed to make the floor non-slip. The thin metal edges dug painfully into my back, and played all sorts of merry hell with my severely-caned bottom.

But I didn't care about that. I couldn't have cared less, about that. Because it was over, at last. My unspeakable testicle-torture ordeal was over. Oh, it was over. It was finally over, thank... Prison officer Billie Jo crouched down, and snarled into my face, "You've got that right - Grass-up! You will, do anything!" she agreed meaningfully.

"You think this is over? You think we're finished? You think I've done with you? Think again - Grass-up!" said prison officer Billie Jo as she stepped up onto my chest; the pressure of her not insubstantial body weight causing the thin metal edges of the lift's bare metal floor grating to gouge painfully into my shoulder blades. I moaned and groaned at this new source of pain.

But then prison officer Billie Jo relieved me of that discomfort, when she kicked off her thin-rubber soled flip flops and stood full-weight on my face, barefoot.

"Because I've not!" she snapped, looking down on me. "Do you think I'm letting you off so easy? Eh? After everything you've done?"

No one had ever stood on my face before, and I was now finding the pressure on my facial bones considerable.

I was immeasurably grateful that at least prison officer Billie Jo's body weight was evenly distributed, with the soles of her warm, slightly sticky bare feet occupying either side of my face. And also that she had acquired a good, assured grip, a surety of purchase which lessened somewhat the chance of her slip-sliding off my face, and stretching my facial skin painfully as she did so.

But then prison officer Billie Jo pushed the lift's button for Level 1.

Because prison officer Billie Jo was standing full-weight on my face, the sudden jolting movement of the lift's ascent caused some of the thin metal edges of the lift's bare metal floor grating to dig agonisingly into the back of my head. The pain was excruciating. But apart from telling me to be grateful I wasn't lying on a bed of nails, she ignored my renewed moaning and groaning noises of complaint and distress.

But the sudden jolting upwards movement of the lift hadn't troubled prison officer Billie Jo a bit.

Before pushing the button for Level 1, she had adjusted her face-standing stance. Standing with the sole of her right foot now over my lower-face: her heel, painfully pressing into my lips; the ball of her foot, agonisingly crushing my nostrils; her toes, curling around and firmly gripping the bridge of my nose - and with her left foot assuredly planted along my forehead, with the pads of her toes firmly pressing down just below my hairline, she was more surefooted than any mountain goat.

To my intense relief, prison officer Billie Jo then stepped off my face, and back onto my chest... But my relief didn't last for long.

Prison officer Billie Jo turned herself around on my chest, so that I was looking at the backs of her legs... The backs of her shapely, well-toned, olive-complexioned legs.

Legs... oh, lovely legs, such lovely legs - great legs... of which I now had an almost unrestricted, almost perfect up-skirt view.

And, being a leg man, I was far from being averse to beholding and appreciating the fabulous sight.

But prison officer Billie Jo's great, olive-complexioned legs weren't the only treasures I had an almost perfect view of...

Because, from my worm's-eye vantage point, I could see right up prison officer Billie Jo's uniform pale-blue short skirt... all the way up, past her smooth as silk, olive-complexioned thighs, to the exciting contours of her shapely bottom... to her uniform pale-blue panties.

Oh, god! I thought. Oh my god!

Despite myself - despite my present and continuing pain and suffering; despite my sadistic subjugation; despite the devastations of my harrowing, abominable affliction - despite everything! - I couldn't help but look.

Thinly, tantalisingly veiled, inside the soft, pale-blue material of prison officer Billie Jo's uniform panties, was the treasure of treasures... the holy grail.

I couldn't help but look. I couldn't help but stare. I couldn't help but ogle. What a sight!

And incredibly, despite this terrible woman's appalling treatment of me; despite prison officer Billie Jo's sadistic subjugation of me; despite suffering her heinously cruel torment - despite everything! - I couldn't help... but want.

And prison officer Billie Jo said, "Prisoner Lightwood... are you looking up my skirt?"

She knew. Oh, of course she knew...

This was what Greystone Prison was all about - prison officers Natalie and Melanie had told me as much, back in the Security Checkpoint building while admitting me into the prison.

And I knew that it was useless to lie. Knew, in fact, that prison officer Billie Jo wanted me to lie! So that she could have more fun with me, administering an extra dose of corrective 'therapeutic treatment'.

"Well, prisoner Lightwood...?"

The lift suddenly jolted to a stop. But prison officer Billie Jo made no move to open the door.

And what's more, I knew that prison officers Bella Donna and Victoria would be standing sentinel outside, ensuring that no one else entered the lift until prison officer Billie Jo was good and ready to come out.

Prison officer Billie Jo suddenly raised her right foot, and with literally breathtaking force she crashed the bottom of her bare heel down into my solar plexus. The air whooshed out of me, and pain; awful, sickly pain, pulsed and radiated from my grievously injured testicles, spreading out to every part of my body. For the second time today, I was seeing bright and sparkly stars; seeing dancing white lights, cavorting in front of my eyes.

"Prisoner Lightwood. I just asked you a question. I've got a nice, cold beer waiting for me down in the bar, and I don't appreciate you keeping me from it. But we won't be getting out of this lift until I'm good and ready. Not until we've finished our little chat."

Somehow, I found the air to gasp, "Yes... Miss Billie Jo. I... I am."

Prison officer Billie Jo again turned herself around on my chest, so that she was again looking down on me. Raising her right foot behind her, this time, and with the top of her foot this time, she delivered a second, even more devastating kick.

This time I had no breath left in me to whoosh out. But the dancing white lights in front of my eyes were now joined by lots of coloured ones, in a shiny commingled spangling of brightly coloured dots. Long seconds passed, and I found I was unable to resume breathing. I thought I was going to pass out, this time.

Not that I wouldn't have welcomed temporary oblivion, right then; I'd have welcomed it with open arms. Welcomed the relief, of oppression free, painless unconsciousness.

"You are what, prisoner Lightwood? Say it!"

This time I didn't know where I found the breath from. I only knew that I must answer; that I mustn't make prison officer Billie Jo repeat herself again. "I - I'm... looking up... your skirt, Miss Billie Jo."

The undersides of her toes were curled over my collar-bones; every one of her ten toe pads, gripping surely into the soft and tender flesh on the other side of them nearest my neck. Her firmly pressing toe pads were causing an awful, dull pain, to add to all of the other pains.

Prison officer Billie Jo had a very strong grip with her toes, I thought. Incredibly strong... A suddenly jolting lift? We could be on a ferry in the middle of the English Channel in a force ten gale, I thought, and even the violent and wholly unpredictable this-way-and-that-way yawing motions of the turbulently pitching and tossing vessel wouldn't be sufficient to dislodge her from her clavicle-clutching toe-grip.

Prison officer Billie Jo then stunned me - shocked me - when she said, "Prisoner Lightwood. I know what you want... You want my pussy. Don't you?"

I couldn't believe what I was hearing.

Never in my life, had I been so startled. I mustn't have heard right, I told myself. In fact, I feared that my balls weren't my only faculty to have gotten damaged today.

"Oh, you needn't look so shocked, prisoner Lightwood. You want my pussy, and I know you want it - really want it. It's as plain as day," prison officer Billie Jo told me, matter-of-factly.

"Unlike prisoner Chapman, who is a virgin - and furthermore, I shall ensure that your wimpy cellmate remains a virgin, until the end of his miserable, useless days - you are actually quite... experienced. Aren't you? You've been... around. You've been 'around the block'. A woman knows, you see. I know. I can tell these things. A woman like me, when she looks at a man like you... can tell many things."

I could barely believe my own ears.

But worst of all - I believed her. I believed that prison officer Billie Jo was speaking the truth. Believed, that she actually could, tell... many things about me.

"You are attractive to women, prisoner Lightwood. Some men have it, and some men don't... sex-appeal, I'm talking about. I bet you are a bit of a lad - sorry: past tense. Past tense, because your sex-appeal is of no use to you now. Not any more. Not in Greystone Prison.

"Yes, I imagine you were a right little Lothario. I bet you were a regular Casanova, adept at sweeping women off their feet, and into your arms... and into bed.

"But, prisoner Chapman - the prisoner who said 'No' to me twice? I know that he hasn't yet become a man - and now he never will. He'll never achieve true manhood... because I'll ensure he never knows what he's missing.

"But you, prisoner Lightwood? You are another matter. Another matter entirely. You are going to miss, a... woman's touch."

When I didn't immediately reply to prison officer Billie Jo's stunning statement; didn't respond, to her shocking observations and chilling assertions, she raised her right foot threateningly again and snapped, "Do not provoke me, prisoner Lightwood - I'll let you have the next one in the balls! I don't care how hurt you are! I said: you want my pussy. Don't you?"

The saying: 'Hell hath no fury like a woman scorned', suddenly sprang to mind. And I wondered how applicable that was to me now: If I was to say: 'No, Miss Billie Jo. I don't want your pussy'.

But, not waiting for my response, prison officer Billie Jo then produced her biggest shock.

Still standing on my chest and looking down on me, prison officer Billie Jo hitched up her uniform pale-blue short skirt, pulled her uniform pale-blue panties down to her ankles and, with her clavicle-clutching toe-grip firmly securing her perch, slowly she lowered 'herself' over my face... Until I was looking up at the pink lips of her vagina, positioned mere inches above my incredulous eyes.

"There! Pussy! Pussy, prisoner Lightwood. My pussy. Look! It's what you want, isn't it? Have a good look... Look!"

I looked... prison officer Billie Jo's importunities were not needed. Her harshly spoken orders were redundant. Her aggressively delivered commands, unnecessary. Her imperiously issued instructions, surplus to requirement. For once, I had no problem with obeying one of her commands.

I looked... Prison officer Billie Jo's womanhood was shaved. Her black, new hair was just starting to show, and her—

"You want it. You want it, don't you, prisoner Lightwood? You want my pussy. Don't you...? Answer me!"

1...56789...12