Jack Brown stepped out onto the mezzanine overlooking the great hall below and his
craggy face broke into a smile. If he had to choose a favourite place in this miserable,
god forsaken prison, then this would be it – standing right here, the air thick with the
barely concealed fear of his charges, trembling hands longing to cover their bared
buttocks as they waited in line for his arrival – It was a pleasure he was quite sure he
would never tire of.
Jack was in especially high spirits this morning, and the new girl was the reason
why.
His eyes were immediately drawn to the pretty little red head as she shuffled bare
foot to the end of the queue, and he smiled as his wife pulled up the terrified girl’s
skirt and tucked it into her belt so that the delicious pink mounds of her buttocks were
fully exposed to him. It always warmed the cockles of his heart to gaze upon a virgin pair
of buttocks for the very first time, and this girl’s pert, but delightfully fleshy orbs
were especially pleasing to his discerning eye. Her flesh was as pale and perfectly smooth
and blemish free as the finest alabaster, and the thought that he was going to be the
first to mark her had his cock twitching in his pants.
It was 7:30am and his girls had already spent an hour scrubbing floors and mucking
out water closets. This was his wife’s department, he had no real interest in that – apart
from the fact that he was able to soften her cruel acts of punishment with his dick - No,
he dealt solely with their education, and he considered their penance to be an important
part of that education. Nobody escaped this ritual, not even little Rose Duke, the newest
and quite possibly the most delectable convict he had ever had the good fortune to lock
up. He was as sure as a man can be that her tight little cunnie had never been visited by
any man. A specimen as fine as her would not remain under his care for long but he was
determined to savour every moment of her time here. His cock was itching to explore her
untouched honey pot…but he wouldn’t be the one to do that. There were other ways he could
scratch that itch and still cash in on her virgin flesh. She would fetch him a princely
sum, of that he was sure.
Most of the girls who passed through his establishment had already sold their souls
to the devil and thought nothing of opening their legs for him or anyone else who favoured
them with a smile or an extra spoonful of broth. There likes were usually sold to the
dockside brothels. Only the ones who refused to comply, served out their miserable
sentences with him, not that he didn’t make good use of their loosened cunnies and foul
mouths, but it would be a shame if one so beautiful and ripe for the plucking as little
Miss Rose Duke, should end her life in such an unfortunate way. It was a rare treat to
have such a beautiful, untouched wench in his midst and he was looking forward to
‘tutoring’ her.
The clock on the wall chimed the hour and Jack Brown licked his lips, adjusted his
trousers, to make room for his growing organ, and headed for the staircase. He could
barely tear his eyes away from the perfect contours of Rose’s quivering buttocks as she
waited for her turn on the whipping bench. God help him, he would love to be the one to
press his hard cock against her virgin cunt and watch that look of innocence in her eyes
turn to one of carnal knowledge. Taking her ripe little cherry was a tempting treat, but
he knew that her worth to him would instantly be halved if he were to succumb to such
baser urges. His eyes wandered towards his wife…It had been a long time since he’d
indulged in a clean, tight cunt.
Jack wiped his brow and took a deep breath. A red bloodied man needed the regular
sustenance of warm female flesh; hadn’t God made them so comely for this very reason?
Jack put aside his thoughts to concentrate on the task at hand and began his slow
descent of the staircase, his immaculately polished boots clipping each steel edged rung
as he made his way down into the hall below. He liked to make a production out of this
daily ritual. He liked to prolong the girl’s agony for as long as possible. He knew they’d
be juicing up between their hot little thighs. In spite of the fear these girls showed on
their faces, and in their trembling fingers, he knew their evil little backsides loved the
sting of his cane. The fact that he made better use of some of these poor souls than the
law actually allowed should be applauded. And, truth was, no one seemed to notice, nor
care, that very few of his girls ever returned to their former lives as reformed
characters. Most people were simply pleased that he was keeping them off the streets, and
didn’t care what became of them once they stepped through the doors of his prison.
At the bottom of the steps he paused.
‘Good morning, girls.’ He smiled as Rose let out a whimper, and noted with
satisfaction that tears had collected, and now brimmed in her long lashes, threatening to
spill down her porcelain cheeks at any minute.
‘Good morning, sir,’ they recited back, without turning their heads towards him.
Their eyes, as instructed, were firmly fixed on the whipping bench set in the centre of
the small stage at the head of the long room – and on the shiny length of cane that would
soon be warmed on the flesh of their errant behinds.
‘Take a good, long look,’ he encouraged, aiming his words at his newest student.
‘Let the sight of this simple rectifier of wrongs burn itself into your sinful brains so
that when you leave here it will remind you to always do as your superiors bid and not as
you feel fit…and remember too, that Jack Brown has an extra special punishment for repeat
offenders who find their way back to my door.’
Jack made his way towards the front of the queue, stopping occasionally to point
out a girl whose cleanliness didn’t meet with his exacting standards. He liked to keep his
girls immaculately clean and handed out a matchstick for each fault he picked up –
matchsticks that would soon be exchanged for extra strikes of his cane when they reached
the front of the queue – before finally climbing the three steps to his podium to stand
beside the whipping bench, facing his flock of nubile young sinners, his throbbing cock
now fully erect and straining against the material of his trousers.
‘Today I am both saddened and heartened to introduce a new inmate into your midst.’
He paused for effect but it was a speech most of the assembled girls had heard many times
before.
‘Saddened because this young girl has chosen a path of evil, yet at the same time
heartened that her foolishness has led her to be delivered into my guardianship instead of
the hangman’s noose or the badlands of the colonies, and with God’s help I will turn her
head away from wickedness and guide her into the service of man with a humble yet willing
smile.’
The girls remained silent, apparently taking in every word he said, but Jack knew
that most of their minds were incapable of focussing on anything other than the well used
wooden whipping bench that they would soon be laying their quivering bellies across, and
of his cane that would cleanse their dirty souls in readiness for the day’s toil.
‘Come.’ Jack beckoned the first girl in line to step up onto the stage and she did
so with only the merest hint of hesitation. Her bare feet hardly making a sound as she
made her way across the rough wooden boards towards him, took the cane from its resting
place, and passed it into his hand before obediently taking up her position over the
curved bench, her trembling hands grasping the smooth wooden handles as Jack Brown
strapped, fist her legs and then her torso, to the bench. Her hands were left free. If she
dared to move them to cover her buttocks, she would receive an extra lash of the cane.
Girls rarely moved their hands. Their fingers remained tightly wrapped around the wooden
handles, knuckles turning white as their knees began to tremble in fearful anticipation.
Jack let her ponder her fate for a few more seconds. This girl was ready to leave
his care. He had already secured her a position as scullery maid…not that her duties would
end in the blackened ashes of last night’s fire. Nor would that be the only glowing ember
she would be expected to extinguish. His girls never left The Reformatory without first
perfecting both oral and anal skills.
Jack moved closer. This girl had handed him no matchsticks so would only receive
the customary daily penance of two lashes.
He lifted the cane and let his eyes pass along the line of waiting girls, relishing
the unease he saw on their faces, before pulling the cane through the air with a loud
swish that seemed to cut through the tense atmosphere with the deftness of a fine sword.
The girl flinched as the cane cracked loudly against her flesh, her whole body
appearing to shorten as her muscles tensed in an attempt to escape the pain but her
position offered no relief and Jack watched with satisfaction as she bit into her lip and
a fresh red welt spread across her quivering left buttock (her right orb still bore
yesterday’s penance) and her legs now quivered in anticipation of his next strike.
Jack didn’t disappoint her and brought it down in a well practised parallel line to
the first. This time he clearly heard her sharp intake of breath and the bench rattled as
her body reacted to this second fiery blow. She appeared to be visibly more relaxed now
that her penance was over for good, but he knew she would be eager to rub at the stinging
pain permeating her pert little behind.
‘You may leave.’ He undid the buckles and she pushed herself off the bench, took
the cane from his hand and quickly replaced it in its holster before descending the steps,
her hands travelling straight to the freshly raised tramlines burnt into her pale skinned
buttocks. She rubbed at them furiously in an attempt to relieve the stinging pain. Jack
watched her take up a position on the far side of the hall before calling his second
sinner to the stage.
This one handed him two matchsticks along with the cane. One he had given her only
moments ago, for the stray hair that had escaped the neat bun she wore, the other had been
handed out by his wife for some other misdemeanour committed, and meant that this girl
would receive four strikes of his cane this morning. But this girl was also wearing a
punishment collar - a leather strap synched around her neck with a smaller leather cuff
hanging from the back of it, to which her right wrist was buckled.
‘What did you do to earn such a punishment?’ he asked.
‘Nothing,’ the sullen girl replied, but Jack noticed the bloody red marks across
her knuckles where his wife had beaten her and guessed that those fingers had been caught
exploring her cunnie. Some girls seemed incapable of exercising any self discipline, and
he doubted that her blooded knuckles would deter this little fire cracker. The thought
tugged at Jack Brown’s cock.
He nodded for her to take up her position across the whipping bench and examined
the flesh on her well rounded buttocks as she did so. The left cheek was still well
bruised and bore the deep red glow of a girl who seemed incapable of obedience, but her
right buttock was even more scarred by his cane. It was difficult for him to find fresh
flesh to punish. This flaxen haired beauty was a hard case, and no mistake. If she didn’t
buck up her ideas soon she would be destined for the stinking hold of a ship bound for the
colonies. Some girls simply learnt to cope with the pain of the cane, and whereas he could
always find a gentleman with a fondness for beating flesh, he also had a commitment to
fulfil to a certain ship’s captain and, if truth be told, he had a mind to teach this
insolent wench a lesson she would never forget. Girls who refused his ‘acts of kindness’
were far too dangerous.
He lifted his cane as far back as his arms would allow - an action that brought a
collective gasp of horror from the assembled group - and brought it down onto the girl’s
buttocks with such force that the wooden bench beneath her creaked under the strain - two
swift and vicious blows to each cheek before dismissing the hussy.
She stomped defiantly off the podium, not bothering to unhitch her skirt nor clamp
her hand across the burning stripes he had laid into her flesh, but Jack was heartened to
see tears glistening in her eyes. He wagered she’d be sleeping on her belly tonight.
Jack swallowed hard, adjusted his trousers and wiped sweat from his brow as Rose
Duke stepped hesitantly up onto the podium, her bottom quivering and unblemished.
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