Climax in Purgatory
What if the true torment of Hell was endlessly reliving life’s most profound sexual regrets?
He awoke in blackness. Dazed and disoriented.
His awareness was slowly coalescing, like the icy rubble of asteroids sinking inexorably towards an embryonic planet. His sense of being returned first, the deadweight of his own body, becoming aware that he was lying on his back, his limbs sprawled out and weak.
Burning sensations began to arrive from his skin, as if he was lying under the blazing sun; yet all around was darkness. Even as his vision began to return, the enveloping blackness remained an impenetrable blur. Whether above him was night sky or dungeon ceiling, it was impossible to tell.
In the gloom, a distant glint sparkled like the Morning Star, but somehow he knew it was the Blade.
* * 1 * *
The ground around him seethed and bubbled. A fierce red glow scorched his face, forcing him to squint at what eventually resolved into fiery ponds of molten lava, which spat and sputtered in every direction. It looked like how he’d always imagined a volcano’s furious heart, a sea of searing incandescence, painful and intensely perilous to behold, like a gorgon’s stare.
His bones ached, accompanied by a dread sensation. Something felt very wrong. He hoped he hadn’t carelessly tumbled into a volcano’s terrible smoking maw, but couldn’t actually remember where here might be, or even how he came to be here. He felt a queasy fear, like he might have made a terrible mistake.
New details slowly emerged from the darkness. He was lying on a boulder, a plate of hot flat rock, coarse to the touch but not jagged, like a granite. The boulder was surrounded by a seething bubbling pool of fire, which provided the only source of illumination. It resembled a room inverted, its ceiling cloaked in darkness, its floor burning with a fiery golden light. Around him were no walls, just billowing curtains of inky noxious smoke.
He noticed he was naked. The baking breath of the surrounding furnace was already roasting his skin, making the side where the hot gusts hit feel painfully tender. The boulder he was lying on was one of several plinth-like rocks that lay in a long meandering line, all partly submerged in this strange frightening sea of fire, like an infernal pathway of stepping stones. The boulders seemed to lead towards a larger rocky outcrop, its outline becoming faintly visible as its smoky shroud began to billow and thin. It was in the same direction that the glinting light was sparkling.
Groggily, he rose to his feet. A searing wind stung his eyes, forcing him to form a visor with his hand. Where he lay, he noticed markings, unnatural ones scratched into the rock, like primaeval carvings. Black writing. Sinister obsidian runes.
Perturbed, he rose to his feet, teetering on unsteady legs as the sluggish magma rivers gurgled and steamed threateningly all around. He soon realised that the rock he was standing on was scorchingly hot, the rising heat already burning the soles of his bare feet. There was another rock a short leap away, so he made the short hop across the fiery crevice. That stone felt marginally cooler, but only momentarily, it seemed any time he stopped to linger, the blistering heat of the ground beneath his toes was propelling him forward again.
The star that was not a star was glinting brighter now, straight ahead. There seemed to be an unsettling impetus behind his movement, like he was being compelled by some malign force towards some kind of ominous beacon, like these bizarre stepping stones were a pathway to a site of punishment. Or sacrifice.
He hopped closer, now two tall posts emerged from the mirk, protruding upwards from the top of the outcrop, looming like vacant flag posts, or empty gibbets. Trepidation made him hesitate, until the increasing heat beneath his feet became intolerable, and he was forced to leap forward onto the rocky outcrop. This was much wider than any of the stepping stones, feeling immediately cooler to his poor scorched feet. The poles loomed above him now, the colour of sooty rusted iron, with shackles dangling ominously from both tops and bases.
He felt his skin prickle, as if long-dormant primal instincts were trying to warn him: that he was not alone here. That some sinister presence was stalking him. Hunting him. But where could he run? How could he run if he didn’t even know where he was?
A shadow suddenly enveloped him, causing him to flinch in fear. Something large had dropped from above, landing beside just him. His eyes instinctively scanned this intruder. He noticed the lithe curves of its feminine form first, only then its chalky white skin, which gave it the appearance of a tall baleful statue.
It - or was it she - was hairless, even her head being completely bald. Her eyes were red, with narrow black feline pupils. Her breasts were small with stubby black nipples, like tiny lumps of coal. Ripples of muscles were visible beneath her limbs and tummy. Her mound was as smooth as the rest of her skin, sloping down to an obvious cleft. She had short black talons, and a gold bangle on her wrist. She was both unnaturally alluring and disturbingly grotesque.
She also had what seemed at first glance to be a tail. He stared between her legs, where a long black leather thong was dangling as far as her knees. It was as thick as two fingers, with a glistening hilt at the top, just where it disappeared into her body.
He racked his memory, trying to make sense of what he was looking at. Folklore had a special name for female demons, didn’t it? He remembered seeing crude medieval paintings, of naked demons sitting astride sleeping men, fucking them in their beds to steal their souls as they came. Succubus - yes that was the word he was looking for; they called these demonic parasites succubi.
“Kneel!”
Her mouth had opened into a snarl, revealing two pairs of fangs amid a row of silvery teeth. Her voice was like a dozen people yelling at once, but not perfectly synchronised, which gave her words an unnerving dissonance. The multitudinous voices roared much louder than he’d ever heard a single person shout.
He kneeled obediently, completely forgetting his nakedness.
“You have been judged,” the discordant voices roared.
He had many questions, but found he was unable to speak.
“I know all your filthy… little… secrets, boy,” the surreal voice of voices teased slowly, each seeming to mock him in a slightly different way.
The demon seemed to take great pleasure telling him secrets he couldn’t remember revealing to anyone else. She knew that many decades ago. he’d get home from school and go straight to his room to masturbate, how he kicked off his shoes and pulled down his trousers to his ankles. How he’d tug and fondle his stiff cock whilst still wearing his uniform. How he’d fantasise about his classmates, and one girl in particular, wondering if she was in her own bedroom right now, with her own fingers beneath her skirt, fantasising about him.
The demon told him she knew all about The Punishment Room, his favourite schoolboy fantasy. How he’d imagine his classmates had been naughty at school, and had been sent to a special room to be disciplined. As the Head Boy, he had the privilege of serving as the Headmistress’s assistant. He would admit them when they nervously knocked on the door, take the note that described their misbehaviour from their trembling hand, and commiserate when he read the punishment they’d been given.
It was his solemn duty to tell any visitor that she would be getting a good hard spanking on her bare bottom. That always made them shudder. Some even burst into tears at that point. He’d console those individuals with a hug as they sobbed onto his shoulder.
He’d help the visitor take off her blazer, hanging it on a hook on the wall. He’d respectfully fold her arms behind her back, then kneel in front of her waist to unbutton her skirt, and guide it down her legs. He’d place his fingers into the waistband of her panties, tugging himself firmly as he imagined her mound and slit being exposed. He’d take his time, slowly lowering her panties to her feet, just so he could savour that most intoxicating of sights.
After she’d stepped out of her discarded garments, he’d hang them on wall hooks too. He’d escort her into the middle of the austere room, and tell her to bend over and grasp her ankles. When her bottom was raised, he’d direct her to part her legs slightly, so he could reach between her thighs and wipe her clean with a tissue. He’d wipe in one long delightfully slow movement, from the top of her mound all the way to her bottom hole.
He realised his eyes were closed, and what he was imagining was unusually vivid. The smoky infernal hellscape had become a distant nightmare. Beautiful mousy-haired Amanda was now bending over in front of him, more real now than it seemed she’d ever been.
He couldn’t believe how exciting it felt to fetch a cane from the hooks on the wall, and place it between Amanda’s perfect cheeks. As if he’d actually just done it. He stood back and admired his handiwork: one naughty girl, bared and wiped and ready to be caned. Sometimes as he played he imagined several girls arrived at once, and he bared and wiped them one by one, so they were all bending over in a row, each with their own cane between their cheeks. Sometimes he imagined having to prepare naughty boys too, but he much preferred picturing the girls in his own year, especially those for whom he harboured crushes.
Oh Amanda! How he wished he’d had the courage to tell her how much he wanted her. How many times he’d dreamt of them both getting so close that they’d finally shared their most intimate desires. In his fantasies, he admitted he wanted to spank her bottom, and she admitted she wanted that too. But the conversation that would have changed their lives never happened. What if the true torment of Hell was endlessly reliving life’s most profound sexual regrets?
Once offenders were properly prepared, he’d press a button to ring a bell in the Headmistress’s office. Within minutes the door would be flung open as if by a sudden gust, and he’d dutifully hand over the punishment note so Miss could decide how many whacks were appropriate. He’d then stand at the side of the room, hands respectfully crossed in front of his waist, to conceal the throbbing bulge that had inevitably developed.
Miss would pluck the cane from the girl’s bottom, holding her open to ensure she’d been properly wiped, before placing the rod across her quivering cheeks. She delivered canings as a sequence of slow hard whacks, pausing between each so both could watch each thin pink line appear, as if it was emerging on a photographic negative.
Sometimes he’d imagine the recipient taking their punishment in stoic silence, others he imagined sobbing tears, which dripped into tiny puddles on the shiny wooden floor. When Miss had finished, she’d hand him the cane to hang up, and instruct the young lady to stand, fold her hands behind her back, and stand with her nose against the wall.
School rules dictated all caned girls had to spend at least 30 minutes with their stripes on display. Miss would leave and go back to her own business, and he would start a timer. His duty was now to ensure those who’d been punished felt their stripes smart, and didn’t cheat what they deserved by rubbing the sting away. It was common knowledge that if a girl was immediately dismissed after a spanking, she’d simply run straight to the lavatory to experience the most amazing orgasm. She might do that anyway, of course, but in the interests of justice it was felt she should have to endure at least half an hour of her sore bottom burning first.
As he got closer, he’d imagine standing behind his classmate in silence as the timer ticked down, with plenty of time to admire her pretty pink bottom. He wondered if Amanda was on her own bed too right now, her fingers dancing between her own legs. Did she keep her cute glasses on as she played? The ones that made her seem so clever and mature. Did she fantasise about having her own bottom smacked too? Or did she imagine being in charge of The Punishment Room, baring and wiping and watching the canings of naughty boys just like him? If only he had asked her.
He had so many questions for her. Had it been an accident that time he’d seen beneath her skirt, or had she intended to flash her snow white panties? The fabric had clung so tight that even in that merest of peeks, he was sure he’d glimpsed the dip of her cleft.
Remembering all this made him so very hard.
“I know all about adorable little Amanda. I have seen everything.”
The surreal voices interrupted his reverie. How could this strange creature possibly know this? He’d never told anyone, not even his most intimate partners.
“I have witnessed every fantasy you’ve ever had,” the voices reminded him.
“I watched as your lust and inaction tainted your soul. And it delighted me!” the voices proliferated as they became louder and more euphoric, as if savouring a triumph.
The demon lifted each of his arms in turn, with a strength that surprised him, placing his wrists in the manacles that dangled from the nearby posts. They clicked shut with a deep and permanent sounding clunk.
The chains began to move, pulling him upwards, forcing him up from his knees, and continuing to rise until he was having to stand on his tip toes.
She scratched his back with her talons, then his throat, then his stiff penis, now jutting so crudely in front of him. He felt the points of her talons intrude between his legs, caressing his scrotum and tracing his bottom hole.
“I waited in your dreams. Knowing you would inevitably come to me.”
What is this place? he thought, still somehow unable to actually speak.
“This is The Reckoning. You have no secrets from me.”
Even…? he wondered.
“Oh, yes. The time you wanked whilst spying on your best friends fucking.”
He wanted to protest. How could she possibly know this?
He and John had been the closest of friends. Wendy had been a fellow student on their course, pretty and vivacious, and part of the clique of six that regularly hung around together. During a break in term, they’d decided to head into the backcountry, and had hired an old farmhouse for a weekend.
He and Wendy had been close, they’d liked each other, often behaving quite flirtatiously. That weekend the group had come back from a walk, had dinner, and the wine had continued to flow well into the evening. He and three of the others had over-indulged, and had staggered off to their beds. Wendy and John had been more temperate, and had stayed up chatting. Everything about that memory now seemed powerfully real, as if it had only just happened a few hours earlier.
He became aware that the demon was now pushing something out the shadows and towards him, something that groaned and squeaked on rusty wheels. Only when it emerged into the flickering lava-light did he recognise it, prompting him to struggle against his shackles instinctively, like a captive animal desperate to be free.
The device looked like a guillotine, a fearsomely sharp angled blade glinting like a twinkling star. It was smaller than the kind of contraption he’d seen in revolutionary paintings, with the blade just above his eye-line. The stocks were at waist height, with a hole that was much too small for his neck, but just wide enough for his penis.
The demon’s taloned fingers grasped the base of his erection and pushed the device forward until he had penetrated the tight little hole. Leather straps were attached to both sides of the frame, which she fastened around the small of his back and buckled tight, so he was unable to withdraw from it. The hole was unexpectedly tight, its sides grasping his shaft like the tightest of cunts. Balanced on his tip-toes, he can feel himself gently swaying in and out.
Now the demon revealed what he’d thought was her tail, was actually a whip. She removed its long phallic handle from her own cunt, already slick with her own juices. He had to admit that this was practical: what better way for a demon without clothes to carry around a punishment strap, than inside her own body?
She began flogging his bottom with the whip, each stinging impact encouraging him to push just a bit deeper into the dread device’s tight black hole.
“Good. Yes,” cooed the succubus approvingly, “Fuck my Castration Machine.”
Just hearing the device being named so blatantly caused a queasy fear swept through his body. But he suppressed his natural instinct to thrash about and try to free himself, wary of accidentally causing the blade to fall.
“Be careful, boy. If you come, I release the blade.”
He tried to relax, and images from long ago materialised in his mind. He was lying in bed. It was dark. There were sounds. He was woozy, disorientated. His head throbbed, his mouth and throat were raspy and dry. Much too much wine.
“Ha! Gluttony!”
He noticed the louder the demon shrieked, the more her voice splintered into several different dissonant voices.Several whacks of the whip seared across his bottom. Dangling from the manacles, he was powerless to defend himself.
As the sting faded, the old memories enveloped him again. The sounds in his ears were growing louder, grunts and moans and cute little feminine gasps, the unmistakable sound of fucking. He sat up, turning his head to determine its source. It was next-door, John’s room.
They were staying in an old house, with thin connecting doors between the rooms that were latched shut when occupied. He got up, and crept towards the noise. Age had made the wood warped and wonky, leaving a clear gap between the door and the frame, enough to make its edges glow. He pressed an eye towards it, and peered into the room beyond.
A thousand thrilling details poured into his mind at once. They were illuminated by the glow of a single candle. Wendy was naked. Wendy was straddling John’s hips, who was lying back on the bed. Wendy was riding John’s cock. Wendy was bouncing up and down joyously. John’s hands were on her hips. Wendy’s brown nipples were stiff in the centre of her small pert breasts. Wendy mewed with pleasure every time she sank deep.
He remembered how his own cock felt heavy between his own legs. Wendy looked so beautiful. So sexy and free-spirited. He realised how much he wanted her.
“So greedy!” accused the demon’s dissonant voices.
He winced as several more stinging blows flayed his backside. He remained fixated on the scene he was spying on, too entranced to tear his eyes away.
Suddenly, a wave of regret surged through him. All those opportunities he’d had to take their relationship further, but he’d been too lazy. He’d been content to lie in bed and masturbate about his fantasy version of Wendy, he’d never been courageous enough to be vulnerable, and risk opening up about how he truly felt about her.
“Sloth!” mocked the demon’s voices in a slow drawling chorale.
The voices laughed as the whip in another reality lashed his poor bottom repeatedly again. In his imagined bedroom he reached back to rub his stinging cheeks, overcome by a queasy feeling of guilt, like a naughty schoolboy who’d realised they’d made a terrible mistake.
He was now aware of another emotion swelling inside him, directed towards John. It wasn’t joy at seeing his best friend enjoy a wonderful fuck with an exceptionally hot date, but the sickly nausea of jealousy. He was resentful that John had his cock inside her, when he knew it should really have been his own.
“En-vy!” teased the voices, like a playground choir might chide a boy who’d carelessly revealed affectionate feelings for someone he could never have.
The scene beyond the door faded momentarily, and he was back on the lava crag, shrouded by darkness. The demon was flogging him enthusiastically, and his cock was pistoning into the hole beneath the blade with every whack.
“Such a silly little boy. Your cowardice cost you your chance with them both. All you’ve ever done with that pathetic little organ is wank with it. I should take away what you don’t deserve.”
He tried to plead his case against emasculation, but found it impossible to utter anything from his mouth. He couldn’t even be sure if he was even breathing any more.
Anger and frustration began to bubble up inside him. Now he was in the room again, watching them fuck and seething with resentment. Fuming at his best friend for his perceived betrayal, infuriated and indignant that Wendy would choose another over him, but most of all, furious at himself for his folly and timidity. It felt as if his blood was boiling, like a bomb inside him, an incipient tantrum waiting to detonate.
“Wrath!” yelled the voices, tinged with their own fury.
For once, he was grateful for the whacking that followed, the fiery pain seeming to soothe a frenzied mind that was ready to explode.
In front of the remembered spyhole he gripped his rigid cock with one hand, muffling his mouth with the other to try to keep his clandestine presence hidden. Each time Wendy sank to the bottom of John’s thick shaft and emitted one of her intoxicating girly giggles, he thrust deep into his grasping fingers.
Suddenly, Wendy stopped riding, and rose from John’s hips. She leaned forward, kissing John deeply, and he heard her whisper: “Finish in my bottom.”
As she turned around and straddled him again, he could see everything for a moment, everything he’d lost and would never have. Her beautiful pink cunt, now puffy and streaked with her own cream. Her cute little bottom, with its delightfully wrinkled little hole in the middle, which she was now manoeuvring over John’s big condom-covered prick. She pushed down on it, moaning as it began to slip inside.
“Oooo. Lust…” whispered the demon salaciously, in the kind of whisper that lovers mew when they’re being fucked deep.
The subsequent whacks just made him thrust deeper. He realised he was fast approaching the point of no return, but was too angry and indignant to really care.
He watched Wendy’s back arch, as John clutched a handful of her short black hair. She came with her lover balls deep inside her bottom, dissolving into thin air like a cloud of dissipating smoke.
In the moments before he ejaculated into the machine, he realised the very worst sin of all was Pride. He’d been too proud to tell Wendy how he felt about her, just as he’d been too proud to dare to be vulnerable with Amanda. He was swamped by a sour and terrible epiphany: he’d spent his entire life allowing his ego to dominate his consciousness, like a gigantic moon completely eclipsing his soul. His ego had convinced him he deserved things because he was better than anyone else. He’d chased status, in the hope of being loved.
He was guilty of Pride. He was guilty of all the sins. He had voluntarily emasculated himself.
As he stared into the darkness, he saw the glinting blade fall.
* * 2 * *
Those passing by on the street might think it was a prestigious office building, with its opulent foyer, a smartly dressed security guard, a few turnstiles screening the short foyer that funnelled visitors into the marbled corridor beyond.
The same passer-by might see a man furtively entering, and pressing his phone down on the turnstile sensor. He has an appointment, so the light glows green, the guard nods politely, and the visitor is admitted. Members of this most exclusive club have no idea what awaits them on their visit, merely that they will be seen to. The algorithm has already decided their fate.
This is a place that respects its members’ privacy, and their boundaries. A private club that isn’t creepy or too sanitised - the kind of place members would always feel a buzz of thrilling anticipation whenever they thought of their upcoming visit.
It had the ambience of an elegant spa, with a menu of 'treatments' clients could discreetly browse and book through their phones. There were packages with optional erotic pamperings, such as waxing, genital massaging, and enemas. Clients who came here to be spanked could choose what shade of pink they'd like their bottom to be, the kind of implements that would be used, and whether they'd like to feel it was a punishment, or something more sensual like a bottom smacking massage. Or one could elect to book one of the highly immersive ‘special experiences’ - and let the algorithm decide which one you received.
This building was the home of Escapade, a company that specialised in creating highly theatrical erotic experiences. When the visitor had made this appointment, what lay in store was never explained in advance, but he had no doubt that it would be dramatic and profoundly affecting.
The philosophy of Escapade was that sexual activity was exercise for the mind. It engaged the imagination, it nourished the brain’s vital chemistry. The company believed experiencing sensual pleasure was itself an act of radical self-kindness. Its very existence was a challenge to the archaic notion that sexual pleasure was some kind of vice. If the world was divided into those who considered quirks to be weirdnesses, and those who believed quirks were a trait of the curious, Escapade catered exclusively for the latter.
Beyond the turnstile and a short walk down the connecting corridor was the main atrium. This was a grand rotunda, covered by a glazed dome that flooded the space with warm natural light by day, and sparkled with artificial stars after dark. In keeping with the company’s theatrical philosophy, the atrium had a theme that changed with every passing month. Now as the end of October approached, the lobby had been given a subtle Halloween makeover to amuse its arriving guests.
The central space was now occupied by five waist-high wicker frames, and on top of each was a giant jack-o-lantern pumpkin. Each had been carved with a different expression, ranging from genially friendly to fanged and fearsome. A gas flame burned within each, slowly cycling in intensity between an ambient glow and a bright fiery blaze. Each lantern’s thick green stalk had itself been carved into smooth realistic-looking phalluses.
One of the pumpkins had a naked woman straddling it, her splayed legs dangling over its bulbous sides. Fascinated, he stopped to stare. Her slit was leaking freely, and had already dripped a long shiny slick onto the pumpkin’s curved orange flesh. As he moved around her he noticed not only had her hands been cuffed behind her back, but she had been well spanked, and the green stalk disappeared between her bright pink buttocks, penetrating her anally. Even standing here he could feel the heat from the lantern’s interior flame, so she must clearly have felt the heat against her sore stinging cheeks.
The sitter was gagged and blindfolded, so it was quite possible she was unaware she had an audience now staring between her legs. He felt the urge to step forward and whisper in her ear: “What did you do that was so naughty, young lady?”
He wondered: just how did naughty did you have to be to end up spanked and put on display, sitting with your bottom stretched on the Jack-o-Lantern of Shame?
He noticed her nipples were covered by sticky labels. At first, he’d thought that was a concession to her modesty, though that made little sense given how she’d been arranged, with her ankles cuffed together behind her, so she couldn’t close her legs. Each label had a four digit number, one slightly bigger than the other. Now he realised they were times, one must have been the time of her appointment, and the other when she’d arrived. She’d been forty minutes late, what a naughty girl.
She was probably some busy executive, who’d arrived here with a sense of arrogant entitlement, expecting her appointment to be rescheduled to suit her. Instead, she’d been treated just like any other silly little schoolgirl who was late for class. A good hard spanking on the bare bottom, and then put on display in the entrance hall as a warning to others.
Latecomers weren’t usually embarrassed like this, so maybe this fate was just a special Halloween surprise. The company did pride itself on its mercurial unpredictability. He checked his watch, much as he’d love to stay and stare at her weeping down her pumpkin seat, there were still several phalluses unoccupied, and unless he wanted to join her, it seemed unwise to dawdle. He should get a move on.
Around the circumference of the lobby were twenty doors, each constructed in different styles and materials. Some were elegantly gilded, whilst others were made of weathered timbers like portals from an ancient castle keep. He’d always been fascinated by Door 14, a mahogany panel embellished with chunky brass pistons, but hadn’t yet been invited to venture behind it. Its appearance suggested some kind of intriguing steampunk fantasy lay beyond.
Each door led to a uniquely different experience. He had simply been told to report to Door 7, an iron-studded panel of timeworn oak, as might be found at the threshold of a church. He used his phone on the door sensor to open it, revealing a stone hallway, which soon turned into a descending stone staircase. The walls were uneven, like he was following a passage hewn out of the bedrock, as if he was descending into an archaeological tunnel, dug into lost catacombs, or a plague pit.
At the bottom of the stairs was a changing room, in keeping with the mediaeval theme, it resembled a bare stone monastic cell, albeit one whose resident had been hoarding modern comforts. There was a concealed fridge full of snacks and drinks, piles of fluffy towels, and a shower with bottles of luxurious body-washes. Every play room had one of these antechambers, they were like airlocks - an interface between the real world and the fantasy world beyond.
He undressed and freshened up under the shower’s warm falling rain, then went to the wardrobe to find what he was expected to wear. Each room provided costumes or uniforms in appropriate sizes for guests to change into, as authentic clothes helped visitors transition into the right mental space for their experience. But he found no garments waiting for him, just a message, not written - but scratched roughly into the wood of the closet: Be Naked.
On a table by an armchair there was a homage to Alice’s Wonderland, a little blue bottle with a handwritten label, reading “Drink Me”. All visitors could elect to take this suspension of disbelief drug before their session began. It would induce a temporary amnesia, helping them forget about the outside world, and where they truly were, greatly enhancing the immersiveness of the experience. He quaffed down the shot, it tasted medicinal, harshly sweet, like a vodka shot without the heat.
He sat down to wait, feeling increasingly euphoric as the drug set to work obliterating his recent memories and any lingering worries, like a classroom duster wiping the blackboard of his mind. At some point his stupor was interrupted by the sound of a tolling bell, the door to the experience chamber had slid aside, indicating it was time to begin.
He approached the dark gap suspiciously, before stepping through into a dim featureless space. The only source of light here was a surreal rotating pillar of clouds. It resembled a portion of a hurricane that had become wrapped around a lamp post, and had kept swirling even after its parent storm had long departed.
The cloud-pillar was called Gail - an endearing pun for what had become the Escapade company’s guide and concierge, a genteel artificially intelligent listener. The cloud would appear whenever its name was called, projected in front of its summoner. It had been designed to be instantly obvious, whatever the setting. He had to admit, it felt less embarrassing to be standing naked in front of an improbable cloud than some kind of humanoid avatar. Clouds were ideal for this kind of Pepper’s Ghost projection, far better than people, whose images just seemed eerie and immaterial. It also had a universal appropriateness, there was no need to worry about gender, or age, or race with a cloud.
“How are you feeling?” inquired Gail, its voice whistling like strong winds through a forest.
“Just fine, thanks.”
“Why are you here?” asked Gail casually.
“Actually, I’ve no idea,” he replied.
Gail floated towards a patch of sand, and asked him to lie down here. He did as he was instructed, making himself comfortable in what felt like a warm sand pit. Around him was a curtain of dark billowing fog. Gail began to dim, and the residual light slowly vanished, shrouding him in darkness. The warm sand scratched pleasantly against his naked skin, and in minutes, he was fast asleep.
* * *
He awoke in blackness. Dazed and disoriented.
In the gloom, a distant glint sparkled like the Morning Star.
He was enveloped by a frightening darkness, so covered in the sand hollow as he waited for his eyesight to adjust. In one direction a dim light was beginning to emerge, like the halo of twilight at dawn. Around him the fog was slowly thinning, revealing an infernal scene, as if his soul had been asleep for a thousand years, and only just awoken in Hell.
There was enough light to see faint colours now, and disturbingly, the ground nearby appeared to consist of several seething ponds of molten lava, which also seemed to be the sole source of illumination. Traversing the bubbling pool was a path of elevated stepping stones that led to a small rocky island. This space was like a room inverted, its ceiling cloaked in darkness, its floor burning with a fiery golden light. There were no walls, only billowing curtains of inky smoke.
Escapade was famous for its theatrical, almost cinematic scenes, combining physical sets with projectors, high definition screens, and speakers to create incredibly vivid settings. The lava might actually be a pool of steaming water, lit from below by submerged red and orange lights, but the drug suppressed his natural scepticism, making the environment seem even more vividly real and perilous.
The rising heat singing his bare soles deterred him from lingering, and encouraged him to jump onto the nearest stepping stone. He began hopping towards the rocky outcrop, its jagged outline with two tall posts becoming visible as its smoky shroud began to thin. It was in the same direction the ominous glinting light was sparkling.
As he arrived, something sinister pounced from the darkness. It resembled a demonic living statue, bald and hairless, with chalky white skin, a mouth fringed by fangs, and fiery cat-like eyes. It was a muscular, clearly feminine figure, with small breasts and a torso of rippling muscles. She exuded an almost regal level of irreproachable authority, her presence emanated the sexual threat of one who fully intended to do as she pleased.
“Kneel!”
Her voice sounded like a dozen voices, each competing to shout over each other. It was an ingenious and disorienting audio effect. It was impossible to argue with, and made him do just as he was told.
The demon, who was a highly experienced member of the Escapade staff, efficiently cuffed her visitor’s wrists and ankles to the adjacent posts, hauling on the chains to raise him onto his tip-toes. Once secured she wheeled a strange contraption out of the shadows, he recoiled, struggling desperately against his manacles when he saw the glinting light was a guillotine blade.
The demon knew things, his deepest and most personal secrets. She told him all about his teenage Punishment Room fantasy. He was shocked this strange creature knew such intimate details, quite forgetting he had already divulged most of his sexual history in the previous visits and conversations. Remembering how he used to fantasise about dear Amanda made him hard, but he realised his peril too late. She rewarded his lack of self-control by sliding his erection into the hole beneath the blade, and fastening the belt behind him to prevent him from pulling out.
At this point he had begun to wonder whether he was in too deep, and contemplated using his safeword. Pleading for mercy was an instinct the amnesiac drug did not suppress, it would halt the scene, and he’d be brought down gently. Although he couldn’t remember it now, he had explicitly asked for an experience that would push his boundaries, so whilst what was unfolding was rather disturbing, it also felt inexplicably exciting.
He was even more astonished when the demon began to talk about the time he’d masturbated as he spied on his best friends fucking. How cruel that at the same time, he could actually hear their moans in his ears, and glimpse flashes of their naked bodies ahead of him in the darkness. Periodically, he’d also feel her whip sting his bottom as she scolded him on his naughtiness.
He began to writhe, gyrating his hips, plunging his stiff cock into the hole of the machine that gripped it so tightly. Even when the demon warned him of the consequences.
He remembered the moment when saw Wendy rise and turn around, her holes gaping as she straddled her lover, when he’d heard her whisper: “Finish in my bottom.”
God. How he had wanted her. Damn it. He had deserved her.
That was when the demon finally released the blade. He saw it flash in front of his eyes, then felt something cold and metallic grip his cock. Then, to his horror, he couldn’t feel anything down there at all. No pain, merely a numbness where exquisite sensations used to be.
The demon laughed in an awful cacophony, unfastening the buckle that had trapped him, and rolling the machine backwards. In a state of stunned shock, he looked down at his own body, and realised he could no longer see his erection, there was simply darkness where his cock used to be.
How could he have known the falling blade was a classic act of misdirection? Whilst his mind had done its best to shield itself from the pain of a horrifying injury, a mechanism deep inside the device had rolled an ultra-black condom down his penis. This, the darkest of all known pigments, absorbed all light, making it all but invisible in the gloomy darkness.
The condom had also been filled with a local anaesthetic, rapidly numbing his cock, so he could no longer feel it. Hence whilst his penis had appeared to vanish from view, he could still feel its weight between his legs, how it still throbbed in time to his own racing heartbeat. He could never have expected being emasculated could feel so arousing.
“Poor boy”, she commiserated, “But let me show you how you don’t need a cock to come.”
The demon resumed flogging him, harder this time. Amid the pain, he seemed to dissociate from himself, as if his awareness was fleeing from his ravaged body. That cherished memory became his sanctuary, as he watched his old friends fuck each other in glorious clarity, imagining himself in that old farmhouse, wanking the cock he could no longer feel.
A growing heat in his bottom reminded him what a naughty boy he was. Somebody strict should have put him over their lap long ago, and corrected his arrogance and disobedience. He should have been the one in the Punishment Room, with lovely Amanda placing the cane between his own pert cheeks. Adorable Amanda in her crisp school uniform, seeping into her panties as their Headmistress cured him of his Pride.
He tried to hold himself back.
But his fate was unavoidable.
* * 3 * *
He awoke in darkness. Dazed and disoriented.
His awareness was slowly coalescing, like the flotsam of a shipwreck being sucked towards a whirlpool. His sense of being returned first, the deadweight of his own body, his back propped against one of the posts from which he’d recently been shackled, as if he’d just laid back and fallen asleep.
“I hope you found that most satisfying,” said the swirling pillar of clouds that resembled the world’s smallest hurricane.
“Unbelievable,” was about all he could manage, barely nodding.
The demon came into view, her chalky body makeup now mostly hidden beneath her fluffy Escapade-branded dressing gown. She checked on how he was feeling, and he replied that he was well. Now her surreal synthetic voice had vanished, she spoke with a compassionate geniality that seemed bizarre given her fearsome teeth and talons.
Instinctively he felt between his legs, where he could feel something squelchy, even though he couldn’t quite see it properly in the gloom.
“Don’t worry! You’re all there!” she reassured, “Let’s get you back to your changing room.”
She helped him to his feet, and into a snug dressing gown of his own, guiding him along the path of ash-grey stones. The exit from Hell was a doorway that resembled a gash in the night.
Escapade took aftercare very seriously, especially for those who’d been through psychologically challenging experiences. The private dressing room provided a quiet space to slowly come down in, well-stocked with chilled drinks and cold towels to soothe the sorest of spanked bottoms. Everything one might need for the journey back to reality.
In the bathroom he’d peeled off the jet black sheath, amazed by how much he’d filled it. His balls ached pleasantly, as if they’d been sucked empty. In the mirror he could see the scratches her talons had left, his bottom had been painted pink by countless overlapping whip-lines.
Seeing all was well, the demon hugged him and they thanked each other for the profound experience they’d shared. Her parting words were “Until next time…”, a comment that made his cock throb.
She took the staff corridor back to her own private office cum changing room, exchanging fist bumps with a pirate captain and Roman slave girl along the way. In her room she could finally kick off her hooves, and remove the prosthetic talons from her fingertips, which made visiting the lavatory, and fetching her own refreshments, much less hazardous.
Now she had time to sink back on her small sofa in a contented stretch. After a short repose she plucked her tablet from the coffee table and checked her schedule. Her next appointment was due to be with a female client. The Staging Team would already be busy, refilling the smoke machines, removing the guillotine and replacing it with a specially constructed device that would make her believe her slit had been sealed, and that she’d become as smooth as a Barbie doll.
Whether one believed in Hell or not, behaviour and consequences were fundamental to the human condition. What we all knew as naughtiness was just an individual's own little rebellion against a world full of rules. The infernal landscape, and the demonic persona she played, were designed to inspire a sense of existential dread, which only served to amplify the latent erotic shame that lay deep within every visitor. Ghosts might not be real, but she knew everyone was haunted by the spectre of guilt.
She read through her visitor’s confession of what she regarded as the naughtiest thing she’d ever done. In the grand scheme of things, it wasn’t very naughty at all. A broken taboo rather than a crime. One night she’d been visiting her Aunt and Uncle and had slept in a spare bedroom, and during the night she had woken, and heard them having sex. She had risen and pressed her ear to her door, becoming extremely aroused by the sounds of their pleasure. That was when she had noticed that one of the bedknobs seemed the perfect size to fill her. So she’d straddled the bedpost, riding along to the rhythm of their moans, timing her incredible orgasm to coincide with her Aunt’s.
Riding the long tapered finial had been so extraordinary, it immediately became her most obsessive fantasy. Back in her own room, she’d push her fingers in deep, trying to recreate the exquisite sensations she’d experienced that night. She even experimented with the handles of numerous hairbrushes, but never found anything that made her come as hard as that bedpost.
So, she began to make excuses to stay with her Aunt and Uncle, insisting she slept in that room even though bigger rooms in the house were also available. She secretly borrowed the house key and had a copy cut, so whenever the yearning became too great, she could sneak into their home on the way home from school, and ride the bedpost whilst they were both still at work.
Perhaps it was the jeopardy of getting caught that was what made it so thrilling. The prospect of hearing the front door unexpectedly open, the shame of being discovered by one or both of them, and getting her bottom smacked as she stood straddling the bedpost. But she always seemed to get away with it.
How perfect, thought the demon, it seems this young lady will finally be getting the comeuppance she’s wanted all these years. She’d arrive on the craggy outcrop to find a bed, sitting there like some kind of incongruous component of a Daliesque dream, with bedposts just like those she remembered. She would make her visitor straddle one, and ride it whilst she was whipped, while the intrusion slowly numbed her. Special effects would complete the illusion, and make her believe her slit had been permanently sealed. It would mess with her mind, of course, but all the best erotic experiences did that.
And whilst her visitor’s imagination was trying to distinguish fantasy from reality, she would be giving her the spanking she had long deserved, whacking her bottom until she reached her own orgasmic epiphany.
She often thought of how similar spankings were to acts of prayer. A meditative ritual, where one freely submitted oneself to a higher authority, there were pleas of forgiveness and earnest desires for understanding. And in the end, absolution.
It really was such a rewarding job.
As the demon read up on her next guest, her first visitor had already showered and changed. He was expected to stay for a while in the aftercare lounge and enjoy some refreshments, to let the drug dissipate, and head off any post-spanking crash. There were even trained therapists available if he wanted to talk about what he’d experienced. But he’d never cared for rules, they were just challenges of ingenuity, created for the clevest to try to evade. He was a busy man, and had an important video conference this evening with the New York office.
As he strode back through the atrium, he noticed two more occupants on the giant pumpkins. Seated on either side of the woman were two men, both with their conspicuously spanked bottoms filled. The one on the left had disgracefully been a whole hour late, and now his tall stiff cock was jutting from between his legs, proudly saluting all who walked by.
The one on the right, who’d been a mere five minutes late, had already ejaculated. His creamy mess was still dribbling from his flaccid member, forming a shiny slick on the pumpkin’s curved surface. He chuckled as he passed them, quite aware of the smarting heat still radiating from within his own trousers. Spanked bums were for silly little boys who got caught.
Questions prompted by his own recent experience were still ricocheting through his busy mind as he marched through the turnstiles and across the foyer. How weird that he’d literally just been to Hell and Back. Was that what really awaited us in the hereafter? Was the true torment of Hell endlessly reliving life’s deepest sexual regrets?
Speaking of which, where was Amanda now? And whatever had happened to Wendy? Did life ever offer second chances? Or did we just experience new challenges, to see if we were now brave enough to grasp them?
He emerged from the building, blinking in the bright sunlight, momentarily disoriented. Now. Which way took him home again?
Left. No!
Right.
Without looking, he veered into the road.
There was a sickening crunch.
He awoke in blackness. Dazed and disoriented.
His awareness was slowly coalescing, like the icy rubble of asteroids sinking inexorably towards an embryonic planet. His sense of being returned first, the deadweight of his own body, becoming aware that he was lying on his back, his limbs sprawled out and weak.
Burning sensations began to arrive from his skin, as if he was lying under the blazing sun; yet all around was darkness. Even as his vision began to return, the enveloping blackness remained an impenetrable blur. Whether above him was night sky or dungeon ceiling, it was impossible to tell.
In the gloom, a distant glint sparkled like the Morning Star, but somehow he knew it was the Blade.
.
.
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@spankingtheatre 2022
What a fantastic story. We all need an Escapade!!🔥🫦