Submitted to: Contest #329

The Protracted, Peculiar, and Probably Quite Pointless Trial of Bertie Masturbine

Written in response to: "Write a story from the point of view of a ghost, werewolf, vampire, or other supernatural creature."

🏆 Contest #329 Winner!

67 likes 83 comments

Christian Funny Speculative

Rather than enjoying the miracle of life, humankind has generally chosen the opposite – they have tried to understand it. More specifically, since the first caveman scribbled on the walls of his home, humankind has questioned what comes afterwards.

Broadly, there are three schools of thought. Some think there’s nothing. Logical, if a bit dull. Some ‘don’t believe in, like, heaven and hell and all that stuff but feel, y’know, like there must be something out there, like, death can’t be the end, right?’ This is the most insufferable school of thought and, incidentally, makes up most of the world’s population.

Finally, some believe that after death our souls are weighed and our lives evaluated. We are then sent either to heaven or hell to live out the rest of eternity. Almost by complete fluke, they are spot on.

Bertie Masturbine flopped down, exhausted, on one of the flimsy plastic chairs lined up against the wall. There were a few others, but most seemed preoccupied. One man seemed lost in thought, occasionally glancing upwards as though waiting for a bus. Another had fallen asleep.

After a short while, his name was called and a laminated brochure thrust into his hands as he was herded through the double doorway.

Welcome to Purgatory’ was written in Comic Sans at the top of the cover. Beneath a set of scales was a short note: ‘Tell us how we did today! Your afterlife experience matters to us and we’re dying to hear your thoughts. Please fill out the Post-Mortem Satisfaction Survey on the 66th page and we’ll be eternally grateful.’

Perhaps it would be alright, Bertie rationalised. After all, it wasn’t like he was the worst person who’d ever existed. In this respect, he was correct. Bertie was not the worst person to have ever existed. He was the fourth.

There were three people worse than Bertie to have ever existed, all of whom happened to be men. The worst woman to have ever existed was the Wicked Witch of the West Coast, who abducted hundreds of children and forced them to read her terrrible movie scripts. Those who survived went insane and were always found on a cliffside or mountaintop, babbling about ‘lazy characterisation’ and ‘lack of stakes.’

In another blow to female representation, the Wicked Witch falls well outside the top ten. She’s languishing at sixteenth between the Evil Captain Bloodbeard, scourge of the seven seas, and Henry Kissinger. The worst non-binary person to have ever existed is unknown as none have yet been sent to hell.

Lord Sigurd the Seal-clubber takes third place. As a youth, he opened a resort outside Uppsala to pursue his passion. Though a commercial failure, it ran for fifty years until the Viking King Eric Bloodaxe closed it down, describing the practice as “uncouth, unsavoury, and medieval.”

In second place is Walter Brideswell of North Somerset: serial killer, organised criminal, and (briefly in his youth) management consultant. All were enough to condemn him to hell, but he made the top three when he founded The Ocean Warming Fund. This was a lobbying group aiming to accelerate global warming so that Walter could holiday at the seaside without having to go via France.

In first place, it’s him. You know who I’m talking about. The person you thought of first when we started on this tangent. He’s in number one. The worst person to have ever existed, obviously.

Bertie was the fourth worst person to have ever existed. Therefore, when he was summoned to the chamber to have his case heard, he wasn’t overly optimistic. He clawed desperately for anything that might count in his favour. There was the time he’d donated $200,000 to sit next to Brad Pitt at a charity dinner. Bertie thought long and hard. He’d slowed down for a cat once…. That might be a bit thin…

As he reached the door, he was shaken out of his reverie by a skeleton wearing a suit and a barrister’s wig. Bertie was surprised, because it was a skeleton wearing a suit and a barrister’s wig. He was even more surprised when the figure began to speak.

“Hello...” the skeleton peered down at a small bundle of notes, “Bertie. How do you do?”

“I’ve been better…”

“Yes, yes, as I recall it is a rather trying experience, death,” The figure paused to readjust his jaw. “How was it for you?”

“It was all so sudden. One moment I was sat in a submarine with a couple of pals, then… hang on, who are you?”

“Oh, forgive me.” The figure held out a dusty, skeletal hand for Bertie to shake. “I’m Baldrick.” Bertie stared at him, bemused, and Baldrick stared back, emotionless. In fairness, it is hard to express emotion without eyes, lips, or skin.

“Alright. I’ll try again. What are you doing here?”

“Ah good question sir.” Baldrick rattled, as though to a dog who’d located a ball. “I’ll be your legal representative for the hearing.”

“You’re my lawyer?” Exclaimed Bertie.

“Got it in one sir, yes. I’m up from Hell this afternoon to help you make your case.” Bertie paused for a long time. That said, it was a short pause for somebody who’d just discovered that their fate for the rest of time was in the hands of a skeletal stranger.

“Do you think I have a chance of making it to Heaven?” Baldrick stared at him. This was a long pause. An excruciating pause that carried the weight of all eternity. Eventually, he spoke.

“There’s good news and there’s bad news.”

“Alright give me the good news.” Baldrick widened his jaw to speak. “No. Stop. Give me the bad news first.”

“As you wish, sir. This morning, I read your file and the bad news is, well, it’s bad. You were very bad, by almost every possible metric. In fact, some of the guys in the office were saying you’d have a shot at the top ten.”

“The top ten?”

“It doesn’t matter. The point is you are a very difficult soul to defend.”

“But I always thought there’s no such thing as bad people, only bad deeds.”

“Afraid not sir, you were a bad person who did a lot of bad deeds.”

“I see.” Bertie paused for a moment. He’d been told similar by various wives, employees, judges, and one time, the Penguin Keeper at Chester Zoo. But, somehow, it struck a chord when put this bluntly.

“What about the good news?”

“Good news?”

“You said there was good news.”

“Ah yes, the good news.” Baldrick shuffled his notes around and pulled out a roll of parchment. “A couple of months ago they changed the protocol due to overcrowding.”

“Overcrowding?”

“Indeed sir, I don’t know what’s going on down there but far too many of you are being born and far too many of you are dying. Therefore, Edict 54,280 was released. It stipulates that it is the responsibility of both places’ representatives to argue why each soul should not be sent there.”

“Baldrick I’m sorry I don’t understand.”

“I wouldn’t expect you to sir,” his wispy voice dripping with condescension – the only emotion he seemed capable of expressing. “The point is both places are overcrowded. Therefore, each hearing now consists of a representative from both places arguing why each soul should go to the other place.”

“But how does that benefit me?” Baldrick leaned forward and inclined his head conspiratorially. Perhaps, if he’d had a face, he would have grinned.

“Why sir, all the best lawyers are in Hell.”

The hearing chamber was designed and built by a tired, overworked angel who’d lost interest in his career and really let himself go. Although we mustn’t be too harsh on him, he had to build over ten thousand of them.

There was no roof, just great, looming, obsidian pillars reaching up into the inky sky. A stone alter was the only permanent fixture, though it possessed an austere beauty that rendered it fairly incongruous among the other furnishings – a small wooden stool and two docks either side of it.

Bertie was directed to the small wooden stool. He had to crouch awkwardly to be seated but he assumed, correctly, that it wasn’t worth complaining. Besides, he was distracted by the murky engravings on the alter before him. Fire, ice, water, earth, blood, and – for reasons incomprehensible to the mortal mind – the number 42.

Meanwhile, Baldrick set himself up in one of the docks and another figure came shuffling into the room, entering the dock on the other side.

“Afternoon Baldrick.”

“Afternoon Gabe.”

“How was the trip up?”

“Not too bad. The air-con broke half-way up which was a shame. Then again, I do live in Hell so…” There was awkward pause. “How was your trip down?”

“Perfect as always.”

“Great.” Nobody spoke. Still, Bertie could swear there were whispers coming from somewhere. They seemed to emanate from the corner of the room but when he looked, there was nothing. Not even a wall, just nothing… Then a voice rang out around the chamber.

“All rise for the honourable Judge Mental!” Bertie leapt up, pleased at the respite from the hard surface of his awkwardly low stool. The silence remained until a frenetic scuffling was heard coming from behind the alter. Suddenly, a small, wizened, bespectacled face appeared over the top.

“Sit down, sit down. If we can get through this quickly, we’ll all be away by five o’clock.” His voice was satin, rich and delicate, soft and seamless, tumbling from a mouth that hardly moved as he spoke. “Who do we have here?” He peered down at Bertie for the first time. “Mr… Masturbine.” There was a short pause. “Oh, for Christ’s sake! This’ll take ages… actually, scratch that last remark, we don’t want any trouble upstairs.” he muttered to someone behind him. “Alright. Get on with it.”

Slightly taken aback, the figure called Gabe began to rattle off his preamble. Unsurprisingly, his motion was that Bertie ought to be sent to Hell for eternity, plus an additional three years for wasting the court’s time with this defence. Then the charges began.

“Count one: smashing his mother’s vase when crawling round the atrium…

Count two: blaming his nanny for the smashing of his mother’s vase…

Count three: failing to disclose the truth when his nanny was dismissed for the smashing of his mother’s vase…”

As the excruciating monologue continued, a look of sincere, deep-seated sorrow and repentance did not trouble Bertie’s face. Instead, he simply looked bored. The judge was hardly paying attention, and the stool was increasingly uncomfortable, no matter how much Bertie shifted his backside.

“Count one-hundred-and-nine: misappropriating monies from the Masturbine Ltd pension fund and transferring them to an account named ‘Shithead’s Stag Do…’

Count one-hundred-and-ten: blaming the misappropriation of monies from the Masturbine Ltd pension fund on a summer intern named Kevin…

Count one-hundred-and-eleven: failing to disclose the truth when Kevin was given a custodial sentence for complex fraud and embezzlement…”

Bertie let out an exasperated sigh. It occurred to him that it was the first noise he had made since entering. Something about the place inspired silence. He turned to look at Bertie who, thankfully, looked very lively for a dead man. He was looking over his papers (especially impressive given his lack of eyes) and assiduously scribbling away.

“Count two-hundred-and-thirty-two: knowingly purchasing jewellery stolen from the Louvre in Paris…

“Count two-hundred-and-thirty-three: attempting to give the jewellery to his secretary, despite assuring his wife that there was ‘nothing to worry about…’

“Count two-hundred-and-thirty-four: unfairly dismissing the aforementioned secretary when she refused to go home with him…”

“Alright, I’ve heard enough.” Judge Mental’s intervention was so unexpected that Gabe continued to speak for thirty seconds before realising he’d been interrupted. “This soul is so indefensibly bad that we need not waste anymore time. Counsel for the defence, keep it short.” Not exactly a fair trial, thought Bertie.

“Thank you, Your Honour.” Bertie was pathetically grateful to hear Baldrick’s voice, even if it was the same disinterested rattle as Gabe’s. “As has been established, my client is a bad person who has done many bad things. Furthermore, he shows no regret for being a bad person who has done many bad things.” Good start. “However, it is my contention that his impact is a positive one. If it please the court, I would like to adduce evidence from the future.”

“Objection!” Gabe’s deathly whisper somehow rang around the chamber. “Future evidence can only be adduced with prior permission from the court and prior disclosure to the opposing council.”

“Indeed, you’re right, and if Judge Mental would like to postpone the hearing so that I can obtain the requisite permissions, he is welcome to do so.” The Judge looked up. “Alternatively, we can dispense with the formalities and continue.”

“Proceed,” barked Judge Mental.

“Thank you. The records show that my client founded the Masturbine Scholarship at Worcester College, Oxford to get more white, upper-class men into academia.”

“We know,” hissed Gabe. “It was going to be Count four-hundred-and-eighty-five.”

“Indeed,” replied Baldrick. “However, three years from now, a Masturbine Scholarship recipient will cure cancer, saving millions of lives.” He paused to ensure the judge was paying attention. “Therefore, the positive impact of my client’s generosity in three years’ time assuages any damage he may have during his life.”

Gabe swung his skull around to stare directly at Bertie. “That is completely absurd. The court has never been inclined to entertain these loopholes and this will not change, certainly not for the sake of this evil, evil soul.” Was he becoming slightly flustered? For the first time since dying, Bertie felt a flutter of hope.

“Surely even you can concede that the law is not clear.”

“The law is perfectly clear, Baldrick. We even sent a short, digestible version down to Earth a few millennia ago explaining how to get into Heaven. The rules are helpfully illustrated by a series of stories which cannot possibly be misinterpreted.”

“Gabe, I’ve had the privilege of liaising with many great legal minds down where I am and they all agree the rules governing entry to Heaven are completely ambiguous.”

“Poppycock!”

The two went back and forth, with Baldrick slinging contradictions and hypotheticals at Gabe, who played a straight bat, dismissing any arguments as irrelevant rabbit holes, foolish misinterpretations and ‘the pointless musings of people who have too much time on their hands.’ Eventually, he made a small concession.

“Listen Baldrick. The basic rule is ‘do unto others as you would have them do unto you.’ The rest are guidelines to assist mortals in achieving this. Furthermore…” he continued as Baldrick attempted to interject, “they are fundamentally deontological. We’ll have none of this ungodly utilitarianism in this court, thank you very much!” Now it was Baldrick’s turn to be indignant.

“Well, that is a radical position! Clearly it is just for a soul to be judged on the consequences of their actions rather than the actions themselves and I’m sure Judge Mental would agree!”

The judge was asleep. Meanwhile, Bertie was growing restless. He wasn’t sure he’d ever been seated this long. Even the long-haul flights to Australia had a beverage cart and a few decent films. This was torture.

They debated relentlessly, flitting from theology, to philosophy, to legal principles, and occasionally considering the subjects in between, the subjects so dull they haven’t been named yet. All the while they strayed further and further from the original purpose.

“…I’m not saying the act of eating an apple is bad, Baldrick. It could have been a banana for all I care, or a plum, or a melon, or a…”

“I know that Gabe,” Baldrick bristled, “but that begs the question, what is the point of the story?”

“The point is to obey the word of God and to resist temptation. I would’ve thought that obvious.”

“Why not just say that?”

“Well… where’s the fun in that?” At this point, the judge stirred. He peered over at Gabe, his eyes listless and empty.

“Thank you. I have taken your submissions so far into account. We will adjourn for now and come back tomorrow.” The stool was lower now, and harder.

“We’re coming back tomorrow?” Bertie’s voice seemed oddly hollow, the indignant bellow which had dominated many a boardroom had faded. Judge Mental peered over at him, and Bertie saw his face for the first time.

His hair ought to be long gone but the wispy white strands remained plastered to his scalp. His skin was parchment. Countless years sat in judgement of the damned were etched into every line of his ancient face, disrupted only by two pale lips which hung open to reveal an irregular set of jagged teeth, jutting out like tombstones.

“Oh no, Mr Masturbine. You won’t be coming back tomorrow.”

“Thank God!” At this, the judge’s eyes glistened. “Does that mean you’ve finally made a decision?” Judge Mental let the question hang, savouring it as the skeletal lawyers packed up their briefcases.

“There’s plenty more to discuss as to your worldly sins, Mr Masturbine. But you will not come back tomorrow. Instead, you will remain seated and wait for us to resume.” At this, Bertie lost it.

“What kind of process is this? I am to sit here indefinitely, listening to these two insufferable lawyers?” He spat the last word like a slur. “All they’ve done is talk in circles about every ethical interpretation of all the dodgy stuff I did when I was alive… for goodness’ sake, how long will this thing take?”

“We expect you to be here indefinitely, Mr Masturbine,” the judge responded helpfully. Bertie huffed in frustration.

“This is literally my worst nightmare. I might as well be down in…”

He stopped and looked around. Both Gabe and Baldrick were staring at him, their skulls cocked slightly to one side. Judge Mental’s black eyes now bore into him, the dry, grey lips contorted in a grotesque smile.

“…oh.”

Posted Nov 16, 2025
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67 likes 83 comments

Grace Urbina
11:40 Nov 29, 2025

“Why sir, all the best lawyers are in Hell.”
This line is hilarious. Great story, and well done!

Reply

W B
19:09 Nov 29, 2025

Thanks Grace, if I’m honest the whole story was written around that line!

Reply

David Cantwell
17:41 Nov 28, 2025

Nice work. You had a lot of fun and it showed. 42

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W B
18:59 Nov 28, 2025

Cheers man, really glad it came across.

Reply

Liesel Armstrong
08:11 Dec 02, 2025

Yes, the 42 made me laugh out loud!!! So clever! We will never be rid of 42....

Reply

Allen Adkins
06:55 Nov 30, 2025

I laughed out loud at Bertie not being the worst... just 4th worst. Congrats on the win!

Reply

W B
12:25 Nov 30, 2025

Thank you so much! Glad it landed 👍

Reply

TJay Earls
14:21 Nov 30, 2025

I laughed out loud multiple times while reading this story! I love how you took religious and philosophical musings and spun it in a way that explored matters that have confounded humanity for a millennia, while adding a humorous undertone. I also noticed how Bertie never once showed any kind of indication of remorse or interest in the trial at all, validating why he's there in the first place. Me, the reader, was sure he belonged there too!

Reply

Denise Lu
18:38 Nov 29, 2025

What a great story. I had fun reading it. Congrats on the win :)

Reply

W B
19:10 Nov 29, 2025

Cheers Denise, glad you enjoyed it :)

Reply

Joni Elbourn
17:08 Nov 28, 2025

Extremely entertaining! Congratulations, well deserved.

Reply

W B
19:00 Nov 28, 2025

Really appreciate it, thanks a lot 👍

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Patrick Druid
22:28 Nov 27, 2025

Okay wow! This is delightful! I've never thought of Purgatory as a courtroom where lawyers argue endlessly! Nice!

Reply

W B
13:07 Nov 28, 2025

Thanks so much Patrick, really appreciated! I thought it would be fun to imagine purgatory/hell as eternal re-litigation of past sins.

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Katy Lindsey
16:01 Dec 01, 2025

Absolutely hilarious, I'm in stitches about the Henry Kissinger mention. This was so clever!!!

Reply

Hazel Swiger
14:14 Dec 01, 2025

This story was great! What a funny, imaginative way to imagine something so dark like death. Congrats on the well-deserved win!

Reply

Albert Hill
18:01 Nov 29, 2025

Had the waiting room of Beetlejuice, new characters that easily could be ! Nice job and great that your putting yourself out there really measures up ! Thank you, al hill

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W B
19:10 Nov 29, 2025

Cheers Al 🙌

Reply

Mira James
14:13 Nov 29, 2025

The comedic spin on purgatory is really inventive and your characters bring the story to life, congratulations on the win!

Reply

W B
19:10 Nov 29, 2025

Thank you so much! Glad you liked it 👍

Reply

Akihiro Moroto
03:55 Nov 29, 2025

Incredible! Congratulations on the win, and thank you for sharing this story!

Reply

W B
19:09 Nov 29, 2025

Glad you enjoyed it Akihiro! Thanks for the kind words 🙌

Reply

Silent Zinnia
20:36 Nov 28, 2025

Nice, congrats on the win

Reply

W B
21:18 Nov 28, 2025

Cheers 👍

Reply

Venice McDuffie
18:02 Nov 28, 2025

Congratulations on the win!! What a great story!!

Reply

W B
19:01 Nov 28, 2025

Thank you so much! 😊

Reply

Saffron Roxanne
17:18 Nov 28, 2025

Fun take. I enjoyed the skeleton's struggle with emotion. Great job! ✨️🎉

Reply

W B
19:00 Nov 28, 2025

Cheers!

Reply

Alex Davis
16:08 Nov 28, 2025

Very funny! Congrats!

Reply

W B
16:28 Nov 28, 2025

Appreciate it 🙌

Reply

John Rutherford
15:56 Nov 28, 2025

Congrats

Reply

W B
16:28 Nov 28, 2025

Thank you!

Reply

Patrick Druid
15:04 Nov 28, 2025

And congrats on the win!

Reply

Mary Bendickson
14:28 Nov 28, 2025

Congrats on the win! 🥳

Reply

W B
14:32 Nov 28, 2025

Cheers Mary :)

Reply

Mary Bendickson
16:13 Nov 28, 2025

Thanks for liking 'Happily Ever After'. Story started with 'Wind Beneath My Arrow'.

Reply

Stevie Burges
11:35 Nov 28, 2025

An interesting story. Thanks for writing and sharing with us.

Reply

W B
13:05 Nov 28, 2025

Thanks Stevie!

Reply

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