Tales From A Teenage Henchman

Von Vapid_Ink

1.2K 124 8

Tim Mitchell--surprisingly competent henchman and high school dropout--begins to reevaluate his career choice... Mehr

Making Headlines
The Letter
No Good Deed
To Catch a Thief
Sparrow
The Many Regrets of Tim Mitchell
No Rest For The Wicked
Good Intentions
Training Wheels for Crooks
Clowning Around
Romancing the Chili Dog

Questionable Life Choices

465 26 3
Von Vapid_Ink

As Tim Mitchell raced out of the bank with a bag full of cash, he thought about a particular piece of advice he wished he'd followed—stay in school. But hindsight was 20/20, and he had more important things to worry about at the moment, so it was little more than a passing thought. Most of his attention was focused on reaching the getaway vehicle with his fellow henchmen.

Carl, a large man with dirty blond hair hidden beneath his cap, reached the van first. Tim entered next with Vic—a lanky twenty-something guy with enough freckles to almost look tanned—bringing up the rear.

They were still missing two of their colleagues.

"Where're Benny and Alex?" Alejandro, the driver of the van said as he watched three of his fellow henchmen pile into the car.

"They fell behind, but I'm sure they'd say to go on without them," Carl said.

"It's what they would have wanted," Vic agreed, knowing full well it was not what they would have wanted. Still, Tim wasn't about to disagree because he didn't want to end up in prison. Tim tried to feel guilty but honestly, he was a bad guy for a reason. Well, two reasons.

Mostly because he was a high school dropout with no real skills and villainy paid better than flipping burger patties. Also, he was a dick. Tim could own up to that much.

"You guys are full of shit," Alejandro said with a roll of his eyes, but he started driving away all the same.

And then he almost ran over their two supposedly fallen comrades.

Both looked worse for wear and Benny was actually limping as Alex dragged him to the van. Both were also glaring at their supposed colleagues as they opened the doors to get in.

"You assholes were gonna leave us behind?" Under different circumstances, Alex might have kicked them all in the shins, seeing as he was too short to actually punch them in the face.

"I was just telling them we should wait up for you," Vic said, and Tim wondered if he actually thought anyone would believe him.

"You're full of shit," Alex said flatly, shutting the door.

"That's what I told him," Alejandro muttered as he finally drove away, seeming too relaxed for someone driving a getaway vehicle after robbing a bank. Granted, he had been doing it for ages.

Still, a sense of urgency would've been appreciated.

"Well, at least you got the loot right?" Vic attempted to change the subject in a not so subtle way.

All five of the men sitting in the back looked around in search of said loot. Tim wasn't surprised to see only his bag sitting on the floor of the van, all on its lonesome. They'd forgotten the loot.

"Do you guys think Penny will ever replace us with more competent minions?" Tim wondered aloud.

"I sure hope not. My retirement plan will be ruined if I have to switch jobs," Benny said, honestly sounding concerned. Tim took a moment to wonder what their lives had become.

If given another chance, Tim would have liked to go to school, get a career, maybe get married if his crippling student debt allowed it. But life had a way of kicking you in the balls and then laughing in your face while it took pictures to immortalize your misery by posting them online—and no, Tim wasn't speaking from experience. So, Tim had ended up as a high school dropout who'd run away from home and fell in with the wrong crowd. Granted, he didn't think he'd done that badly.

And at least he still wrote home to let his poor mother know he wasn't dead, because he wasn't heartless. Most of the time.

Still, Tim had to admit, as far as leading a life of crime went, he was doing pretty well. Mostly because he'd run into a decent enough villain who'd agreed to take him in. Probably out of desperation. Tim would take what he could get.

That villain was Penny—or as she was most commonly referred to by the media, Penny Dreadful. She was, as her name suggested, dreadful at coming up with names. Coincidentally, she was also dreadful at villainy.

Truly, it wasn't Penny's fault. She tried hard enough to be an evil mastermind, but it just wasn't in her to be a maniacal villain. Even if generations of her family had succeeded where she had failed so miserably. It was a touchy subject the henchmen usually steered clear of.

It wasn't that Penny was cruel to them. On the contrary, she was very good to her henchmen, but she had a tendency to take their failures as proof of her personal villainous shortcomings. That explained why she looked like she'd just been told her puppy had died when her henchmen returned with a meager amount of loot, instead of punishing them like any decent villain would.

Personally, Tim thought the kicked puppy look was worse.

"Hey, come on Penny, we got some loot," Benny said as he leaned on Alex, trying to cheer her up.

Somewhere amongst the other villains watching it all go down, someone snorted. It was probably Susan. Goddammit Susan.

"My mother was right, I'm a terrible villain!" Penny said in a croaky tone thanks to the flu that'd kept her home. Her long dark hair was a mess, her skull patterned night gown looking rumpled, and there was a look of defeat on her face even as she wore her favorite pink fuzzy socks. This was not the first time Penny brought up her mother's disappointment and Tim was fairly certain it wouldn't be the last.

One of the henchmen who'd been watching from behind Penny patted her back consolingly while a henchwoman handed her a tissue. Next to Tim, his fellow henchmen squirmed uncomfortably at having upset their boss.

"She told me, you know? She said, Penny, you're too nice for the life of a villain, and she was right. But no, I had to go and prove I was a villain. And now look at me. I don't even have an archnemesis!"

Tim felt bad for Penny, really, he did, but he didn't understand why he had to get lumped in with the others. He hadn't forgotten his share of the loot.

Honestly, and they wondered why Tim was always employee of the month.

"We can always try again?" Vic tried.

"What's the use? I'm already the laughingstock of all the other villains," Penny said, sounding resigned. Apparently, she'd gotten over her need to break into a self-deprecating monologue. Instead, she plopped down on one of the bean bag chairs in the lounge of their lair. It was a nice lair.

Penny's dark eyes swept over the group of henchmen who'd failed her so miserably. Tim didn't mind it all that much, mostly because he was the only one who'd done his job, but his fellow henchmen were shifting on their feet, refusing to meet Penny's gaze.

"Guys, I'm sorry but I'm going to have to punish you this time," Penny said, voice wavering. She sat up straighter in her pink beanbag chair and attempted to look tough. Tim thought it was a decent attempt, even if she failed thanks to the hot pink socks and the short pause she took to blow her reddened nose. "You're banned from this week's taco Tuesday."

The outrage was immediate.

"What, but this week we're having carne asada!"

"I was making margaritas!"

"Can't you just break my other leg?"

Tim rubbed the bridge of his nose and wondered if he should laugh or cry. He decided he'd to that later. There were more important matters to tend to at the moment.

"Since I actually didn't fail miserably, can I not be punished?"

"Yes Tim, you may be exempt from the punishment."

Tim ignored the downright betrayed expression on his fellow henchmen's faces as he left them to face the not so formidable wrath of Penny.


# # #


If there was one good thing that could be said about Tim's life as a henchman, it was that at least he didn't have to worry about rent and crappy neighbors. The lair Penny had set up for her underlings in an old warehouse was roomy and pretty comfortable. While most of Penny's minions didn't live there, it was still a busy place. Mostly because, as their base of operations, they all ended up spending a lot of time at their lair.

Besides, someone had to keep Penny company.

Tim was, often enough, one of those in constant company of Penny. Not that he minded much. She could be fun when not despairing about her failures.

Even so, sometimes, Tim wondered why he stuck around. Sure, the money was good, but there was only so much one could expect out of a life of crime. As much as he enjoyed working with the other henchmen and Penny, Tim couldn't see himself pulling off heists for the rest of his life.

The image of old man Tim running away with a bag of cash on his walker—complete with tennis balls on the legs—flashed in his mind. He shivered at the thought.

No, Tim would rather not be a henchman until he broke his hip, thank you very much.

And so, after three years of service to Penny's not-so-noble cause, Tim decided it was time to move on to better things. In hindsight, he shouldn't have made his announcement to all of his minions, but they were like family and Tim didn't want to keep them in the dark.

"Guys," he said that very night, standing in front of all the others at their lounge. "I've decided to quit and go back to school." The effect was immediate.

Every pair of eyes focused on Tim, a couple of guys stopped in their game of foosball—one taking advantage of this to score before also turning to Tim—and there was a precious few seconds of absolute silence.

Then, all hell broke loose.

"Why?"

"You're abandoning us?"

"School is for nerds!"

"Why don't you love us anymore?"

Tim knew he should feel touched at the response his announcement had garnered. He still thought the backlash to his decision was a bit much.

"Okay, first off, I'm not abandoning you." Tim ignored the cough that sounded suspiciously like the word lies. "I've just been thinking about this, and I don't know if I want to keep doing this for the rest of my life. I'm almost twenty. Soon I'll be an old man like Benny."

"Hey!"

"Besides," Tim went on, ignoring Benny's indignant cry, "I don't know if I want to be known for the rest of my life as an evil dick."

"Just because you're a dick, doesn't mean you can't be a good dick," someone said rather unhelpfully. From amidst the crowd, someone snorted.

"That's what she said!" called out someone who sounded suspiciously like Susan. Goddamnit Susan.

"The point is, I'm going back to school," Tim said, trying to keep things on track. "Now Imma go talk to Penny and you all can go ahead and discuss how I'm heartlessly abandoning you."

As Tim walked away, he could hear them all muttering. Really, he should have known things wouldn't be that easy.

Tim didn't know it at the time, but that was the moment operation "Keep Tim Evil" began.


# # #

Hey everyone! 

If you've been reading my stuff for a while, then you might have realized I've posted this story before. Because of various reasons, it had to be pushed aside and was initially rushed. Since then, I've taken the time to look it over, fix some typos and do some art for this while also writing more chapters. So, here's a newly edited version for you all, now with illustrations of Tim and company's various shenanigans! 

Hope you all enjoy it and, as always, thank you all for your support!

Oh yes, and just in case. 

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