Pretty Sweet - Eddie Munson X Henderson Sister Reader
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Summary: Dustin Henderson always leaves Hellfire early to keep his older sister far away from Eddie Munson’s obvious crush, but one forgotten character sheet ruins everything and gives Eddie the perfect chance to finally charm her right in front of Dustin’s horrified eyes.
Word Count: 1.5k
There was a reason Dustin Henderson always left Hellfire Club five minutes early, and it wasn’t because he had to make it back for curfew.
It was because you, his older sister, picked him up.
And because Eddie Munson, Dungeon Master with a flair for dramatics, had developed a hopeless, obvious crush on you the first time he saw you waiting by your car, tapping your fingers on the steering wheel to whatever song was stuck in your head.
Dustin had caught the look instantly.
“Don’t even think about it,” he had warned Eddie that very first day, grabbing his backpack like it was a shield. “I’m serious, Eddie. She’s off-limits.”
Eddie had only grinned, popping the cap on his marker. “Off-limits? Henderson, she drove you here. She’s literally right there. In the parking lot. Breathing the same air as me.”
“Exactly the problem!”
And so a system was born—one Dustin upheld with military precision. Every campaign night: five minutes early. No exceptions. No stragglers. No chance for Eddie to “accidentally” walk out at the same time.
Until tonight.
Tonight, the dice betrayed him.
A natural 1.
Not in the game, oh no, Dustin had rolled a 20 for that, but in real life, fumbling for his bag and realising too late that he’d forgotten his character sheet somewhere in the mess of snack wrappers and graph paper.
By the time he sprinted back into the room, Eddie was already strolling toward the doors, humming something off-key, twirling his ringed keys around his finger.
And outside—right outside—you were leaning against the car, Hawkins’ sunset painting you in gold.
Dustin skidded to a halt. “No, no, no. Abort mission. Turn around. Eddie, don’t go out there!”
Eddie froze mid-step, eyes lighting up with the slow-building grin of a man who finally caught the monster he’d been chasing.
“Why’s that Henderson, you tryna hide something from me?” Eddie looked ahead, over Dustin's shoulder, with a large grin on his face. “Ah, someone?”
Eddie didn’t wait for Dustin’s answer. He brushed past him with that maddening, self-satisfied swagger, boots thudding on the linoleum as he pushed open the doors. The warm evening light hit his face, and he squinted dramatically, as if he’d just stepped into some divine realm—your realm. You glanced up at the sound, lifting your head from whatever you’d been scribbling on a notepad, and your eyes met Eddie’s.
He nearly tripped.
“Hey,” he said, suddenly softer, suddenly shy, like someone had reached into his chest and squeezed. “Uh—hi. Didn’t know you were the designated Henderson chauffeur tonight.”
You gave him a small, amused smile. “I’m always the designated Henderson chauffeur.”
Behind Eddie, Dustin groaned loudly, breaking the air. “Oh my god. Y/N disengage, get in the car, and drive”
Eddie ignored him entirely. “Well, lucky us.”
You raised a brow. “‘Us’?”
Eddie cleared his throat. “Uh—me. Lucky me.”
Dustin threw his hands up. “No. Nope. Eddie, abort. Retreat. Go back inside and pretend this never happened—”
You tugged open the passenger door for your brother. “Dustin, it’s fine, get in the car. Let him talk. You never let me meet your friends”
Eddie visibly perked up whilst Dustin visibly died inside.
Eddie placed a hand over his heart, staggering back a step like he’d just been given divine permission to breathe.
“You hear that, Henderson?” he said, eyes shining with theatrical triumph. “Your sister wants to meet your friends. Specifically me. Mostly me.”
Dustin shoved his backpack into the car with a force that suggested he wished it were Eddie instead. “I hate this. I hate both of you. I’m telling Mom.”
“You do that,” you said, rolling your eyes. “I’m sure she’ll be devastated to hear that someone finds her daughter interesting.”
Eddie snorted, then tried to disguise it as a suave laugh. It absolutely failed.
You shut Dustin’s door before he could protest again and turned back to Eddie, crossing your arms lightly over your chest. “So. Eddie Munson.”
He straightened like someone had just called his name at roll call. “That is me. In the flesh. In the leather.” He gestured vaguely at his jacket. “And the denim.”
You fought a smile. “Dustin talks about you a lot.”
Behind the rolled-up window, Dustin slapped both hands against the glass. “NO I DON’T.”
Eddie beamed. “Oh yeah? All good things, I hope.”
“Depends what you consider ‘good.’” You smirked. “Lots of yelling. Something about unfair campaigns. A dramatic monologue about you killing his character two weeks ago.”
Eddie gasped, affronted. “I didn’t kill his character. He threw himself into a pit trap after I explicitly told him not to.”
Dustin yelled through the closed window: “YOU SAID IT WASN’T A TRAP!”
“I lied! That’s storytelling!” Eddie shouted back, no longer looking at him, still looking at you.
You laughed, genuinely, bright and warm, and Eddie looked like he could live off that sound for a year. He rubbed his palms against his jeans, suddenly restless. “So, uh… since fate has clearly intervened tonight—thanks for the nat 1, Henderson—I was thinking… maybe… if you’re not too busy sometime, we could… I dunno.” He shrugged, eyes flicking up to meet yours. “Hang out? Maybe grab something to eat? Talk without your brother trying to tackle me?”
You tilted your head, pretending to consider it even though the smile tugging at your lips gave you away.
“That depends,” you said. “Would Dustin survive the shock?”
From inside the car, Dustin pressed his face to the window, eyes wide with horror. “PLEASE DON’T ENCOURAGE HIM.”
Eddie placed a hand on the car roof, leaning in closer, hopeful and helpless in the same breath. “I’ll take my chances.”
You cut him off. “Maybe.”
Eddie blinked. “Maybe?”
You shrugged. “Maybe we can hang out,”
Eddie grinned, slow and stunned and triumphant. “I’ll take a ‘maybe.’ ‘Maybe’ sounds like a strong ‘yes’ waiting to happen.”
Eddie’s grin was still stretching across his face, wide and triumphant, when he moved toward your car. He hooked his fingers around the handle like he had done it a hundred times before, although the truth showed in the careful and almost reverent way he pulled the door open. Inside, Dustin snapped his head toward him, eyes narrowed into the kind of death stare usually saved for mortal enemies or, apparently, potential brothers-in-law.
“Don’t you dare,” Dustin warned, his voice high with panic and disbelief. Eddie leaned down just enough to meet the younger Henderson’s eyes directly. The two of them froze, locked in an entirely ridiculous yet absolutely serious battle of wills.
Dustin’s glare promised violence. Eddie’s stare promised trouble.
The tension held for a moment. Then Eddie’s expression shifted slowly, showing a smug smile before he lifted his hand in one deliberate motion and flipped Dustin off right in his face.
“You absolute—!” Dustin sputtered, smacking his palm against the window with enough force to rattle the whole door.
Eddie had already stopped paying attention. When he turned back to you, the mischief fell away instantly. His posture straightened, and he pushed the door open a little more with exaggerated gentleness, almost as if he needed you to know he did have manners, even if he used them selectively.
“There you go,” he said, his voice softer. “Wouldn’t want the designated Henderson chauffeur to deal with any complications.”
You could not help smiling. There was something undeniably endearing about how quickly he could shift from menace to sweet. “Thanks,” you said, sincere despite Dustin’s meltdown.
“Anytime,” Eddie replied. The word came out like a promise, and his grin grew smaller and warmer. He looked like he was trying very hard not to bounce on the balls of his feet.
Inside the car, Dustin made a dramatic noise that sounded half wounded animal and half outraged brother. “I cannot believe this. He flipped me off. In front of you.”
You shut his door before he could work himself up further and moved around the car to take your seat behind the wheel. Through the windshield, you caught Eddie backing away with that same stunned, proud smile on his face. He lifted a hand in a small wave. You returned it before starting the engine.
The moment the car rolled forward, Dustin erupted.
“Why are you smiling?” he demanded. He twisted in his seat with an expression that accused you of committing several crimes. “He insulted me. He flipped me off. He is trying to date you. How is any of this funny?”
You shrugged lightly as you merged onto the road, fingers tapping the steering wheel in a rhythm you did not think about. “I do not know, Dustybun. Maybe because he is sweet.”
Dustin made a strangled noise and slumped dramatically into his seatbelt. “Sweet? Sweet? Eddie Munson is not sweet. Eddie Munson is chaos in denim.”
“It could be worse,” you said with a tiny smirk.
Dustin threw his hands up in complete exasperation. “How? How could this possibly be worse?”
In the rearview mirror, you caught one last image of the parking lot. Eddie was still standing there, fists raised, bouncing on his heels like someone celebrating a long-awaited victory. He looked absolutely thrilled.
You had to admit, it was pretty sweet.
