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ms-nesbit · 5 months

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Sweet home chicago (jason todd x afab!reader)

chapter one

Rating: 18+

Warnings: eventual smut, swearing, father figure dick grayson, skater tim drake, sad jason todd :(

Summary: dick and tim trick jason into taking a vacation in chicago. There, he meets someone he hopes to never forget.

Note: im sorry for dipping, yall. I really had some important things to take care of.

ao3

Amber and rose peeked through the hedge between the array of buildings on Michigan Avenue. Jason blended himself with the sea of tourists and chic aristocrats. He didn’t necessarily stick out like a sore thumb, as there were a few Chicagoans dressed casually like him; even in the late-November evening, he sported his signature red hoodie and straight fit jeans, tattered and dirty near the hem. No matter what, he wanted to appear mildly stressed, only mildly, so as to not draw more attention to himself than his six-foot-four frame already did.

He wondered how he got here. Was it the phone call from Dick, or the two dozen from Tim? Could it have been neither, and he perhaps wanted to rush the plane during the busiest season, nudged in a lousy middle seat between an obnoxious preteen and a middle-aged woman watching poorly edited, extremist conservative media? To be fair, Jason treated himself to Portillo’s once he left the airport - a well-earned reward for not lashing out at the self-absorbed individuals beside him.

He stepped briskly, moving in sync with the less-anxious of the crowd toward the shopping district notoriously named Magnificent Mile. On his left ear, he heard the excitement in the tune of indistinguishable conversations and the season’s final water taxis boarding; in his right, a wireless earbud, softly playing his childhood favorite, Diana Ross and the Supremes.

Once he reached the other end of the bridge, he strolled to the sidewalk in front of Tribune Tower, pulling his phone out and indiscreetly sending a message of his coordinates to-

A call. “As much as I love the smell of fish, garbage, and the crooked CPD, why did you and Tim want me here?” Jason was more curious than upset, but he’d rather not disclose his true feelings to his brothers.

“C’mon, Jay, it’s the Windy City! You ever been to Chicago?” Dick asked. “Beautiful everything here. Tim’s at the Van store up the street, and I’m grabbing a slice of pizza across from ya. You wanna come over and get a slice, grumpy? You get a little hangry sometimes.”

Jason sighed, and his stomach grumbled in response to the offer. “Alright, but I’m not goin’ outside. I sat next to some wackjob on the flight who sounded like she needed to be in the looney bin, and I’m not lookin’ to make friends.” As he spoke, he quickly turned his head before dashing across the busy street, waving off a car blaring its horn at him. “What’do’ey have?”

“How about you see?” Dick approached Jason, smiling mischievously. Jason ended the call, moving his eyes to Dick’s hands behind his back. “Guess what I got?”

“Dick, I’m not in the mood for games-”

“Ta-da!” Dick shifted in his coat, revealing a white box with a drawn pizza and the name Lou Malnati’s on it. Jason pretended like his mouth didn’t water at the smell of grease and garlic. “I had ‘em make a classic cheese with those square slices. How about we sit down on the riverfront and talk?”

And talk. No matter the temptation, be it a buttery, gooey pizza right under Jason’s nose, he still believed it wasn’t worth the compromise of having to make more than small talk with others. “Listen, Dickie, as much as I appreciate the offer, I don’t think I’m ready to talk about-”

“Dude, this isn’t about Artemis, if that’s what you’re about to say.” Dick shrugged in his beige peacoat, a piece of his thick, navy, knitted cardigan spilling from his waist. “I just want to, y’know, see if you want to go to this thing tonight.”

Jason cocked a brow in his theatrical manner. “So you and Tim badgered me, had me fly all the way to goddamn Chicago, all to just talk over some overpriced pizza?” Around him, he felt the glare of customers, but he doubled down, giving them knowing looks. “I’ve been here. Want a real place? Go to the goddamn place off Clark and Dickens. You’ll thank me later.”

Dick rolled his eyes, already tired by Jason’s heels in the sand. “Always gotta be a drama queen. Just…come with me. I’ll explain once we’re out of earshot.” His voice was hushed, signaling Jason to follow suit. They walked together to the riverwalk, sitting on the cold high-risen edging. Dick delicately opened the lid of the box, revealing the savory American delicacy and motioning for Jason to take the first slice.

Once Jason reached for the slice, taking his first bite and stretching the rosemary-seasoned cheese from its bed atop the crust, Dick began. “Tim and I were thinking that the three of us could use a break.” Jason grumbled indistinctly into his pizza slice, swirling the string of cheese around his tongue in a tight noose. “Bruce has been a handful lately - I mean, he always is - and I think it would be a good lesson for him to finally be on his own instead of taking us for granted, y’know?”

Jason nodded, rearranging his food to one side of his mouth so he could speak with the other. “You do know that Bruce is probably better off without me, right? Since I-” he swallowed the food, kissing the excess sauce and garlic from his teeth, “leave a ‘pretty big mess’, as he says.”

“You also help. Gang-related crime decreased about 37 percent when Red Hood regularly patrolled, and the Gotham Gazette did a poll, based on before and after Red: thanks to Red Hood, 6 out of 10 female Gothamites feel safe walking home at night, compared to the 3 out of 10 prior to Red Hood’s introduction.”

The statistic surprised Jason. He was used to the smearing from Justice League’s best, so it was nice to hear a compliment for a change. “And Timmy’s on board with this?” He didn’t hesitate to take a second slice, while Dick left the pizza untouched.

“He was the one who coined it.” Dick looked out at the river, mildly put off by Jason’s shameless eating habits. “We were patrolling one night and he just said it out of the blue. I get it, though.” He pursed his lips, staring wistfully. “I couldn’t tell you before because then you wouldn’t agree to it.”

Dick was right: when he’d offer to take Jason in after they reconciled, Jason refused. Though not Bruce’s blood son, Jason was comparably stubborn, sometimes surpassing the Dark Knight. “And where are we gonna stay?”

“That’s the best part.” Dick finally reached for a slice, folding it in half and dipping a chunk into his mouth to cut from the slice. “Tim hacked into Bruce’s business travel account and used some of his points to book a stay at some fancy place called Waldalf…lemme check.” Dick reached into his peacoat pocket and pulled out his phone, checking the reservation. He continued to chew, as did Jason, and Dick leaned over to show Jason the reservation email. “Astoria. It’s a couple of blocks here, I think. Worst case, we can just use a taxi or Uber there or something.”

“I’m banned from using Uber.” Jason said nonchalantly, squinting at the details on Dick’s pristine phone screen before looking the name up for himself. “I can walk as long as I can have another slice.”

Dick blinked at Jason blankly before glancing at the remnants of the pizza. “Take the small one right there.” Removing a wrinkled, discolored restaurant napkin from his back pocket, Jason snatched the slice with an asymmetrical, genuine smile, now holding a slice in each hand. Dick bit his tongue in his mouth to keep himself from laughing. If he hadn’t held a slice in his, he would have snapped a photo to send to the family group chat. “We’re already checked in, so just bring whatever luggage you have with you.”

Jason looked up from his slices like a deer in the headlights. “Sorry, I didn’t think to bring anything other than the usual.” With a slice, he vaguely gestured to his dirty clothes.

“I was…expecting that.” Dick chuckled lightly. “I brought you some clothes so you could go out and enjoy yourself for a change.” He spotted Jason’s eye roll. “You’re in your twenties, for crying out loud. Enjoy yourself! Make a friend. Would it kill you to just live?”

As Jason shook his head, a few strands of grey fell from his messily combed back hair and onto his forehead. “What, is coming back from the dead and seeking vengeance to blood-thirsty psychopaths not living?”

“No, it’s not.” a voice came from the other side of the riverwalk, by the bustling street: a lanky-built male, wearing a beige Santa Cruz sweatshirt and dark jeans, strolled on his skateboard toward the brothers. “And by the way, Jason, you look no different than the bourgeoisie skimming the racks at Urban Outfitters over there.” Jason’s frown dropped at Tim, already bugged by him. “Me and Dick were basically wanting you to, y’know, socialize like a normal human being. I know you’re an introvert, I get that, but you’ve gotta, y’know…converse.”

Jason stood from the platform, brushing the suggestion from his broad shoulders. “Jesus, and you wonder why I don’t want to hang out with you guys.” he made an excuse and walked back toward Michigan Ave, finishing his slices along the way.

“By the way, Dick.” Tim nudged Dick with his elbow, showing him a photo of zoomed-in Jason, a few minutes earlier, smiling goofily with his two slices of pizza pie.

Dick erupted into laughter, doubling over and nearly knocking over the box.

“You got the terrace suite?” Jason muttered in blustering shock. “Bruce is going to be so pissed.” His lips stretched into a wide smile.

He plopped onto the sleeper sofa, sprawling his limbs out to relax. Dick assigned Jason to the couch (“Finder’s keepers!”), while Dick and Tim each slept in their separate rooms. “We already received a warning about how you’re dressed, Jason, so if you could please promptly change into something more appropriate, I’m sure this stay would be more enjoyable for all of us.” Dick managed to remain calm while conveying, despite the fatherly-level of disappointment underneath his skin.

Heeding Dick’s advice, Jason made his way to Dick’s room, where he opened up the luggage Dick neatly packed for him: a pair of dress shoes, two pairs of socks and boxer briefs (all red, for continuity’s sake), along with a lightweight, tightly knitted sweater, t-shirt, long-sleeve undershirts, and two pairs of slacks (one beige, one black). Jason sighed halfheartedly, bummed by the array chosen for him. He knew, of course, it was his responsibility to select his own attire, but of course he’d forgotten it, lost in the chaos of his everyday life; Dick anticipated Jason’s reaction, and packed something nonetheless, and although grateful, Jason still hesitated to express it.

While Tim and Dick explored the depths of downtown, Jason immersed himself into the room, quietly exploring the channels that Astoria offered.

Knock, knock. “Housekeeping!”

Jason yelled back, “Come in.” while munching on a bag of corn chips on the couch, eyes lasered on the television screen.

The housekeeper, wearing a black and sky blue uniform, pushed his trolley in. “Are you enjoying your stay, Sir?”

Jason shrugged. “My ma was a housekeeper for a bit. Don’t worry about the ‘sir’ stuff, it’s all good.” The response was new to the employee, who stood for a moment before excusing himself to clean the bathroom and bedrooms.

“Sir,” the housekeeper returned, gripping the trolley behind him with a single hand. “Would you mind vacating the room while I clean, or should I return if you are…busy?”

Jason looked at the chip crumbs on his hoodie before looking back at the housekeeper. “I’ve no problem leaving. I’ve gotta change, so I’ll go the other room. Could you just lock the door when you leave?”

“Absolutely, Sir.” the housekeeper said before Jason shut the bathroom door, slacks and sweater in hand.

—

Stepping out from the courtyard of the hotel premises, Jason wandered down the corner, unable to prevent himself from making grotesque faces at the high-end stores nearby. The breeze chilled the skin on his face to the point where it eventually felt like he was kissed by needles, and he unlocked his phone to find a place to settle down and (hopefully) eat. Out of the corner of his eye, he noticed an approaching blotch of yellow and blue, to which he immediately hailed down. A taxi parked along the curb, and Jason hopped in. “Could you please take me away from here? Some place with some good food?”

The driver gave Jason a look of uncertainty, pondering before nodding and starting the meter.

Jason sat back and relaxed as giant metallic letters standing proudly on top of clear, godliness glass storefronts began to disappear, one by one, until they were replaced with bulletins and signs, and tented storefronts matched with painted, worn down brickwork.

He exhaled in relief. Despite living with Bruce and his luxurious lifestyle, the unspoken language of wealth was still foreign to Jason. He didn’t understand why the affluent would whisper, and why evil would poison their tongue and burn away at their heart once their financial wealth accrued.

After slipping the taxi driver a couple of hundred dollar bills, Jason abruptly left the vehicle, reading the name of the restaurant to himself. “Like the song…?” he asked the driver, who nodded.

“Different spelling, different things.”

Jason inhaled nasily, chest rising. “Alrighty, thanks, man.”

The driver nodded once again before waving and merging back into traffic. Jason entered the restaurant and was instantly greeted with sweet and savory notes, causing Jason’s stomach to cramp in pain. He walked up to the counter, so clean that he could almost make his reflection out, and waited for an employee to serve him. While he waited, he studied the menu: sandwiches, soups, and more appetizers to choose from. He chewed on his bottom lip, distressed when deciding between pasteles (mix of plantain mix and meat, wrapped in a banana leaf) or mofongo (stuffed plantain).

“When you’re ready, I can take you.” A voice notified him as he stood like a bronze statue before the menu.

He didn’t take his eyes off the photos above the counter. “Sorry about this, I’m a first timer - what are your pasteles filled with?”

“Usually pork or chicken, but we make them with cheese now since there are some vegetarians.”

“Could I have just pasteles, one with cheese filling and one with chicken?” Jason asked.

The clerk pressed a button on the register, which was a tablet with a brightly lit screen. “Sure thing. Anything else?”

“Yeah, and…pastellitos de guayaba? Can I have that, too? And water.”

The clerk pressed the screen a few times, noting down Jason’s order. “Of course. For here or to go?”

Jason finally tore his eyes from the menu to look at the clerk, and his mouth fell open at the sight of the clerk: hair was tightly curled, coiled from their roots; lips plump and glossy, appearing much more enticing to Jason than the food he ogled at.

“Here.” he stuttered, feeling heat rise up to his neck. The clerk smiled at him, and they placed their hand on their wide hip, bringing Jason’s eye to it.

“It’ll be ready in a bit. We’ll bring it to your seat, yeah? Sientate.” They motioned with their nose at the dining area, a selection of polished wooden chairs and tables to choose from.

Before he could ask for their name, the clerk rushed to the kitchen of the restaurant, repeating his order to the rest of the staff. Jason watched them walk away, their bottom half swaying in the leggings they wore, before he realized his leering and chose an empty seat and table near the colorful mural.

Thoughts rushed to the tall man’s head, some impure ones welcoming themselves for the first time since he and Artemis parted. Their relationship was, in short, complicated, and neither of them were fully transparent toward another, leading to the inevitable diffusion of the once-kindled fire; it didn’t break Jason’s heart, but rather disappointed him, and he felt that his fate of inescapable loneliness was encapsulated.

The clerk reappeared from the kitchen, holding two plates of food. They walked past Jason, ignoring whatever eye contact he attempted to make at them, and attended to the table diagonally from his. “Y te quedas a tu mama, ok?” They spoke warmly but sternly to the couple, before leaving with a grin. “And you,” they pointed at Jason, “your pastellios should be ready in one to two minutes, okay?”

Jason nodded frantically, popping an optimistic grin. “Can’t wait.”

“I know.” they winked at Jason before turning back around and walking through the revolving door leading to the kitchen. Jason felt something distant in his stomach. Perhaps hunger?

In a few minutes, the mysterious clerk returned, holding what Jason hoped was his food. When they arrived at his table, settling the plates down delicately before handing him cutlery and a glass, he beamed first at the food, then at the beautiful clerk. He didn’t know which he was more excited for. “Thank you!”

“Not a problem.” they returned his smile, eyes glistening at him. “Our chef is working on something else for you to carry out, free of charge. Can’t let you starve out on us, right, big guy?” their eyes briefly scanned Jason’s figure, which caused Jason’s cheeks to flush a bright pink.

They’re hitting on me, the fuck. “Thanks! I was hoping maybe I can come back, get your name?”

“Oooh, I like the sound of that.” their voice dipped an octave, and Jason swore he felt his pants tighten under the table. He shifted in his seat uncomfortably. “How about I save you the trouble and tell ya now, that way next time you can take me out for dessert?”

Jason smirked at them, slowly checking their figure out before focusing his attention back on their eyes. “Sure.”

“It’s y/n.” they purred, reaching their hand to rest on Jason’s bicep. Their skin was soft, yet calloused. “And you are…?”

“Jason.” he grinned. “Sorry, I’m new at this.”

“Don’t worry.” they assured. “I’m here if you need anything. And if you decide to take me on that offer, my number is in the check right there.” they pointed to the black checkbook beside the plates of food. Jason’s skin was burning under their touch, and when y/n had to leave, Jason felt a twinge of sadness when they retracted their hand.

Unraveling his cutlery from the napkin, Jason made sure to make an important phone call before his vacation ended.

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