Firsts

Anna is sixteen

Anna was stunned when Charlie showed up at the bunker out of the blue one Thursday morning in June. She was even more surprised to find that it was her, Charlie wanted to hang out with.

"I'll take great care of her," Charlie promised Dean, standing directly beside him and looking up at him exactly the way Anna always did when she was pestering him. "We'll be gone three days tops. She'll call every night. No booze or drugs, I promise. Stuff's overrated anyway."

Dean set his beer down and sat at the kitchen table, giving Charlie an appraising look. "Where the hell do you even want to go?" He asked.

Anna perked up from her spot on the counter, socked feet dangling above the ground. That was progress right there. Before, Dean had just said no. Now he was asking questions.

Charlie smiled deviously. "Pride," she said.

Dean's expression changed to one of fear. "No," he said firmly, pointing at Charlie, then at Anna who was beaming at the mere thought of going to Pride with the coolest woman she knew. "Don't even start, Anna," he told her seriously. Her excitement only grew despite his answer. "No," he repeated at the look on her face.

"What's wrong with pride, Winchester?" Charlie asked with her arms crossed over her chest, looking thoroughly unimpressed by his reaction.

"Nothing," Dean answered rapidly. He raised his hands in surrender. "Nothing wrong with pride, Charlie. Okay? Pride's fine. Hell, it's awesome."

Anna couldn't help herself— she bounced once on the counter, feeling closer to a yes already.

"No," Dean said again, though, one finger pointed at her. "Don't get excited, Runt. It's not happening."

"And why is that?" Charlie demanded. She put her hands on her hips. "Do you not trust me with your sister for a few days? We're not going hunting."

"Yeah, and that's the only reason we're still discussing this," Dean said and took an aggressive swig of his coffee. He set it back down firmly on the table and stood up again. Pacing over toward Anna, he looked at Charlie and gestured to the kid behind him. "She's sixteen, Charlie."

"I know," Charlie retorted.

Anna made a face at her brother for insinuating she was a friggin' child. She got a snicker out of Charlie for the rage in her expression, but Dean never even noticed the look.

"What about it?" Charlie pressed on.

"So, she's too young."

"Too young for what?"

"For… I don't know… It's a lot of people, okay?" He argued defensively. "It's a lot of drunk people who aren't spatially aware. And I don't want you losin' Anna in a crowd like that." He ran a hand over his face. "Look, I know you want to, okay?" He looked back at Anna, "I know you wanna go too. I just… maybe next year, okay?"

Charlie made an annoyed face. "So we can have the same fight next year? Not happening. I want her for three days. Just three. She'll call you. We'll be careful."

Dean held Charlie's gaze for a long moment. She didn't waver or back down. "Where is it?" He asked in a strained voice.

Charlie smiled broadly, winking at Anna over his shoulder. "New York City."

Dean's expression filled with horror again. "Fuck no."

"It's my favorite and it's not that far."

"No, Charlie."

"Dean, come on," Anna begged. "New York," she repeated. "That's, like, the biggest pride parade in the country."

"Exactly my point," Dean told her, avoiding her hopeful eyes. "The answer's no. Drop it."

"In your dreams, I'll drop it," Anna scoffed. She looked to Charlie for help and wasn't disappointed.

"Sam would say yes."

Dean gave Charlie a dangerous look. "Don't even try."

"He would," Charlie insisted. "And I'll get him out here, and the three of us will wear you down until you say yes."

Dean threw his hands up and turned away in frustration. "Fuck," he swore, and Anna knew he'd given up. "Fine," he said, turning back toward them. "Fine. But if anything happens to her-"

He was interrupted by Anna jumping off the counter to hug him tightly. "Yes, thank you! Oh my god, I'm going to New York. Thank you, thank you!"

Charlie was smiling ear to ear at him, but Dean's expression was not one of joy. In fact, he looked deeply unhappy.

()()()

Anna shoved a bag of makeup into her duffel and listened patiently to Dean's hundredth recitation of the rules.

"You better listen to Charlie. And you stick to her like glue, understand me? Like glue."

"Yeah, I got it," Anna promised. She folded a pair of black denim shorts and stuffed it into her bag. She smiled briefly over her shoulder at her older brother. "You can quit worrying, Dean. We're gonna be fine."

Dean shook his head at her, jaw clenching rhythmically. "It's in the job description," he informed her dryly and crossed his arms. "No funny business at this thing, alright? I mean it. No alcohol. You touch anything worse than alcohol and you'll be grounded til you're my age."

"Not within your power, but I hear the message," Anna allowed with endless patience. She zipped her bag and swiveled so she could sit on the bed next to it.

Dean inhaled deeply, then dropped to a crouch in front of her and sighed. There was a different seriousness coming into his eyes now. Concern, deep and cautious. "Listen," he said and waited for her to look into his eyes. He seemed to be searching for something in hers, but she didn't know what exactly. So she just looked earnestly back at him, waiting to hear what he had to say. "I want you to have fun, okay? But if your depression thing rears its head, I don't want you keepin' that secret."

Anna swallowed and looked pointedly away from her brother.

"Hey, I mean it," Dean pushed, tapping her knee with his knuckle. "I don't care if it's embarrassing or you don't want to worry anyone or whatever other bullshit you can think up. I'm not havin' you run off or hurt yourself because Charlie doesn't know about what goes on in your head. You get that?" At her continued silence, Dean asked again, "Do you hear me, Anna?"

"I hear you," Anna mumbled, ducking her head so her curly hair covered half her face. "Just don't tell her," she requested. "Please don't. I just want to have fun."

"You will, Rugrat," Dean told her and gave her a warm, charming smile. "Charlie will make sure of that." His eyes softened, but his smile started to fade as he added, "But it's my job to keep you safe, so just humor me and be in touch, alright?"

"Okay," Anna agreed amicably. She lifted her chin and wrinkled her nose at the worry she could still see in Dean's face. "We'll be fine," she told him for the thousandth time and kicked him lightly.

()()()

"You got sunscreen?" Sam asked her as Anna handed Dean her duffel and watched him put it in Charlie's car.

"Yep."

"Water bottle?"

"Not an amateur," Anna reminded him with a soft punch to his arm.

Sam put a hand on the top of her head and ruffled her hair just a little. He was always like that— more careful than Dean about messing up her appearance when he teased her. "Just checking," he told her. "New York in June? It's gonna be hot."

"Not as bad as the summer we spent in Texas," Anna countered. She reached up to take Sam's wrist and pull his hand off her head. But she pulled on his arm just enough to make him tilt toward her and then back. "Ease up. You're starting to sound like Dean over there. He's worrying enough for every adult on planet Earth."

Sam snorted at the truth of that, watching Dean lecture Charlie one last time on the other side of the car. "Yeah, he means well."

Anna half-smiled. "I know," she said truthfully. She bounced on her heels and said, "See you in a few days," holding out her hand for a fist bump.

Sam shook his head at her and grabbed her in a bear hug. "Be safe, Ladybug. Take care of Charlie."

"Course," Anna agreed easily, face squished against Sam's chest. If she was honest, that last instruction had surprised her. But it was something she did instinctually in a lot of ways— keeping an eye on people and helping when there was something wrong. Winchester trait, though none of them were exactly experts at it.

"You be safe too," Dean was telling Charlie even as she rounded the car with one hand waving him off. "I mean it, Charlie. Anyone gets fresh, you show 'em that right hook. Girl or guy. And-"

"Dean," Charlie cut him off and turned to look at him with a brilliant, carefree smile. Sunlight glinted off her red hair, making her look somehow more cheerful. "We'll see you in three days."

Dean looked like he wanted to say a million things. But they were likely things he'd already said a hundred times over. He restrained himself. Instead he looked at Sam and said, "You trust these two together?"

Sam laughed, looking at the mischievous smiles on both girls' faces. "Not even a little bit."

"Yeah, me neither."

Anna stepped forward to give Dean a quick hug. But when she tried to pull back, she was held tightly against her brother. "Dude," she grumbled, embarrassed that Charlie was standing right there to see this shit. "It's only three days."

"Yeah," Dean said gruffly. He had on his tough guy face when he let her go. "I don't know what you're so worried about, Munchkin. You'll be fine."

Anna laughed in spite of herself. "Shut up," she told him in exasperation and opened the passenger door.

"Hopeless," Charlie said and smiled.

()()()

They were an hour into their drive when Charlie proved to Anna how much cooler she was than Sam or Dean for the millionth time.

"Play me some of your music," she requested and tapped a couple times on her car screen. The heading said Bluetooth, and there was a button for pairing.

So Anna pressed that button and pretended she wasn't in awe of Charlie having a car with a touch screen. Not to mention letting Anna pick the music. It was unheard of. Maybe she could pick one of Dean's cassettes. But she certainly couldn't play music off her phone in the Impala.

"You sure?" Anna checked, already scrolling through her playlists.

"Well, I don't think you want to listen to 80s pop the whole way to New York," Charlie predicted. "And you probably don't want video game soundtracks either. And those two things pretty much make up my entire Spotify library, so…"

Anna laughed. "I wouldn't have minded, but since you offered…" She opened the playlist she and Kate usually listened to when they were chatting and painting their nails or baking. Girl in Red's hornylovesickmess was the first song to come on, and Anna almost skipped it instinctually. She wouldn't have played that song for her brothers after all. But she paused halfway to the button. "You gonna freak out over the word horny?" She asked Charlie.

Charlie straight up giggled, "You poor thing. What have they done to you."

"Oh, you don't even know," Anna said eagerly. She would take any opportunity to complain about her experience as a teenage girl who had lived exclusively with men her whole life. "When I was like twelve, I said the word blowjob one fucking time and Dean lost his shit."

Charlie's laughter got louder and giddier at that. "Oh, I can picture that," she said. She did her best Dean impression, which essentially just meant she dropped her voice an octave and tried to do a smolder as she said, "That's just wrong, Rugrat."

Anna laughed so hard at the imitation that she doubled over in her seat. She needed more people in her life who felt safe making fun of Dean. "Spot on," she praised and did a chef's kiss. "Dude, you should have seen it. Took like two days after I said that for both of them to try and give me the sex talk."

"Oh my god, no," Charlie said through her laughter. "Don't tell me— it went badly."

Anna snorted at the memory of that day. "Neither one of them could commit to telling me anything, so they kept making each other take over. Dean kept doin' these hand gestures. Truly disturbing."

"Sounds traumatizing," Charlie agreed, still grinning. "I don't know how you do it," she admitted. "All that testosterone all the time? I could never."

"Yeah, I don't know," Anna sighed. "They're not all bad. Just pretty weird about feminine stuff."

"Well, that's not all, though," Charlie told her. "I've seen your room. You don't have anything fluffy or nerdy in there. It's just wrong. You're sixteen. You've got bands and comics and tv shows you like. You should have… stuff."

"Oh," Anna mumbled, a little uncomfortable with the scrutiny of her life. "I mean, that's not their fault. I just… I don't know. It's weird. We never used to stay anywhere long enough to decorate. And it just feels pointless now."

"Pointless?!" Charlie gasped. "My walls are lined with Comic-con memorabilia, Winchester. You better take that back."

Anna laughed, feeling more at ease again. "Okay, I'm sorry," she said. "Just for me, it's pointless."

"Why?" Charlie pressed, tone light. "What's so pointless about fun? Your room is your safe zone as a teenager. You gotta make it more yours."

"But it's… I don't know… it feels dumb," Anna admitted. "I don't have that much stuff. I can't buy posters and plushies and stuff. I feel weird just asking for new clothes."

"My point exactly. Those boys don't like shopping. Admittedly, I don't either most of the time. But Hot Topic? I love me a Hot Topic. Or Spencer's. But don't tell Dean I brought you there. Newbury Comics," she added, merely thinking out loud at this point. But her energy was contagious, and Anna found herself getting excited.

"Are you saying what I think you're saying?" She asked with hope filling her core.

"We're going shopping!"

()()()

Anna had never actually heard of Spencer's before. But once she'd explored the whole store, she understood why Charlie had told her not to mention this trip to Dean.

"You have a vibrator?" Charlie asked her as Anna stared in mortified shock at the back wall.

"Uh, no," Anna stammered. "Should I? I mean, is that a girl thing?"

"There's no should," Charlie corrected her. "Just, you know, if you want one… you can get one. No weirdness."

Anna's eyes went wide. "I… guess I never really thought about it. I mean, how would I even… I don't think I know how to… Yeah, I'm good, I think," she finally said.

Charlie smiled sympathetically at her. "You don't have to be magically comfortable with this, Anna. I just think you should know that you're allowed to embrace your sexuality however you want. And your femininity."

"That's a weird word."

"Hey, I was making a point."

Anna wrinkled her nose, cheeks pink with embarrassment. "Sorry."

"Shush. No sorries. You want one, get it. You don't, we'll move on."

Anna stared at the wall for a second and took a deep breath, trying to get her nervous system to accept that this moment didn't need to be tense and awkward just because there were vibrators a foot in front of her. "Dude, these are crazy," she snickered, struggling to get her shoulders to loosen a bit. "Is that one a pickle?"

"Yeah, I don't get the appeal," Charlie told her. "I don't really want a pickle in my vagina, personally. But I'm also very gay, so, you know. That could have something to do with it."

Anna nodded, exhaling shakily. "Yeah, this is too much," she admitted. "I'm too stunted for this."

"Stunted?" Charlie repeated, sounding almost upset. "You're still a kid and this is new to you. Those are two different things."

"Yeah, I know," Anna said shyly, looking down at her sneakers. She felt suddenly tired. And her brain was taunting her. She'd thought maybe the whole depression thing would leave her alone for just a couple days so she could have fun with Charlie. But it seemed like her stupid brain was as easy to set off as ever. "I just, you know, I'm kinda messed up, Charlie. I don't… I don't think I'm that good at being a girl."

"Hey," Charlie scolded, brushing her hand over Anna's head in a way that was almost sisterly. God, she wished Charlie was her sister.

"Sorry," Anna muttered. "I'm a buzzkill lately."

"Stop apologizing," Charlie instructed. "You gotta learn to be nicer to yourself."

"Yeah, that's not really my vibe," Anna told her and turned around suddenly, trying to find a good distraction. "They have keychains?" She asked. "I have a pretty sick keychain collection on my backpack."

"Yeah, real smooth," Charlie quipped but followed Anna across the store anyway.

()()()

By the time they checked into their hotel room in the city, it was dark outside and Anna was exhausted. She wasn't used to doing so much and seeing so much. It was exciting but tiring. She didn't have the serotonin for this shit.

"I'd say that's a pretty good haul," Charlie remarked as she and Anna carried in their shopping bags.

"I've never bought this much stuff in one day before. Like ever."

"Well, I expect you to drag Sam and Dean to every geek store within a hundred miles of the Batcave now."

Anna grinned at the thought of Sam and Dean perusing a Newbury Comics and pretending not to be as excited as she was. Suddenly, she wanted to show her brothers all the cool stuff she'd gotten.

She was saved the embarrassment of being way too old to eagerly call Dean when Charlie said, "Hey, you should probably call Dean soon. Knowing him, he'll drive all the way here just to chew us both out."

"Yeah," Anna said with a very fake eye roll. "Guess I should." She pulled her phone out and made a face at just how quick Dean was to answer her facetime. "Dude, get a life."

"Ha ha," Dean deadpanned. "You guys get there okay?"

"Well, I'm alive, aren't I?"

"Extra funny tonight," Dean said dryly. "I take it you and Charlie are already up to no good?"

"So much mischief," Charlie said from behind her, and Anna grinned.

"Dude, we went shopping," she told her brother. "Like real shopping. Like to a mall with three floors. It was huge."

"Oh great. So you won't need to go the mall in Lebanon anytime soon," Dean teased, and Anna saw him take a swig of beer.

"Very funny," Anna grumbled.

"So, what'd you get, Rugrat? Band shirts?"

"Dude, think big. Charlie has a magic credit card."

"That's terrifying," Dean admitted. "Go ahead, kiddo. Give me the reveal. I'm dying of suspense here."

Anna reached behind herself and pulled out three separate posters. "Dude," she said. "Fall Out Boy. Paramore. MCR," she recited, tapping a different poster each time. She set those aside and reached back in to her bag. "Plus hoodies. Plus, look-" She held up five keychains of various bands and one of Rick and Morty.

"Good God, Runt, that backpack is gonna be so weighed down, you won't be able to walk."

"That's such a dad joke," Charlie observed. She sat beside Anna on the bed.

"No, that was an observation," Dean replied defensively. "Here's another observation: You're feeding her obsession with that mad scientist cartoon."

"It's called Rick and Morty," Anna said impatiently.

Charlie wrapped an arm around Anna's shoulders so she could lean in and show her face on the call. "Uh, for the record, Dean, not knowing what a show is called even though she's said the name a thousand times is also giving dad energy."

Anna wrinkled her nose and surprised herself shortly thereafter with a yawn.

"You okay there, Champ?" Dean teased.

Anna pouted. "Yes. Shut up. Real shopping is tiring. It was a three floor mall and we walked the whole thing like five times."

"Two times," Charlie corrected, then made a face and said, "Which is basically five. I'm tired too. But the merch…"

"Worth it," Anna agreed wholeheartedly.

"Alright, alright," Dean grumbled, but he was smiling at them both as he shook his head. "You two behave yourselves and get some sleep, okay?"

"Hey, we're perfect angels," Anna griped.

"Believe that when I see it," Dean snorted. "Love you, kid."

"You too," Anna said through a sweet smile. Dean didn't say that very often. And in a strange way, it felt really good to be missed. She was used to being the one left behind, wondering whether anyone needed or wanted her at all.

She wasn't doing anything as important as saving lives, of course, but it still felt good to be out and about. Traveling. Exploring. Trying things for the first time. She'd seen a whole wall of vibrators today, and Anna had been the most awkward one present. That was a first.

"G'night, Dean," she said softly.

"Night, Rugrat. Night, Charlie."

Charlie waved bye at the camera and waited for Anna to hang up. "You guys are so cute," she said once Dean was gone.

"Dude," Anna groaned.

"I'm sorry, but that's goals."

"Shh."

"Oh! Also. He holds his phone like an old man. Like with the camera low at the most unflattering angle."

Anna laughed out loud. "Oh my god, yes! Thank you! Sam refuses to admit it, but I think it's just because he's only four years younger and he doesn't want me to call him old. But, like, Sam's not out of touch. So… God, Dean is not old enough to act as old as he does."

()()()

Getting ready for the parade was almost as fun as going to it. Anna didn't often get to hang out with other women, and it was so much fun to put on makeup and pick outfits without being teased for wanting to look nice. It was like hanging out with Kate, except Kate was Anna's age.

Charlie was like… like the big sister Anna had always dreamed of having. She let Anna borrow clothes and makeup– makeup she was a little surprised Charlie even owned, if she was being honest.

"So, tell me about this parade. Is it, like, the Macy's parade but cooler?"

Charlie laughed at her. "Not really, no." She opened an eyeshadow palette and removed the plastic sheet from the middle of it. "It's not really about the floats, actually. It's mostly just a lot of people with a sense of community hanging out and being kind to each other. It just feels really, really good to be a part of it."

Anna looked at her with soft green eyes. "How many people?"

"I don't know. Thousands, I guess."

"Woah," Anna breathed, trying to wrap her head around that. "I don't think I've seen that many people in one place. Like, ever."

"It's a big city," Charlie told her. "It'll be crowded, but people take care of each other pretty well. There are even these groups of nurses from different hospitals who go around handing out sunscreen." She snickered, "We're still gonna get a sun burn."

Anna wrinkled her nose at that. "That's inspiring," she said sarcastically.

Charlie smirked at her and said, "Hey, there will be inspiration. People give some good speeches."

"Speeches?" Anna repeated. "It really isn't like the Macy's parade."

"It's not about the parade," Charlie reiterated. "There are floats, and they're great. But the best part is just seeing everybody be so unapologetic. It's like going to a convention or LARPing, and everyone is dressed up and geeking out as hard as you are. You get to just exist. It's awesome sauce."

Anna smiled softly at the thought of that. But her smile faltered after a second. "Do you think I belong there? I mean, Charlie, I don't even know if I'm gay or not."

Charlie looked dubiously at Anna. "Kiddo, I would be stunned to find out you were straight," she said very un-gently.

Anna was surprised into momentary silence. "I have a… a kind of boyfriend… ish."

"Mhm," Charlie murmured and didn't backtrack on her earlier statement at all. She didn't even flinch.

"I'm not really sure about anything," Anna admitted, watching closely to see Charlie's response.

She wanted to know what her friend knew. She wanted to have some intimate knowledge of herself and queerness and the world. But she didn't know shit. She didn't know anything about herself, knew very little about the queer community, and knew even less about the world.

She felt so out of place everywhere she went. Anna hoped like hell this wouldn't be just another version of that feeling.

Charlie set her palette down and gave Anna her full attention. "Anna, you're into this. I saw the look on your face when I said people get to just exist at Pride, and it was the face of someone who wants that."

"Yeah," Anna mumbled and looked down.

"You don't have to know anything for sure at sixteen years old. Just have fun with this!" she encouraged and gave Anna a light punch in the arm. "And play some music! We've got glitter to put on!"

()()()

The sun was unrelenting throughout the day, making Anna's feet hurt as the heat from the pavement bled through her sneakers. But she barely noticed. There was so much else to take in.

Charlie was right about how many people there would be. Anna stuck close to her friend, trusting that Charlie wouldn't let her get lost. But she couldn't keep herself from wanting to see every single thing she could.

She hoped she wasn't gawking too obviously at all the parade goers. Everybody was so… free. Happy. Anna had never seen so many rainbows or so much glitter in her life. It was amazing.

"You like energy drinks, right?" Charlie asked her, voice raised so Anna could hear her over the constant noise around them.

Anna's eyes went wide. "Yeah," she shouted back, hoping she'd heard right. Energy drinks? Count her in.

Charlie smiled gleefully and pointed down the road from them where a group of people with branded t-shirts were handing out energy drinks… for free. Free.

Anna bounced excitedly on the soles of her feet, then felt silly and childish and forced herself to stop. But to her right there were three or four fully-grown adults bouncing just like she had been, dancing and cheering the brand name, waiting for their turn to caffeinate. Anna smiled even as she felt somewhat confused. Was joy that easy? It almost didn't make sense.

But maybe all the freedom went hand-in-hand. Maybe being unashamed of your gender and sexuality meant you could be unashamed of your excitement about your interests and about new experiences. Maybe it was okay to be anything here. Not just gay.

Anna felt a longing for the briefest moment. A longing to exist in a space like this forever.

Then she was handed an energy drink, which she cracked open immediately with a giddy thank you that made the worker smile brightly at her. "I love these," they said. "I literally wear this shirt on my days off."

Anna laughed, "I would too!"

Charlie slung an arm over her shoulder and pointed to a group of people across the street from them singing a Queen song.

Anna watched them for a second and suddenly found herself feeling sentimental. Classic rock mixed into this parade made her think of her brother. "Hey," she called, looking up into Charlie's face. "I think Dean is bi."

Charlie laughed, "You think? He taught me to flirt with a man!"

Anna giggled at that. But her heart ached underneath the buzz of excitement. She wished Dean was capable of coming to a parade like this. She wished he could let himself be free. Maybe he didn't want to do half the stuff these people wanted to do. Maybe he didn't want to dress any differently or act any less manly every second of every day. But Anna wished he could. She wished he wasn't locked up so tightly.

She wished it wasn't partially her fault that he was. That he'd had more time to think about himself and his identity when he was her age and a little older instead of raising his siblings.

She was distracted from those thoughts by a speech starting up. The speaker talked about police brutality, intersectionality, and the erasure of queer black history. Anna learned more in five minutes than she had in an entire semester of US History last year.

The day continued with the same high energy. People danced and shouted and sang and laughed and loved. Anna saw more queer couples than she ever had before, and they were all unabashed.

Her head started to ache along with her feet as she finished her third energy drink without even touching a bottle of water. A nurse with blue hair handed her a tiny bottle of sunscreen and said, "Enjoy the parade, baby."

By the time they left, everything had started to feel surreal. Anna was exhausted, and Charlie seemed pretty wiped too. But they were laughing and smiling as they complained about their sore feet and trudged up the stairs to their hotel room.

"So, what did you think?" Charlie asked as they each collapsed onto their respective hotel beds.

"As advertised," Anna said with a satisfied smile. "Fucking awesome."

La Fin