guest12 prompted "Would you ever write a chapter about a young Stefan and high school Damon? The one flashback in this chapter was so cute! It'd just be so interesting to see Damon beginning to step in as Dad, especially how he's low-key parentified while other kids his age don't have the same responsibility."

So from this point forward, this fic will bounce around between past, present and future. I've gone back and labeled each chapter with the date they take place in.

TW: Child abuse + parentification

February 2002

Damon pulls a long sleeved gray t-shirt over his head and checks his clock. He's got 10 minutes to get to Aubrey's house. It took him 6 months to get her to agree to a date. Usually, he's able to just schmooze a little and give a wink. Aubrey lead him on a cat and mouse chase. At least now he can drive over than walk or take a bus. God bless Giuseppe's rare moments of guilt for getting him a Mercedes when he got his license.

He's only halfway out the door when the cordless phone rings. Damon looks in the mirror in the entry way as he attends to his bangs and answers.

"Yeah?"

"I'm looking for the parents of Stefan Salvatore."

Damon frowns. "Uh, they're not here. But I'm his brother."

There's a bit of shuffling. "Ah, you are on the pick up list." Damon nods as if the person can see him. "I'm Sylvia Newton here at Westmere."

"Is Stef okay?" Damon stops fiddling with his bangs.

"He's fine. The issue is no one's come to collect him. Pick up was at 3:15."

Damon pulls the phone back to check the time on the screen. 3:45.

Another glance at the large calendar in the entry way reminds him that today is Lily working some Daughters of the American Revolution function. With Stefan starting kindergarten, she went back to volunteering. That meant hiring Andrea, a sophomore at Siena College, to tend to him 3 afternoons a week. It allowed Damon to keep up his own obligations, including football.

Where the hell is Andrea?

"I'll be right there," Damon says instead of asking a dumb question that Mrs. Newton can't answer. "But I'm about 15 minutes away."

"That's fine, Damon. We're here until the after school program lets out at 4:30."

Once he hangs up with the secretary, Damon calls Aubrey. It goes to voicemail. She's probably getting ready herself.

"Hey, uh, Aubrey…I gotta cancel. I'm sorry. There's been an emergency with my brother. I'm sorry. Raincheck? I'll see you tomorrow."

Damon drives as fast as he can without risking a ticket. He never liked Andrea. Sure, it helped that he could see his friends and play football. Yet, when he came home, he often found her on the phone while Stefan played by himself. He rarely had been given a snack. Damon did all that before attending to his own homework. More than once, Andrea cut off early and asked Damon to say he offered to watch Stefan. He tried to talk to Lily about it but she brushed off his concerns, claiming Stefan loved Andrea.

Stefan sits in one of the chairs, hugging his Spider-Man backpack to his chest. A familiar pout is on his lips. He's in his puffy red jacket and gray beanie. Damon tries to put on a brave smile.

"Hey, Stef."

The 5 year old's eyes light up. He drops his backpack and dashes over. Damon scoops him up and tosses him in the air, catching him with ease. He blows raspberries into his neck and tummy to get a giggle. Any trace of sadness has disappeared. Even Damon finds it hard to be upset when he sees how happy Stefan is.

"DayDay! You're here!"

"Yes, I am. Couldn't leave my baby brother here, could I?" Damon swoops up the backpack and puts it over his shoulder.

"Where's Andrea?"

"She had something come up, so she asked me to pick you up," Damon lies.

Stefan's eyes light up. "I get to ride in your car? You never let me."

"Today is a very special day."

He taps Stefan's nose and turns to the desk. Mrs. Newton is watching on with a smile on her face.

"Do I need to sign him out or anything?" Damon asks.

"No, dear. You two are all set to go. I'll speak with your mother later."

Damon nods. He should figure out a way to get in contact with Lily at the function, having been taught better to reach out to his father at work.

Damon carries Stefan all the way out to the car. He straps him into the backseat and checks the belt. In their parents' cars, he's still in a booster seat. Given Damon just passed his probationary license, he hasn't been allowed to drive Stefan and therefore, doesn't have a seat of his own. It's not too far of a drive.

"Keep this on, alright?"

Stefan nods. "I'll be safe, Day."

"That's my good bunny."

Damon gets up front and pulls out of the lot. He wonders if he could pester his dad into getting him one of those new cell phones. A few people in his grade have them after all. It'd make moments like this a lot easier.

"How was your day?" Damon asks, peering into the backseat through the rearview mirror to make sure Stefan isn't getting out of the seatbelt.

"Good! We had show and tell. I brought Bunny. Everyone thought he was the coolest!"

"Because he is the coolest," Damon agrees.

"But Nora brought her mice. Did you know you could keep pet mice?"

"I did know that." He turns on his blinker at a red light.

"I got to hold one. It crawled up my arm! It felt so cool!"

"That sounds like a good time."

"Do you think Mommy and Daddy would let me have mice?"

Damon chortles. "I don't think so, bud." He catches a slight pout in the mirror.

"Why?"

"Because Mom doesn't even like the mice that come into the house uninvited."

"But these would be invited," Stefan argues. "I'd take good care of them. You'd help. You help me with everything."

Damon smiles as he turns into their part of town.

"I do, you're right. But you're a lot of responsibility. Not sure I want to take on some mice too."

"Fine. What about a puppy?"

"Puppies are a lot more work than mice."

Stefan huffs. "What pet can I have?"

"Let's start you off with a rock."

Stefan bursts into a fit of giggles. "Day! Rocks aren't pets!"

"I used to have a pet rock," Damon says, honestly. "Put googly eyes on it and everything."

"That's silly."

"They don't need food or water. Or much at all."

"I want a puppy. Or a mouse. Or a bunny."

"How about hot chocolate?"

Stefan nods excitedly. "Okay!"

Damon sighs in relief. The last thing he needs is Stefan bugging Giuseppe for a pet. His father is still mad that Lily made him get rid of the hunting dogs after they bit Stefan one too many times. The 5-year-old is too forgiving and was sad to see them go. Damon did all but cheer.

Once they're inside and everything's hung up, Stefan sits at the table. Damon realizes Lily got rid of that booster seat. Stefan is finally able to reach their high table without it. Damon isn't sure why that makes him sad.

Stefan is happy with the Oreo appetizer he has while Damon starts on the cocoa. He glances over at the answering machine but the light is off, indicating no new messages. Damon holds back a sigh. He tries to call the banquet hall Lily is at but no one answers.

He waits a while for the hot chocolate to cool a bit before pouring some into a Looney Tunes mug then one advertising his school's football team. He hands the latter to Stefan.

"Be careful," he warns as he adds the whipped cream. "It's cooled down but it's still warm."

"I'm a big boy Damon, I can handle it." He grins at the mug. "This one's yours."

"Well today we'll switch it up. You drink from that one, I'll have yours."

"Okay!"

They cheers and Damon settles beside him, stealing an oreo. Stefan tells him more about his day, Damon listening intently. He never really had this as a kid. Lily did more volunteering back then. Damon had a string of equally emotionally absent sitters. Often he'd try to go to friends' houses just to have someone to talk to. He smiles along, even as Stefan goes on 5 separate tangents.

After the hot chocolate (which Stefan only got a little on his shirt), Damon brings him into the living room and gives him control of the remote. He builds a pillow fort and they huddle beneath it. Stefan's current obsession is "Recess". Damon hates about half the characters but watches along as he strokes his baby brother's hair and cuddles him on his lap.

After an hour of watching the antics of a bunch of bratty kids during recess, they hear the front door open. Stefan jumps off Damon's lap and dashes into the kitchen, happily screeching "Mommy!" The older brother is quick to follow behind. Stefan is frozen in the kitchen. Damon frowns when he finds Giuseppe instead of Lily. He puts a hand on Stefan's shoulder.

"Dad, you're home early."

"Yes, I am." Giuseppe looks between the two. He spots the chocolate on Stefan's shirt. "You're a mess already." His eyes scan the kitchen. Damon tenses up. There's still a bit of cocoa powder on the counter. He also left the empty whipped cream can out. "This place is a sty."

"That's my fault." Damon instantly steps in front of his brother. Giuseppe's eyebrows are knit together as he glares at his eldest son. "I was going to clean up, I swear. But it was my idea to make hot cocoa. I just wanted to make something special for Stef."

"I see."

Stefan clings to the back of Damon's shirt. The older brother turns around and gives him a brave smile. Stefan is pouting again, his eyes wide.

"Are you in trouble?" His voice is soft, scared.

"How about you go finish your show, hm? I'll talk to Dad."

"But…"

"Go on." Damon pats his back.

Stefan hesitates but eventually obeys. Damon turns back to face his father. Giuseppe's nostrils flare.

"I made a fort in the living room, too," Damon confesses. "But I'm going to clean it up, I promise."

"You think I enjoy working all day and coming home to a mess?" Giuseppe's voice is low. That's more dangerous than his yelling.

Damon shakes his head and straightens up a bit. "No, sir."

"You're the older brother. It's up to you to set an example."

"Yes, sir. I'm aware. I just…"

He doesn't have time to anticipate the backhand. It burns his cheek something fierce. Still, Damon bites hard on his lip and keeps the tears in his eyes.

"Did I ask for excuses, boy?" Giuseppe asks, snarling his lips.

"No, sir."

"No, I didn't. You'll clean this mess and the one in the living room." He looks around the room, clicking his tongue. "Where the hell is Andrea?!"

"I wanted to talk to you about that, sir," Damon says, ignoring the mark that's inevitably forming on his cheek. "I got a call from Stefan's school telling me that she never showed up. I am not making excuses, but that's why there's a mess. I was trying to keep him occupied."

Giuseppe nods. For a moment, his anger seems redirected. "And your mother?"

"At an event for the DAR, sir."

"Of course," he mutters, shaking his head. "Go on, clean up your mess. Then attend to your brother. Get him in new clothes." Damon nods. Giuseppe smacks his bottom. Damon jumps. "What was that?"

"Yes, sir."

"That's what I thought."

Damon waits until the master bedroom door closes to whisper "I hate you". It goes beyond hate. Long ago, Damon longed for his father's approval. He'd do anything to be praised. But then Giuseppe struck Stefan for the first time. All the then 2 year old did was refuse to clean up his toys. He had a bruise on his cheek for a week.

At that moment, Damon began hating his father. And in a way, he resented Lily for not doing more.

Damon quickly cleans up the kitchen before heading into the living room. The TV is off and the pillows put back. Stefan is trying to fold the blankets. Damon swoops in.

"Hey, Bunny Boy, I've got that."

Stefan looks up at him and frowns. "You have a boo boo."

Damon touches his cheek. "This thing? My clumsy butt tripped and hit it on the fridge. But I'll be fine." He ruffles his hair. "I'll fold these then we'll get you changed."

Stefan chews on his lip. "Daddy yelled at you."

Damon shakes his head. "It's fine. He's just a little cranky, you know? I should've known better than to leave that mess in the kitchen."

"I could've helped."

"Nah. That's my job." Damon expertly folds both blankets. "Now, what shirt are we thinking?" He joists Stefan onto torso. "Ninja Turtles? Maybe Mickey Mouse?"

His brother still frowns. Damon lightly pinches his cheek. That gets a small smile.

"Turkey shirt?" Stefan asks.

"Seems good to me."

It doesn't take much to distract Stefan once he's changed. Damon keeps him in his room as they play with his action figures. Giuseppe retires to his study with scotch. Eventually, Damon hears a soft cough from the doorway. He glances up and sees his mom. She's staring at his cheek. Damon quirky shakes his head and gestures to a distracted Stefan. She nods and forces a smile.

"Angel?"

Stefan looks up with a grin. "Mommy!" He darts right into her arms. She lifts him up and kisses his cheek. "Damon picked me up from school! And we had hot cocoa and built a fort! Now we're playing trains."

"Oh, that sounds like a very special afternoon." Lily settles him back on the floor.

"Did you have fun at your party?"

"I did, yes." Lily looks back at Damon. "You can start your homework."

"Are you sure?"

Lily nods and takes Stefan's hand. "You come help Mommy with dinner."

The little boy nods. "Okay." He waves to his brother. "Bye, DayDay."

Damon smiles and ruffles his hair. "Bye, Stef."

The subject of Andrea isn't brought up until Stefan is tucked into bed. Giuseppe and Lily call Damon into the dining room. The patriarch settles at the head of the table while Lily sits beside him, Damon on the other side.

"Andrea has been fired," Giuseppe says.

Damon holds back a sigh of relief. "Did she say why she didn't show, sir?"

"She claims to have forgotten. Regardless, we cannot let this go forward."

"Of course, sir."

"However, that leaves a gap in care. Your mother has made a commitment to the Daughters of the American Revolution and cannot back out of it. Until we can find another nanny, you shall pick Stefan up from school and tend to him."

Damon frowns. "Sir, I don't mean to question you. However, what am I supposed to do about football? As well as soccer when the season starts?"

"You'll bring him with you."

Damon wants to argue. He wants to say this isn't fair. How can he possibly practice and keep an eye on Stefan? It'll mean he can't go out with his friends until Lily comes home. He's got his homework too.

Aubrey's probably not even worth considering at this point.

But he can't tell his dad "no". Not if he wishes for his bottom to stay pain free and his other cheek clear.

"Yes, sir," Damon complies.

"Very well." Giuseppe pushes back his chair and rises to his feet. "This will save us money in the long run. Perhaps the arrangement shall be permanent until you start college."

"Whatever you want, sir."

Giuseppe casts him a weary look but says nothing more as he exits the room. Damon looks at Lily. She simply smiles.

"Stefan prefers you anyway," she says. "And you love taking care of him."

Damon does. He knows he's about the only one who does it right. Suddenly, he feels guilt for resisting this at all.

"Whatever I can do to help. May I be excused?"

"Of course."

Damon heads upstairs. He settles in front of the computer he received for Christmas. Giuseppe should be getting ready for bed, so it's safe to use the dial up.

"You've got mail."

There's a singular message from "goodcharlotte1986" with lyrics from "Little Things" in the signature.

I'm not the girl guys blow off, Damon. Clearly wasn't worth it.

-Aubrey

Damon deletes the email and pulls up the IMs to see which of his buddies is online.

There'll be other girls.

As always, let me know what you think and feel free to leave prompts! There will be future installments of him dropping in various places and the slow reveal to everyone, but that will all come in due time! So let me know if you want to see anything else. :)