Life’s Lessons - Adventures In Babysitting
AO3 Link: Read Here
Pairing: Mechanic!Dean x Female!Teacher!Reader
Word count: 4,019
Summary: Dean and Y/N spend a weekend looking after Sam and Eileen’s son. Looking after the baby brings up the conversation of children, as Dean puts the plan of proposing in motion.
Warnings: It’s literally just fluff. Like so much fluff. Implied smut.
A/N: Time stamp #4 is here! This one brings you right up to the proposal in the epilogue of Life’s Lessons. I’m taking a little time stamp break to bring you all something in maybe late June/early July, and I’m so excited about it! As always, happy reading and enjoy! :)
Dividers by @firefly-graphics
Life’s Lessons Saga Masterlist
Y/N smiled, watching on as Sam and Eileen took care of their son, Elliot Patrick Winchester. It had been 2 and a half months since he arrived, and the Winchester family had never been more excited to have a new addition, especially one so adorable. Sam and Eileen somehow just knew exactly what they were doing, becoming pros at handling everything that comes with having a baby instantly. Knowing them pretty well now, Y/N had a brief thought that Sam must have researched anything and everything to do with pregnancy and babies. A book could never tell you exactly what to be prepared for, but they were a good guide, and the new parents were making it work and doing a great job.
However, Y/N could see how exhausted they both were. They had been going non-stop and hadn’t had any sort of a break, which she could see they desperately needed. She and Dean had talked between them that they should babysit and give them a Saturday off for now, so they could catch up on much needed rest. Now that Elliot had started to sleep through the night a little more, she knew that she and Dean could handle it.
Dean walked out of the bathroom, having freshened up just after Y/N, for lunch that they brought over to Sam and Eileen’s apartment. Eileen told them that she missed them and wanted them to come over, so they picked up some food along the way and made it to their apartment pretty quickly.
“There’s my man,” Dean said, smiling as he saw his nephew in Eileen’s lap. He walked over and instantly picked him up from Eileen, holding him close as he began to walk around the apartment.
Y/N watched on as he cooed at the baby, making funny faces and just being all around amazing. She had to admit that after seeing Dean with her nieces, and now his own nephew, it was beginning to stir feelings within her about seeing Dean as a father.
“Did you tell them what we talked about?” Dean asked, as he turned around to face her.
“I was about to,” she replied, before turning to look at Sam and Eileen. “Dean and I think you guys really need a break, so whenever you want us to, we’d love to take Elliot off your hands for a Saturday.”
Sam and Eileen smiled at them, both looking more than a little relieved at the offer. “That would be amazing,” Sam sighed, a small smile on his face. “I mean, we wouldn’t want to burden you-”
“It’s not a burden, Sammy,” Dean interjected, stopping his brother from thinking there was anything wrong with the idea. “You’ve been at this since the kid was born, you gotta relax.”
“Thank you both. That would really help us, we definitely need to recharge,” Eileen signed, smiling as she looked between Dean and Y/N.
“You’re welcome,” Y/N signed in return, smiling at Eileen.
The next weekend, Sam brought Elliot over to Dean’s house, complete with all the things that he would need for his little stay with his uncle and aunt. Both Dean and Y/N were excited to look after the baby, while the new parents were just relieved to sleep the day away.
Sam arrived in the late morning, giving Dean and Y/N enough time to clean up before he got there. Y/N held the door as Sam carried the baby into the house, followed by Dean carrying Elliot’s bag and portable crib. He set them down in the living room, as Sam put the carrier down on the coffee table, with Elliot sitting inside, looking around inquisitively.
“Thanks again for doing this, guys,” Sam said, as he leaned over Elliot and undid the straps to take him out of the carrier.
Y/N smiled brightly at the baby as she held her hands out, instantly taking him from Sam. She held Elliot close, kissing his forehead as she gently rocked him. Dean looked over, smiling as he saw the baby in Y/N’s arms. She looked good like that, and he had a sudden thought about what she would look like with their baby in her arms.
“You’re so welcome,” she told Sam, looking up at him. “And you pick him up tomorrow at whatever time, no rush. Okay?”
Sam laughed, slightly as he nodded. “You got it.”
Sam gave them a rundown of what to do with Elliot, what time to feed him, when to put him down to sleep, and a few other things to know. For the most part, he would be easy to take care of, and Sam made them promise to call if anything happened that they couldn’t handle.
“We got this, Sammy.” Dean walked over to Y/N, wrapping his arm around her shoulders.
“Yeah, and it’ll be good practice, right?” Sam joked, chuckling slightly.
“Yeah,” they both said, agreeing without hesitation.
Sam was taken aback, considering his comment didn’t seem to get the standard freak out reaction from them, both of them as calm as ever. His expression turned into a small smile, already knowing that even though he had teased Dean about it, his older brother was going to be a great dad when it was his turn.
“Alright, I’m going to head out.” Sam leaned over, kissing Elliot’s head softly, before leaning in and kissing Y/N’s cheek. “Have fun.”
Y/N laughed and looked down at Dean’s nephew, nodding. “We will.”
Dean walked Sam to the door and said goodbye, shutting the door and walking back into the living room. He smiled at Y/N as she looked over at him, the thoughts he was having before coming back to him. He pushed them away, knowing it was way too soon to be thinking that way, even though they had already talked about it. In fact, they were about to be one step closer to that reality. A few weeks ago, he had gone to his parents’ house, wanting to talk his mom about how he wanted to propose to Y/N. He told her that he wanted to use her ring that his dad had given her, which she had kept for him to use some day. Nearly in tears when she heard that he was going to ask Y/N to marry him, Mary had agreed straight away and had given him the ring.
The plan was in motion now that he had the ring, and Dean already knew how he was going to propose. At the house that he had been renovating with the help of his friends and some professional help, after a night out. He couldn’t think of a better place to do it than the house that they would spend the next stage of their lives together in.
Dean got to work on fixing the portable crib, opening the contraption in the living room and staring down at it. It definitely looked more complicated than it probably was, so he would just have to take it one step at a time, trying to remember what Sam had told him. His first attempt was completely wrong, making him start all over again. Y/N watched on, amused by Dean’s attempts to set the crib up, rocking Elliot back and forth. Groaning loudly and cursing inwardly, Dean kicked the crib with frustration.
“Who designed this thing? NASA?” he complained, his face pulled into a frown.
Y/N pressed her lips together, trying not to laugh. “There’s instructions for a reason, babe.”
“Please,” he scoffed as he looked down at the crib. “Those are just there to confuse you even more.”
“Well, for the sake of your nephew, you should probably have a look at them,” she informed him, turning slightly to show him Elliot’s eyelids drooping with sleepiness.
“Fine,” he huffed, picking up the manual.
Within a few minutes, he had figured it out and assembled it securely. Y/N walked over slowly; Elliot now completely asleep in her arms. She leaned down and gently put him in the crib, relieved when he didn’t wake up. She looked down at him, smiling softly as she watched him sleep peacefully. Dean stood next to her, his expression resembling hers as he looked down at his nephew.
“He’s so cute,” she whispered, reaching out to lightly run her finger over Elliot’s little hand.
“Yeah,” Dean agreed, his voice low like hers.
“I’ll get started on lunch,” she stated, turning and kissing his cheek before she walked into the kitchen.
Y/N made some sandwiches for lunch, Dean and her sitting in the living room as they ate and kept a watch over Elliot. After lunch, they washed up and cleaned up the kitchen, trying not to make too much noise and wake the baby. Their attempts weren’t enough, as Elliot woke up and started fussing. Y/N went to him, picking him up and holding him close until she realized he needed a diaper change. Making quick work of setting things up, she started to change him, cooing and making faces at him to distract him.
Dean watched from the kitchen, knowing she couldn’t see him. He felt the familiar feeling he had earlier return, as he watched her smile and play with the baby while she changed him. He turned away to finish cleaning the kitchen, not wanting to get distracted by what he was thinking, but still smiling as he washed the dishes, those same thoughts still very much in his head.
The rest of the day continued in much of the same way. It had been relaxing for the most part, Y/N getting in some reading as she laid on the couch, checking in on Elliot every time he needed attention. Dean did the same when she couldn’t, both of them tag teaming pretty damn well, whether it was to feed him or change him, or just be with him when he needed. It was good practice, sure, but more than anything, it just solidified that he and Y/N could handle just about anything together.
Dean made dinner as Y/N sat on the couch, Elliot in her arms as he looked up at her. She smiled as she ran her finger over the small tuft of brown hair on his head, his slightly chubby cheeks which would no doubt get bigger, his little nose and chin. One side of his mouth quirked up, an attempt to smile as he looked up at her.
“Alright, dinner’s ready,” Dean called out, bringing two bowls of pasta to the table.
Y/N got up from the couch, slowly putting the baby into the carrier, and carrying him on to the dining area. She set him on the table across from them, smiling as she sat down, seeing him quite content to be with his family. Dean pulled a face at him, but his morphed into an unamused one, the baby showing quite a personality already.
“That face right there is so Sam,” Dean said, laughing as he looked at his nephew’s blank expression. “He’d always do that when he didn’t like a joke I’d make. Guess the kid takes after his dad in that, too.”
Y/N laughed as she took a forkful of pasta, looking between the baby and Dean. “Maybe that’ll change when he’s older.”
“Better,” Dean muttered as he ate.
Y/N pursed her lips in thought, wondering if she should voice the question that suddenly came into her head. “So… when we have our own…” she trailed off as she looked at him, her cheeks heating up at the subject.
“Uh huh,” he mumbled, smirking. He was amused at her reaction and wanted to see where she was going with this.
“Well… how-how many do you want?” she asked, hesitantly as she bit her lip.
He hummed as he sat back in his chair, taking a sip of his beer. He put the bottle down, looking over at her. “Well… two’s good, I like the thought of two. Like me and Sammy.”
She nodded, smiling. “Like me and Jill.”
He nodded, as he thought about the idea of two kids. Suddenly, flashes of his recurring dream he had had so many times over the years came to him. In the dream he had three kids, two boys and a girl.
“The idea of three though…” he started, as he looked at her. “I don’t know, I guess it feels… complete.”
Y/N beamed, trying to hide her face as she smiled wide. “I like the idea of three, too.”
“Awesome,” Dean muttered, unable to contain his smile either. “Though, god help me if we have a girl,” he stated, shuddering.
“Why?” she asked, laughing lightly. She looked over at Elliot, giving him a once over before turning back to Dean.
“I’m going to go pretty crazy with a girl. I mean, when she starts dating… nope, you know what? She’s never dating.” Dean shook his head, as he sipped his beer, not wanting to think about it anymore.
Y/N laughed as she shook her head. “That’s not going to be in your control, baby.”
“Yes, it will,” he countered, not listening to reason. “Especially if the boys are anything like me.”
“I think you’re pretty great,” she said, leaning closer to him.
Dean scoffed as he looked at her. “You didn’t know me back then. Trust me, you would’ve hated me in high school.”
She shook her head, completely disagreeing with him. “I don’t know, seems like you were the rebel and bad boy type, but you have a quiet and kind side too. Feels like I would’ve totally had a crush on you, Dean Winchester.”
“Really?” He raised an eyebrow, leaning closer to her.
“Oh yeah,” she whispered, moving in and kissing him, passionately. She pulled away after a moment, smiling. “If those boys turn out to be anything like you are now when they grow up, she’ll be fine.”
Dean smirked, sipping his beer before he continued to eat. They didn’t say much else on the subject after that, continuing their meal as they kept an eye on Elliot. That conversation told them everything they needed to know. Neither of them could wait for the day they had a child of their own.
After dinner, Y/N cleared up while Dean took over on Elliot duty, feeding him. Once he was done, Dean wheeled the crib into his bedroom and started to get Elliot ready to put him down for the night. Once she had cleaned up, Y/N walked down the hall to the bedroom. She smiled as she heard Dean talking to the baby, leaning against the doorway as she watched him changing Elliot’s diaper. He squirmed around, getting a little restless.
“Hey, you know what? I’ll pay you money if you stay still,” Dean joked, as he leaned over the baby.
Y/N laughed quietly, shaking her head at Dean’s attempt to calm the baby. She watched as Dean secured the diaper, buttoning Elliot’s onesie back into place and slowly picking him up. He held his nephew close, making her feel things she had no control over in that moment. She couldn’t wait to see him as a dad, this little glimpse as an uncle proving that he would excel at it. She laughed again as Dean started humming “Smoke on the Water” to Elliot.
“Dean,” she started but stopped when he shushed her. He rocked the baby, and she could see Elliot’s eyes closing.
“It’s working,” he whispered to her. He walked over to the crib slowly, still humming.
“Okay, if I put you down, you gonna be a man about it?” he asked his nephew, quietly, despite knowing he wouldn’t get an answer.
Dean slowly laid Elliot down, smiling when he saw him fast asleep. He looked at Y/N and smiled in relief. He cleaned up and put everything back in its place, washing up in the bathroom. He ushered Y/N out of the room as he left the door open, slightly ajar.
They walked down the hallway and dropped onto the couch in the living room, Y/N immediately curling into Dean’s side. She laid her head on his shoulder, her arm wrapped around his. She smiled softly as events of the day played through her mind again.
“We did good today,” she said, looking up at him.
“We did,” he agreed, leaning down and pressing a soft kiss to her forehead. “You were awesome.”
She smiled as she wrapped her arm tighter around his. “So were you.”
They moved in and met halfway, their lips pressing together, a slow kiss between them. Y/N shifted back slightly, allowing Dean to wrap his arms around her waist as hers moved around his neck. He moved into her, his hands gently pressing into her back as he laid her down on the couch.
“This is so high school of us,” she laughed between kisses.
“The rebel and the babysitter… yeah, sounds about right.” He chuckled as he leaned in again.
She hummed against his lips, chuckling lightly. “More like the nerdy babysitter.”
“Even better,” he mumbled against her mouth. “You know how I feel about your little teacher clothes.”
They continued to kiss passionately, pulling each other as close as they possibly could. Dean removed his lips from hers, moving down to her neck, leaving small kisses and nips along her skin. His hands slid down her body, pushing up her shirt and feeling her warm flesh against his palms. He reached for the edge of it, pulling it up slightly, when a sudden wail from the bedroom startled both of them. He jerked back, hovering over her, as he looked down the hallway to where his nephew was now crying.
Dean groaned, shutting his eyes. “Of course Sammy’s kid is a cockblock.”
Y/N burst into laughter, cupping her hands over her mouth, as her shoulders shook from how hard she was laughing. She felt the couch shift as he got up, hearing him walk away down to the bedroom. She sat up and fixed her shirt, getting up from the couch and following behind him. When she got to the room, she saw Dean leaning over the crib.
“Alright, kid. What’s going on, huh?” he asked, as he reached in and picked up Elliot. Holding him close, the baby started to calm down, small whimpers leaving his mouth before his eyes started to close. “Ah, someone just wanted a little extra attention before he completely passed out, huh? I get it.”
Y/N walked closer and wrapped her arms around Dean’s waist, looking down at Elliot as he held him.
“Hope this means you’ll get some proper shut eye, and I can score with your aunt here,” Dean whispered, looking between the baby and Y/N with a small smirk.
She shook her head as she rolled her eyes, a smile tugging at her lips. “You’re insatiable.”
“When it comes to you, damn right I am.” He leaned over, kissing her and lightly nipping at her lower lip, causing a small moan to leave her.
“Not in front of your nephew,” she scolded playfully, looking up at Dean when he pulled away. “You get him to sleep, I’ll go find something for us to watch.”
“Okay.” He kissed her once more, winking at her before she turned around and walked out of the room.
He bit his lip and looked down at Elliot, smiling. “She’s pretty great, huh?” he asked, seeing Elliot look up at him.
“She’s really gonna be your aunt soon, if she says yes,” Dean said, quietly. “And then hopefully you’ll have some cousins to cause trouble with, soon too.”
Elliot’s eyes drifted closed again, a small sigh as he fell asleep again. Dean kissed his head softly and gently laid him down again, smiling as he didn’t jostle from the movement.
Dean shut the lights off, leaving the bedside lamp on for some brightness, before he left the room and walked down to the living room to join Y/N.
The next morning, Dean and Y/N tag teamed just as well as they did the day before, before Sam arrived at noon to pick Elliot up.
Y/N kissed Elliot’s forehead, frowning as she handed him over to Sam. She watched as the father strapped his son into the car seat, feeling a little sad to be giving him back already. Looking after him had naturally been a challenge, but she loved it so much and loved seeing Dean with the baby, too. Sam turned to them, smiling as he hugged each of them.
“Thanks so much again for doing this,” he said, leaning against the car.
“You’re welcome,” Y/N said, smiling. “I just hope you and Eileen got the rest you deserve.”
“Oh yeah, we definitely did. I think we slept for like 7 hours, didn’t get up until the late afternoon,” Sam told them, laughing slightly.
“Good. You needed it.” Y/N rubbed her hand up and down Sam’s arm, before stepping back and standing next to Dean.
“Always happy to look after the little guy, you just say the word and we’re ready, Sammy,” Dean added.
“We really appreciate that.” Sam tossed his car keys up before catching them again, a small smile on his face. “Alright, we better go. Eileen’s missing him already.”
“Tell her we said hi,” Y/N informed him, as she and Dean watched Sam get into the car.
“I will,” Sam agreed, sitting in the driver’s seat with his window down. “We’ll do something soon.”
They both gave Sam a small nod and waved as they watched him drive away from the house.
They walked back in and Dean closed the door, immediately swooping behind Y/N and pulling her close. She laughed as she leaned back and kissed him; the kiss instantly heating up.
“The kid leaves and the first thing you do is this?” she asked, her eyes closing as he kissed her neck.
“Damn right, I didn’t get any last night because of him,” he replied, between laying kisses on her neck and shoulder.
“You know, that was just a taste of what life is going to be like with a baby,” she informed him, chuckling at him as he stopped kissing her and pouted.
“Damn,” he whispered. “Are we really sure we wanna have any?”
She smacked his arm around her playfully, laughing as she shook her head. “Yes.” Turning around in his arms, she wrapped her arms around his neck, wagging her eyebrows at him. “Besides, think of how much fun we’ll have making them.”
Dean visibly shivered as he looked down at her, moving down to kiss her, a little more hunger for her behind it this time. He hummed against her lips, pulling away slightly. “Maybe we should start now?”
She shook her head but smiled at him. “Give it a little time, babe.”
“Fine.” He frowned but it quickly morphed into a smirk. “We’re still gonna have sex right now, though, right?”
“Obviously,” she replied, with a little ‘duh’ expression.
Kissing her again, he picked her up as her legs came up to wrap around his waist. He carried her into the bedroom, but pulled away slightly, smiling.
“Hey,” he said, softly getting her attention away from his lips. “How about dinner next Saturday? Just you and me… we haven’t done that in a while.”
“Yeah,” she said, biting her lip as she smiled. “I’d love to.”
“Awesome,” he smirked, leaning in to kiss her again.
Sometime later, as they laid in bed wrapped up in the sheets, Dean held Y/N close. Both of them were content, basking in the peace that came after the intense love making, knowing they didn’t have to speak and fill the silence. He smirked as he thought about his plan, and how she had unknowingly agreed to a night out that would change their lives forever.
It was a lot of pressure, and it could just as easily completely backfire on him, but Dean was certain that things were going to be okay.
With Y/N by his side, they always were and hopefully if she agreed to be his wife, they always would be.
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