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wayward-dreamer · 3 years

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Life’s Lessons - Part 4

Title: Life’s Lessons - A Lesson in Self Control

Pairing: Mechanic!Dean x Female!Teacher!Reader (eventual)

Other Pairings: Dean x Lisa, Female!Reader x OMC – Ethan (past, mentioned)

Word Count: 6,612 (thoughts, song lyrics in italics)

Part Summary: After Charlie witnesses the looks between Dean and Y/N outside the school on Friday, she convinces Y/N they should go out for drinks. At the bar, Charlie and Y/N bond, as she opens up to Charlie about Dean but also her past. After several drinks, Y/N goes home drunk and gets a little help from a friend. The next day brings a little embarrassment, but also brings up feelings within Dean and Y/N, that they know they shouldn’t be feeling.

Warnings: Swearing, Alcohol Consumption, Mentions of cheating, Mentions of reader’s ex, Talk of Emotional Abuse, Mentions of a physical incident against reader, Drunk reader, Embarrassment, Dean being sweet (yes, that’s a warning), flirting, forbidden feelings

Music: Deeper in the Water by The Lone Bellow (playing in the background while Y/N is baking scene), Wherever I May Roam by Metallica (Dean and Y/N backyard scene).

Life’s Lessons Spotify Playlist

A/N: Thank you to everyone for your wonderful comments on this series so far! I’m so glad you’re all enjoying it! This part is a little heavier, so please read the warnings. Please share your thoughts with me, I love hearing what you all think! Happy reading and enjoy! :)

Dividers by the wonderful @firefly-graphics! Check her out for all your AU needs!!!

Life’s Lessons Masterlist

Y/N took off her red glasses, smiling as she looked at her students. She could see them all flicking their eyes up at the clock every now and then, wondering when the bell would ring. She found it amusing as she tried not to laugh. It was Friday and they couldn’t wait to get out of there and start their weekend fun. She couldn’t wait herself, hoping to have some time for herself, call her family and maybe go see a movie.

Unfortunately for her students, they still had some time before they could leave, using that time to take the notes for the criteria set for their book reports. She watched as they all scribbled in their notebooks hurriedly, wanting to get out as soon as the bell went off.

“Make sure it’s personal to you” she told them as they wrote. “Books have a way of really affecting us, so I want you guys to choose something that really had a big effect on you.”

Some of them mumbled an “okay” while others nodded.

Suddenly, the bell rang, and they all sprung up at the same time. It was like how smaller children got excited for ice-cream.

“Alright, don’t all head out at the same time! You’ll plow each other out of the way!” she laughed.

“Sorry, Miss Y/L/N” one student called out.

“Have a great weekend, guys!” she called out in return.

Y/N walked out of the room as well, following them down the hallway and out of the school building. She smiled as students were being picked up by their parents, getting on the bus home or their bikes and riding home. She spotted a parent of one of her students notice her, walking over to her.

“Miss Y/L/N?” the woman asked.

“Yes” Y/N smiled, offering her hand.

“Oh, it’s wonderful to meet you, I’m Carol. Amy’s mom” she said, shaking Y/N’s hand.

“Wonderful to meet you, too” Y/N agreed.

“I just wanted to come and introduce myself and welcome you” Carol said, a bright, peaceful smile on her face. “I know it’s already been a couple of weeks, but I hope you’re loving Lawrence.”

Y/N nodded. “I’m definitely warming up to life here.”

“Well, Amy’s really fond of you. English is already her favorite subject but she’s so happy to have someone like you teaching it” Carol complemented her.

Y/N beamed, her heart soaring. It was always great to hear when kids enjoyed a subject and the way you taught it.

“She’s a great student, so that definitely makes it easy” Y/N told her.

Carol blushed, delighted by the complement for her daughter. “Well, we better go. I’m sure we’ll see you around.”

“Of course,” Y/N said. “It was great to meet you.”

As Carol walked away after saying goodbye, Y/N looked around as the crowds of children started to clear. She spotted Charlie and was about to walk over, when she noticed who she was talking to. Dean was leaning against his car, aviators on and laughing at something Charlie just said. Ben was sitting in the car, waiting for Dean. She didn’t realize that Charlie knew Dean too, but she really should’ve made the connection considering she knew Cas, and Cas knew Dean. She thought about going over there, but she didn’t want to interrupt them. Plus, after what happened the other night at dinner with him and Lisa, she wasn’t sure if she should go over there.

“Y/N!” she heard her redheaded friend call out and she knew she had to go over.

She smiled as she walked over, trying to prepare herself to be near Dean again. He looked so damn good in that moment, and she was finding it hard to look at him.

“Thanks to your car, I know you already know each other, so I don’t have to introduce you” Charlie laughed, as she nudged Y/N with her hand.

“Yeah.” Dean took his sunglasses off and Y/N saw that he was looking directly at her. She was suddenly nervous again.

Dean took her in, dressed in a black dress that hugged her body in just the right way. Her red glasses were tucked into the neckline of her dress, and he had a sudden urge to see her wearing them. Mind outta the gutter, man he thought to himself as he looked away from her.

“I didn’t realize you guys were friends” she said, as she stood in front of Charlie and Dean.

Charlie smiled as she looked at Dean. “Yeah, have been for years.”

“Charlie’s like the little sister I never wanted” Dean teased, smiling cheekily at her. Charlie punched him in the arm, and he laughed.

His gaze moved from her back to Y/N. He hadn’t been able to get her out of his head since the first time he met her, but even more so after what happened at her house.

Charlie noticed how Dean and Y/N were looking at each other and dropped her head, smiling without them seeing.

“I better go” he said, suddenly, putting his sunglasses back on. “Lisa finished work early and we’re going to Sid and Olivia’s for dinner.”

“Tell them I said hi” Y/N told him, trying not frown as she wished he had stayed longer.

“Sure thing” he nodded. He moved in to hug Charlie, kissing her head.

Y/N watched as Dean got into the car and drove off, the car roaring down the road. She turned to Charlie and her face dropped into a frown, when she saw her friend grinning at her.

“What?”

“You like him” Charlie stated.

Y/N stared at her in shock, before scoffing a laugh. “You’re insane.”

“On the contrary, I’m completely sane” Charlie countered. “And you denied it a little too quickly, so it has to be true.”

“Charlie…” Y/N trailed off, not knowing how to respond to that.

“I think we need to get a drink together” Charlie suggested. “We haven’t gotten a chance to hang out outside of work yet.”

Y/N grinned. “Sounds great.”

“Tonight?” Charlie asked.

“Name a time and place, and I’m there” Y/N responded quickly. She was excited to go out and see what Lawrence was like on a Friday night. She knew it wouldn’t be much for a small town, but she also knew she needed to know how the nightlife was here.

“Ditch the rental at home and I’ll pick you up” Charlie said, as she started to walk away. “I’ll be there at 7!”

“See you soon!” Y/N called out as they both made their way back in to collect their belongings, before they headed home.

When she got home, Y/N relaxed for a while before she needed to get ready. She freshened up and got dressed into black ripped skinny jeans and a dark mustard sweater. She put on her black heeled ankle boots, ran a straightener through her hair quickly to get the kinks of the school day out and applied light make-up. She picked up her black leather jacket and her bag, just in time when she heard two quick honks of a car horn. She picked up her keys and walked out, closing the door behind her. She walked down the porch steps and smiled at Charlie as she walked over, getting into the car.

Y/N and Charlie made their way to the town square, lined with shops and some restaurants. Deciding they were hungry too; they grabbed a quick bite to eat. Conversation over at the diner mainly consisted of work and minor things, because Y/N had a feeling Charlie wanted to talk about personal things over drinks. After they ate, they walked down the street and past a couple of dive bars, the loud music and chatter filtering out to the streets. She felt better knowing there was something going on in this town and that it wasn’t as sleepy as a place like Rhinebeck. Though Rhinebeck did have its own charms.

Y/N followed Charlie, arriving at the place where they sat at the bar. She and Charlie sat on the bar stools, the bartender immediately coming over to them.

“What can I get you, ladies?” he asked, smiling at them.

“Gin and tonic, please” Charlie replied, smiling back.

Y/N thought it over for a second before she replied. “A vodka martini.”

“Sure thing” he muttered before moving down the bar to mix the drinks.

Y/N and Charlie both took their jackets off, settling in. The bartender put their respective drinks in front of them and then went to serve other customers. Charlie picked up her glass and turned to Y/N.

“To surviving your first two weeks” she said, smiling.

“Well, thanks for making it easy for me to settle in” Y/N smiled back, clinking her glass against hers. “I really mean it. You and Cas have really helped me and supported me, so… thank you.”

“No need to thank” Charlie waved her off, taking a sip of her drink. “So… let’s get to the real reason we’re here…”

“Oh god” Y/N groaned.

“Oh yeah” Charlie smirked. “You like Dean.”

Y/N laughed a little to herself. She didn’t beat around the bush, this one.

“Yeah. I do” Y/N admitted, feeling slightly relieved to say it out loud. “At first, I really just thought it was a crush, something that would just go away after a couple of days. Then… then the butterflies stuck around and they’re not going away. Every time I see him… I just want to be near him. All the time. I know two weeks is way too soon to be feeling like this about someone I just met, but-” she explained but Charlie shook her head, cutting in.

“I don’t think the length of time matters to Oxytocin” Charlie advised her.

“I’m not quite at the love stage yet. In fact, I hope I never get there because that’s going to get me into trouble” Y/N countered.

“Which is unfortunate because I think you two would be adorable together” Charlie confessed, a guilty grin on her face.

“What?” Y/N scoffed, not quite believing what she just heard.

“I’m sorry, it’s just… the way he was looking at you, even just for a few seconds, I haven’t seen him like that in a really long time” Charlie said, a sad smile on her face.

“Oh god” Y/N groaned, her face dropping into her hands. “Charlie, what are you doing to me?!”

“I know, I know” Charlie shook her head, not knowing what else to say.

“I can’t” Y/N shook her head, taking a large sip of her martini.

“I know, and I wasn’t telling you to go for it at all. I’m sorry” Charlie apologized, sipping her drink.

“It’s okay” Y/N reassured her, patting her back. Once they had both calmed down, Y/N turned to her friend. “Oh, they came over for dinner on Monday. I wanted to thank Dean about the car, and he came over with Lisa.”

“Really?” Charlie asked, a little shocked. “She actually came over?”

Y/N nodded. “Seemed like she didn’t want to be there, though. I mean, she was okay, she didn’t say much, which I don’t really care about, but she was kind of cold with Dean.”

Y/N looked at Charlie and saw that she looked like she wanted to say something but was contemplating whether she should or not.

“Okay, look…” Charlie started, trying to find her next words carefully. “I’m just going to tell you this, and it’s in no way saying that you have to do something, I just think you need to know, now that you’ve brought this up.”

“Okay…” Y/N didn’t know where she was going with this, but she listened anyway.

“Dean and Lisa have never been good for each other. They had a one-night thing, it was great for both of them, but that’s where it should’ve ended. Things were fine at the start, but once they got past the one-year mark, is when things started turning. Two years in, it got pretty bad. I mean, Dean doesn’t know for sure… but he thinks that she might’ve slept with someone else when she went home to visit her family. Things haven’t been right for a while now. Between not trusting her and them fighting at the drop of a hat all the time… it should’ve ended a year ago” Charlie explained.

“Wow” Y/N sighed, shaking her head.

“The only time we see him happy is when he’s at work or when he’s with us and she’s not around. Hell, I don’t particularly think she likes any of us, and we’ve tried really hard to include her. She never really wanted to do anything with us and would only come out with Dean if she wanted to prove things were okay. After a while, we just stopped trying to get her to like us” Charlie went on.

Y/N couldn’t imagine anyone not liking Charlie or Cas. “Seriously?”

Charlie nodded, a glint of anger behind her eyes. “She’s never encouraged him with the business, she’s always put him down for his choice in friends. She claims it’s to make him see that he’s better than them, but she’s just forcing him to think things he never would.”

There was a long silence between them, as Y/N processed everything Charlie just told her. She and Charlie were only just starting to become friends, so she could’ve easily said she didn’t believe her. She did, though. Charlie looked genuinely hurt, which meant everything was true.

“Fuck” Y/N whispered.

“Yeah” Charlie said, raising her eyebrows. “Dean’s generally a happy, care-free guy but for over a year now, I know he’s been hurting. He just hides it behind his larger than life personality. I just want to see him as his old self again. He thinks that if he stays, maybe things will just fix themselves, but they won’t. They haven’t yet and they certainly won’t the longer he stays in this relationship.”

“Wow” Y/N sighed again.

“So, that’s all I want to say” Charlie finished. “I’m not saying you have to do anything about it, but I want you know the reality, and maybe not hate yourself so much for having the thoughts you’ve been having.”

Y/N nodded. Hearing it made her feel slightly better, but worse now that she knew what he was going through.

Another silence fell between them as Y/N thought about everything Charlie said.

“It scares me” Y/N looked down into her glass, shaking her head. “Feeling something so quickly for someone I just met. I’ve never felt a connection like this before. Not even with Ethan.”

“Ethan?” Charlie asked, confusion written on her face.

Y/N bit her lip. She didn’t realize she had never mentioned him to Charlie. “My ex.”

Charlie nodded slowly, immediately understanding. “I’m guessing things didn’t end well if you’re so far away from New York.”

“No, they did not” Y/N muttered after a sip of her drink. “He uh… he was really controlling of me. He’d tell me how I shouldn’t dress up and be too revealing, but then somehow… somehow, he’d tell me that I didn’t try hard enough either, that I wasn’t attractive enough. My job wasn’t good enough. I… I wasn’t good enough. I didn’t… I didn’t think it was something that was a problem, no matter how much anyone told me it was. I thought he’d… he’d say the things he did because he just wanted me to be better, but it was to stroke his own ego.”

“Scumbag” Charlie muttered; her face morphed into anger.

“Yeah” Y/N laughed, bitterly. “I couldn’t see it until the night he hurt me. I thought he was doing those things because he loved me, but love isn’t making a person hate themselves to make yourself feel better.”

“You said he hurt you…” Charlie trailed off, worried that she’d uncover feelings that Y/N had buried.

“Just once, he pushed me and I ended up in hospital with a concussion” Y/N said, her words choking around the lump in her throat. “Once I was better, my parents helped me get my things out of his apartment. It wasn’t an easy transition; I kept seeing him everywhere. I tried to get a restraining order against him, but his family had money and probably paid someone off, so he never got charged with one. He eventually left with his new girlfriend, but that didn’t mean it got better for me. It took some time, a year of therapy before I left, but I realized that I wasn’t going to let anyone do that to me ever again. That place… I didn’t want to leave my family but there was too much of him there. So… now I’m here.”

“I’m glad you are. Y/N, you’re… shit, you’re fucking amazing and I hate that someone made you feel like you’re not” Charlie said, quietly, her eyes watery.

“I really know how to tell a story, huh?” Y/N jested, trying to lighten the mood again, as she blinked to keep her tears from falling.

“I’m glad you told me, that you could trust me with that” Charlie said, a small, empathetic smile playing at her lips.

“I’m sorry” Y/N shook her head, feeling awful at her sudden confession of her past. “I shouldn’t have brought it up when we’re here to have a good time.”

Charlie took her hand in hers. “No, please don’t apologize. I really am glad that you did. I’m so glad I know you.”

Y/N smiled at her. She knew Charlie would hear the story and wouldn’t pity her but be there for her and listen. She held Charlie’s hand, squeezing it. She was glad to have met the woman sitting in front of her.

“You know… Dean would never do that to you, right? To anyone” Charlie told her.

Y/N nodded, closing her eyes. “I know. I don’t know how I know, but I just see him, and I know that he’d never do that.”

“And that’s what scares you, right? That he’d never do that, that you feel so much and that he’s with someone else?” Charlie asked.

Y/N looked at her and didn’t say anything. Her face said it all. Charlie just nodded, before taking the last sip of her drink.

“I need another drink” Y/N said with a small chuckle, having finished her martini.

Charlie just smiled as she flagged down the bartender.

Another drink turned into two more after that. Y/N understood what Charlie said clearly, but that didn’t mean she was going to take the words and run with them. Why risk everything on what could just be a crush? She was wrong, 2 weeks was absolutely a ridiculous amount of time to suddenly fall for someone. She was overthinking things.

She was thankful when Charlie dropped the subject of Dean, having said what she needed to about how she felt towards Lisa, knowing Y/N would interpret everything the way she needed to. She also felt a huge pressure lift off her chest when she told Charlie about what happened with Ethan. It had been a year since the break-up and since she had started therapy. Her last session before she left had left her feeling relieved. Coming to Lawrence had been the best decision, even with her situation with Dean. Charlie was amazing and was glad she spoke up and told someone who she really trusted.

They eventually moved onto talking Charlie and Dorothy and Y/N found the redhead incredibly cute in that moment, as she gushed about her girlfriend.

Y/N knew that once the fourth martini went down, she had to get home. She was well and truly drunk and all she wanted to do was sleep it off. Just forget them ever talking about Dean.

As they left the bar, she stumbled slightly as they walked down the road. She needed to get an Uber and be alone in her thoughts now, her mind reeling with their conversation but vodka, too.

“Are you sure I can’t take you home?” Charlie asked, concern all over her face.

Y/N chuckled as she shook her head. “I’m sure, I’ll be fine.”

“Okay” Charlie agreed, reluctantly. “Message me as soon as you get home.”

An Uber quickly pulled up a few moments after she called it, and Y/N got in. She smiled and waved at Charlie. “Thanks for tonight.”

“You’re welcome. I’ll see you Monday” Charlie smiled.

Y/N leaned back against the seat, looking out the window. She really didn’t need man drama while she settled into a new town. She had had enough of it back home in her previous relationship, that one almost ruining her mental state. She was still recovering, even if had been a year since they broke up. Memories of him and imagining him around town, even after he left, were what made her decide to leave too. The last thing she needed was to be with someone. That being said, someone could argue with her that it was time to move on and find something better, something more meaningful.

Well, that something would have to come from somewhere else because it sure as hell wasn’t going to come from Dean. As much as she was attracted to him, he was with someone. No matter how unhappy the relationship was. Her mind floated to something Charlie told her. That it was possible that Lisa cheated on Dean.

He was sweet and caring, nurturing and compassionate. Gorgeous as hell and insanely hilarious. Who could ever cheat on him? People had their flaws, but that didn’t mean you give up on a person. His flaws couldn’t be as bad as her ex’s.

The Uber pulled up outside her house. Y/N steadied herself as much as she could as she got out. The car pulling up caught the attention of Dean, however, as he was sitting on the front porch, beer in hand. He watched as Y/N stumbled up the stairs of her porch and tried to open the door to her house.

Dean put his beer down on the stoop and got up from the stairs, walking across the street. As he walked up her porch stairs, Y/N turned around and smiled at him, indicating to Dean that she was quite drunk.

“Dean” she slurred happily, her eyes sparkling.

He tried not to laugh as he walked over to her. “Doing okay there, sweetheart?”

“Sure am” she giggled in her drunken state. “Just trying to get my door open.”

Dean watched as she tried to put the key in but kept missing the keyhole. He stepped forward and took the key from her hand, putting it into the lock and opening the door with ease.

“Thanks” she beamed.

As she went to walk through the threshold, her foot caught the edge and she stumbled. With quick reflexes, Dean caught her arm and pulled her into his body.

“Whoa, Y/N” he exclaimed, cradling her to his body.

She let out a loud cackling laugh, completely unaware of her near injury. Knowing that this wasn’t going to end well if she kept at it by herself, Dean bent down and lifted her legs up as he cradled her body. He lifted her into his arms as he carried her into the house, trying not to dwell on how good she felt in his arms.

“Ooh” she gasped, as her arms wrapped around his neck. “You’re very strong, Dean.”

She couldn’t help but lean her head on his shoulder, the intoxicating scent of cologne driving her crazy.

He ignored that as he walked down the hallway and into her bedroom.

Dean gulped as he looked around, the realization that he shouldn’t be standing in her bedroom hitting him suddenly. He quickly walked to the bed and laid her down, watching her eyes flutter as the alcohol she had consumed took control.

“Have to… have to text Charlie” she mumbled, the alcohol making her sleepy.

Ah, so that’s who she went out with he thought as he took off her shoes and pulled the covers over her.

He picked up her bag and fished around quickly, finding her phone. He didn’t look in, knowing that a woman’s handbag had things in there he had no business seeing.

Y/N unlocked her phone and handed it to him, flinging her head back to her pillow.

Dean bit back a laugh as he messaged Charlie as Y/N.

Hey, made it home safe. Thanks for tonight.

He added that in because if she was this drunk, then clearly she had a great time with his friend. Who wouldn’t?

Dean placed her phone on the nightstand and was about to walk away when he heard her stir.

“You’re really sweet, Dean” she mumbled, only one eye looking up at him as her face was smooshed to her pillow. “Why can’t all guys be like you?”

Dean shook his head. She was really out of it. “I wouldn’t say that, Y/N. I’m not someone to be compared to.”

“I think you are” she said, a soft smile on her face. “I think you’re something special, Dean Winchester.”

A smile spread on his face, but it dropped quickly. She wouldn’t remember saying it in the morning, so it was best not to dwell on it.

“Goodnight, Y/N” he whispered.

“I could get used to you in my life” she whispered, as she drifted off into slumber.

Dean felt a pang in his heart at her words. She may have been drunk, but it had been a while since someone had something like that to him. He couldn’t let her words affect him like that, though. He was with someone else and he needed to make that work again.

Dean slowly walked out of her room and back down the hall. He took out his wallet and took out the Advil tablets he kept in there, leaving them by her coffee machine. He picked up a napkin and quickly scribbled a note on it, before leaving her house. Hopefully she wouldn’t remember all of that in the morning and they could avoid the awkwardness that would follow.

The sunlight from the windows streamed into Y/N’s room. It warmed the covers she was wrapped in, causing her to stir. She groaned as she lifted her head, feeling the heaviness of last night’s drinking session with Charlie. She sat in bed as she tried to recall what happened last night. Her eyes widened as she remembered, everything quickly rushing to her head.

Dean had helped her into the house. Dean had most likely helped her into bed. Dean had been in her bedroom.

She couldn’t remember if any words had been exchanged. Had she said anything that would cause her embarrassment?

Y/N slowly got out of bed and picked up her robe, wrapping it around herself. She picked up her phone and walked out of her bedroom, into the kitchen, as she needed coffee as soon as humanly possible. She looked at the time. It was 10 in the morning. She had really been knocked out last night. She walked over to her coffee machine and was about to start filling it, when she noticed something out of the corner of her eye.

A slip of Advil tablets and a note laid next to the machine. She smiled as she picked up the note, scribbled in all-caps.

HOPE YOUR HEAD DOESN’T HATE YOU TOO MUCH IN THE MORNING.

-D

Her stomach flipped as she bit her lip, reading over the note again. She liked his handwriting. It said so much about him.

She quickly took the Advil before she made her coffee and breakfast, two eggs and a little bacon. You had to have bacon on a Saturday morning, especially if you were hungover. That’s what she felt.

The rest of her afternoon consisted of paying bills and doing some work for her classes, once her head was feeling slightly better. She made a mental note to actually go see a movie next week with Charlie. Maybe they could invite Cas’s girlfriend along, as she was dying to meet Meg. After doing her work for the day, she decided to do a little baking. Saturday afternoon baking was something she did often back home, and she wanted to keep that going here in her new house.

Y/N decided on making an apple pie, one of her favorites. As she got all the ingredients together, she decided to make two, wanting to take one over to Dean as a thank you for helping her last night. Hopefully he liked pie. She turned on one of her softer playlists, as cooking or baking needed some kind of music in the background and something soft was good for her head right now.

An hour later as The Lone Bellow graced her ears, she took out two beautifully golden pies from the oven. She put them on the kitchen bench and went to shower, having still been in the same clothes from last night.

Once she was freshened up, she walked out in dark blue skinny jeans, a white tank top and a pink and white plaid shirt over the top. She took a red and white checked cloth and wrapped it around one of the pies, making sure it stayed warm as she walked over. Slipping her phone into her back pocket, she shrugged on a light jacket to shield her from the light breeze. It was starting to get colder and she wondered what winter would be like here.

Y/N left her house and walked over to Dean and Lisa’s, pie in hand. She was a little nervous and hoped that Lisa wouldn’t be there, so that she could talk to Dean alone. She was slightly ashamed of herself; he was technically a parent of a child she was teaching, and he saw her drunk. She really hated herself for it and hoped that they could talk and come to an understanding.

She quickly walked up the porch steps and rang their doorbell. She waited patiently for a few seconds, before she rang the bell again. Again, she didn’t hear anyone coming for the door. Even the Impala wasn’t in the driveway. They had probably gone out as a family. As she walked back down the porch steps, she heard some music and clinking sounds coming from the back of the house. Wondering if maybe Dean was at home, she walked around the corner to their backyard, the sounds of Metallica’s Wherever I May Roam becoming louder as she got closer. The sight that greeted her caused her eyes to widen and her heart to beat wildly in her chest.

Dean was leaning over the engine of his car with the hood open. He was wearing blue jeans that hung on his hips in the most perfect way, highlighting his cute butt. His dark grey t-shirt defined his physique, the material stretching across his chest and biceps. His arms and face were covered in grease from the car, but that only added to the hotness he was showing at that point. When he turned around and noticed her, he smirked which just killed her dead on the spot.

“Hey, I didn’t hear ya coming out here” he said, walking over to her, turning the music down a little as he walked past his little radio.

She blinked a few times, trying to get out of the trance he put her in. “I rang the bell a few times but then I heard you out here.”

He nodded as he jerked his head towards the car. “Yeah, I gotta work on her from time to time, make sure she’s still runnin’ properly.”

“Well, she’s gorgeous. I wouldn’t want her to fade away either, if I was you” she smiled.

He smirked as he looked at his priced possession. “Dad would tear me a new one if I ever did.”

She laughed a little before a silence fell between them, only the sounds of the song being heard.

And the road becomes my bride And the road becomes my bride I have stripped of all but pride So in her I do confide And she keeps me satisfied Gives me all I need And with dust in throat I crave Only knowledge will I save To the game you stay a slave

Now was as good a time as to bring up what she needed to.

“Dean, I just wanted to say thank you for helping me last night” she started but he waved her off.

“Don’t mention it, sweetheart” he smiled.

He really had to stop calling her that if she was ever going to get anywhere with this. If only he knew what that did to her.

“I know it might’ve felt like just a nice gesture, and it was, but… Dean, I’m really ashamed and I really, really hope you don’t see me differently now” she confessed.

Dean frowned, not sure what she meant. “Why would I do that?”

“It’s just that… I’m a teacher, and I’m supposed to be a certain way. You’re practically a parent to a child in my class, and you shouldn’t be seeing me like that, like how I was last night-” she rambled but the feel of his hands on her shoulders stopped her.

“Y/N, it’s really okay. I’d never tell anyone about that. I mean, shit. You gotta let loose once and a while, too. Maybe someone else would judge you for that, but I never would” he told her, his voice calming her.

“But-” Dean shook his head when she protested.

“Honestly, Y/N. It’s fine. That’s just between you and me. Okay?” he reassured her.

She sighed in relief. “Okay.”

“Good” he winked at her.

Her lips pressed into a thin line as she looked down, trying not to think about that wink.

“It’s just… I didn’t say anything stupid to you, did I? If I did, I’m so sorry” she apologized.

Dean remembered everything she said last night. It had kept him up for an hour and a half as her words circled around in his thoughts.

“Nope” he lied. “Though you did mutter something about finding Christopher Walken sexy.”

Y/N eyes widened. “What?!”

Dean guffawed loudly, shaking his head. “Oh my god, you should see your face.”

She reached up and smacked his arm, causing a small “ah” to leave his lips but he kept on laughing, as he rubbed his arm.

“You’re such an ass” she shook her head, trying not to smile at the sound of his laugh.

His laughter died down as he composed himself. “That was too easy.”

“I don’t think you deserve this pie now” she gestured to the wrapped-up dish in her hands.

His eyes lit up as he looked between her and what was in her hand. “Pie? You-you made me a pie?”

“Yeah, I did, as a thank you for last night but I don’t think I want to give it to you now” she pretended to be upset, riling him up.

“Y/N…” he said, looking her right in the eyes. “Please.”

Jesus. She was putty in his hands. This wasn’t good. She couldn’t do this with him. In that moment, all she could do was hand over the pie with a polite smile. She couldn’t let him think that she was wanted to keep going on this banter of theirs. That was dangerous and she wouldn’t be that person.

She quickly handed it over. “Since you asked so nice.”

His eyes and smile grew brighter, as he giddily lifted one corner of the cloth and smelt the cinnamon and apple.

His eyes rolled back as he moaned lightly. “Damn, that smells amazing. Thanks, Y/N. Seriously.”

“You’re welcome” she said, laughing slightly at his reaction. “I take it you like pie.”

“Like?” he scoffed. “More like obsessed.”

“Good to know” she giggled as she watched him take another whiff. “I better go.”

“Oh, before I forget. Your car should be ready on Wednesday” he told her.

She smiled with a sigh of relief. “Amazing, thank you.”

“So, I’ll see you at the shop on Wednesday” he said, his thumbs rubbing over the cloth around the pie. He was itching to dig into it.

“Yeah” she nodded. “Bye, Dean.”

“Bye. Thanks again” he lifted the pie as he thanked her.

Y/N smiled as she walked away, rounding the corner and disappearing.

As soon as she was gone, Dean walked into the house and put the pie on the kitchen counter. He washed his hands and wiped them down, his mouth salivating as the delicious scent of the pie wafted through the kitchen. He opened a drawer and took out a fork, unfolding the cloth from around the pie dish. He licked his lips he looked down at it, stabbing his fork in and digging up a big bite. He blew on it and shoved it into his mouth. The flavors exploded as he closed his eyes in delight.

“Fuck, that’s good” he mumbled to himself as he swallowed down the mouthful.

It had to be the best pie he had ever had, not including his mother’s because that wasn’t a fair fight. Did Y/N really have to be so perfect that she made an amazing pie, too? How the hell was he supposed to stay away from her if she did things like this?

You just have to he thought as he wrapped the pie up again, for later. You can’t keep doing what you’re doing with her.

If this was ever going to remain friendly, then he had to stop turning on the charm, even if that was second nature to him. She made everything so easy. Things hadn’t been easy for him in a long time.

Between what she said in her drunken state to him (she may have been drunk, but she still said it. So, it had to be true, right?) and now bringing him this pie, it was getting harder to resist her. He knew was starting to feel something for her, even if it had only been a couple of weeks. He hadn’t felt like this since the first time he was with Lisa. Once they actually got together, the spark fizzled out quite quickly as comfortability took over. Now, even that wasn’t there.

Maybe it’s only meant to be comfortable. Maybe the spark isn’t meant to stay as you get comfortable with your partner. Though, that didn’t seem right to him. If you were really in love, then wouldn’t the spark stick around?

He had never been more confused about what to do, but he knew what the right thing was. It was to stick it out with Lisa, and that’s what he needed to do.

No matter how much he thought about Y/N.

As Y/N walked towards her house, her smiled dropped. What happened back there wasn’t just a friendly neighborhood chat. That was more. Much more. That was something two people did when they’re getting to know each other as more than friends. That was banter and flirting and messing around with each other with silly jokes. There were looks that made her tingle all over, and polite words that comforted her.

He made everything so easy. What she was beginning to feel for him was so much more than what she had felt before. This feeling wasn’t even there the first time she met Ethan. She knew she was fooling herself when she said this was just a little crush.

As she entered her house, Y/N was determined.

Dean Winchester was not going to have an effect on her.

He just wasn’t.

-x-

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#Life's Lessons #Dean x Female!Reader #Dean x Female!Reader Series #Dean x Female!Reader Fanfiction #Female!Reader Insert #Mechanic!Dean #Teacher!Reader #Dean x Reader Fanfiction #Dean Winchester Series #Dean Winchester Fanfiction #Dean Winchester Fanfic #Supernatural Fanfiction

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curtisandlewis · 6 years

Text

Happy Trans Girl Day Pride!!!!

Much more will be added to this!

Jerry unlocked the door to the suite he shared with his partner Dean. He held the hand of a lovely young woman as he stepped inside. “Here we are my Dear. I usually don’t bring women here because my partner has a habit of barging in at the exact wrong moment. But I saw him go off with a girl of his own so we should have the place all to ourselves. Go ahead and sit,” Jerry said gesturing to the couch. “What was your name, sweetheart?”

“Roberta”

“Would you like a drink, Roberta?”

“Umm...I think I should go to the bathroom.”

“Okay. It’s the second door.” Jerry went ahead and made them both Gin Martinis with olives instead of pickled onions, of course. He handed Roberta her drink when she came back and she drank it all in one gulp. Jerry stared at her in shock as he took a sip of his drink.

“Before this goes any further there’s something I should tell you.”

“Alright,” Jerry said taking another sip of his drink.

Roberta bit her lip. “You have to promise me you won’t get angry.”

“Okay.”

“I mean really promise me. This is going to be a big shock and you might lose control...And I need reassurance you won’t hit me.”

“HIT YOU? Of course I wouldn’t. Not even if you were a Nazi.” Jerry hesitated. “You’re not from Irvington are you?”

“No, I’m from Pleasanton, California.”

“Oh, Okay,” Jerry said relieved. “Yes. I promise I will not get angry and I will certainly not hit you. Please just tell me what it is.”

“I think you better sit down.” Roberta set her drink down and looked even more nervous than before. “I think the easiest way is just to show you.”

“Okay.” Jerry’s heart fluttered in his chest. He felt like he was in an old gangster movie and about to get shot by the beautiful temptress. But she made him promise that he wouldn’t hit her. Would he hit someone with a gun? Roberta stepped closer to the couch. She slowly lifted her dress. Jerry watched as the material went up her legs and to her thighs. This was it she was reaching for her gun he was sure of it. He guessed there were the worse ways to go than looking at a beautiful woman in her garter belt and panties. He gripped the couch and prepared for the bullet but nothing happened. “Honey...What am I supposed to be seeing?”

“Look at the panties. There should be something...Off.”

Jerry stared at the undergarment. They were very nice panties. White satin with lace trim. Her thighs were quite nice too. Now that he was sure he wasn’t about to get wacked he was feeling horny again. He thought about caressing her milky white thighs while licking them then sticking his tongue deep in her. “Oh...” There was a noticible bulge in the fabric. He looked up at Roberta “You have between your legs what I have between my legs?”

Roberta nodded.

THAT’S IT? “I thought you were sent by the mob to kill me, Roberta!”

“What!” Roberta dropped her dress. “Why would the mob want you dead?”

“Who knows! Those people are extremely sensitive. You know I have a heart condition,” Jerry said drinking his martini. Then it occured to him what Roberta said before. “Did somebody hit you?”

“Yes. One time. I was much younger then and he was older. Men don’t...they don’t like when they find out. They feel tricked. Even though he put his hand up my dress when I didn’t want him to.” She looked away as if she was reliving that horrible moment in her mind.

Jerry was outraged. “Even if you were a man he has no right to hit you.”

Roberta looked at Jerry. Their eyes locked. She sat beside him. “You don’t see me as a man in a dress?”

“Do you see yourself as a man in a dress?”

“No.”

“Then it would be pretty silly if I saw you that way. You forget I AM a man in a dress and I can tell the difference. The first time I wore a dress I was twelve years old and I’ve done performanences in drag ever since. There’s been PLENTY of men that have mistaken me for a woman. I’m damn good at my job. They got angry when they found out, sure. But I can’t imagine them getting violent. Though, now that I think about it I was pretty lucky. People don’t know this but Dean was there to protect me. He doesn’t want people to know how long we’ve really known each other. There was one scary guy but Dean beat the hell out of him before he could touch me.” Jerry thought back to all those men in the stripclubs that made him uncomfortable. That would masturbate out in the open and scream disgusting things at the strippers as if they were objects to be fucked and nothing more. He was pretty sure atleast a few of those men wanted to fuck him too. Even if he wasn’t wearing a dress. He saw one put his hand in his trenchcoat, no doubt touching himself. Jerry felt sick. He locked himself in his dressing room and cried. It was before he met Dean. Thankfully, the man didn’t come near Jerry. It was easy for Jerry now to see a man be so cruel as to hurt her. Especially if they were like Dean. He knew Dean would never do anything like that but someone like him who was taught the same ridiculous rules. If they had the same insane beliefs then yeah they would probably think they would magically turn into a homosexual by being attracted to a woman. They probably would turn violent if they felt their heterosexuality was threatened. People like Dean they’re taught their heterosexuality is all they have. If they lose it then they’re nothing. “Those men could have really hurt me.” Jerry lightly put his hand over Roberta’s on her knee. “He had no right to put his hand up your dress either. I’m so sorry that happened to you.”

“I’m okay,” Roberta said with a slight smile. “I wasn’t planning on any of this. I wasn’t going to go with you but you picked me. Out of all of those girls you picked me. Why did you pick me?”

“You’re very beautiful, Roberta and I liked the way you laugh. You also have a nice ass if I’m being completely honest...”

Roberta giggled. It was nice to see her smile. “I knew you were a good person but...Why are you taking this so well?”

“I’ve been around the block. I know about girls like you. It’s not as shocking as you think. You’re not the first of your kind you know.”

Roberta looked down. “Have you been with a girl like me before?”

“No. You’d be the first one.” Jerry held Roberta’s hand with both of his. “My feelings haven’t changed. I would still very much like to have a lovely evening with you but you have to promise me something.”

“What is it?”

“When you’re asked about this night it’s very important that you say all you did was suck me or give me a handjob whichever is the most believable.”

Roberta looked confused. “Oh, you want them to think I didn’t tell you my secret.”

“No. In fact it’s better if you say after you told me I was ONLY comfortable with you doing those things to me.”

“I don’t get it. Why would you want people to know we had sex? Wouldn’t it be better for them to think that after I told you I was asked to leave?”

“No! I come off as a total prick. Listen, I don’t give a fuck if they know that I see you as a sexy woman and that you got me hard. I saw you and I wanted to have sex with you so we came back here and had VERY HETEROSEXUAL sex. That part is key!”

“Very heterosexual?”

“You know, follows the rules.”

“The rules?” Roberta looked more confused by the second.

“Didn’t you have guy friends growing up?”

“Not really,” replied Roberta. “All my friends were girls.”

“Same here.” In other circumstances Jerry rejoice in finding another rational human being but this meant that he would somehow had to teach the insanity that he never understood himself. “Ok. Here’s the deal. You are a woman and that means ANYTHING I do to you or you do to me is het-er-o-sexual like how a guy can get sucked by a woman and it’s not considered homosexual even though that’s a common way for two men to have sex. Are you following me?”

“I think so...”

“And the rules say I can be sucked by anybody even a homosexual and still be completely heterosexual.”

“...what! But you had sex with a man...who enjoys it. You had your cock in his mouth and he liked it...”

“Exactly!” Finally someone who gets it. “To rational people like us if two men are having sex and enjoying it they’re probably not heterosexual. But Society or these people...I don’t know which created their own reality...The way it was explained to me is that if you’re receiving then you are male but if you’re giving then you’re the female. The worse-the second to worse thing a man can do is suck another man. He not only is instantly seen as homosexual but loses all his manhood...and becomes a woman...in a sense.”

“So that’s what happened to me.”

Jerry laughed. He knew she would have a good sense of humor. “Can you understand why it’s important for people to think I refused to be anywhere near what’s between your legs?”

“I don’t understand,” replied Roberta. “But I understand.”

Jerry smiled to reassure her. “I’m taking a big chance and maybe I shouldn’t because I just met you...I just always got to be a non conformist....” Jerry took a deep breath. “You have to promise me that you will never tell another living soul what I am about to tell you OR anything we do together tonight.”

“I promise,” said Roberta slightly shaken.

“Your solemn word.”

“You can trust me.”

“I sure hope so. I’m trusting you with my life, Roberta. You had a secret and I’m about to tell you mine.”

Roberta swallowed a lump in her throat. “I won’t tell anyone.”

Jerry let go of Roberta’s hand. “Ok. My secret is I don’t follow the rules. I can go down on you if you want. I was thinking about doing it before your surprise. I like to give people pleasure. I like to hear the person I’m giving sex to moaning and coming. I like to taste them. I like to feel them in my throat...”

“...But I’m the only woman you know-” The realization hit her. “You had a cock in your mouth. You had a man’s cock in your mouth.”

“Yep.”

“But you’re not homosexual.”

“Nope”

“You fuck women?”

“Yep!”

“You fuck men and women?”

“Bingo! Am I your first one?”

“Yes. I guess we’re each other’s firsts.”

“That’s why I felt I could trust you, Roberta. We’re very different but we both know what it’s like to have a secret.”

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