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dean-winchester-is-a-warrior · 3 years

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Dear Fucking Diary: Entry the 8th - The Long Weekend

Pairings: Dean x Fem!OFC (Daisy)

Explicit 18 +/Warnings: None. Some kissing and implied smut. Brief mentions of an abusive relationship. Some angst. Lots of fluff.

Word Count: 4,358

DFD: Series Masterlist

Series Summary: I’ve been tasked with writing in this fucking diary like a some teenage girl. It sucks, but who else am I going to talk to about the incredible hottie who lives next door?

Chapter Summary: 8th Entry: Technically this is the 8th, 9th, 10th, 11th, 12th, 13th, and 14th entry. It was a tough weekend okay! But my week is looking up!

A/N: This series has popped into my head from out of nowhere. It was supposed to be a whole other thing, but then it just morphed into this. (Cause I needed more series to work on! 🙄😄) Hope you like it, I should be releasing a new entry every few days, and I think there will be about 7 or 8 entries 9 or 10 entries 8 entries and an epilogue. The first entry is short and sweet, but most of the others will range between 1000 and 3000 5000 words. Thanks everyone!! 🥰

A/N 2: So, this is the final entry in this series, excluding the epilogue which I will post by the end of the week. I hope you enjoy it and the epilogue to come. It's possible I may write some drabbles about Dean and Daisy in the future. I like them. 😁

The awesome divider at the bottom is created by @talesmaniac89

So, it's Friday night, didn't hear from him all day. But I mean, that's normal, he had to work, I had to work. I JUST saw him this morning. I mean, whatever. It's fine. He'll probably text tomorrow. I'll write again later.

Saturday night now. I haven't talked to him since he dropped me off at my apartment yesterday morning. It's about ten o'clock. I'm going to bed now.

This is good, though, right? I mean, it's not like I want him to be all clingy or stalker-ish. I had enough of that crap with the previous asshole. So. No. This is good. No clinging, no demanding, no - anything.

So, I guess I have my answer

I guess I was just stupid

I feel like I'm gonna

I don't want to write about this.

But shit! Writing here has been really helpful so - what the hell!

It's like two in the morning. I couldn't sleep earlier, so I tried painting. I think I did some decent work actually. This latest painting is all sharp edges and shades of green. I can't imagine why. But I like it.

Anyway, about twenty minutes ago I heard loud banging and voices in the hall, coming from the direction of Dean's apartment. I told myself it was none of my business even as I was quietly opening my door and peeking out.

Dean was leaning against the wall while a tall, gorgeous, leggy blonde used his keys to open the door.

He was dressed nicely, in suit pants and a white dress shirt and tie. But the tie was loosened and his crisp, white, button down was all rumpled and only partially tucked in.

Did the blonde untuck it? I wondered.

Then he threw his arm around her shoulders and he seemed a little tipsy as he leaned in toward her.

"...just so beautiful." I could hear him say in the same awed voice he'd used with me.

He stumbled forward a little and the blonde giggled under his weight and pulled him into the apartment, shutting the door behind them.

And since then I've just been sitting here thinking what a fucking idiot I am.

I mean, mooning over him and telling myself I was in love, and thinking that maybe we had some kind of future.

I mean Jesus Christ, Daisy.

It wasn't like he hid things from me! I knew what kind of "dating life" he enjoyed. He didn't explicitly say,

"This is a one time thing."

because he probably assumed I would figure it out.

But no. Not me. Guy sleeps with me one time, and I get all swoony and romantic, and stupid. I blame you for that a little, DD. You might be making me think I'm an actual teenager again.

Well, in the real, adult world, hot guys fuck you and forget you. Fucking Lois. But she was probably right. Why would he stay with his frumpy, needy neighbor when he could move on to the next hot blonde.

I was a good time. That was it.

I don't wanna write anymore.

So, he called me yesterday which was Sunday, and texted too. The text just said:

Hey, hope your weekend's going good.

I didn't answer the phone or text back. I don't know what to say. He's probably just trying to ensure things aren't gonna be weird in the hallway from now on.

Or who knows, maybe he couldn't find the next blonde, or redhead, or whatever and just thought, well hell, easy access right next door.

Either way I'm taking off for Dr. Hailey's right away, she's making up our last missed appointment before I start work. I'm gonna tell her about everything and listen to her tell me how stupid it was to rush into something physical with someone.

It's not gonna be fun!

Well, it definitely wasn't fun, but it was really enlightening. I'm writing quick while I'm on my break at work.

So, basically when I told her about Dean and asked her what she thought, Dr. Hailey said this:

It was your choice to make, whether or not to pursue a sexual relationship with your neighbor, and I can't tell you whether it was a good choice or a bad one. It's not my place.

You're a grown woman and you are the only one who can know your body and your own sexual needs, therefore you have to take responsibility for your actions and decide what they mean for you.

If you feel like the night is a regret, figure out why you feel that way, and don't make the same mistake in the future. If you feel like you are satisfied that it was a good night, a good time with no future, then accept that and move on.

But if you believe that your feelings for him are more than physical, more than what can be explored and enjoyed in one night, then decide whether or not to pursue something further - whether that be an actual relationship, or simply a friends with benefits arrangement.

I couldn't believe my quiet, reserved, has to be in her mid-sixties, therapist actually told me friends with benefits was a viable option. I thought she was gonna be all judgey. Or tell me my choices were made by my hormones alone and were therefore, stupid.

I mean, not in so many words, of course, but you know, whatever that translates to in doctor-speak.

But if I'm being honest, (and I've certainly managed to be that, here in these pages) Dr. Hailey is pretty great, actually.

And completely right.

I need to stop acting like a petulant kid or some kind of woman who's been wronged. Dean didn't promise me anything; he doesn't owe me any kind of loyalty. We made absolutely no declarations of any kind and he's perfectly allowed to go out and bring home as many other women as he chooses.

I'll just invest in noise cancelling headphones. Or move out.

Shit. Okay, truth. It's gonna suck to see him waltzing in and out with all those lucky women.

Because even though he didn't make any promises that I can hold him to, I was so sure that our night together meant something more than just good sex. To both of us. I felt connected to him in a way I had never felt with anyone before.

But I was probably just being naïve.

And I was being a jerk not responding to his text. I mean, he was just trying to be friendly. Or, if he was reaching out to see if I'd be interested in round 2, could I really blame him? Maybe he's thinking about a friends with benefits thing too.

Here's the thing - I definitely want a round 2, but FFS, the first round sent me into three days of pouting and staring at my phone. I don't know if I could manage a friends with benefits thing because...I don't wanna be friends.

Oh shit! Don is scowling at me, my break's over!

Well, this day ended a hell of a lot better than it started. This might be a long entry, but well...

Okay, so, this evening I came home from work and Dean was standing by his door.

I smiled at him and he smiled back, both of us surprised and awkward.

"Hey." I said, as I moved passed him, walking toward my door.

"Hey, wait." He said and I stopped and faced him God, he looked fantastic. Unsurprisingly. He was wearing black jeans and a gray sweater. He looked so cozy I just wanted to snuggle him.

"I just..." He trailed off and then rubbed the back of his neck. "I called yesterday, I don't know if..."

Before he could finish what he was saying, the same blonde from Saturday night walked out of his apartment.

In spite of all my earlier plans to be totally cool with whatever Dean wanted to do - I was gonna be light and breezy - I felt a white hot jab of jealousy as I looked up into her beautiful face and bright smile.

"Oh, hi." She said, kindly. And I felt myself give an incredibly rigid smile back.

"Hi." I tried to unclench my jaw, but it didn't really work and the word still came out through gritted teeth.

Dean frowned a little and I kicked myself. Jesus, talk about NOT being cool.

I tried harder to unfreeze my smile.

Dean pointed toward me in introduction. "Jess, this is my neighbor Daisy. Daisy, this is my soon to be sister-in-law, Jessica."

His words took a second to penetrate my brain and I just repeated stupidly, "Sister-in-law?"

Dean smiled a little knowingly and nodded. "Yeah, they flew in Friday afternoon to celebrate the engagement. They've been staying with me."

Before he could continue a giant of a man came out of the apartment door carrying one suitcase and wheeling another.

"Jesus Jess," he said to his fiancé, "you should have brought another suitcase for all the crap you bought."

He noticed me then. "Oh, hi!"

Dean did the introductions again. "Sam, this is my neighbor, Daisy." He nodded at Sam. "And Daisy, this is my little brother, Sam."

Sam smiled deeply showing adorable dimples. "Oh, wow! You're Daisy?"

I nodded. "Oh, wow! You're his 'little' brother?" I asked with finger quotes.

They all chuckled.

"Yeah," Sam answered, "I outgrew the shrimp over here by the time I was sixteen."

Dean casually punched his brother in the arm and I winced at the force behind it but Sam just laughed.

"He's still sensitive about it." He smiled and I could see a hint of mischief enter his expression.

"It's so great to finally meet you. You're all we heard about all weekend."

Another, harder punch connected with Sam's arm but he continued without seeming to notice.

"We dragged him out for an impromptu celebration slash karaoke night on Saturday, but he was no fun cause all he kept talking about was his incredibly gorgeous neighbor he'd gone out with the other night."

Dean punched him again and Sam laughed.

Jess laughed gently too and also couldn't seem to stop herself from teasing her brother-in-law-to-be.

"Yes, just hours and hours of, 'You know, Daisy said this and Daisy said that.' and over and over again, 'God, she's so beautiful.' That's all he kept saying, all night." She lowered her voice to an approximation of Dean's deep tone. "Jess, seriously...just so beautiful."

Dean groaned. "Oh, come on, you're just being cruel 'cause you know I won't punch you."

I recognized the words I'd overheard on Saturday night and my heart leapt. He had been talking about me. I couldn't keep the smile from my face. Hell, I knew I was beaming, even if I was also blushing almost as brightly as Dean.

Jess smiled brightly at me and put a hand to her mouth like she was confiding a secret. "He was right, by the way. I think you two make an adorable couple."

Dean spoke loudly without looking at either Sam or Jess. "Okay, well, way you two go! Don't wanna miss your flight home."

They laughed at his none-too-subtle dismissal and Sam pulled him into a hug. Dean hugged him back, thumping him on the back, before turning to give Jess a decidedly gentler hug.

"Safe flight." He said squeezing Jess into his side and slapping Sam on the back again.

I waved to them both. "It was so nice to meet you. Congratulations!"

They waved and said their goodbyes and Dean and I were left standing awkwardly in the hall.

He smiled at me and nodded toward my apartment. "Could I, uh...could I come in for a minute?"

"Yeah." I hurried over to my door and let us both in to my apartment.

As I took off my coat, Dean approached my kitchen table and the painting I'd put there to dry. It was a kind of mountain landscape in a vaguely post-impressionist style.

It was also, all a reaction to him and what I felt about him while I was painting.

"Wow!" He said with genuine appreciation in his voice. "This is beautiful." He noticed the signature at the bottom, a little daisy flower.

His eyes were wide when he looked back at me. "You did this?"

I nodded, half wishing I'd put the thing in the closet with all my others. I'd never let anyone see my work and it felt a little like being naked in front of him again.

I'd painted and drawn when I was a kid and all through high school. But I stopped, writing it off as frivolous and not a viable career.

I'd only taken it up again after I left The Monster behind.

"Wow!" Dean shook his head again as he looked back at the painting, tilting his head.

"It's...I don't know...like something wild. It's almost angry, like the angles of the lines, but it's full of these calm, soothing colors too. That probably doesn't make any sense. It's just a really amazing combination."

I shook my head. "No, it makes sense. Do you know a lot about art?"

He smiled. "I know nothing about art." He said, repeating what I'd said about cars. "But I know it's pretty."

He shook his head. "No, beautiful."

I smiled, accepting his compliment without argument for the first time and congratulating myself on that. Dr. Hailey would be proud.

Thinking about her made me turn to sit on the couch and pat the spot beside me.

Dean walked over and sat down; each of us were turned toward each other, ready to talk.

I decided to dig right in and just go for it.

"So, I saw you and Jess in the hallway on Saturday night and I absolutely thought she was another hook-up and that's why I didn't answer the phone or text you back yesterday."

Dean just nodded and smiled. "Yeah, I figured that might be the case when you almost broke your jaw saying hi to her."

I closed my eyes and shook my head. "Look I'm really sorry about that, it was..."

Dean held up a hand. "No, wait. Can I go first?"

I shrugged and nodded. That was probably best since I still wasn't a hundred percent on what I was going to say to him.

Dean, I would like to be friends. NOPE

Dean, let's just leave the night behind us and go back to being neighbors. Double NOPE!!

Dean, would you be willing to try a friends with benefits arrangement? M'eh! Not really what I'm hoping for.

Oh, but also maybe I don't just wanna be friends, because I think I'm falling hopelessly in love with you and I'd kind of like to get married and have endless sex and lots of babies. You up for that? Fuck - this might be closest to the truth, but it might be a little too much after only one date.

Yeah, I figured it was smarter to let him go first.

"I wanted to call you. All day on Friday. Hell, all weekend. I picked up my phone constantly, I wrote and erased a dozen text messages. I knew I wanted to talk to you, I just had no idea what I wanted to say."

He took a deep breath and rubbed his hand down his face. "So, I don't date. I mean, I never really have. In high school, it was all about taking care of Sam, taking care of everything my Dad was too busy to manage.

I just didn't have time, or money for that matter, to date anyone. So I had a series of hookups, usually with slightly older college girls who weren't interested in anything long term either and were happy to take a goofy, horny teenager and help him learn a trick or two."

His smile turned sexy and I silently thanked those unnamed heroines for their service to the sisterhood. He had learned his lessons well.

"Even after high school finished, it was all about getting Sam into Stanford. I made sure I put in extra hours at the garage, worked two other jobs to try and pay for tutors and SAT prep courses, and to help add to what my Dad managed to squirrel away for Sam's tuition.

Again, I just didn't have time for anything serious or long-term. And by this point, I didn't see the need. I liked what I had."

He shrugged. "The sex was fun, easy, we made each other feel good for the night, occasionally two, but it was never anything more."

He frowned. "Sometimes, I thought about trying for something more, but most of the women I met weren't interested in something more either and I didn't know how to find what I wanted."

He scoffed. "Hell, I didn't even know what that was."

He looked at me and smiled, but there was trepidation in his voice and expression.

"And then I met you." He inched closer to me on the couch and I felt my pulse kick up a notch.

I was a little blown away by what he was saying and it was making me kind of sad for him.

It sounded lonely, like all his efforts and all his work had been for someone else. He hadn't allowed himself to spend any time thinking about what he wanted.

Like, he obviously didn't begrudge Sam his education and was clearly incredibly proud of him. But who was taking care of Dean? Where was his college tuition? Where were his helpers, his champions?

He took my hand in both of his, covering it completely. "I told you I wanted you from the first moment I saw you." He shrugged. "But that I was used to. I knew that feeling. That physical pull. Never this strong, maybe, but I knew how to handle it. Or figured I did, anyway."

He shook his head. "What I wasn't at all prepared for was how interested I became in you after we met for real. You banged on my wall and it was so funny to me, such a badass move - telling your jackass neighbor to shut the fuck up."

I blushed a little and ducked my head, remembering how embarrassed I'd been about that.

"Then I met you and you were this quiet, shy little thing. It was such a contrast and I was just so intrigued. Then we started hanging out and I saw that you were smart and funny, sarcastic, but genuine. You're real and kind and I just..."

He shook his head and chuckled. "I'd never met anyone besides Sam and Bobby that I felt so comfortable with, someone who just...I don't know...just fit."

He caught my gaze and I could see nervousness there. "I don't know, does that make any sense?"

I nodded. "Yes. Perfect sense." I whispered.

A little of the nervousness in his eyes dissipated. "And I didn't really know what to do with that. But it occurred to me that maybe we could actually just be friends. I'd never had many friends and never really any female friends, not close ones anyway.

So, I told myself sex was off the table so we could stay friends." He chuckled. "Except that did not work out the way I'd hoped."

He shifted closer and then pulled me into his lap. I wasn't about to complain.

"Because every time I was near you," he continued, his voice dipping low, "I found myself wanting you more and more, certainly more than anyone that came before you."

He took the opportunity to kiss me gently, mouth closed but warm, and I wasn't complaining about that either.

He placed soft kisses along my jaw before he pulled back; the heat in his gaze made my head fuzzy. I tried hard to focus on what he was saying.

"So, probably inevitably, Thursday night happened and it was so incredible." He closed his eyes and I felt like I was seeing the visions that were flashing behind his eyelids and it caused a riot of butterflies to take flight in my belly.

He opened his eyes and I saw worry mixed in with the heat. "So, all day Friday, I wanted to call you. I wanted to tell you that you were incredible, that I wanted..."

He was silent for a bit and then threw up his hands. "And that's why I never called you, because I had no idea what I wanted. I didn't want just a one night stand, had never wanted that with you, but it had become embarrassingly obvious that I couldn't just be friends with you either. So, what friends with benefits? Maybe, but..."

He stopped and shook his head and shrugged. I was struck by just how similar our thought processes had been over the weekend. We probably should have talked about this stuff before we slept together, or at least the morning after.

But hey, the pain and confusion had created a pretty piece of art. Just looking on the bright side.

"So, here I am," he said and he leaned his forehead against mine, "admitting that I have absolutely no idea what I'm doing. This is all brand new, uncharted territory for me. So, I'm asking for your help in figuring it out."

He cupped my cheek. "And I'm asking what you want."

I laughed. "I have absolutely no idea."

When he frowned at me I shook my head. "I've been having almost the exact same conversation with myself all weekend."

I sighed. "Look, I've dated more than you, sure, but I'm terrible at it. Previous boyfriends include," I started ticking them off on my fingers, "the guy who was dating me so he didn't have to pay rent, the guy who tried to convert me to some kind of cult, and then my...last boyfriend. We were..."

I trailed off and swallowed hard. I had never spoken to anyone outside of Dr. Hailey about my relationship with -

Keith. His name was Keith.

And he was not a monster, he was just a man. A selfish, narcissistic, power-hungry man, who used me to make himself feel strong and in control, and I didn't see the signs until it was too late.

No, that's wrong. I ignored the signs until I thought it was too late.

I never talk about him. I never even name him in my own head. But then I'd never shown anyone my art before either. Today was a day for firsts.

"I got out of a pretty bad relationship about a year ago. He was..."

I trailed off and couldn't think of how to explain him.

Dean's jaw was set and his gaze was intense as he looked at me. "He hurt you."

I shrugged. "Not physically."

"Hurt is hurt."

I nodded. "Yeah, it is. And he did hurt me, tried hard to break me. It took me a really long time to pull myself away from him. We were together about four years. Finally, little over a year ago, I managed to walk away from him, but it wasn't easy. And I'm just starting to remember who I am, what I look like out of his shadow."

I dashed away an unexpected tear and jutted out my chin. "And I like her. I like her a lot."

Dean ran his fingers across my cheekbone and tucked my hair behind my ear. "So do I."

I smiled and nodded. "My point being, that..." I chuckled. "I have no idea what I'm doing either. This is uncharted territory for me too. But..."

I shifted my position so I was straddling his lap and facing him. I had figured out what I wanted and I wasn't going to shy away from it. I heard Dr. Hailey's voice in my head telling me to take ownership of my life.

I still kind of hate that expressions like that are part of my vocabulary now. But hey, truth is truth and it was time for me to own my life.

I took his cheeks in my hands and took a breath. "It's gonna be new for both of us, and there's gonna probably be a learning curve, but I would really like to try. Try to see what comes of us dating. For real dating. Exclusively."

I was momentarily worried that I might be pushing too much too fast, but Dean's face broke into the wide, blinding smile that may end up being the death of me.

"Okay. Okay, yes. Let's do this." He kissed me, laughing, our teeth scraping against each other.

Eventually our laughter died down and the kiss turned carnal, deep. When I reached for the hem of the sweater he was wearing, he stilled my hands and grabbed on to my upper arms fiercely, pulling me close.

"I might be bad at this and I might screw up. But try not to be too mad at me, okay? I promise I'll be trying."

I nodded. "Me too."

His smile was sweet as he bent his head to give me a soft kiss on the forehead, like we were sealing a pact.

Then his smile became wicked and he whispered in my ear. "I also promise that every time I screw up I'll make it up to you in a very effective manner."

I shivered and climbed off his lap, pulling insistently on his arm. "Well, it never hurts to build up some brownie points ahead of time, you know."

He growled and leapt up, chasing my squealing form down my hallway.

That was about five hours ago and we basically didn't leave the bed all evening. Let me tell you that boy has wracked up some serious brownie points.

I'm scared, but so very excited, DD. I can't wait to write about what happens tomorrow and the next day and all the rest of the days.

Things look bright. I mean, really fucking bright.

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