Summary: You had a fling with Dean fifteen years ago and now he wants back into your life, but like all things, it’s complicated.
Characters: Dean x Reader, Sam (mentioned), OMC Dylan
Word Count: 4756
Warnings: smut, unprotected sex, oral (female receiving), slight angst
A/N: Italics are memories
It was days like this that were the hardest. The days where your mind decided to replay one of the best weeks of your life.
Fifteen years ago you lived in this small coastal town in southern Maine with your mom. Every summer, for as long as you could remember, you worked in your mom’s bar. The summer of your senior year was no different. It was going to be the last time you worked there before you left for college in the fall. The town was buzzing with tourists and the bar was full but still, you noticed him right away. He was tall with a cocky smile and the greenest eyes you had ever seen.
Your breath caught in your throat when he noticed you staring at him. Heat flushed your face as you quickly looked down concentrating on wiping down the bar. The next time you looked up he was gone. You retrieved clean glasses from the kitchen and walking back out you almost squeaked when you saw him sitting at the bar. You stayed behind the bar stacking the clean glasses when he leaned over.
“Hey, sweetheart,” he said smiling at you. “How ‘bout a beer?” he asked.
“How ‘bout some ID?” you asked cocking your eyebrow.
He couldn’t be much older than you and you’d just turned eighteen. He laughed and licked his lips.
“Sure,” he said reaching into his back pocket.
He pulled out his wallet before handing you his ID. You looked at it and looked back up at him.
“So, Freddy, what brings you here from Minnesota? By the way, you look great for 48,” you laughed handing his ID back. “Nice try.”
“Shit,” he looked through his wallet again. “Sorry, that was a joke, my brother, he…”
Green eyes handed you another ID. You looked down at it and handed it back to him. Hmm, 23.
“Ok, Dean, what’ll it be?”
He smiled, his cocky grin finding its place on his face once more.
“What’d you recommend, sweetheart.”
“We’ve got a nice blonde on tap,” you suggest.“
Then I’ll take that.”
You poured his beer setting it down in front of him before going back to stacking glasses. Dean stayed at the bar drinking his beer and looking around. As you stacked your last glass he caught your eye.“
So what’s your name, sweetheart?”
“Why do you want to know?”
“I always like to know the names of beautiful women.”
You laughed; he was cheesy, but also kind of adorable.
“My name’s Y/N.”
“So Y/N, when do you get off?”
Not interested,” you rolled your eyes. “But they’re plenty of other girls you could convince,” you gestured to the bar then turned to head back to the kitchen. “Have a good night.”
“Hey, Y/N, sorry I didn’t mean it like…”
You stop waiting for him to continue.
“I’m actually down from the university. I’m in the journalism program and I’m writing an article about old ghost stories. Do you know about Captain Lord’s Mansion?”
“Everybody does,” you turned back laughing. “But just between you and me,” you leaned over to him whispering, “it’s just a tourist trap.
”You leaned back your nose filled with his scent; leather and beer and something else you couldn’t name.
“Still I’d love to hear what you know.”
You still weren’t sure if he was serious but you checked your watch.
“I’m off in about thirty. If you stick around I can sit with you for a bit and tell you what I know.”
“Thanks,” Dean smiled and this time it was wide creating faint crinkles around his green eyes.
After your shift, you and Dean sat at a booth in the back of the bar while you told him all about the stories you’d heard about the mansion. You were surprised that Dean listened intently, asking intelligent and thoughtful questions since you really thought he was after something else. The conversation eventually turned more personal and you learned that Dean had a younger brother that he didn’t see very often, he loved his car, a ’67 Impala, and classic rock. He was engaged and interested in learning more about you too. Soon it was the last call and Dean was asking you for your number.
“In case I think of anything more questions for my story.”
You’d had such a nice time with him you figured it couldn’t hurt so you obliged. Dean gave you a quick kiss on your cheek before he left.
The next night you were working again and halfway through your shift Dean walked in. You couldn’t help smiling when you saw him. He walked straight over to where you were busing a table.
“Hey, sweetheart,” he said leaning over the table.
“Hey, Dean. Back again?”
“I’m actually here for the week, Y/N. You think you could show me around on your next day off?”
“Well, I have tomorrow off. What’d you have in mind?”
You and Dean spent the entire next day together. You went to the old mansion, showed him all of your favorite spots in town, and that night you ended up back in his motel room. You’d told yourself that you wouldn’t sleep with him but he was sweet and handsome and he said just the right things; besides you were leaving in the fall anyway.
That night would stay etched into your brain so that even fifteen years later you would still feel the way he dragged his finger down your naked body leaving a burning trail of goosebumps as he went. You would still see the way his cocky smile didn’t fully hide his excitement and nervousness. You would still taste the beer on his lips when he leaned in to kiss you and how that kiss grew deeper when you kissed him back. The way you moved around each other like magnets; always keeping a hand on one another. But what you would remember most is when you were on the edge, moaning his name and his green eyes found yours and you came together. After that, you’d be spoiled for other men. Dean Winchester would take his time with you, exploring you, worshiping you, learning what made you moan. No one before or after him would handle your body the way he did.
Unfortunately, remembering the best week of your life inevitably leads to you remember the worst day of your life; the day Dean Winchester smashed your heart.
You were sitting on Baby outside of his motel room as he was packing up to leave.
“It was fun, sweetheart, but you knew this was going to end eventually,” he said dropping his duffel in the trunk of his car.
“Dean,” tears welled up in your eyes, “you don’t mean that. What we’re doing, this is different…”
“You’re wrong,” he looked at you with those beautiful green eyes. “It was just sex.”
That was the day you learned that you can live even after your heart shatters into a million pieces. That was the day you decided to never let anyone into your heart again. Every time Dean looked at you or kissed you or made love to you, you could feel in your bones that he cared deeply for you. So when he told you that you didn’t mean anything to him you realized you couldn’t trust yourself in love; your judgment was flawed. Three weeks later you had the second-worst day of your life; when you found out you were pregnant. About nine months later when your son was born you had the best day of your life. And every day spent raising your amazing boy had been better than the next. Still, every time you looked into his beautiful green eyes you saw him, the man who ripped your heart into pieces and (unknowingly) sewed it back up.
And now here you are fifteen years later running the bar your mother left you after she died. You never did make it to university but you’ve never regretted your choice to have Dylan. He enriches your life in ways you never could have imagined. And while there are many hard days, there are also days where he makes you prouder than anything ever in your life.
You shake yourself from your trip down memory lane. Your mind always seems to wander when you have to do menial tasks like reorganizing the boxes in the storeroom. You check your watch, it’s time to open the bar and get ready for the lunch crowd.
An hour later the place is humming and you’re busy behind the bar. Like kismet there he is walking through the door to your bar. The same green eyes and bowlegged stride, but his face has an edge that wasn’t there all those years before. Your palms start to sweat and you reflexively wipe them on your jeans. Dean hasn’t spotted you yet and you almost duck under the bar. As you’re waffling in your decision he spots you. That cocky grin that’s burned into your brain spreads across his perfect face and you groan inwardly as butterflies take flight in your stomach.
Dean’s POV
I spot her across the room behind the bar. Fifteen years since I’ve seen her and she looks just like I remember. Solitary is a special kind of hell. Not seeing another face, not hearing another voice, or touching someone else is the worst torture. For six long weeks, I’d nothing to do but think and that’s what I did; I thought about my life. Surprisingly I kept coming back to the week I spent with Y/N so long ago. Of my many regrets, the lost chances, and broken hearts, Y/N, her face is the one that haunted me the most while I sat in that cell. Her hair is pulled up into a ponytail, her cheeks are rosy and there are dust motes clinging to her shirt and hair. When she looks at me her lips part in a perfect little O. My mind bolts to when I watched her fall apart underneath me making that same little O. I take a deep breath before crossing the room to lean against the bar.
“Could you recommend a good beer, sweetheart?”
I give her my best smile as I swallow down the fear crawling up my throat, hoping that she’ll at least talk to me. The yearning to be seen and touched is worse now than it was when I was stuck in that goddamn cell. I know I don’t deserve her forgiveness but I’m going to try to earn it.
—-
You almost pinch yourself; it must be a dream or a nightmare. Dean is standing in front of you asking for a beer as no time or heartbreak has passed between you. You stand rigid, unable to speak for fear of yelling or crying or laughing or, at this point, a combination of all three.
“Y/N?” Dean looks at you questioningly.
You decide to let your anger guide you, but you don’t want to make a scene so you lean closer.
“What are you doing here?” you hiss.
“I was in the area so I thought I’d stop by and see if you were still around.”
“Ok, you did that; here I am; now you can go.”
“Oh, don’t be like that, sweetheart.”
“Don’t call me sweetheart. And be like what, Dean? Like some girl, you had a fling with a million years ago and then left when things got a little too serious for you?”
“Well, when you put it like that…”
“Just go,” you cross your arms.
You’re well-practiced at keeping people at a distance.
“It wasn’t like that, you know?”
“Like what?”
“I didn’t want to leave. I had to.”
You scoff, but his eyebrows are knitted together with sincerity as he leans closer to you resting his elbows on the bar.
“My dad needed me and I knew I couldn’t stay with you,” Dean continues. “I figured if you thought I didn’t feel the same way about you you’d be able to move on.”
“So shattering my heart was you trying to help me move on?”
“I cared about you Y/N; it killed me to leave you. All I wanted was to stay here with you.”
You lean across the bar, your face inches from Dean’s.
“Why are you coming to tell me this now? After all these years? What’s the point?”
“I had a lot of time to think over the last month. Actually, that’s all I did,” Dean doesn’t take his eyes from yours. “I thought about my whole life, all the things I’ve done, wished that I’d done or wished I’d done differently. You came to my mind many times, so I made a decision. If I made it out I would come to find you. So here I am coming to tell you that I wish I would have been honest with you.”
This is not what you were expecting, you lean back unable to speak and unable to quell the intense desire to touch him; the magnet inside pulling you back to Dean. Before you can say anything one of your employees is at your side with a question.
“I’ve gotta handle this,” you say to Dean.
Walking back to your little office with your employee and leaving Dean at the bar fills you with relief. The pull he has on you is still undeniable and it was taking all of your wills not to reach out to him. A few minutes later you emerge and he’s still waiting at the bar.
“I’m pretty busy at the moment.”
“It’s ok; I’m staying at the Fontenay Terrace Motel, Room 12. Come over after work.”
You put your hand on your hip giving him a hard look.
“To talk,” Dean says holding his hands up.
“Fine. I’m done at six, I’ll come over after.”
“Ok, see you soon Y/N,” Dean gives you a smile before walking out the door.
Just before six, you call your son letting him know that you’ll be late coming home and to eat the leftovers for dinner.
“Got it, Mom. Don’t worry about me.”
“Thanks, sweetheart, I’ll see you in a little bit.”
You need to freshen up so you walk down the hall to the bathroom chastising yourself for wanting to look good for Dean. You check your hair and make-up in the mirror before leaving to meet him. Your mind races with thoughts of what’s to come as you drive to the motel. Should you tell Dean about his son or should you just let it lie?
Dean’s POV
I’m more nervous than I thought I’d be. Seeing her again, remembering the smell of her shampoo, the way she absentmindedly drew her fingers over my skin when we were cuddled together and how she would giggle when I kissed her side. My throat tightens and I swallow hard. The lingering loneliness from lock-up has yet to fade. I bought a six-pack of Y/N’s favorite beer and flowers from the convenience store down the street. Sam texted to see how everything was going but I sent a vague response. Sam didn’t understand why I had to drop everything and drive from Kansas to Maine. But he’d never met, Y/N; he was at Stanford and I was hunting on my own when I met her. ‘Let it go,” Sam said, ‘what’s the point in finding her now after all this time?’ I didn’t tell Sam that I wasn’t planning on doing anything about my feelings until I met with Billie. Even now the reaper’s cryptic remarks snake through my mind as I sit waiting for Y/N to show.
“When the time comes I kinda hope it’s not you,” Billie said looking down at me.
“What? Why?” I asked confusion furrowing my brow.
“Maybe I’d like to see you right a few wrongs before you go.”
“Is that supposed to mean something to me?”
“I don’t know, Dean, any ghosts haunting you lately?”
—-
You pull into the motel parking lot when you see Baby parked right in front of room 12. You smile to yourself, you can’t help it. You loved that car from the moment you heard Dean talk about her. And when you finally rode in her you understood why he loved the car so much. You park next to the Impala taking a moment to look at yourself in the rearview mirror. With a deep, calming breath you climb out and walk over to room 12. You knock and wait, you hear Dean moving around inside, and then he’s opening the door filling up most of the doorway. Your heart pounds in your chest and heat blooms deep inside you, you groan inwardly at your body’s betrayal.
“C’mon in Y/N,” Dean says holding the door open for you.
You step inside and notice the flowers and a six-pack on the table as you take off your jacket. You smile and then grumble to yourself for smiling before turning around to face Dean.
“So,” you say swinging your arms back and forth. Relax Y/N, you think, shoving your hands in your pockets.
“Here have a seat,” Dean says pulling a chair out from the table.
You sit down as he sits in the chair across from you, leaning forward with his elbows on his knees.
“You want a beer?”
“Sure.”
“You still like this one?” he asks twisting the top off and handing one over to you.“
I do thanks.”You sip your beer while looking around. You catch his eye and he smiles, but you glimpse a flash of nervousness he’s trying to hide. Dean takes a drink of his beer then sets it on the table.
“So, this is more awkward than I thought it would be,” he says.
“Yeah, it is,” you laugh.“I just had to see you. I can’t explain it…”The pull to touch him is almost unbearable. Like magnets, you keep moving closer to each other.
“What happened to you?” you ask leaning forward.
“Nothing important,” Dean brushes away the question. “What’s important is that I wanted to see you and to let you know that I was wrong and I shouldn’t have left as I did.”
“Why did you say it?” you ask and your voice is barely a whisper.
“I knew,” Dean huffs. “I knew we didn’t have a future together and it would be easier for you if you hated me.”
“Well that’s idiotic,” you roll your eyes in frustration. “I never hated you, not really, I…”
“I’m sorry,” Dean reaches out gripping your wrists in his hands. “I was young and dumb.”
His hands around your wrists send waves of desire right down to your core. Even after all this time he still has this effect on you.
“It’s in the past, there’s nothing to be done about it now.”
You lean back slipping out of his grip. You’re starting to think meeting in his motel room was a bad idea. You’ve got to get out of here before you do something wildly stupid. You grab your beer off the table and take a long pull and Dean mimics you.
“Well, this was a fun trip down memory lane, Dean,” you stand. “Thanks for the beer and the apology, but I’ve got to go.”
“Y/N, wait,” Dean stands catching your arm.
He pulls you closer to him, his hand tilting your head up, forcing you to look into his perfect green eyes.
“I want to know you again.”
“I can’t, I’m sorry; I can’t go down that road again,” you cast your eyes downward. “I barely survived last time.”
“It can be different, I promise,” Dean cups your face. “I had a long time to think about it and there’s no one I need as I need you.”
Dean dips down gently brushing your lips with his. He’s tentative but you feel the urgency behind it. His lips are warm but his tongue is cold from the beer as it slides into your mouth and the sensation of cold and hot mixing together is enough to make your knees buckle so you lean into Dean as he pulls you tighter.
Dean’s POV
I can’t let her leave without showing her how I feel. I kiss her tentatively at first but as soon as she responds I wrap my arms around her waist pulling her against me. Her arms slip around my neck and I groan as she drags her fingers through my hair. My body aches with longing as the six weeks of solitary and the memories of her mix in my mind. I slide my hand under her shirt unable to deny the need to feel her skin against mine.
—-
Pulling back from the kiss you look up at Dean. You can’t do it again; if you were on your own maybe, but your son needs his mother not a vacant shell of a person. Your stomach tightens and your chest feels hollow. Should you tell him about Dylan? When you thought he’d just used you it was easy to answer that with no, but now, it’s complicated. His searching eyes rake over your face as the hunger behind them spurs your desire to give in to him.
Dean pulls you tighter bringing your mouth to his demanding you to let him in. You part your lips and softly moan into his mouth urging him on. Pulling his flannel off his shoulders you break the kiss long enough to remove his shirt and yours. His hands are like fire and ice on your skin and as he pulls you to him he lets out a low growl the moment your skin is against his. You capture his lips more urgently than before as you slowly walk backward stopping once your legs bumping into the bed. You both quickly remove your jeans leaving them in a pile on the floor. You unhook your bra crawling back onto the bed as Dean follows, his body hovering over yours. He trails his tongue down your neck nuzzling between your breasts before taking one into his mouth and slowly circling your nipple as you arch your back against him. He moves across to the other breast and does the same. He makes his way down your stomach to your hip, his scruff on your sensitive skin making you giggle. Dean smiles as he pulls your panties down slightly nipping and kissing your exposed skin. Fire burns at every place his lips touch your skin. You lift your head grabbing his hair making him look up at you and the playful wink you’re expecting is replaced with naked desire. Dean slides your panties off before pushing himself between your legs.
He plants soft kisses up your thighs and over your folds before he flicks his tongue up and through working his way to your sensitive bundle. He swirls circles around it with his masterful tongue before gently sucking it between his lips. You grip his hair harder.
“Oh, Dean.”
He smiles and hums as he slides a finger into your wet core. He slowly drags it out adding another finger as he pushes back in. He continues to move in and out dragging along your walls crooking his fingers against your sensitive mound.
“Oh, god!”
“There she is,” Dean whispers. “You taste just like I remember, sweetheart,”
His full lips suck on your clit as his pace increases. The coil in your belly tightening as you grip his shoulder. After a few more thrusts an intense orgasm rips through you and you clench around his fingers. Your legs grip Dean’s head as his fingers work you through your climax. He slows his fingers before sliding them out. He stands removing his boxers and positions himself between your legs again. You look up at him and notice more scars lining his body, but he is just as glorious as you remember. Kneeling between your legs he pauses looking at you asking for permission.
“Yes, Dean, please,” you whisper.
He rubs the tip of his cock over your slick folds before pushing through moving slowly allowing you to adjust as he fills you. When he finally bottoms out he groans and grips your hip with one hand before he slides back out and thrusts back in. The movement is slow there’s no rush; like he wants to feel every part of you. You wrap your arms around his neck as he leans down capturing your lips again. He lifts your leg over his hip getting deeper and pumping into you faster as you lift your hips to meet his. His kisses move from your mouth to your throat to your shoulder. His lips feel like they’re everywhere. He rolls his hips increasing the friction until you feel the familiar coil tightening inside you once again. Dean wraps his arm around you, pulling you tightly against him. He slowly trails soft kisses up your neck to your ear.
“I’m close; I want you to come with me, Y/N.“
You kiss him wrapping your legs around him.
“I’m close too,” you whisper.
Dean tilts his hips and starts to thrust faster thrumming against every nerve inside you. You come calling his name his cock twitching as you pulse around him.
“Oh, Y/N!“
Dean hugs you tightly to his body as he comes, his erratic thrusts slowing. You lay together, his heavy breaths creating goosebumps down your neck and spine, as you both come down. Finally, he lifts up onto his elbows and looks down at you.
“That was better than I remembered,” he smiles, crinkles forming around his eyes.
“Yeah, it was,” you laugh.
He rolls onto his side leaving his arm draped across your body. You turn your head to look at him lightly stroking his arm with your fingers. Your body is languid but your mind begins to race. You know you need to tell him about Dylan, but you’re not sure how.
Dean’s POV
I look over at Y/N; she’s the most beautiful woman I’ve ever seen. I leave my arm lying across her body. After so many days alone it feels good to be close to someone again. I watch her, she looks sated just like me, but there’s something in her eyes. Apprehension?
“I have to go,” she says suddenly breaking away from me.
She rolls off the bed quickly dressing before grabbing her bag. I’m still trying to get my jeans on as she bolts out the door. I throw on my boots before grabbing my keys and jumping into the Impala. I can’t let it go this way. My jaw clenches as I follow her car. When she finally pulls into her driveway I realize it’s her mom’s old house. I pull over to the side of the street before jumping out of the Impala as she climbs out of her car and starts up the walk.
“Y/N, wait!” I call.
—-
As you’re walking up the front walk you hear someone calling your name. You whirl around to find Dean crossing the street.
“You followed me?”
“You didn’t give me much of choice, sweetheart,” Dean says striding over to you.
“You need to leave, now.”
“Mom?” you hear Dylan call from the front door.
“Go back inside, sweetheart,” you call back.
“Who’s that?” Dean asks.
“My son,” you say unable to control your clipped tone.
“Your son? But he’s, like, what, thirteen?”
“Fourteen almost fifteen,” you whisper.
“Mom? You ok?”
“I’m fine Dylan,” you turn to look at him. “Go back inside. I’ll be there in a moment.
”Dylan stubbornly stands on the front porch waiting.
“So, what, you had him right after you started college?”
“I never made it, Dean.”
“What’re you saying, Y/N?”
You open your mouth but the words don’t come.
“What is it, Y/N?” Dean reaches out gripping your arms.
Hearing the anxiety in his voice you know that you need to tell him the truth, you take a deep breath.
“That week with you,” you sigh. “I got pregnant.”
“What?” Dean’s arm drops.
“I got pregnant, I had a boy, that’s Dylan,” you motion to your son who is still standing on the front porch.
You put your hand to Dean’s cheek and look into his gorgeous green eyes.
“Dean you have a son.”
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