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This Time...

Summary:

I can finally rest now, but… I can't help but feel regret, can't help but wish that I had a little more time– to make things different.
‘Oh Jack…. I wish my children could've at least had the chance to meet Dean, or Bobby, hell– maybe even dad. Meet Cas, Jack, Ellen, Jo, Ash, you and so many more. If only I had..a little more time..’
Breathe in.

Breathe out.

Breathe in.

Breathe out….

And then

...Nothing.

 

Wait... what?

 

"Hello, Sam Winchester."

 

Sam Winchester dies surrounded by his children. He regrets not being able to do more and that his children never had the chance to meet their family. With a heart full of pain and regret, a Time Deity offers Sam a once-in-a-lifetime opportunity: to go back to where it all began and prepare for a better tomorrow. But the deity has a surprise waiting for Sam when he returns to the past—one that could change everything. Follow Sam Winchester on his journey to the past.

Notes:

Hello everyone! This is my first ever fanfiction so please be kind!

(Please excuse any mistakes I may have made, I'm writing this alone so if it sounds weird it's cause I've literally never done this before😅 Also I
have no idea how tags work😅 if you have any advice please comment below! Please and thank you!)

(Also I hope this sounds like a fanfiction and not a college essay lol)

Enjoy the story!!💕

(See the end of the work for more notes.)

Chapter Text

Breathe in.

Breathe out.

Breathe in.

Breathe out.

Ba-thump.

‘Oh Jack…I'm so tired…’ My breath escapes me in soft bursts, I hear soft footsteps approach. My son. Dean Jr.
He’s always been light on his feet, careful not to wake me—especially when my nightmares were too much. But I would always know when he was there.

‘Because you're my son’

It used to drive him crazy that he could never sneak out as a teenager.

Jr. leans forward on my bed—a white hospital bed installed into the middle of my bedroom, designed for comfort, or so the doctor claimed when he told us how much time I had left. It looked out of place, a white hospital bed surrounded by warm yellows and browns of the walls and furniture. Dean would’ve been proud of my son’s reaction at the news: a snarky remark, denial, followed by threats. I couldn't bear to see my son so distraught, so I held on as long as I could for him.

"Dean would've loved you," I always told my boy, whenever he would ask what he was like.

Another set of soft footsteps clicks from behind him. A voice, quiet and hesitant.

"How is he? Is he—"

The last words are muffled, like I'm underwater. ‘Oh... I can't... hear her…’

I turn my head slowly. My daughter stands there, black blazer with a white blouse underneath and a black pencil skirt. She looks so grown up. Her hair—short now, ‘just like my mom's when she was revived’. A soft, almost bitter smile tugs at my lips, at remembering how well that turned out.

She catches my gaze and returns it, albeit her smile is more sad than bitter, she steps closer to the chair beside my bed. Back when I was coherent, she always complained about how uncomfortable it was. Now, she looks like she never wants to leave it.

"Hey, Daddy... I—it's me, Marilyn. I, uh—"
Her voice cracks. She always hated goodbyes.

"I got an interview—a job interview. I—" She sniffles, rubbing her eyes with the sleeve of her blazer. "I'm gonna be a lawyer!"

A choked-out laugh escapes her, but it’s shaky.

I smile weakly. ‘That’s my girl.’

I reach out, and she takes my hand, squeezing it tight.
Across from her, Dean Jr. looks up, a smirk pulling at his lips. "Nerd."

She snorts, rolling her eyes. "Dick."

‘Bitch’

‘Jerk’

A sound leaves my throat—an attempt at a laugh, but comes out more like a cough. They turn to me immediately, worry etched into their faces.

Dean Jr. sighs and shifts carefully onto the bed, placing a hand over mine.

"Dad... it’s okay. You can go now.”

I try to smile, but it feels more like a grimace. My eyes flicker to my daughter, who shudders, silent tears slipping down her face. She licks her lips, forcing a smile. It looked just like mine when Dean passed—pained, reluctant.

‘Like father, like daughter.’

My vision starts to blur. From tears or from...something else I can’t tell.

"Yeah, Daddy... we’ll be okay. Just rest now."

I take both their hands and hold them close.

"We’ll take care of each other."

Finally, That’s all I needed to hear. I sigh, gaze drifting toward the ceiling. The world fades.

Somewhere in the distance, the heart monitor wails.
But I don’t care.

I can finally rest now, but… I can't help but feel regret, can't help but wish that I had a little more time– to make things different.

‘Oh Jack…. I wish my children could've at least had the chance to meet Dean, or Bobby, hell– maybe even dad. Meet Cas, Jack, Ellen, Jo, Ash, you and so many more. If only I had..a little more time..’

Breathe in.

Breathe out.

Breathe in.

Breathe out….

And then

...Nothing.


Wait... what?

I see..my children and….myself? Frozen at the moment. An out of body experience. I look down at my wrinkled hands. ‘Literally, an out of body experience.

A voice cuts through the void.

"Hello, Sam Winchester."

No.

No. No. No. No. NO.

I turn slowly, my stomach twisting into knots

A little girl stands before me, arms crossed, head tilted. She has long blonde hair that reaches just below her waist, almost the same length as Marilyn’s when she was younger. Her eyes, though—they seem as if she is seeing everything and yet nothing, like she’s watching multiple things at once.

She huffs, looking almost disappointed.

"What? Never seen a ‘cosmic being’ before?"

I blink. My mind is still catching up.

"Who—no. What are you?" My voice is hoarse.
She smiles, but there’s something ancient about it.

"Come. We have much to discuss."

She snaps her fingers—
And suddenly, we’re somewhere else.

A park. A dirt trail stretching ahead. Birds chirp in the distance. A breeze rolls through, carrying the scent of fresh earth and blooming flowers.

I flinch. The last being who could snap me into another location was—

My hands curl into fists. ‘Old habits die hard.’

"Relax, Winchester," she says, glancing back at me. "I’m not here to cause problems."

I untense, but the embarrassment of my reaction lingers. I glance down at my hands—

Wait.

They’re smooth. Unscarred. Stronger.

Younger.

"I suppose you can guess what it is I can do," she says, an expectant look on her face. "That’s your first hint."

I flex my fingers. My skin is unwrinkled, my joints no longer aching. My body—it's as if I’ve been rewound.

I look back up. She seems... taller? No, older. She was six or seven when we first arrived. Now, she looks closer to nine or ten.

She’s aging as she walks forward, slowly, but it's there.

My breath catches.

"Time," I say. Almost to myself.

She stops. A bright grin spreads across her face.

"RIGHT!”

I flinch. Not the reaction I was expecting.

She clears her throat, looking slightly embarrassed. "Ahem. I mean, yes. You’re correct." A faint blush dusts her pale cheeks—though now, I notice the light specks of acne forming on them.

She’s still aging.

We continue walking, side by side.

"I’m glad you caught on quickly," she muses. "Games are a waste of time. But when I'm like this I usually can't help myself," She mutters, gesturing to her small form, glancing up at me. "Although... I was curious about your thought process. So—what gave me away?"

I watch her, noting how her face is losing its childish roundness. The acne is fading, replaced by sharper features.
"The constant references to time," I answer. "Me suddenly being young again. And you... aging."

She hums, eyes locked on the trail ahead. "Fair enough. I didn’t make it difficult to figure out—I don’t like wasting time explaining things."

Then, she turns to me, all traces of playfulness gone.

"Time is always moving. And I don’t like to wait. So let’s get to the point."

She picks up the pace. Almost as if she's nervous about something.

I pick up the pace, too.

"How would you like to go back?"

Silence.

My breath hitches, but I don’t let myself react—don’t let myself hope.
"Go back?" My voice is low, careful. "To where? My time is up."
She smirks.
"Ah. Ah. Ah. I decide that. Well—Death and I, technically. It’s more of a... collaborative effort."
She sighs, folding her arms.
"So, Sam Winchester. You up for another round?"
I shook my head and, without hesitation, scoffed out a quick, “No.”

It was a gut reaction. A truth.

Only after the word left my mouth did I fully register what she was asking. I glanced toward her. She looked older now— If I had to guess, she was maybe eighteen, or a young-looking twenty-one.

She scoffed right back, giving me a slow once-over, her lips curling into an irritated, almost teasing smile. It made her seem like just a normal teenager.

"You didn’t even think about it!" she huffed. "The least you can do is take a second to consider it."

"I thought you didn’t like wasting time," I shot back, glancing away.

The park looked peaceful. It reminded me of all the times I took my kids out for walks, how they’d tire themselves out, and I’d always end up carrying them home. I could almost hear their laughter, their tiny hands grabbing at mine, their sleepy murmurs as I held them close.

"Unless it’s to think," she snapped. "Why waste time making mistakes when you can avoid them in the first place?"

I sighed, rubbing a hand down my face. "My answer's the same. I’ve lived a good life. I won’t risk it just to go back and live it over again."

She picked up her pace, moving ahead of me. Then, as if she couldn’t bear to let the conversation die, she turned—walking backward so we were still face-to-face.

A slow smirk stretched across her lips.

"Even if it’s to save Dean?"

I froze.

‘She didn’t.’
She giggled, spinning back around and continuing down the trail. By the time I snapped out of it and caught up, she looked older—mid-twenties now, maybe a little more.

My jaw clenched. My voice came out sharp. "Dean died the way he wanted to—alright? He went out swinging. He would never want me to—to—"

The words got caught in my throat. I exhaled sharply.

"To risk his sacrifice just so I could see him again."

She stopped walking just long enough to glare at me. And then, just as quickly, she kept going.

"He died to a rusty old nail in a barn, with his little brother begging him not to leave him.”
Her voice was sharper now, quieter, but every syllable cut deep.

"He died pathetically."

A hot rush of anger flared up inside me. I scoffed, my tone thick with disbelief. "Of course you’d say that. Dean was right. All you cosmic beings are the same. Treating us like your damn playthings—just—"

"Is THAT what you think this is?"

For the first time, she faltered. Not much. Just a fraction of a second.

But it was enough.

She let out a short, humorless laugh, shaking her head, her blonde curls bouncing with the movement. Her voice was quieter now, almost… disappointed.

"Of course that’s what you think. But I’m not the one with regrets, Sam."

My walk stiffened. Each step taken almost robotically.

"You said it yourself—you wanted to give your children a chance to meet the people you knew, the people you loved. I can give you that chance. But no—you’re too busy drowning in guilt, obsessing over what other people wanted."

Her head snapped toward me, and for the first time, her irritation bled into something sharper. "Seemingly wanted."

She turned away again, shaking her head, muttering, "You won’t even consider the offer.”
Silence stretched between us.

By the time either of us spoke again, she looked like she was in her early thirties.

She exhaled, the fight gone from her voice. "Although… I knew you wouldn't react well, that you would refuse. " Her steps slowed, and for the first time, she seemed hesitant. "A lot of things can go… wrong after all."

A flicker of something crossed her face—regret, maybe. Embarrassment. "Even if I am on your side…" She looked down at her feet as we walked.

I hesitated. Then, finally, I asked, "Then why suggest it? If you know the consequences—if you already knew my answer—why?”
She sighs, her face creasing into lines that don’t fade. They stay, etched in place. She’s probably reaching her mid to late thirties now.

She gives me a serious look.
“You, out of everyone I could possibly go to with this, don’t carry as much guilt as you do. You’re right—Dean has earned his peace, truly. But what about you? Are you truly content with how things ended?”

I look at her skeptically. She chuckles softly to herself, then gazes ahead again.
“I know what you’re wondering. ‘Why me?’ ‘Why now?’ And my answer to that should be pretty clear.”

She looks me dead in the eyes, and I shudder at her gaze. Her eyes are the color of gold honey—almost like Jack’s. As I keep staring, I see an ancient, ticking clock deep within them.

Her wrinkles are becoming more pronounced, especially around her eyes—like she’s aging faster, like she’s already reaching her forties.

‘Is her aging accelerating? What happens when we reach the end of this trail?’

She doesn't stop walking, her blonde curls start to straighten with her age, grey streaks her hair in different places.

I try to hold on to her shoulder but she keeps her moving anyways.

“What happens when we reach the end of this trail?...” My voice comes out soft, hesitant. I feel as if I already know the answer, but had the need to ask her anyway. She smiles serenely at me.

“Scared, Sam?” She laughs softly, “Now, don't dodge the question.” She flicks her hair to the side, a few strands falling out. My face twists, bitter again. I run my hand through my own hair– short and soft. Just like back when my hair barely went past my ears.

“What do you want me to say? ‘That I wished things were different?’ ‘That I wished it turned out better?’ Because I'm pretty sure you already know the answer, or else you wouldn't be asking me, but–” I sighed, frustrated. ‘Anything with cosmic beings always makes me frustrated’. I take a deep breath, hesitating before answering, “I– I– I just can't..” it all comes out in a rush. My mind goes right back to Dean. The last thing he said. His last damn words—words he fought to get out. His final wishes.

“I will find a way, okay?” My breaths quick, uneven, “I– I will find another way–”

“No. Man, no. No, no ,no, no bringing me back, okay? You know– You know that always ends bad,” He smiled, that weak, stubborn smile. His breath slowing, rasping.

I breathe in deep, like it’ll help, like it’ll shake the memory loose, but it doesn’t. ‘Don’t think like that, Sam. You’ll see him again soon. Just... deal with this. Move on.’

Time looks at me, eyes sad, pity. She's at least in her early fifties, hair being more grey than blonde, but she doesn't seem to notice, or care. I imagine this is what mom would've looked like if Jack hadn't– I shook my head.

“Dean's at peace, and I'm okay with that. I'm not bringing him back–”

She cuts me off, “And I'm not asking you to. I'm asking you to go back. Not Dean.” She looks ahead, golden eyes that almost look too strong for her face, “And Dean's peace… Dean's peace doesn't have to mean death. You could change that– without burden or–or consequence weighing on you. This is a one-time offer.”

She looks at me, like she's waiting for some kind of response. I look away, because to that, I really don't have one.

‘If it's me..that's going back…’ I pause, my mind racing, ‘ if it's me and not Dean too…maybe…maybe I could change things?’

Like the cat that caught the canary, she drives it home, voice full of certainty, “You can change things Sam Winchester. You may not be able to change everything, but you can keep people from dying, you already know all the steps, all the– big ‘plot twists,’ all the wrong decisions– you just need to make sure to pick different choices.”

I chuckle, light hearted, but hollow, “You make it sound so simple. So easy, but….”

“I'll be all alone… Nobody will understand what I've gone through... how much I've changed. Would it all really be worth it?”

She’s pushing her sixties now—her face lined with fresh wrinkles, hair fully gray and thinning. Maybe a strand of blonde here and there, but it blends so well with the gray you'd barely notice.

“I know, I know, you don't want to be alone. You've been through so much and—see here? This is exactly why I want to send you back. You've suffered for so long, being alone. Sam, what have you got to lose? Tell me now—what's really stopping you? And don’t give me any more bullshit about what Dean would've wanted, or wouldn't have wanted. Tell me, Sam. Be honest, you hear?”

‘She even talks like she’s in her sixties now.’

She sighs. “You can live again, Sam. Not just survive—like your brother wanted you to. Find a better ending for you... and for your loved ones.” She stumbles, her legs unsteady. Walking isn’t easy for her anymore. Her hair is fully gray, face worn and lined.

“Don’t you want to see Dean? Just one last time?”

I wince, but I keep walking, mind racing.

Breathe in…
Breathe out…

It doesn’t even feel like air’s reaching my lungs, but the motion keeps me calm. And that same stupid thought keeps ringing in my head:

‘What have I got to lose?’

“If I go…” I hesitate, lick my lips, thinking. “If I agree to go back... what happens?”

Her eyes light up with excitement. “You go back, you change things. Save lives. Maybe give Dean a better ending. Who knows?” She shrugs like she used to when she was younger, but the movement makes her wince. The pain shows in her eyes—she’s probably closer to her seventies now.

‘She seems so frail. I know she’s not—but still.’

“You’ll never know what you’ll miss unless you take the chance.” Her tone shifts—serious, tired. Like she’s done trying to convince me. “Take the chance, Sam.”

“Okay.”

“Look, if you really don’t want to, then—wait, what?” Her eyes widen a little.

I laugh, quick and dry. “I said ‘okay.’ I’ll do it. I’ll… go back.” I throw my hands up, then let them fall. Exasperated.

Her smile brightens. “You’re serious?” I nod, nervous. “Oh man, this is going to be great! Oh, Sam—I’m so proud of you!” She hugs me tight.

‘For a little old lady, she sure hugs tight.’ I pat her back, awkward but genuine. ‘For some reason, she reminds me of Garth and Donna mixed into one.”
‘It’d be nice to see them, too…’

“Okay, okay… so… what now?” I ask, unsure.

“Oh! Right, right. Here’s what we’re gonna do.” She lifts her hands and slams them together—bam!—a golden shockwave blasts from her palms, nearly knocking me over. Between her hands, she pulls them apart slowly—and there, floating, is a tiny hourglass no bigger than my pinky. Gold sand flows upward, not down.

She gestures for me to crouch—frail as she is—and suddenly, sting! A sharp pain hits my left ear. I snap upright.

“What the—what was that for? What the hell did you do to my ear?” I reach up, feel something dangling.

It’s the hourglass.

She summons a mirror with a wave of her hand, then hands it to me, eyeing me critically. “Hmm… yup! You look great, love.” She pats my arm, grinning—her teeth decayed and chipped.

“What is this?” I look at the mirror—there it is, the hourglass. Gold, with a black gem hanging from it.

She brushes back her hair—clumps fall out, but she doesn’t seem to care. She’s probably well into her eighties now.

She points at the hourglass. “That, my dear, is how you’re gonna summon me when you get there. Take it off, and on top, you’ll see a gear.” She mimics the motion, like we’re playing charades. “Turn it twenty-four times. That gives us a full day to chat. And trust me, you’ll have questions when I send you back. I've got a surprise waiting for you.

She smirks—all-knowing. She’s aging fast now. Hair almost gone. Teeth? Nearly all fallen out.

She grabs my arms, pulling me down to her level. I stare into her clock-like eyes and shudder. ‘She’s surprisingly strong.’Her grip is tight, hands wrinkled—but decaying. I grimace, glancing back up—

—and flinch.

All that’s left is an empty skull staring back.

“Time’s up, Sam Winchester.”


Tuesday, November 2, 2004. 12:12 am

Beep!Beep!Beep!
Beep!Beep!Beep!

My breath caught—sharp, ragged, wrong. I shot upright, chest heaving, the nightmare’s claws still tearing at my skin. My shirt clung to me, soaked in sweat, freezing cold. The darkness around me felt too close, too real.

My eyes darted wildly, trying to ground myself.

Movement flickered at the corner of my vision. They stirred—a muffled groan—and the figure beside me sat up.

Blue eyes met hazel.

My breath hitched.

“…Jess?”

Chapter 2: Back to the Beginning

Summary:

‘I'm back.’

 

I slick my bangs back and take a deep, shuddering breath. I look at the hourglass dangling on my earlobe and rub my fingers on it gently, in thought.

 

‘I'm young again… No wrinkles, no gray hair….’

 

“Sam?...”

Notes:

Hello again!

This was originally gonna be a one-shot, but i decided to add another chapter! If you see any mistakes please let me know down below!

 

Hope you enjoy the story!!💕

(See the end of the chapter for more notes.)

Chapter Text

Tuesday, November 2, 2004. 12:12 am

Beep!Beep!Beep! Beep!Beep!Beep!

My breath caught—sharp, ragged, wrong. I shot upright, chest heaving, the nightmare’s claws still tearing at my skin. My shirt clung to me, soaked in sweat, freezing cold. The darkness around me felt too close, too real.

My eyes darted wildly, trying to ground myself.

Movement flickered at the corner of my vision. They stirred—a muffled groan—and the figure beside me sat up.

Blue eyes met hazel.

My breath hitched.

“…Jess?”


Beep! Bee–

She yawns, clicking the stop button on the alarm clock. Hair a mess, she wipes the drool from her lips.

“Mmmm... who else would it be, silly?...” She gives me a sleepy peck on the cheek, before her eyebrows furrow. “Sam? What's wrong?…”

She glances at the clock, actually looking at the numbers. “It's midnight…? The alarm clock must be busted. Let's go back to sleep, babe.” She brushes my bangs—probably covered in sweat—to the side. “Sam?…”

“Yeah... uh—I'm fine now. Just go back to bed. I'm gonna… go to the bathroom real quick.” I get up quickly and make my way to the door. Before my hand reaches the knob, I look back toward her. She’s already back under the covers, blonde hair sticking out. ‘I'll miss you…’

I take a deep breath before opening the bathroom door. I look in the mirror. My face is pale and covered in sweat—but it’s undeniable now.

‘I'm back.’

I slick my bangs back and take a deep, shuddering breath. I look at the hourglass dangling on my earlobe and rub my fingers on it gently, in thought.

‘I'm young again… No wrinkles, no gray hair….’

I glance toward the calendar on the wall, marked up with class dates. I chuckle, remembering why we hung it in the bathroom in the first place.

“I can't believe you forgot about that test!” I laugh, wrapping my arms around her shoulders.

“It’s not my fault,” she says, pushing me playfully with a small smile. “I just can't remember when we have tests.” She shrugs, like it’s no big deal.

“We have a calendar in our room. Just check it before you leave.” We walk up the stairs to our apartment. She gives me a look.

“Not all of us are early bird risers. By the time I’m out the door, I’m already late! I barely have time to brush my teeth, let alone look at the—”

She stops in her tracks and gasps. Turning toward me with a smile on her lips, she grabs my face and kisses me deeply.

“You’re such a genius, babe,” she giggles, grabbing my hand. “Come on! You just gave me an idea.” We laugh as we practically run up the stairs.

The memory fades, bittersweet.

‘This time… I won't let her die.’

The date catches my eye. ‘She’s supposed to die today. Maybe I can convince her, last minute, to visit her family before I leave—’

I look at the year.

Wait… 2004? Then she won’t die until next year. Same date, but different year. If I leave now, Brady probably won’t even consider her important.

‘Brady.’

‘How am I gonna deal with that?’

A frustrated sigh escapes me before I hear a dull thump—not from the bedroom, but from the kitchen. I step out of the bathroom into the bedroom, and the bed shifts.

‘If Jess is still asleep, then…?’

I walk into the kitchen, but it's too dark to see anything. I switch on the light to see better and—

“Sam?...”

I jump, turning toward the small voice. My eyebrows furrow as I spot a child—probably three or four years old—standing in the middle of my living room by the coffee table, which seems to have moved an inch. He must have bumped into it in the dark.

“Who?...” I squint at the strange child, because I know for sure that no kid has ever been in this apartment before, with me and Jess. But something about him feels familiar. ‘Blond hair, blue eyes, that Castiel-like head tilt.

“Jack!?” I whisper-yell.

No way do I want to wake up Jess because of this. The child—Jack, my mind confirms—practically lights up. He runs straight toward me, wrapping his arms around my right leg and nearly toppling me over.

He looks up with a childish grin. “Sam! You look so different!”

I bend down to his level and gently shush him. “Sorry!” he whispers, his tiny hands muffling his voice.

“It’s okay, I just didn’t want you to wake up my gir—uh—ex-girlfriend, Jess.” I whisper back.

I pull him into a hug before letting go. “You’re not the only one who looks different, you know. I mean, if you can’t tell already.” No longer did he look like his late teens or early twenties, but instead the age we thought he would've looked like.

“Hehe… you’re right! I’m so little!” he giggles softly. “My plan worked!”

That makes me pause.

“Wait, Jack. What plan? What do you mean by that?” I take his shoulders gently and look into his eyes. He shrinks in on himself, guilt written all over his face.

“I—I—I heard your prayer, Sam. Right before you died. I talked to Time, to see if she could convince you to go back in time.” He stares at the ground, ashamed. “I just wanted to be with you again. I liked listening to your prayers. You always talked about Dean and you, back when it was just about finding your dad. Before I was born. You had so many regrets. I thought... I thought you’d want another chance. I’m sorry…”

I sigh, tired. “It’s okay, Jack. I just wish we could’ve talked about this first. Between me and you and not Time” I think back to my conversation with Time, ‘This must've been the surprise she was talking about.’

“I’m not mad though. In the end, it was still my choice.”

‘She points at the hourglass. “That, my dear, is how you’re gonna summon me when you get there. Take it off, and on top, you’ll see a gear.” She mimics the motion, like we’re playing charades. “Turn it twenty-four times. That gives us a full day to chat. And trust me, you’ll have questions when I send you back. I've got a surprise waiting for you.”’

I touch the hourglass hanging from my ear in thought.

Jack beams with a toothy grin. He seems so small and innocent, it makes me forget that he’s actually God now.

‘Wait a minute…’

“Jack, are you still God?”

He looks down, definitely guilty. “Uhhhm... no.”

“Jack! You mean to tell me Chuck is in control again!?” My heart pounds wildly at the thought, my vision blurring at the edges. I snap out of it when I see Jack wince, and guilt immediately crashes over me. A sound comes from the guest bedroom, and we both glance toward it.

“Wait here. We'll talk about this later.”

I get up and move stealthily toward the door. Jack grabs my arm, his voice urgent but quiet. “Wait, Sam! There’s something else!”

I ignore him and reach the guest bedroom, cracking the door open just enough to peek inside. There’s something in there. I push the door open slowly—and freeze.

My breath catches. Two baby car seats rest on the bed, one draped with a pink blanket, the other with a blue one. Jack steps in behind me, but I can’t tear my eyes away from the seat in front of me. I lift the soft blue blanket and gasp—a baby boy, maybe a year and a half old, sleeps soundly inside. Faint snores rise from the second seat as well.

‘I don't want to hope. I don't even want to think but…,’ I reach in and gently tug down the baby’s navy-blue shirt, revealing a small mole on his collarbone. My breath hitches, tears welling in my eyes as I carefully lift him from the seat.

‘Dean Jr.’

“Hey, baby boy… look at you...” My voice is hoarse, thick with emotion. ‘It’s been too long since I’ve held my son like this.’

“That’s your real surprise, Sam.”

I flinch, momentarily forgetting Jack was still there. I turn to him, eyes wide. “You brought them here?”

“Well, Time did. I just helped a little,” he shrugs. “I wanted you to have them with you. Don’t worry—they won’t remember anything. It’ll be just as if they were born at this point in time. I was hoping to tell you before you walked in here, but you wouldn't stop. ” He scratches the back of his head.

I chuckle wetly before taking a deep, shuddering breath. Jr. lets out a soft, contented coo—shifting sleepily into a more comfortable position. I take a second to enjoy the moment before snapping out of it and gently laying Jr. back into his seat. He whines briefly before settling down. I glance toward Jack, who is on his tiptoes, peeking at my children. I chuckle, and Jack notices, blushing in embarrassment.

“What about their records? If someone looks into me—and trust me, they will—they’ll question my relationship to my kids, including you.” Jack smiles at the comment before replying, “Don’t worry, Sam. I made sure all the documents list their mother as a Jane Doe who passed away. Well… in hopes no one looks too deeply.”

I ruffle his hair affectionately. “You’re a Winchester, alright. Good thinking.” Jack’s smile brightens even more.

“We should probably hit the road soon. I don’t want to spend too much time here. My ex could wake up at any time, and I don’t want her asking questions about you guys.” I walk toward the door into the living room. Turning to Jack, I whisper, “Stay here and watch over the babies. Don’t wake them—please.” The please was more urgent than suggestion, but Jack doesn’t seem to mind. He gives me a thumbs-up.

I head toward the bedroom and quietly, quickly pack all my essentials. Jess stirs here and there, but luckily, she doesn’t wake. I pause, glancing at all the old photos of the life we had built together.

‘A life I could never have again.’

I sigh, finishing my packing. Slowly, I creep to Jess’s side and place a soft kiss on her forehead, tears welling in my eyes. She sighs contentedly.

‘Goodbye, Jess. I’ll make sure no one hurts you again…’

I grab a piece of paper and write her a short note, a small goodbye.

‘Jess,

I hate that I have to tell you like this but I have to leave.Things are happening that are out of my control, I hope you have it in your heart to forgive me and I wish you the best moving forward. Don't wait for me, I'm sorry, but I'm not coming back to Stanford.

-LoveBest wishes, Sam Winchester’

I folded the note and left it on the dresser. I looked back one final time.

Bag in hand I make my way to the door. I cross the living room and into the guest bedroom, I find Jack trying to explain everything to the babies.

“And so your father prayed to me so that you two could meet your uncle—who you,” he points at Dean Jr., “are named after.” He smiles at them and nods, as if confirming to himself that they understand.

I let out a soft laugh, catching Jack’s attention as he turns around. “Oh! Sam! You’re back!”

“Yeah, come on. We should get going now.” I grab the car seats and shuffle toward the door. Jack opens it for me.

As we make our way down the stairs, Jack offers, “I can summon a car for us if you'd like, Sam?”

I shake my head. “No, Jack. I don't want you using your powers.”

Jack frowns but doesn’t argue.

We walk down the street. I stop now and then—the babies shift and whine with each movement, but thankfully they don’t wake. I glance around at the cars, considering which one might be easiest to steal or hotwire.

I spot a car not too far away—a 2003 black Volkswagen Jetta. It's a bit beat-up compared to the more popular cars of this era, like Honda Civics or Toyota Priuses. I head toward it as quickly as I can, carrying two car seats and a bag packed with supplies.

Setting the children and the bag down, I shimmy the handle to check if it’s unlocked. No luck. Glancing around, I crouch down and unzip my bag, pulling out a rag and wrapping it around my arm. I cover my babies to make sure they don’t get glass on them before slamming my arm against the window.

The alarm blares loudly. I hop inside as quickly as I can to turn it off, hotwiring it to start as I do so. It takes a few seconds, but it’s enough for the kids to wake up and start crying.

“Jack, sit in the front—I’ll strap them in.” He quickly makes it to the front. “Wait! Take this!” I hand him my bag. It looks ridiculous giving a four-year-old a duffle bag half his size, but he makes it work.

I quickly strap in my kids and try to shush them softly, but they were so startled by the sound of the alarm that they can’t stop crying. I look around and see lights flicking on in the windows of nearby buildings.

‘Shit. I need to make this quick.’

I find pacifiers attached to the handles of the car seats and place them in their mouths. They quiet down a bit, but soft cries still escape. I glance over at Jack.

“Ready, Sam?” he asks, adjusting his seatbelt.

I chuckle weakly. “Ready as I’ll ever be...” Jack smiles at me, then looks back at the babies.

He shushes them and talks to them, but I can’t hear his words—too focused on the sound of my own heartbeat. I take a deep breath and adjust my seatbelt. In the rearview mirror, I catch a glimpse of the hourglass dangling from my earlobe.

‘This time, time is on my side.’

Notes:

Hey again! Did you enjoy this chapter? Tell me what you think down below! Thanks for reading!💕

🥹👉👈

Constructive criticism only! 😞🙏

(This is my plan for this series, but remember I'm not required to follow through if I don't want to, but I kinda want to explain why it's set a year earlier than when Jess is supposed to die.

I want this story to have a pre-series, where is just focuses on Sam and his relationship with his kids + Jack, ((don't worry for all the Dean or John fans lol, I'll write about them at the end of every chapter to see what they're doing)) also I want to rewatch the first season before starting so while thats happening I'll write the pre-series)

(Don't worry it won't be too long! Im actually on like episode 5)

(So this story is kinda like the Epilogue story, basically a starting point, at least for me just to see how well it does or if I like it. ((So far I do lol))

So basically:
This Time... - Epilogue
This Time... - Pre-series
This Time, Time is on My Side! - Series
??? - prologue(?) Idk

Notes:

Hey everyone! Did you enjoy the story? Tell me what you think down below! Thanks for reading!💕

🥹👉👈

Constructive criticism only! 😞🙏

(Also should I leave this in first person or change it to third?)

Inspired by Second Chances by Nephilim22

Series this work belongs to: