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Seeing Double

Jack Abbot x F!Author!Reader x Grant Reilly

Summary: your casual friend with benefits slash sort of sugar daddy, Jack, invites you to meet an old army buddy of his. You end up with far more than you bargained for.

C/W: age gap (unspecified but as per usual, all my reader characters are implied to be in early/mid thirties) / friends with benefits situationship / vague sugar daddy arrangement (Jack likes to spoil you) / threesome (M/F/M) / oral (F!receiving, M!receiving) / dirty talk (they both have filthy mouths) / PIV (unprotected, wrap it up folks) / zero risk of pregnancy / cum eating / enthusiastic consent / graphic description of sexual activity (duh).

Notes: This one might end up with a part two, if requested? IDK, this fic is for my oomfies in the Salt & Pepper discord server.

Word Count: 5.5k

You wouldn’t say that you have favourites, per se. It’s hard to describe a casual situationship as anything but that, but you’d say that Jack Abbot treats you better than every ex boyfriend you’ve ever had.

You’d met him by chance, in the most ridiculous meet cute way. Something you’d write about, in fact.

You had been in your local bookstore, silently celebrating your first traditionally published novella. After three years of self publishing, dealing with Amazon (ew) and indie contracts, you’d scored a deal with a traditional printing house.

It had been kind of surreal, seeing your name on a book in a chain bookstore, something you’d dreamed of since your age had been in single digits. You’d been stealthily signing a couple of copies, hiding them in the stack, too lost in your own world to notice the older man when you’d taken a step back and almost tripped right over him.

Holding a copy of your book to your chest, you’d felt warmth rush to your face, embarrassment almost entirely overwhelming you when you realised he wasn’t not just some older guy, but handsome. Broad shoulders, salt and pepper curls, bright hazel eyes, and, if the black scrubs he was wearing were any indication, a doctor.

“Oh, god, I’m so sorry,” you had said, mortified, but he had just smiled at you, a lopsided little smirk that made the creases at the corners of his eyes more prominent.

“Don’t be. Yours?” He had asked, nodding at the book and pen in your hands.

You had been surprised, nodded, half expecting him to say something derisive about chick lit and porn in written form, but he hadn’t. He’d just smiled at you again, told you he’d noticed you signing a couple of the books.

He had been curious, sweet, bordering on flirty, and when he’d picked up a copy of your book and asked you to sign it for him, you’d taken a risk and added your phone number beneath it. You’d never expected anything to come from it, but he’d sent you a text just a few hours later.

Over the next few months, you’d gotten to know Jack better. He was an emergency medicine physician, a senior attending at a level one trauma centre. He worked the night shift. He was an army veteran, a widower, an amputee.

He was your friend, first and foremost, but you were comfortable enough with each other to let that friendship blur into sex without any sort of expectations.

Jack was still grieving his late wife, and you weren't really looking for anything serious; you wanted to primarily focus on your career, on letting your creativity bloom.

It was a good, practical, happy arrangement. Jack was lonely, you were lonely, and he made far more money than a guy who was technically single could ever need, in his words.

So while a lot of your relationship was built on friendship, on keeping each other company, there was also a part of it that was decidedly built on erotica.

Sexts, heated makeouts, long afternoons or, on his days off, nights of multiple rounds of mind blowing sex. You had no idea how a man of fifty had the stamina that Jack does, but you sure as hell had no complaints.

While you weren't together, there was an exclusivity to your arrangement. You both had attachment issues, but the maturity to know it and discuss it.

Said discussion had come about when you'd been discussing the idea of not using condoms anymore; you had had permanent contraception done in your late twenties, so it wasn't like you were going to get pregnant any time soon. Or ever, for that matter, which you preferred.

"Why would I seek out anyone else's company, sweetheart? We get along just fine, don't we?" Jack had said.

Regardless, he'd provided you with a screening to put your mind at ease, even though you hadn't asked.

You'd been pretty upfront; like him, you weren't looking for a label, but you liked the relationship you had. You weren't interested in having this sort of thing with anyone else, not when Jack was so good to you.

He took you out to nice restaurants, occasionally bought you little gifts. Jewellery, books, little trinkets for your bookshelves at home.

For a not boyfriend, he was considerate, too. He'd bought your favourite skincare products and perfume to leave at his place, bought you flowers for each chapter of your next novel you finished.

When your laptop had crapped out on you, he'd replaced it as soon as he'd heard about it.

You sometimes weren't sure if you felt right about letting him spend so much money on you, but he'd just waved his hands.

"Don't exactly have anyone else to spend it on. Besides, I like spoiling you. You deserve it, and you don't expect it. Just like I don't expect anything in return."

Sometimes you accompany him to events if he wants a plus one. You're beautiful, according to Jack, and he likes showing you off.

"My girl's a writer," he would say proudly each time he introduced you to somebody, so open and confident that nobody judged your choice of career.

Tonight is one such night; Jack tells you he has an old army friend coming down from Boston for work. A chef, he says, owns a Michelin star restaurant up that way.

They're catching up for a couple beers and rounds of pool at a bar Jack likes, and he wonders if you'd like to come along.

You don't see why not. This isn’t totally out of the ordinary; you hang out with Jack often enough, have met his best friend once or twice. Besides, you know – and like – the bar he’s talking about.

By around six thirty, you’re stepping into the bar in a pair of high-waist jeans, a deep wine red tee that shows just a peek of midriff, and a washed out black denim jacket. Cute, put together, but casual enough that you don’t feel like you’re trying too hard.

That’s another thing you like about Jack; you never feel like you have to be someone you’re not. He’d told you once – whilst he was inside you, of all times, your wrists pinned above your head in one big, gentle hand – that he didn’t care if you were wearing a casual grungy look or a pretty dress, he was always one step away from pushing you against the nearest wall. That he thought you were beautiful no matter what you wore.

It was difficult to hear things like that and not feel a little something for him, though you knew that was pretty natural, and not something to be explored. Not right now, or necessarily ever.

You spot Jack by the bar, leaning against it casually, looking far too good in a black t shirt and cargo pants, talking to someone you can’t quite see.

You’re not too sure what to expect; he hadn’t told you much about his friend, only that his name was Grant, he was ex army like Jack, they’d done a couple of deployments together, and he was from Boston.

You were expecting another guy around Jack’s age, like his friend from the trauma centre, sure. What you decidedly were not expecting, was for him to so closely resemble Jack.

Grant stands a little taller, has a bit more ease to his posture, which after spending so much time with Jack, you recognise as a trait the latter doesn’t have due to being an amputee.

His hair is a little longer, more of a tangled mess of salt and pepper curls than Jack, but he’s no less built, has stupidly thick biceps that are on the border of obscene peeking out of a white t shirt. White shirt, black jeans, laced up dark boots.

You’re staring and you know it, cough and blink rapidly, completely missing the almost knowing smirk that the two gorgeous older men share.

The bar is a nice temperature, the music loud enough to be heard but not overbearing, so you can still hear each other talk.

You slot into the conversation nicely, find Grant just as easy to talk to as Jack, even if he seems a little more cautious, a little more careful.

Two pints and a couple of games of pool later, and the three of you seem to be getting along just fine, all comfortable with each other, laughing and joking. You can tell they’ve known each other a long time – over twenty years, Grant tells you when Jack goes off to grab another round of drinks after they finally get you to agree to play a round, rather than just watching.

That explains their easy dynamic, you think as you step around the pool table, try to balance the cue properly in your hands.

It’s not that you don’t know how to play – you most certainly do – it’s just been a while and you’re not so confident around this incredibly handsome near stranger. After a couple of failed attempts at lining up a shot, you huff, consider just giving up.

Grant watches you for a moment, as if trying to decide something, then circles the table and tilts his head slightly, before he steps behind you, your back against his chest.

His firm hands are gentle as he adjusts yours, guiding your body into a different stance. “There you go. Now try.”

His voice is low, raspy, just like Jack, but there’s a little more hoarseness to his. You suppose that’s to do with having to be heard over the sounds of the kitchen, which must be deafening.

Close to your ear, you have to resist the shiver that threatens to run down your spine. He’s so warm and solid against your back, his arms against yours as you line up your shot with his help. You sink the right ball, look up just in time to meet Jack’s eyes as he returns from the bar; you feel your face heating again, feel almost guilty, until you notice the smirk on his face, the glint in his eyes.

For the first time this evening, you start to wonder whether he has an ulterior motive for inviting you out tonight. More importantly, you realise, you want that to be the case.

You get your wish at around nine, when the bar starts to get busier, filling up with college students, and Jack suggests heading back to his place. Not just you and him. The three of you.

The suggestion isn’t entirely surprising; he’s made a comment or two about the idea of bringing a third person into the mix once or twice. Never another woman, though. Jack gets off on getting you off, on having control of the situation, sure, but he’s not interested in making you watch him fuck another woman.

However, what he does like is the way you look when you’re overstimulated, totally fucked out and needy. He likes spoiling you, after all, and this is no different.

You end up sitting between the two older men on Jack’s couch, feeling a little nervous and giddy until Jack kisses you first, clearly the more extroverted of the pair. That or perhaps he’s simply more comfortable with you.

Regardless, when you break apart, it’s entirely clear that the other man is interested, based on the way his hazel eyes are dark with desire as he looks at you.

Somehow, you get the feeling that he won’t be the one to initiate; he seems kind of shy, at least not the same kind of introvert as Jack. That doesn’t bother you, not in the slightest. In fact, you think it’s kind of endearing. Endearing and attractive.

You lean in to kiss him, brush your lips against his at first; it’s not a case of you being nervous, more the idea of making sure that he’s okay with it too.

At first, he doesn’t move, but then perhaps two heartbeats later and he’s pulling you in closer. Two pairs of big, warm hands roam your body as you lean into him, part your lips and let him lick into your mouth.

He kisses differently to Jack, of course. Jack kisses with a sort of self assurance, a quiet confidence. Grant is a little more cautious, not quite hesitant, but with the air of taking his time to figure out what exactly you respond best to.

Idly, you hope that translates over to everything else, too.

You find yourself pressed between them both, alternating between who you kiss while the other kisses your throat, only pausing when the three of you get to your feet, stumble, all three of you almost giggly, to Jack’s bedroom.

“’s easier in here,” he’d said, nodding down at his right leg, or rather, the half of it that’s titanium. Not like you needed an explanation; you’d long since learned to adapt to the physical limitations that came with Jack’s disability.

Grant doesn’t question it either, but that isn’t surprising – they’ve known each other for so long, you suspect since before Jack lost his leg.

You expect there to be a certain amount of awkwardness, or at least to be a bit uncoordinated, considering there’s three of you. Somehow, though, it just works, and you manage to get both of them shirtless.

That in itself is an achievement, considering they work together to get you naked; you’re gently pushed backwards onto the bed while Jack sheds his pants, sits on the edge of the bed to remove his prosthetic, before he’s settling himself behind you, unclasping your pretty lace bra and tossing it aside.

His warm hands cup your tits as you feel his hardened cock pressing against your ass, making you inhale sharply. You love his cock. Are intimately familiar with the thick, heavy length of him, the freckles at the base, the vein along the underside that, when you drag your tongue along it, always makes him groan.

The mystery here is Grant.

The other man removes the rest of his clothing with that same sort of quiet caution, that same caution finally giving way to blatant desire when he sees the way you look him up and down, slowly.

Fuck, he’s handsome. His biceps and pectorals look like they could be carved from marble, there’s a slight softness to his belly, and like Jack, he’s covered in freckles.

“Beautiful,” you breathe before you can help yourself, and only then do you let your gaze wander further south.

With the physical similarities between the two men, you shouldn’t be surprised by the fact that his cock is pretty, too. Just as thick, slightly curved, achingly hard.

You’re about to say something else, but then he’s joining you on the bed, gives Jack a look before the latter is adjusting you so that the other man can settle comfortably on his belly between your thighs, nudging them apart and settling there.

Slowly, agonisingly slowly, he brushes two fingertips along the damp fabric of your panties, has the audacity to smirk as he looks up at you. “Soaked,” he all but murmurs, raspy voice soft as his fingers hook into the waistband of your underwear.

He waits for you to lift your hips so he can pull them down slightly, then tugs them the rest of the way down with his teeth.

You whimper softly as the ruined fabric is tossed aside and he settles himself back between your spread legs, planting open mouthed kisses on your inner thighs.

That he’s a tease doesn’t remotely surprise you. What you like is the way he occasionally glances up at you as he kisses inwards, as if silently checking in with you.

Perhaps it’s because you’re so used to Jack, who knows you and your body so well by now that he touches you with a sort of ease that only really comes after months of intimacy, but this sends a thrill through you.

Speaking of Jack…

He resettles himself behind you, leans in to kiss along your bare shoulder, up your neck, his hands still cupping your tits, thumbs brushing back and forth across your nipples slowly.

“You gonna be good for us?” He breathes into your ear, just as Grant presses an open mouthed kiss to your core, making you whimper and nod.

“No, you use your words,” Jack corrects you almost immediately, settling into that comfortable, confident dominance that you adore.

Just as you open your mouth to answer, Grant chooses that exact moment to circle your clit with the tip of his tongue, moaning as he drags his tongue through your slick folds. You whimper again, go to roll your hips without even thinking about it, but then just as quickly as he started, he’s pulling away from you, just a little, looking up at you with a little smirk on his face. “Jack asked you a question, honey.” His warm breath fans across your sensitive skin. In that moment, you think you might do anything, say anything, so long as it results in getting his mouth back on you.

“Y-yeah, I’ll be good.” You answer shakily, breath catching in your throat as you feel the purr of approval rumbling in Jack’s chest as he resumes kissing your throat.

Based on the way he touches you, featherlight brushes of his fingers across your nipples, smoothing his palms over your curves and back up again, he’s pleased with your answer. He keeps one arm wrapped around you, the other resting at his side.

Meanwhile, Grant resumes the slow, almost languid licks of your folds, intermittently sucking on your clit, moaning into you as you drip slick onto his tongue.

He’s so busy with work, the first to admit he has no life outside of his restaurant. No real hobbies, certainly no time for anything resembling a stable relationship. Hell, he doesn’t even remember the last time he spent a night with someone that wasn’t just a quick hookup.

Grant’s always loved going down on his partners. Loves the way it makes them react, loves the intimacy, and there’s a part of him that just loves the taste. You’re no different, reacting beautifully as he makes out with your pussy, drinking down your slick and teasing your entrance with two fingertips.

He eats you like you’re the most delicious thing he’s ever tasted, making absolutely zero effort to disguise the way he moans into you, the obscene slurping of his tongue and the filthy groan he gives you when he finally pushes his fingers inside you.

“Ohhh, god-” you gasp as he presses one last kiss to your puffy clit before he’s wiping his mouth on your inner thigh, sitting up as he slowly curls his fingers inside you. Jack shifts behind you and you realise he’s stroking his cock with his free hand.

“’s okay, baby, ‘s okay to want him, too-” Jack purrs into your ear, the hand that isn’t wrapped around his thick shaft sliding down to circle your clit in time with the warm fingers pressed knuckle deep inside your pussy.

You kind of assumed that was the case, but it’s still almost relieving to hear him confirm it out loud, so blatantly stated.

“Your pussy’s delicious, honey,” Grant murmurs, rests his head on your thigh for just a moment, looks up at you with pussy drunk eyes.

He kisses his way back up your body, pausing to pay more attention to your nipples, kissing and licking them, making you writhe against Jack, who laughs softly in the vicinity of your ear.

“Gonna tell us what you need, honey?” Grant breathes, brushing his lips against yours, massaging your g-spot before he slowly pulls his fingers out of you, making you whine pathetically as he maintains eye contact, licks his fingers clean with an obscene groan.

“Inside-” you breathe as Jack’s fingers circle your clit. “Want you both-”

The older men exchange a look, silent communication, a smirk, before Jack removes his hand too.

“Up you get, sweetheart. Turn over for us, yeah?”

You do as you’re told, turn onto your front, wait for Jack to move back a bit so he can lean against the headboard. Once he’s settled, you crawl up the bed to get closer to him, feeling the mattress dip a little as Grant moves up behind you, runs his palms over your ass as you settle on your hands and knees, giving him a beautiful view of your slick soaked folds, your soft skin.

Meanwhile, you’re very distracted by Jack’s cock. Fuck, you love his cock. It’s thick and fat and the perfect length, a smattering of freckles dusting the base.

You can’t help yourself – you lean in and press little kisses along the underside, from base to tip. Jack looks down at you, brushes his hand over your cheek as you look up at him, keep eye contact as you kiss the fat tip of his cock, already drooling precum.

Behind you, Grant holds your hips in one hand, grinds against you slowly, resting his equally gorgeous cock on your ass for a moment before he shifts again, wraps his hand around his shaft to guide the tip to your dripping entrance.

You’re so fucking wet. He doesn’t remember the last time someone wanted him so badly. In a moment of briefly selfish relief, he’s glad you’re not too preoccupied with blowing Jack just yet, so he can hear the moan you give him as he presses a couple of inches deep inside you.

He lets out an almost whimpering groan at the feeling of your warm, wet walls enveloping him, the way you angle your hips to give him better access.

“Oh, fuck,” he murmurs, his hands on your hips to steady himself as he slowly stuffs you full of his cock. Your attention is back on Jack by now, sucking on the tip of his cock again, before you take him in deeper, flattening your tongue so you can lick him at the same time.

It’s filthy, obscene, the way you moan around him as Grant’s hips finally meet your ass, the soft, breathy groans he rewards you with, the low almost growls Jack gives you from above.

You start to bob your head, trying to silently demonstrate how much you love sucking his cock as the other man starts to move, slowly grinding against you until he’s so deep you think he might kiss your cervix. Your appreciative moan is a little muffled, but it’s enough to encourage him.

They move almost in sync, Jack gently rolling his hips up, just enough that he’s encouraging you, whilst Grant starts to give you slow, shallow thrusts, letting you get used to the stretch of him inside you.

“Fuck,” he groans softly, breathless, “fuck, your pussy is perfect, baby-”

The praise makes you tighten around him, brief and involuntary, which draws a truly obscene groan from him, a rumbling purr that’s almost immediately echoed by Jack as you swallow around his cock.

Jack loves when you blow him, loves how sloppy and passionate you get with it, drooling all over him as you lick and suck, moaning around him as Grant picks up his pace behind you.

He steadily builds up a good rhythm, eventually giving you full, heavy thrusts, shifting to plant one foot on the mattress to give him better leverage. His hands are firm on your hips, but not bruising, guiding you back onto his cock to meet his thrusts.

“Nngh, mmmffff, fuck-”

He’s vocal, raspy voice dropping an octave lower as he grunts and groans, practically purring as he feels you getting tighter around him. The entire time as he works you up to the edge, you keep giving Jack all your attention with your mouth, wrapping one hand around the base of his shaft and stroking him, making him grunt.

“Mmmffff, shit, sweetheart, your fuckin’ mouth-” Jack groans, cups your face in one hand, brushes his thumb back and forth across your cheek.

“Doesn’t she take our cocks so well?” he asks, looks over your shoulder at Grant. Both of the gorgeous older men are a little flushed in the face, hazel eyes dark, pupils blown wide with lust.

“Nnh, such a good girl-” Grant agrees, giving you a particularly deep thrust that has you mewling.

You’re getting so close, hovering right on the edge of your climax, and they know it. Jack can tell by the change in pitch of your moans, Grant can feel you getting tighter around him, the increase in your already copious slick.

“Ohhh, you’re getting close, aren’t you, sweetheart?” Jack coos knowingly, “c’mon, we both wanna hear what you sound like when you cream all over his cock.”

Taking that as permission, you pull back from his cock, albeit a little reluctant; he really does taste delicious, clean and slightly salty, but there’s also a part of you that wants to focus entirely on your own impending orgasm.

Without having to focus on trying to make Jack feel good at the same time, you can give over to your utmost base instincts, letting yourself get lost in the feeling of Grant’s velvet soft cock pressing in and dragging out of your soaked pussy, moaning obscenely when one big hand leaves your hip to circle round, press his fingers to your swollen, aching clit and start to draw tight little circles around it.

That’s all you need, you think, you’re right there, but then he leans down over you, blankets his body with your own, just to be able to purr into your ear.

“There you go, honey, just let go. Let go for me, nnn; I’ve – I’ve got you...”

That’s what finally sends you crashing over the edge, your moans echoing around the bedroom as the tension in your core snaps, your thighs trembling with each wave of the intense, sudden orgasm.

He can feel a little trickle of your cum and slick soaking his cock, dripping out around him and onto the sheets, but all that serves to do is make him throb inside you, just prolonging your orgasm as he holds you against him.

You’re dimly aware of Jack’s familiar grunts; through the haze of your climax, you register him in front of you, one big, freckled hand wrapped firmly around his cock, giving his shaft a few slow, precise strokes as he watches his friend fuck you.

And god, does he.

Grant fucks you through your release, just keeps going, clearly chasing his own orgasm now.

His thrusts become more erratic with each one, grunting on every second impact.

“Mmff – mmm – nnngh -”

He makes no attempt to be quiet, and neither does Jack; their deep, masculine groans mingle with your breathy, high pitched moans as the room echoes with the lewd, wet sound of Grant’s hips colliding with your ass, Jack stroking his cock, matching the rhythm.

You know the tells of when Jack’s close; you lean forward again, wrap your lips around his cock, replace his hand with your ow, stroke him and bob your head, hollowing your cheeks and swallowing around him until he’s groaning, bucking his hips up involuntarily.

“Mmmm, yeah, that’s it sweetheart, suck my fucking cock-”

He runs his mouth when he’s close, so filthy that it makes you shiver, determined to get him there; just as you look up at him, make eye contact, he groans, tips his head back, giving you a beautiful view of the prominent muscle and veins in his neck, before he’s spilling down your throat.

You swallow every drop, lick him clean as Grant works you up to another orgasm; it’s only when Jack’s pulled his softening cock out of your mouth, brushed his thumb over your bottom lip, that his friend pulls out of you, gently maneuvers you onto your back.

He carefully pushes one of your thighs up to your chest, lowers it to wrap around his waist as he presses back inside you, groaning appreciatively at the way your walls almost immediately begin to flutter around him.

“Ohmygod, yes, fuck me-” You beg, your moans almost immediately swallowed in a filthy, greedy kiss, your fingers flying to his broad shoulders, scrabbling for purchase.

Thankfully, he’s merciful, gives you what you ask for, starts to all but pound you into the bed, breaking the kiss to nuzzle into the side of your neck, giving you intimate access to the huffed, breathy, whimpering moans he makes as he chases his release, fucks you through your second orgasm.

It’s only when you’re on the way down that he finally falls over the edge too, groaning a long, drawn out moan as he fucks his spend deep into you in a series of deep, erratic thrusts.

You gasp and whimper, still taking shuddering breaths and mewling softly by the time he eventually starts to go soft inside you. He stays above you, so you wrap your limbs around him, stroke his broad, freckled back as he peppers your shoulder, neck, and face with little kisses.

After he eventually pulls out of you, he follows Jack’s directions to the en suite, brings warm washcloths and a towel to help you clean up. Jack slips his prosthetic back on, heads out to the kitchen to grab chilled water for the three of you, giving you a lovely view of his ass as he goes.

The three of you work together to strip the bed, change the sheets, thanks to you completely ruining the existing ones, before finally, you’re lying in clean sheets between the two men.

“Mm, that was unexpected,” you hum, trailing your fingertips over Jack’s chest, brushing through the soft greying curls that grow there.

“Good unexpected?” Grant asks, and you turn your head to give him a long, slow kiss, breaking it to repeat the gesture with Jack.

They may look alike, but their kisses, confidence and mannerisms are so different. You kind of love it.

“Very good,” you assert, and both men laugh, exchange knowing smirks.

“Well, man, I guess you know what this means,” Jack says, lightly trailing his fingers up your sides, over your curves.

“Mm?” Grant sounds just like you and Jack, exhausted and satisfied. He genuinely doesn’t remember the last time he felt this way.

“No being a stranger.” Jack clarifies, and you giggle as his friend tuts.

“You know I have the restaurant. And you work a ridiculous schedule, too.” Grant hums, “but, I’m pretty sure I can find time. And hell, if you ever find yourself in Boston...”

You nod eagerly, too blissed out to try and be coy. As a matter of fact, you will be in Boston relatively soon for a book tour, and Jack has promised to come with you.

“We’d love to catch up with you again, but you know, she’s a big girl, she can always come visit on her own,” Jack purrs, curls into your side, nuzzles against your shoulder.

Grant raises an eyebrow at you, a silent question. You turn to kiss Jack’s temple before you lean up to kiss the other man again, liking the plush firmness of his lips. “Mm, it’s a date,” you confirm, and you swear both men give you approving little purrs as you finally settle down to sleep.

Part 2? Let me know!

do not repost or use my work to train AI.

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