A Halloween to Remember (Chuck)

A/N: A Halloween to Remember was a commissioned one-shot originally written in October of 2018! Posting it now for people to enjoy.

Themes: NTR, Humiliation, Master/Slave

-x-X-x-

Sarah Walker, CIA Agent and all-around gorgeous femme fatale, had royally fucked up. It wasn't a feeling she was used to, this sense of failure. It was Halloween Night, and she was on a mission. It was supposed to be a simply one too. Nothing overly complex, a very straight-forward retrieval job. Except, the microchip, extremely important and very sought after by her Agency… was currently in the wind.

No, that wasn't entirely correct. Sarah knew where it was. She was actually staring at it, right now. Jeffrey Barnes, disgusting slob and balding old man, had accidentally taken the bag it was in and put it in his pocket by mistake. At least, she assumed it was a mistake. No… she knew it was a mistake. Jeff had been vetted by more than just the CIA this way and back. He was no spy, no enemy agent. Which meant she had to treat him with the kid gloves.

None of her normal tactics could be put to use here. She couldn't let on that the microchip was overly important, or she might end up blowing her cover to Jeff. Hell, Sarah wasn't even about to let Chuck or Casey know about what had happened. This was HER screw-up after all, and so long as she got it fixed before the night was out, she'd be perfectly fine.

But that meant she had to go another route when it came to getting what she wanted from Jeff. Luckily for Sarah, there was a Halloween Party happening just after work that she'd been planning to go to, leaving her with the perfect attire for what she would have to do. Slipping into the back, regretfully and reluctantly taking her eyes off of the prize, Sarah very quickly strips down and changes into her Halloween costume.

Once she's done, she looks at herself in the mirror of the woman's bathroom, biting her lower lip as she makes sure her witch's hat is just right, and her corset is low enough to show off her cleavage, but not too low to reveal areola. Because of course Sarah Walker was dressed as a sexy, slutty witch. Halloween was the time of year where a woman could get as sexy as possible without being judged for it. It was the one time of year where it was permissible for a grown woman with her gorgeous figure to play dress-up outside the bedroom.

She'd been looking forward to flaunting what she had all night long at the party, but not giving it up to any man. It'd be a good reminder to all of them that she was both beautiful and out of their league. And then, once the night was over, if Chuck was especially good, she might just let her boyfriend have some fun with her. Or not. It was her choice.

Now though, Sarah found herself having to use her sexy witch's costume in a way she never wanted to. Luckily, by the time Jeff leaves for the night, there's no one else around as he makes his way to his car. Sarah, having been sneaking about on the side of the Buy More building, waiting for him to come out, quickly makes her way into the parking lot as well. Once she's a few dozen feet away, she turns her fast walk into a seductive one, smiling sultrily as she calls out to the slobbish loser.

"Jeff! Hey~"

Blinking, Jeff turns to the sound of his name. The balding older man's eyes go wide as he makes out what she's wearing and how she's currently dressed, and his jaw drops open in shock, even as Sarah suppresses her disgust in favor of being all smiles, all the time.

"Looking good, Jeff. Hey, you going to that Halloween Party tonight?"

Jeff blinks even more rapidly at that, all while trying to get his mouth to actually work.

"Uh, I, uh… Halloween Party?"

Her words finally permeate his mind, and he frowns slightly.

"… I wasn't invited to a Halloween Party."

Of course not. No one would have wanted him there, not in a million years. But Sarah doesn't SAY that, nor does she let any of her derision or irritation with the man show on her face. Even now, she can see the bag with the microchip hanging out of his inside coat pocket. Oh, how easy it would be for her to cold cock him and just take the bag. Then she could hand it over and get to the party before it got much later…

But no, that had too much potential to blow her cover. That was why she was doing this. Smiling brightly, Sarah just laughs a little.

"Well, I was thinking of blowing it off anyways, to be honest. It didn't look like it was going to be much fun, especially not with you there. Hey, why don't we go back to my place for a drink instead?"

Jeff just stares for a moment, truly bewildered and baffled. Then, he outright asks the obvious, though Sarah supposes she shouldn't be that surprised.

"Are… are you flirting with me, Sarah?"

He'd probably dealt with enough rejection and misunderstandings in his life that he wanted to be sure. Sarah would have preferred to make this whole thing seem like a misunderstanding as well, but it looked like she'd have to dig herself a little deeper here…

"Maybe I am, Jeff. Maybe I've always found you a little attractive, and just haven't really known how to express it…"

For a moment longer, it seems like Jeff doesn't believe her. But then he seems to decide to just see where this goes, his frown turning into a goofy smile as he bobs his head up and down.

"Alright then! Lead on!"

Oh… the idea of him driving with her in her car was… NOT what she had in mind, but how could she say no now. Keeping the fake smile on her face as she turns and leads the way over to her car is a titanic effort, made even more so when Jeff spanks her ass from behind and she's forced to just smile and take it. She's disgusted in truth, but in the end, what else can she do but go along with this until she has Jeff alone?

-x-X-x-

They make it to her hotel room in no time at all, Jeff whistling at the fancy (to him anyways) lodgings. Sarah does her damnedest not to wrinkle her nose in distaste, especially when he pushes up against her from behind while she's fiddling with her room key, his arms wrapped around her waist and his nose brushing against her neck as he inhales her scent. Instead, the undercover CIA Agent turned sexy witch wiggles her bottom against his growing erection and coos slightly, before escaping his grasp as the door finally opens.

"Sit down, I'll get us some drinks!"

While Jeff sits on the bed, Sarah hurries over to the hotel room's mini bar, at the same time reaching into her cleavage to take out the vial she has there. Rather than give Jeff a night to remember, she's going to give him one that he can't help but forget. The smile on Sarah's face turns positively wicked as she spikes the balding slob's drink, and a shudder of almost pure delight runs down her spine as she considers how easy it'll be to downplay it if Jeff ever tries to talk about what happened tonight. He won't remember anything, so it'll be very simple to just label him a liar.

Genuine smile still on her face, Sarah turns around with both drinks in hand, only to nearly jump in the air when she finds Jeff behind her rather than still sitting on the bed. So lost in her own plans, she'd completely missed his movement. God she was out of it tonight. More than that though, while she holds out Jeff's drink to him, he takes it and immediately sets it down on the counter behind her. Sarah's eyes try to track towards the spiked drink, only for Jeff to grab her by the face and kiss her heatedly.

Squirming in his grasp as he ends up shifting so his arms are around her and he's kissing her, Sarah can't help but be repulsed… at first anyways. Her eyes inevitably widen as Jeff turns out to be a REALLY good kisser… the best kisser she's ever had. But then, sometimes such talents can come in a terrible package. Its just… its really hard to remember how much of a disgusting slob Jeff is when her eyes are lulled shut and she's being kissed and groped a-and… Sarah whimpers into Jeff's mouth as he squeezes her ass cheeks with both hands quite roughly. She whines when he rubs against her chest through her costume.

It shouldn't feel this good, but it does. Before the femme fatale knows what's happening, she finds herself being pushed back onto the bed, her eyes opening again as she looks up to see Jeff stripping down, his own gaze fixated on her and burning with unadulterated lust.

"Screw the drinks. I want you now, as much as you want me. Gonna fuck you, Sarah. Gonna fuck your little witch booty so hard."

Sarah's eyes are wide, and her nostrils are even wider as they flare at his words. She's never heard Jeff speak like that before… and to be fair, she's never had ANY man speak to her like that before. One might think she wouldn't like it… but the problem is, she does. And the more Jeff strips down, the more he stares at her with those hungry eyes, the more turned on Sarah gets.

That's her biggest secret, in the end. She's created a mask for herself and she wears it so well that at times she forgets it's a mask. She plays so many roles, but even her 'real self' is just another act. Sarah Walker might have slept with many men in her past, from sexy secret agents to even her current kind and sweet boyfriend, Chuck. But Sarah Walker was always in control, both of herself and the men she slept with.

However, Sarah wasn't always Sarah. Once upon a time, she'd been born Sam Lisa… and Sam was the kind of girl who'd had the worst sorts of fetishes, the most humiliating, anti-woman fetishes one could imagine. She'd always secretly desired to be the submissive sex pet of a cruel, sadistic master. Someone who treated her like an item, who insulted her, who reduced everything she was to nothing but a little cum dump whore.

Sarah had known from the get-go, even back when she'd been Sam that these desires were wrong. They were degrading, and demeaning and she had to be better. She'd spent her entire life doing her best to BE better… but now, faced with Jeff as he was now, acting like this… he was bringing her fantasy to life, much to Sarah's shock. Especially when he finally pulled down his boxers and out sprung the biggest, fattest cock she'd ever seen in her life.

"Like this, slut? Yeah, I bet you do. Look at it long and hard, because its gonna be going in you long and hard in a moment."

Despite the cheesy line, Sarah can't help but feel another spike of pleasure at Jeff's confidence. While she'd been hiding behind her confident, cocky CIA Agent persona, it seemed Jeff had been hiding a perverted, misogynistic mind of his own. They were just lucky to have found each other. Wait… lucky? Sarah can scarcely believe what she's thinking, but she doesn't put up any sort of resistance when Jeff climbs onto the bed and over her, spreading her legs wide and yanking her costume's leotard to the side beneath her witch's skirt, exposing her wet little cunt.

At the same time, he tears down her top, causing her breasts to pop out of their confines. The corset had been more than tight enough, so Sarah hadn't bothered with a bra, especially because she didn't have one that worked within the color scheme of the costume. Not on her, anyways. Still, now her tits are completely exposed… and as Jeff leans in, pressing his massive cockhead up against her cunt lips and slowly spreading them open, while also slobbering his way across her chest, Sarah can't bring herself to mind all that much.

She's enjoying it, even moaning along with his molestations, his rough, domineering actions. Though, she does begin to mind when he doesn't stick it in right away. That juicy massive schlong of his remains at her entrance, Jeff teasing her folds but never fully penetrating her. Eventually, Sarah can't take it anymore.

"P-Please…"

Finally pulling back from her breasts, having licked and slurped and even bitten at her tit flesh, Jeff grins wickedly.

"Please what? Please… Master? Say it, Sarah. Say it you little whore. We both know you want to. We both know this is exactly what you want, a strong man who will take control of you and steer you clear of your slutty ways."

Sarah's lips tremble, as does the rest of her. Oh god, he's right. He's right, and she hates herself for it, but she does what he says.

"Please… Master. Please, put it in me. Please f-UCK MEEEE!"

Sarah's eyes very nearly roll back in her skull right on the spot as Jeff thrusts into her in the middle of her begging. The proud CIA Agent is reduced to nothing more than the slut he's called her out for being as he takes her to pound town right then and there. Sarah's legs wrap around his waist, and her arms wrap around his neck. Jeff kisses her, but its even more domineering than before. He's in complete control, and they both know it. They both know she'll do whatever he says, whatever he wants. Her insides clench down and squeeze along his length, and Sarah moans into his mouth as she cums on the spot, an explosive orgasm that is soon followed by many, many more.

He fucks her like she's nothing more than a piece of meat, treating her like she's nothing more than his filthy fleshlight. And as he does so, he disparages her as well, eventually pulling back and holding her by the throat, looking down into her eyes and sneering at her as he very lightly restricts her airways.

"You're a whore, Sarah. You're a filthy cum dumpster who needs to be taught a lesson by a REAL man. Luckily, you came to the right place. I'm not gonna let up until you know your PLACE!"

He stays true to that, and Sarah's eyes do end up rolling up in her head as her jaw hangs open and she cums again and again around his big, fat, pistoning prick. Jeff fucks her until kingdom cum, and then he fills her womb with his seed like he doesn't have a care in the world. After doing so, part of Sarah expects it to be over. She thinks that it's done, and she even feels disappointment at that.

But Jeff isn't done, not by a long shot. Before the humiliated, freshly-fucked femme fatale can even truly recover, the disgusting slob has turned her over onto her front and lifted her hips up. There's a LOUD rip as Jeff tears the back of her cheap sexy witch's costume apart completely, and then he's spreading her ass cheeks wide and thrusting his messy prick right up against her anus.

Sarah's eyes go wide as he unknowing hits another one of her major fetishes, and having her asshole penetrated so fast, so hard, and so deep sends her into a spiral of self-loathing and bliss. But Jeff isn't content to let her sit idly as he fucks her back door. Reaching out, the older man grabs Sarah by her hair, fisting it and pulling her head up off the bed as he continues to fuck her.

"I find sluts are always the most honest when they've got a thick log of meat up their asses. So, tell me… why? What about Chuck?"

Sarah blushes deeply, even as she finds it quite easy to be honest in this moment.

"F-Fuck Chuck… I've found s-someone better!"

That gets a rueful chuckle from Jeff.

"He is a bit of a loser, isn't he?"

Jumping on the chance to disparage her boyfriend, the addled CIA Agent does just that, even as her anal plundering continues.

"H-He is! He's a loser, a-a, mm, shit stain! His d-dick isn't even half your size, M-Master!"

It feels like she's being brainwashed, almost. But this has always been beneath the surface. Jeff is just the perfect combination of disgusting, misogynistic, and domineering in bed to bring it to the surface. Chuck's kind, humble demeanor had attracted Sarah Walker, CIA Agent. But Jeff was the kind of man who'd always shamefully attracted Sam Lisa, slutty little cum dump whore. Now, her original identity was bleeding into her cover, and Sarah was becoming just as much a slut and whore for Jeff as Sam already had.

He cums inside of her as she's realizing that, filling her bowels with his seed like he did her womb. But its not over. They fuck for hours more, long past the end of the Halloween Party. Sarah's phone buzzes a few times, and she almost wishes Jeff would have her pick up and answer it, knowing that its probably Chuck asking her where she was. But her beloved Master doesn't seem to care for the idea, or he just doesn't think about it. One way or another, he's too busy plowing her silly in the end. Eventually Sarah just passed out, her mind going white as she falls into the sweet embrace of oblivion.

When she wakes up, she has Jeff's dick in her mouth. He's asleep in her cum stained, messed up bed. Slowly, Sarah withdraws his cock from between her lips, trying to ignore how good it tastes. Slowly, the truly fucked-up witch crawls off the bed and walks with shaking, trembling legs over to Jeff's discard pants. She takes out the chip he'd accidentally grabbed and hides it in her drawer.

Then, she tries to tell herself to leave. To get away from Jeff and come back when he wakes up in the morning and gets out of her hotel room. It's the small part of her that's still Sarah Walker, CIA Agent who says to do as much. It's the small part of her that thinks there's a chance she can still remain uncompromised.

Sarah knows better, she does. She already is compromised. Crawling back into bed, Sarah joins Jeff in bed once more, laying her beautiful body over his flabby, slobbish one and falling asleep with her head on his hairy chest, fantasies of him in her mind. She knows she's finally where she belongs… with her one, true Master.

-x-X-x-

Only, the next morning, Sarah wakes up late in the afternoon to find Jeff long gone. He'd fucked her so hard and so thoroughly with that big cock of his that her body had needed all day to recuperate. Days pass, and when she finally sees him again at Buy More, the balding older man ignores her like nothing happened.

Telling Chuck that she just didn't feel good and had gone straight to her hotel to rest had worked like a charm, and she'd gotten the microchip to her superiors, so she was in the clear there too. But neither her relationship with Chuck or her position as an undercover CIA Agent held true priority in her mind anymore. Instead, it was Jeff, and she spent most nights masturbating to the thought of Jeff fucking her. She doesn't even let Chuck touch her anymore, doesn't even let him lay a finger on her. He's probably getting suspicious, but Sarah could care less.

Jeff was right. She had been a slutty whore, sleeping around with everyone. But now all she wanted was to be JEFF'S slutty whore, to be by his side and cater to his every whim. She needed him… and when she finally cracked and tracked him down, she discovered that he needed her as well. It was clearly serendipity, not Jeff's perverted nature that led her to saving him from a pair of police officers who were interrogating him for groping a woman on a subway car.

Sarah, without a second thought, rushes to defend her Master.

"Gentlemen, I hate to interrupt… but Agent Sarah Walker, with the CIA."

Three pairs of wide eyes turn towards her as Sarah presents her credentials, the two police officers surprised but after looking at her papers, believing her. Jeff meanwhile, is simply completely and utterly floored, his jaw dropped open and a gobsmacked expression on his face as Sarah flashes the two officers a smile.

"I've been hunting this perv for a while now, boys. This is a bit outside your paygrade, so leave it to me, alright?"

The policemen are easily swayed by her charming smile, and her status as an Agent with the CIA. Never in a million years did Sarah think she would be doing something like this, but for Jeff… she'd do anything. Its only the work of a few moments before she and Jeff are alone again, hidden away in a nearby alcove, the police officers long gone.

"Sarah? What the hell?"

"Let's make one thing clear, Jeff. I'm willing to strike a deal with you. You want to hear it?"

"U-Uh… s-sure?"

Blushing a bit, and squirming even more so, Sarah bites her lower lip as she tries to act like she's in charge.

"Its really… really simple. A-An exchange, even. I'll give you all my resources, my cash, my information as a CIA Agent, my home… but you… you have to fuck me like you did the other night and be my Master from now on. What do you say?"

Jeff just stares at her for a long moment, and then the goofy smile is back, and he pulls her in for a deep, tongue-filled kiss, even as he eagerly gropes her ass cheeks with both hands. Sarah happily goes with it, wiggling her firm badonkadonk back and forth in his grip and pressing up against his slobbish front as she lets him put his tongue down her throat.

When they pull apart a moment later, its because Jeff ended the kiss, and Sarah is left flushed and panting for breath as he smacks her behind.

"Should have known, slut. I'll accept your deal… but there's one more thing you have to do for me."

Sarah opens her mouth to protest, but Jeff just spanks her again. She breaks immediately, shuddering her way through an orgasm as she holds herself up using him for support.

"A-Alright… what is it?"

-x-X-x-

The next day, eyes bulge out of their sockets as Sarah Walker walks right into the Buy More wearing nothing but a sexy black dress that shows off plenty of leg and cleavage, as well as a black choker that goes with it. The CIA Agent walks right up to Chuck and leans in close.

"New orders from the highest authority, Chuck."

He blinks at that, even as Sarah smiles slightly, speaking quietly enough that no one can hear them.

"We'll still be working together, but our time as boyfriend and girlfriend comes to an end now."

Chuck's face falls immediately, his heart breaking quite clearly before the entire store. Sarah feels a tendril of pleasure at seeing the pain in the kind man's eyes, knowing that it would make her beloved Master happy.

"Sorry it had to be this way Chuck. Oh… and sorry for this too. My superior said to make it look good."

Then, she raises her voice.

"How DARE you cheat on me, Chuck!"

Her hand rears back just as Chuck's eyes widen in surprise. Sarah slaps the man right across the face, and then follows that up before kneeing him in the balls. As Chuck falls to the ground in quite a lot of pain, while the rest of the people in the store try to commit the flash of black lace that showed up when she lifted her leg to memory, Sarah stands over him, feeling quite powerful in that moment.

"You're a pervert, Chuck. Just because I wouldn't play into your sick fantasies, you went and paid a hooker to do it for you."

With his reputation ruined in the eyes of everyone, Sarah walks right past Chuck and towards another man entirely. Jeff manages to fake looking surprised quite well as the gorgeous blonde in a black dress grabs him by his lapel and kisses him right on the lips. The two end up making out in front of everyone, even as Sarah shudders in orgasmic delight. She's never been happier.

-x-X-x-

A few weeks later, and Sarah has to amend that previous thought. NOW she's never been happier. Having called in a few vacation days, she'd taken Jeff on a beautiful vacation to Hawaii, using up a portion of her savings to do so, and to make sure they got to stay at the most luxurious, premium resort. Now, she walks out onto their private deck with its beautiful view wearing nothing but a sexy red bikini that barely covered more than her nipples and her slit, humming to herself happily as she places the drink she's made for him right next to Jeff.

This one isn't drugged, of course, and Sarah actually feels bad about that to this day. She'd confessed what had happened to Jeff after she'd broken up with Chuck. That very night, she'd explained why she did everything she did, and how she'd managed to lie to herself and everyone around her for so long about what she truly wanted. She'd explained that while her feelings hadn't initially been genuine, they were now, and that there was nothing she wanted more than to be Jeff's little slave-whore for the rest of her life.

He'd required some convincing… and even after he said he believed her, she'd been in the dog house for weeks. Not a literal doghouse, despite the black leather collar she wore in private with him now, emblazoned with the word 'BITCH' on the front of it. But her punishment had been legendary nonetheless.

Smiling down at Jeff, Sarah makes sure to stand properly straight, her posture perfect and her tits jutting out in his direction as she speaks.

"Dinner is ready, beloved."

Jeff chuckles, eyes twinkling.

"Its good to see you've learned your place in the kitchen, cum dump."

A small shudder runs through Sarah at the disparaging remark, her heart fluttering with desire and arousal.

"Mm, yes Master… I can't wait to learn more recipes for you when we get home too…"

She was still a CIA Agent, for now. But that didn't mean she wouldn't be the best live-in houseslave she possibly could be for her delicious, manly Master. As Jeff rises from his chair and takes his drink with him, Sarah happily allows him to wrap an arm around her waist, his hand falling to her ass where he gropes her bare butt cheek, the bikini bottoms doing absolutely nothing to cover the vast majority of her derriere.

Together, they walk inside, towards the table where his meal is waiting for him. There's no place setting for her of course, but then Sarah is quite looking forward to extracting HER sustenance from Jeff's cock. Her place while her Master eats is either by his side if he deigns to put some scraps in her doggy bowl, or beneath the table, sucking his dick as enthusiastically as possible. Either way, she belongs on her knees, not in a chair, and she knows that quite well.

Before they can get to the table however, Jeff stops them and sets his drink down, grinning at Sarah.

"The meal smells delicious, but I want some pictures first. Going to post them all over my Facebook so everyone back home knows how much fun we're having."

Sarah just smiles happily, even as Jeff brings up his phone to take some selfies. Given how she's dressed, even if its not uploaded by her personally, there's a chance she could actually lose her job if her superiors decided she was being 'improper' on social media. But the blonde could care less. She had more than enough money saved away and if the CIA did fire her, she could always write a book and make oodles of cash off that.

All of it would go to Jeff of course, all of it would go to her beloved Master. Posing lewdly and rubbing herself up against the balding older man, Sarah makes kissy faces at the camera, and then happily exchanges saliva with Jeff when he turns to kiss her. They make quite the dichotomy, her gorgeous, beautiful body pressed up against his flabby, slobbish form. Jeff wouldn't change for her though, and Sarah didn't want him to.

She didn't care how he looked, it was how he acted, how he treated her that she loved. Of course, the big fat cock was a plus as well. Watching Jeff pull away and post the pictures, the blonde femme fatale can't help but smile sunnily. She continues to smile, all the way to the table where she happily kneels under it to begin sucking her Master's cock. Slurping and sucking on it, Sarah has a thought that only spurs her on to be more enthusiastic, bobbing up and down on Jeff's dick until she's deep-throating it and beginning to gag.

The world may never know Sarah Walker was a spy, but they'll certainly know how much she adores and loves her Master, Jeff.

-x-X-x-

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