Disclaimer: I do not own the characters in Chuck and have no association with anyone involved in the show.
Authors note: This story takes place in Season 4.
Keywords: Anal, FF, Toys
by MTL ([email protected])
"Exc... excuse me." Ellie stammered, convinced she must have been more drunk than she thought because she couldn't possibly have heard her brother's girlfriend right.
"I said, get on the bed and bend over." Sarah said like this wasn't something completely out of the ordinary, the blonde then stepping forward moments later to comfort her friend, "You wanted my help right? With Devon's little... request?"
"Well yes but I was expecting... I don't know, some advice or something." Ellie said.
"And I told you, there's nothing I could say that you can't find on the Internet, and no words could really prepare you for the feeling of taking a big hard cock up your ass." Sarah said, "Which is why the best way I can help is to, well... show you what to do."
Ellie's eyes almost popped out of her head, "Oh, erm, I, thanks but I'm not gay."
"Neither am I, and that's not what I was suggesting." Sarah said, quickly cutting Ellie off before she got the wrong idea, or more accurately the right idea, "I'm not suggesting we have anal sex, just that I show you how to properly loosen up your ass hole. Because trust me, no matter how much instructions you give them even the nicest of guys will awkwardly shove a couple of fingers up your ass, and then their cocks, and you'll probably hate it, but let him do it now and then when you really want something. But, if you let someone who knows what they're doing take their time to gently stretch your ass hole out it can be one of the most pleasurable experiences you'll ever have. And trust me, if you let me help you practice for a couple of days by the time you're bending over for Devon your ass hole will crave the feeling of getting fucked. You'll be a total anal whore, ready to fulfil everyone of your husband's desires."
It may have been the three glasses of wine Ellie had consumed to work up the courage to ask the blonde's advice about anal sex but Sarah seemed to be making a lot of sense. Ellie was still a little worried though, "O, ok... what... what exactly would you do? To help me practice I mean."
"Oh, just use my fingers, and maybe a small dildo, to stretch you out back there. Get you used to the feeling of something sliding in and out of your ass hole. Show you it isn't as scary as you might think." Sarah said, a little smile crossing her face, "Hopefully show you why I love anal so much... show you how good it can feel to have something inside your ass... moving in and out... fucking your little ass hole."
Ellie blushed and silently thought this over. It was crazy she was even considering something like this, but if Ellie was going to try anal sex it seemed to make a lot of sense for her to dip her toe in the water so to speak. This way she could feel what it was like to have something invading her ass hole without getting Devon's hopes up, and she would be in the hands of someone who had taken it in the ass before as opposed to someone who'd only dreamt about anal sex.
So Ellie pretty much made up her mind, but she was still nervous about it so buying herself a little time to calm her nerves she asked, "Have you done this before?"
Sarah smiled, "Maybe once or twice."
"Ok... ok, ok let's... practice." Ellie said, very slowly getting on all fours on the bed.
For a moment Sarah lost control of herself, a look of lust crossing her face as Ellie presented the spy with her ass. Luckily Sarah was able to come to her senses before Ellie could turn to catch her staring or licking her lips, which only happened briefly, Sarah able to keep herself in check as she quickly retrieved a bottle of lube and then got on the bed behind Ellie. When she slowly, carefully pulled down Ellie's pants and panties revealing the other woman's ass Sarah lost control again, this time Sarah reaching out and grabbing two handfuls of Ellie's perfect butt before gently caressing the prize in front of her.
"You have a beautiful ass Ellie." Sarah said softly, squeezing the round but firm cheeks of Ellie's butt.
"Thanks." Ellie blushed, not sure what to make of Sarah's actions.
"Devon is a lucky man." Sarah said, able to stop herself saying anything further as she pulled apart Ellie's butt cheeks and lustfully studied the other woman's ass hole for a few seconds. Oh how Sarah would have loved to lick that puckered hole, or slide her mouth and tongue all over those beautiful cheeks, or even go after Ellie's pussy which looked encouragingly wet. But one thing at a time.
"You're going to have to relax, ok?" Sarah said, as she let go of Ellie's cheeks and quickly applied a generous amount of lube to the fingers of her right hand. Once there was plenty of lube on her fingers Sarah used her left hand to gently spread Ellie's left ass cheek, the blonde giving herself as much room as possible to get at the brunette's ass hole.
Ellie gasped as she felt a wet finger gently touching her virgin rosebud and immediately tensed up. Luckily Sarah didn't try to force her way into Ellie's butt. Instead the blonde just gently rubbed some lube onto the brunette's back hole, Ellie finding the soft caressing of her butt hole oddly comforting, the touch slowly coaxing her to relax.
Of course that was Sarah's plan, the spy waiting until she was convinced her friend couldn't be more relaxed before firmly sliding a finger into Ellie's back door.
"Ah!" Ellie cried out, more in surprise at the suddenness than actual pain. In fact there wasn't that much pain at all. It wasn't the greatest feeling ever, but it wasn't unpleasant. And for the most part that was how it continued. Even when Sarah added a second, then a third, then finally much later a fourth finger the experience was far from what Ellie had expected. Then she moaned. She couldn't believe it, but it actually started feeling good. Really good.
It took a while for Sarah to get a moan out of Ellie, but it was totally worth it. That little sound meant Ellie was Sarah's. She might not know it yet, but she would very, very soon.
Of course getting that moan had been a lot of fun as Sarah had loved every second of slowly stretching out Ellie's shit hole. She had adored fingering her friend's ass, only adding additional fingers when she was absolutely sure the other woman was ready, working then gently to further open the brunette's butt hole, gently caressing the soft yet tight walls of Ellie's rectum. It was marvelling at the tightness of the other woman's back passage which was Sarah's favourite. This was partly because it proved to Sarah she really was doing Ellie a favour by stretching out this tight little hole, but in truth Sarah just liked the way Ellie's butt felt clamping down on her fingers. It made her horny, made her want to give this cute little virgin ass a real stretching.
"Ellie... I've stretched your ass hole as wide as I can with just my fingers. I could fist you, but I think what we really need now is depth. So I'm going to get a nice long dildo so I can stretch the deepest part of your ass, make sure it's nice and ready for your husband's big cock. Are you ok with that?" Sarah smiled as Ellie moaned a enthusiastic response. Deciding to push her luck Sarah added, "Good, I'll go get one of my toys... in the meantime, you don't have too, but it might help if you fingered your ass hole. That way your ass hole stays nice and loose."
Following another positive moan from the brunette Sarah removed her fingers from Ellie's ass, a smile crossing the blonde's face as she watched as one of Ellie's hands immediately shot to her backside and inserted two fingers into her already loosened butt hole.
Sarah watched Ellie shamelessly finger her own ass hole for a few moments before quickly yet quietly sneaking over to her toy draw, opening it up and retrieving her favourite type of toy, namely a strap-on. It was extremely tempting for Sarah to pick one of the bigger models, but for her boyfriend's sister she chose a nice 8 inch model, expertly strapping it around her waist after removing her pants and panties, and then moving back onto the bed so that she was kneeling behind Ellie again without making a sound loud enough to disturb the moaning brunette.
By now Ellie had three fingers in both her pussy and ass and was using the palm of one of her hands to rub her clit. From the way Ellie was moaning Sarah guest it wouldn't be long before her friend came. Sarah could let that happen, put her strap-on away, hand Ellie a vibrator and leave her to it, or something like that, but Sarah just couldn't resist. She had resisted going after Ellie for so long, too long, and now Sarah was going to make Ellie hers.
Grabbing hold of Ellie's hands Sarah used enough pressure to stop their movement without hurting her friend. There was a whimper of disappointment from Ellie before Sarah quickly said, "Ellie, I thought you wanted to practise for Devon. Make sure you're ready to take his big cock up your ass."
"I do." Ellie whimpered.
"Then stop trying to make yourself cum like a little slut." Sarah said deliberately firmly before then just as deliberately softening her tone, "Trust me, I'll let you cum soon enough, if that's what you want, but we need to get this big cock of mine inside your ass while it's still nice and loose and ready to be fucked. But it's up to you. In a second I'm going to let go of your hand. You can make yourself cum if you want and we can call it a day, maybe try again tomorrow if you want. Or you can spread your ass cheeks for me. Make it easier for me to get my big cock in your tight little ass. You choose."
Letting go Sarah watched with bated breath for a few seconds, and then smiled widely as she watched Ellie slowly reach back and spread her ass cheeks, submitting to the butt fucking Sarah so wanted to give her.
Sarah took longer than necessary lubing up her dildo, admiring the sight of Ellie offering up her ass hole to be fucked. It was a beautiful sight, one which Sarah wanted to commit to memory, something she would treasure forever. Then Sarah did something else that she would treasure forever, that being taking Ellie's anal virginity. Sarah took Ellie's anal cherry slowly, placing the head of the dick against her friend's previously unviolated butt hole and then gently increasing the pressure so that the tight ring of flesh was slowly forced open until the first few inches of strap-on cock slid deep inside Ellie's virgin ass.
Ellie let go of her butt cheeks and cried out in pain, but it wasn't as bad as she feared, and for that she was very grateful to Sarah, who unnecessarily apologised, "I'm sorry. It always hurts at first, but trust me, you'll be begging for more in no time."
Those last words made Ellie blush because she didn't doubt them. Before tonight she hadn't even dared to touch her ass hole, but Sarah's fingers, and then her own, had felt so good inside her butt, and she was so horny from the initial anal play that what Ellie had imagined being unbearable pain with Devon was very much bearable and faded quickly. It wasn't even that bad when Sarah began pushing a few more inches into Ellie's rectum, and then when Sarah started slowly pushing those few inches in and out, beginning to butt fuck Ellie, the brunette doctor moaned in pleasure.
The pleasure seemed to increase with every thrust, Ellie barely even noticing any pain as Sarah gently pushed more and more of the strap-on into the brunette's bowels until Ellie felt the blonde's hips smacking into her butt cheeks. This shocked Ellie a little at first because she had been so distracted that she hadn't realised that Sarah had strapped on a dildo. Ellie thought Sarah was just going to get a small hand held dildo, but this made sense. After all Sarah was trying to prepare her for anal sex with her husband. That was what Sarah was still doing, right? So using a large strap-on dildo would obviously better help prepare Ellie for that. Obviously.
It wasn't like Sarah wanted to butt fuck her or anything. And the idea of Sarah being the one to give Ellie her first butt fucking wasn't an incredible turn on or anything. Sure, Sarah Walker was the most beautiful woman Ellie had ever met, and Ellie had thought about being with the blonde, about kissing her, sliding her hands all over her body, and using her tongue to... but Sarah was her brother's girlfriend. Nothing ever could or would happen between them.
Luckily this was just practice so it didn't count. And because it didn't count Ellie was free to become lost in the feeling of that dildo sliding in and out of her ass hole, giving her powerful sensations of pleasure she had never felt before tonight... sensations she wanted more of. She... she wanted more.
Realising Sarah had officially been proven right and that it was a matter of time before she begged for more Ellie decided to make it sooner rather than later so that she could get more of that wonderful pleasure, the young doctor softly moaning, "More."
"I'm sorry, what was that?" Sarah teased.
"More! I want more. Please give me more." Ellie begged.
"And by more... you mean?" Sarah smiled, deciding to push her luck.
"I... I..." Ellie blushed. With her mind racing Ellie quickly realised this made sense too. She was practising to have anal sex with her husband, therefore she had to play the part. Besides, she knew what he liked to hear. So gathering up her courage Ellie softly moaned, "Please... fuck me! Fuck my ass! Please Sarah, fuck my tight little ass hard!"
Sarah was briefly taken aback by just how verbal Ellie was. Then deciding to push her luck even more Sarah asked, "Is that what you want? For me to fuck your tight little ass hard?"
"Yes Sarah, please fuck my tight little ass hard! Oh God, fuck it as hard as you can! Oh it feels so good, mmmmmmmm, fuck me hard!" Ellie begged, and then realising may be Sarah wanted specific words added, "I'm begging you, give me more. You were right. Mmmmmm, you were so right. This feels amazing when done right, and you do it so right, mmmmmmm, so fucking right. Oooooh, so fucking good. Ohhhhh fuck me, please Sarah, fuck my tight little ass. I need it. I need you to fuck me. I need you to make me cum. Please, I'll do anything."
There was a pause, and then Sarah laid down so her breasts were pressing into Ellie's back and her lips were next to her ear, the spy then softly asking, "Tell me, is it Devon who gets off on the dirty talk, or you?"
Ellie blushed and stammered, "I, I do it for him."
"That's not what I asked." Sarah said.
Again Ellie blushed, and then after a pause admitted, "We both do."
"But you a little more than him, huh?" Sarah pushed, smiling when Ellie gently nodded her head, "Would you like me to talk dirty to you? Call you a slut? Treat you like a filthy little anal whore I found on the streets?"
"I want you to make me cum." Ellie whimpered, and then after a beat added, "Please, I'll do anything."
"Then answer my questions." Sarah pushed.
Again Ellie whimpered, then blushed, then admitted, "Yes. Yes, please talk dirty to me. I love it. Mmmmmm, I love being called a slut, a tramp, a whore, ohhhhhh, and I love being treated like one."
"That's what I thought." Sarah said, leaning in even closer to Ellie's ear, "Now, here's the deal. In a moment I'm going to start fucking your tight little ass hard until I make you cum harder than you've ever cum before. Then I'm going to keep ass fucking you, making you cum over and over again until you get me to stop or pass out. But first I want you to promise me something..."
"Anything!" Ellie quickly interrupted.
Sarah smiled, then continued, "Don't go running to your husband the moment we're done. You let him ass fuck you now you'll both enjoy it, but you probably won't cum. But if you give me the rest of the week to properly train you it will be the best sexual experience of your lives. I promise. All you need is a week of practice with me and you'll be such an anal whore you won't be able to go a day without a serious butt fucking."
The next few seconds seemed like an eternity in Ellie's mind as she struggled not to just say yes and really think about what Sarah was suggesting.
When Sarah had suggested a week of practice before letting Devon fuck her back there it had seemed like a reasonable timeframe. Now Ellie was sure she had all the practice she really needed, and while Ellie could just about convince herself that another woman fingering her ass or sliding a dildo in and out of her ass wasn't technically anal sex... although now she actually thought it through it was really silly, another woman slamming a strap-on in and out of her ass until she came definitely seemed like anal sex. Lesbian anal sex. Which meant even by agreeing to continue she was knowingly cheating on her husband, and now she was on the verge of agreeing to cheat on him for an entire week.
But how could she possibly say no to a week of this amazing pleasure?
Ellie opened her mouth, and despite feeling like she should be saying no or at least being hesitant she instead said, "Deal. We can practice for the whole week. Maybe longer, if you think it's necessary. Just please, fuck me."
Sarah smiled, straightened herself up, grabbed on tightly to Ellie's hips and began increasing the speed of the sodomy.
The whole time they had been talking Sarah had been lazily pumping Ellie's pooper, not fucking the other woman's butt as hard as she had been before the conversation so Ellie would concentrate on her words. Now Sarah wanted Ellie to concentrate on the pleasure she was giving her, which proved to be an extremely easy task.
All of the slow butt fucking had loosened Ellie's rectum to the point that the brunette was so ready for a hard ass pounding that no matter how quick or hard the thrusts became Ellie continued mindlessly begging, "Yes, more, give it to me, mmmmmmm, oh, make me an anal whore. Oh God Sarah fuck me. Fuck me, fuck me, fuck me, fuck me, fuck me, fuck me fuck me fuck me fuck me fuck me! OH FUCK! FUCK MY ASS! OHHHHHH SARAH!"
Hearing Ellie screaming her name like that and fucking her perfect bubble butt was literally a dream come true for the woman who called herself Sarah Walker. She loved Chuck more than anyone or anything, but she had a passion... a need to fuck other women. Luckily for Sarah hearing about her lesbian exploits was a huge turn on for Chuck, who loved her enough to let her fool around with women, and he even 'suffered' through the occasional wild threesome. But she couldn't expect him to be ok with her desire to fuck his sister, so Sarah kept it to herself. Unfortunately that meant Ellie became forbidden fruit. Sarah had tried so hard to resist, and really she deserved credit for lasting as long as she did, but when Ellie had dropped this opportunity in Sarah's lap the blonde spy could no longer resist.
Part of Sarah had been hoping she could fuck Ellie once and get it out of her system, but deep down Sarah knew that was a long shot. The more time she had spent with Ellie the more Sarah had grown to like her in every conceivable way, and now she was literally slamming Ellie's beautiful butt Sarah knew not even a week would be enough. She had to make Ellie hers. She would make Ellie hers.
By now Ellie's cries had become completely incoherent, but the other woman was clearly enjoying herself. If her squeals of pleasure didn't prove that then the fact that she was shamelessly slamming her own butt back against the bowel busting thrusts certainly did.
Believing Ellie was too distracted to be able to hear her, or even understand her, Sarah said softly, "Your ass is mine Ellie.
Until you give your ass to Devon it's mine. Your ass belongs to me. I own it."
Sarah had hoped her words would sink into Ellie's subconscious, make the other woman want to be with her, and if Sarah was honest partly to fuel her own ego. What Sarah wasn't expecting was for Ellie to then scream out, "YES! OHHHHH YEEEESSSSSSS! OH IT'S YOURS SARAH! MY ASS IS ALL YOURS! MMMMMMMM OH, IT BELONGS TO YOU! MY ASS BELONGS TO YOU! YOU OWN MY ASS! IT'S YOURS!"
Sarah was so surprised the rational thinking part of her brain completely shut down and she began hammering Ellie's ass a lot harder than she should ever fuck a previously virgin ass. But Sarah couldn't stop herself. Just like she couldn't stop herself loudly asking, "What does that make you? If your ass is mine what does that make you?"
"YOUR ANAL WHORE? YOUR ANAL SLUT? YOUR SLUTTY ANAL WHORE?" Ellie offered.
"No, it makes you my bitch!" Sarah growled as she brutally fucked Ellie's butt, "Until you give your ass to Devon you're my bitch!"
"OH GOOOOOOOGGGG YEEEESSSSS! I'M YOUR BITCH!" Ellie squealed with joy, "I'M YOUR BITCH SARAH! MMMMMMMM, YOU OWN MY ASS AND THAT MAKES ME YOUR BITCH! OOOOOOOHHHHHHH FUCK, I'M GOING TO BE SUCH A GOOOOOODDDDDDD BITCH FOR YOU SARAH! I MMMMMMMMM, I OHHHHHHH, I'LL BEND OVER WHENEVER YOU THINK WE NEED TO OOOOOOH PRACTICE. I'LL BEND OVER SO YOU CAN FUCK THE ASS YOU NOW OWN. I'LL... I'LL OOOOOOOOHHHHHHHH SAAAAARRRRRAAAAAHHHH! YOUR BITCH IS GOING TO... YOU'RE GOING TO MAKE YOUR BITCH CUUUUUUUMMMMMMMMM!"
For a brief moment Ellie thought she came so hard she had pissed herself, but quickly realised she had squirted. Ellie had never done that before but now she just couldn't seem to stop, amazing orgasm after amazing orgasm making her explode like a volcano as her mind turned to mush. Soon Ellie was beyond thinking, her entire world revolving around the ecstasy echoing through her body as a result of that dildo slamming in and out of her ass hole.
The rest of the world melted away for Sarah too, her world mainly focusing on the pleasure she was receiving from the stimulator inside the strap-on bashing against her clit and the incredible mental stimulation of fucking the beautiful bubble butt of a woman who had been forbidden fruit for her for so long. However Sarah was also concentrating on the feeling and sound of her hips smacking into Ellie's nicely rounded ass cheeks and the sight of her cock brutally pounding in and out of the other woman's butt hole. But most importantly Sarah paid close attention to Ellie herself, waiting for the brunette to either beg her to stop or to pass out.
Either seemed like a logical possibility but Ellie couldn't seem to get enough of the now extremely rough lesbian anal sex, screaming hysterically with what Sarah was sure was joy until her voice faded and she slumped face down on the bed. Sarah immediately stopped, waited a moment and then started to pull out, only to hear Ellie softly moan, "No... more... please Sarah, fuck my ass. Fuck your bitch's ass."
Sarah bit her lip. She should stop. Ellie's ass was going to be incredibly sore as it was and further ass fucking would only make that worse. But that feeling was something Sarah had grown to love as it reminded her of the naughty things she had done, and the idea of Ellie's ass feeling sore, maybe so much so the other woman couldn't even sit down, was an incredible turn on. Add that Sarah was so close to another orgasm and the blonde just couldn't resist beginning to gently pump Ellie's pooper again, quickly building up speed until she was again brutalising the brunette's butt hard and deep.
Ellie whimpered in pleasure at first, then grew silent as Sarah squeezed a couple more orgasms out of them both thanks to another passionate round of girl on girl butt fucking. Then Sarah repeated her earlier process of stopping and slowly pulling out. Ellie didn't utter a sound even when the head of the dildo was pulled from her ass hole with a gentle pop, leaving the so recently virgin hole stretched open wide.
Licking her lips Sarah spread Ellie's ass cheeks and studied the other woman's stretched out shit hole, the spy becoming lost in staring at that little crater until she heard Ellie stir, and then softly moan, "Sarah, what are you doing?"
"Just admiring how sexy your freshly fucked ass hole looks." Sarah said, still lustfully staring deep into Ellie's bowels.
"Oh." Ellie blushed.
"Don't be embarrassed. I love it. I love walking around with a gaping butt hole. It makes me feel like such a dirty little anal whore." Sarah confessed before smiling softly, "Is that how it makes you feel?"
The answer was yes, but Sarah was left to correctly guess the right answer as Ellie buried her face in the covers as she whimpered softly in shame.
Dropping the subject Sarah let go of Ellie's ass cheeks, and lay down in front of the brunette doctor, "Do you want to know what else makes me feel like a dirty little anal whore?"
"What?" Ellie asked, not sure if she wanted to know the answer or not.
"Ass to mouth." Sarah said, her eyes dancing back and forth between her strap-on and Ellie's lips, making it clear what she was suggesting. When Ellie gave her a look of disgust Sarah quickly added, "It's not for everyone, but like anal it's not as bad as some people might think. And if someone was practising for her husband, she might want to try it during practice as opposed to the actual thing. See if it turns her on as much as getting fucked up the ass."
There was a long pause and then Ellie hesitantly lent forward, closed her eyes tight and quickly opened her mouth to swallow the head of the cock. Ellie automatically scrunched up her face in disgust, but the flavour wasn't nearly as bad as she thought it would be. Relieved Ellie began to gently suck on the head of the dildo, her eyes flickering open so she could look up at Sarah.
The look of lust Ellie saw in Sarah's eyes was an incredible turn on which pushed Ellie to work harder, the young doctor bobbing her head up and down on the big dick which had just been in the deepest part of her ass.
This turned Sarah on even more, the blonde gently beginning to stroke Ellie's hair and moan, "Yes, that's it. Clean my cock. Clean it of all your slutty little ass juice you dirty little anal whore. Suck it. Mmmmmm, yeah, suck my fucking cock you dirty little cock sucker. Oh yes, that's a good cock sucker. That's a good bitch."
Encouraged by Sarah's words Ellie sucked on the cock even harder, both women thinking how much they were looking forward to the next time that they got to... practice.