Rewarding Ruby

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Ruby Hale is rewarded by her new boss.
5.5k words
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Part 1 of the 4 part series

Updated 06/09/2023
Created 08/29/2018
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MTL17
MTL17
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Disclaimer: I do not own Agents of SHIELD. I do not make any money from the writing of this story.

Author's note: This story takes place after Season 5 of Agents of SHIELD, but deviates from canon.

*****

"Agent Hale, my office. Now!"

Ruby Hale sighed, stomped into her boss's office, and exclaimed, "What? I did everything you said, and I didn't even kill anyone!"

"I know." Daisy smiled, "This isn't about scolding you."

"Oh." Ruby quickly changed her tune, shoving the door closed behind her and then slowly closing the distance between them, "Sooooo, this is more like a reward?"

"Officially it's a debriefing, but we can call it whatever you want." Daisy smiled, pulling the younger girl into her arms.

"Rewards sounds good to me. Let's do that." Ruby grinned, already leaning in, "And I know exactly what I want."

Ruby then kissed Daisy Johnson, the new Director of SHIELD, right on the mouth. If anyone had ever told Ruby that she would be kissing the Director of SHIELD she would have laughed, and probably killed them. Especially if they had said that it would be right after her first mission is an official Agent of SHIELD.

If instead they told her she would be kissing Daisy Johnson she would have been intrigued, as she had been infatuated by her for a very long time, and while that had mostly been about beating her even then she won't have been able to deny she had something of a girl crush on her. Maybe even a full-blown crush, if she was being honest. But she never thought anything would actually come of it.

Just because Ruby had never seriously imagined it happening didn't mean she wasn't disgustingly happy right now. Working for Hydra had been a misery, and things stand there and gone better with her Mom in charge, but the organisation was once again defeated, SHIELD standing tall with the rest of the world complete with her mother in jail where she could visit her.

And where SHIELD could use her as leveraged, if Ruby ever stepped out of line, but she wasn't focus on that right now. No, Ruby was fixated on receiving the reward she had earned from her new boss, and maybe sort of girlfriend. Although because Daisy was responsible for Ruby not being in a cell alongside her mother should make sure she enjoyed it too.

They both certainly enjoy their kiss, which was why Ruby wasn't in a hurry for it in to end, taking time to squeeze Daisy's butt before breaking the kiss and growling, "This is mine now, right? You promised!"

"I said one day, maybe, if you're good." Daisy reminded the other girl, "And completing one mission without killing everybody is hardly what I call good."

"But you promised!" Ruby whined softly.

Daisy briefly considered this, before frowning, "So what?"

"Excuse me?" Ruby frowned.

"What would you do if I don't keep my word?" Daisy gently pushed, "What would you do?"

Ruby almost showed how upset that idea would make her, but she quickly realised she was being tested, and did her best to answer as calmly as possible, "I would be deeply disappointed, but I wouldn't hurt anyone."

"That's not very convincing." Daisy grumbled.

"I promise to be good no matter what. I, I like being an Agent of SHIELD. I like helping people. It feels good, to be good." Ruby admitted softly, hating that she not only had to say it, but that she meant it. But it was worth it to get what she wanted, especially as she got to add with a wicked grin, "And if I don't get my reward soon, I'm going to stop having sex with you."

"Really?" Daisy chuckled, leaning in slightly as she had in a husky voice, "Do you really think you can do that?"

"Wanna see?" Ruby challenged.

There was a extremely long pause, and then Daisy sighed, "Alright."

"Yes!" Ruby pulled back and exclaimed, even doing a fist pump which made her feel like a total dork, but she just couldn't help it.

"Let me finish." Daisy quickly put a stop to Ruby's celebration, "I'll make you a deal."

"No more deals. Bend over and give me your ass." Ruby demanded, "That was the deal, and I'm collecting."

"Then how about a challenge." Daisy quickly offered, knowing it would peak her lover's interest, "You go first, then if you're still up for it, then you get your turn."

"Ass for ass? Intriguing..." Ruby thought it over, knowing that Daisy was using her competitive nature against her, but she just couldn't resist the offer, "Do I get to eat your pussy first?"

"If you want that to be part of your reward, go for it." Daisy grinned.

"Then we have a deal." Ruby purred, closing the distance between them again.

"I thought you said no more deals?" Daisy teased.

"Shut up and kiss me, before I change my mind." Ruby tried to threaten, although it came out as more of a giggle.

The first kiss had been initially soft and gentle, at least by their standards, but this was hard and rough right from the start, and Ruby didn't even waste a second before reaching down to grab two handfuls of Daisy's hot little ass. It had been the Holy Grail ever since Daisy had taken Ruby's anal cherry, and there was no way that Ruby was going to be denied having it tonight.

But she was used to jumping through hoops, so what was a couple more? Especially when she enjoyed them both so much. And as much as Ruby's dark side was screaming at her to take what she wanted it would be so much more satisfying when Daisy realised she had no more options left but to bend over her own desk and spread her cheeks.

For now Ruby was satisfied with just kissing the older woman, and caressing her charms. Most of her attention was on Daisy's butt, because how could it not be when she was so close to making it hers? But Ruby's credit she gave Daisy's tits at least some attention before going for her prize, both with her hands and then eventually also with her mouth as she unzipped Daisy's uniform and literally tore her bra out of the way.

But Ruby was never really big on foreplay, so after only a few brief moments of going back and forth between Daisy's tits she yanked down that uniform so it was around the other woman's ankles, pushed her boss backwards until she was sitting on her desk, and then buried her face in between her legs.

"Oh hell yeah, mmmmm, that's it Agent Hale. Earn your reward." Daisy gleefully encouraged.

Daisy liked foreplay, and more to the point getting a nice, long pussy licking, and sometimes when they were alone in her quarters Daisy would insist on receiving that treatment from Agent Hale. Especially whenever Ruby let her tie her down. But even then it was a risk, because Daisy was quickly learning that being The Director of SHIELD meant that she was always on the clock, meaning they had been interrupted more than once.

Luckily no one in SHIELD barged into her quarters or office uninvited, but it may be a matter of time before someone had no choice, and they got an eyeful of a pretty blonde head in between her legs, or with her strap-on buried in the 19-year-old girl's butt. Which was more of a turn on that should be.

Even if the chance of getting caught had been a massive turn on Ruby's tongue would do the trick as it expertly worked over Daisy's cunt. To Agent Hale's credit she was able to restrain herself just long enough to deliver half a dozen gentle, albeit not slow, licks which most ignored Daisy's clit before going in for the kill.

In this case that meant spitting on Daisy's pussy, rubbing that saliva in with her fingertips and then pushing a finger inside of her. As it didn't take much for Daisy to yet turned on, especially by Ruby, the finger slid in easily and cause Daisy to cry out with pure pleasure, which she continued doing as the new member of her team began fingering her, again with a surprisingly restrained pace.

That didn't last very long as with a wicked smile Ruby increased the pace of the finger fucking and even began to curl that finger upwards to attack Daisy's G-spot. Not satisfied with that alone Ruby began licking around her finger, before inevitably sliding her tongue upwards to flick Daisy's clit over and over again.

Then Ruby took it into her mouth and sucked it forcefully while adding a second finger into Daisy's cunt, which was easily enough to push the older woman over the edge of orgasm. But Daisy didn't allow herself to go over it. Not just yet. No, Ruby needed to earn the privilege of making her cum, and more importantly Daisy was determined to squeeze a little more enjoyment out of this first.

Eventually though Daisy just had to squeeze every last bit of pleasure she could out of what was happening to her, so she reached down to grab hold of pretty blonde hair, pushed Ruby's face deeper into her cunt and practically growled, "Yesssssss, that's it you little bitch, eat me! Eat my pussy you fucking slut, oh fuck yeah! Mmmmm fuck! Oh God, you fuck me so good, Agent Hale. Oooooooh, you must really want your reward. Huh? Well how about some cum? Would you like that? Huh? Would you like me to cum in that pretty face of yours? Mark you as my pussy eating slut? Or at least, more than you already are? Huh? Ohhhhhhh yesssssss, earn your reward Agent Hale! Mmmmm, earn it good! Oh fuck yeah, use your fingers just like that, ohhhhhhh fuck, mmmmmm Gooooooodd yesssssssss, fuck me! Fuck me! Ohhhhhh yeahhhhhhhh, oh Agent Hale, aaaaaaahhhhhhh fuckkkkkkkkkkk!"

While in the past Daisy had tried to keep her voice down she quickly realised that was impossible with Ruby around, so for better or for worse she had soundproofed her office for occasions like this. Which meant she could be as loud as she wanted to be, yelling abuse at Ruby are beginning to grind her cunt against the other girl's face.

This meant that she came sooner, and more frequently, but it was worth it to remind Ruby who was in charge, at least for now. No! She was still in charge. Just before she started cumming so hard it was difficult for her to think coherently Daisy promised herself that into what happened she would remain the top with Ruby. No other outcome was acceptable.

Ruby was equally determined to achieve the other outcome, but right now she couldn't be focused on that. Not when she was concentrating on making Daisy Johnson cum for her, which right now was an overwhelming need which Ruby was helpless but to give in too, which was unusual for her. Not the giving into her desires part, she was very familiar with that, but Ruby wasn't exactly the giving time.

Not when it came to pleasure. No, Ruby was very giving when it came to pain, but the desire to actually give pleasure was very new to her. But then this was Daisy Johnson, and Ruby broke all the rules for her. She would do anything for her, which was why she allowed herself to bottom for so long. Well, mostly.

Eating pussy definitely seemed like a submissive thing to Ruby, but fingering felt dominant, which was why she tried to include it every single time she went down on Daisy. Sometimes she wasn't able to because her hands were restrained, but at times like this she took full advantage and used her fingers to remind Daisy that she wasn't a total bottom.

That, and of course to make Daisy feel good, and most importantly at the moment, make her cum. Which she always did, over and over again, and this time was no exception. Of course Ruby was very proud of this. She just wasn't as proud of what she did next, or at some point during the finger fucking and clit sucking combo. Which was of course replace her fingers with her mouth and tongue.

Occasionally she could resist the urge, but this wasn't one of those times, and ultimately Ruby wrapped her mouth around Daisy's entrance and drink deep from the other girl's cunt. Which was addictive enough when it was just filled with her regular cream, but when the other girl was overflowing with cum like this Ruby went berserk, swallowing as much as she could while the rest ended up on her face.

True, Daisy pushing her face into pussy and then grinding herself against her had a lot to do with it, but Ruby should know better. This was total bottom territory, and despite herself Ruby just couldn't help but get lost in that for a few minutes if it meant she got to swallow more of yummy Daisy's cum.

It was at times like this Ruby truly thought it wouldn't be so bad being a pure bottom, as long as Daisy was her top. Oh yes, as long as a total bad ass like Daisy Johnson, a.k.a. the infamous Quake, who literally had the power to destroy the world, was the one dominating her like this Ruby didn't really mind at all.

Especially considering what was about to happen to her, which would make Ruby feel even more submissive, and cum like a total bottom. But once again Ruby was just about able to remember what she truly wanted, and the fact that it was fairly within her grasp, giving the strength not to beg to be Daisy's bitch once she got the chance when she was finally pulled out of the other girl's twat and then roughly kissed.

After enjoying tasting herself on Ruby's lips and tongue for a minute or two Daisy broke that kiss and ordered, "Now, Agent Hale, YOU, bend over."

"Yes, Director Johnson." Ruby grinned cheekily, quickly standing up and taking off her uniform, before bending over her boss's desk and taunting, "Abuse your power like all good leaders, and fuck my teenaged ass."

Daisy almost didn't hear that as she was so busy drooling over Ruby's cute little butt. Unfortunately she did, and it made her cringe a little. Technically her conscience should be clear as Ruby was 18 the first time they had sex, but the girl was still about 10 years her junior, which made her feel like a bit of a creep.

Combined with the fact that she was Ruby's boss should have been enough for her to put a stop to Ruby's advances when the younger girl originally came onto her, but she was just so hot, and it had been so long since Daisy had another girl to play with. Then there was Ruby's perfect little ass, which Daisy hadn't been able to resist taking and making hers, just like she was about to do again.

So pushing Ruby's taunting out of her head Daisy kicked off what was left of her uniform, quickly retrieved a strap-on dildo from under her desk and then strapped it on in front of the tiny 19-year-old, who just grinned sadistically back at her.

That continued to be the case as Daisy covered the toy in lubricant and then slowly circled the desk so she was behind her pray, taking a few more long seconds to admire her prize before dropping down onto her knees and burying her face in that cute little butt.

At first she just breathed in the smell of the other girl's fuck holes, before reaching down slightly so she could slide her tongue from Ruby's clit all the way up to the top of her ass crack, then just licking the crack before finally concentrating on Ruby's butt hole.

Which had the other girl crying out, moaning, whimpering and eventually taunting, "Mmmmm, that's it Director Johnson, eat me! Eat my tight little ass! Oh fuck! Oooooooh God, that feels so good. I love the feeling of my boss's tongue worshipping my little ass hole. Mmmmm, but not as much as I love feeling it inside my butt. Oh yes, come on Director Johnson, shove your tongue up my ass! Tongue fuck that tight teen ass hole of mine, and get it nice and ready for your big fucking cock. Butt fuck me with your tongue! Mmmmm yeahhhhhh, butt fuck me with your fingers! Oh God, butt fuck me with your cock! Just butt fuck me Director Johnson! Yeahhhhhhh, reward me for my successful mission. Reward me by fucking me in the ass, boss lady. Oh fuck! Yessssss, ohhhhhhh, fuck me Quake! Oh fuck!"

Again Daisy did her best to ignore the annoying girl, who was only technically still a teenager, and just focused on eating Ruby's ass. To get serious with that, and to oblige one of the other girl's requests, Daisy used both her hands to pull apart Ruby's butt cheeks, first so she could get plenty of access to lick that forbidden little hole, and then to push her tongue inside it.

After months of nearly non-stop butt fucking Daisy's tongue slid through Ruby's ass hole fairly easily, and she was able to get pretty deep, and then fuck her with it. But even that wasn't going to be enough preparation, something Ruby had actually mentioned. Which was okay, because Daisy had just the thing.

Namely her fingers, which were still covered with lube, making it real easy to slide first one, and than a second one deep into Ruby's hot little ass. Which of course made the well-trained anal slut moan and cry out with pure pleasure, which in turn made Daisy smirk and finger her hard.

If they were back in Daisy's quarters she may risk stretching this out for a little longer, or try some other toys to further stretch Ruby, or even give the other girl a pussy fucking first. Although even then it was hard for Daisy to resist the thrill of sodomising the dangerous little blonde and she certainly didn't try very hard now, giving Ruby the bare minimum that she needed before straightening up to her full height, ready to take what was hers.

Daisy then smacked Ruby's butt nice and hard and ordered, "Spread 'em Agent Hale! Spread your cheeks and show me that pretty little hole I own, so I can fuck it and show you who's boss."

Ruby glared as she slowly reached back to spread her cheeks, silently promising it would be for the last time. Oh yes, before she left this room Daisy Johnson would be the one spreading her cheeks, giving Ruby the chance to break her and turn her into her little up the butt bitch. No other outcome was acceptable.

So Ruby might as well enjoy being submissive while it lasted, although that was a little difficult during the weird sensation of having her shit hole stretching wider than it was ever supposed too so a large dildo could slide through it and into her ass, even making the bad ass Ruby Hale let out a sharp cry of pain. Even worse it was followed by an embarrassing whimper, which Ruby tried to stop, but it happened every time.

Luckily something else that always happened was that Daisy gave her plenty of time to relax, before pushing forwards nice and slowly, and unlike the first few times there were no patronising words which were meant to be encouraging, or cooing which was some how meant to be soothing.

No, there was complete silence between the two women as one stuffed the other's butt full of dildo, until Daisy's thighs came to rest against Ruby's cheeks, announcing every inch of that strap-on was deep within her ass. There was another pause, before Daisy started gently pumping her hips back and forth, causing the cock to slide in and out of Ruby's ass and thus officially beginning the butt fucking. Which was when things started getting really, really embarrassing.

It was humiliating enough to bend over and allow herself to be sodomised. When Daisy had initially bought it up Ruby couldn't imagine anything more gross, weird, and most of all humiliating, but what was far worse was feeling pleasure from such an obscene act. And not just enough to make the experience bearable, but increasing amount to the point where she just couldn't stop herself from moaning in pleasure.

She was good at hiding it, and given that she was on the verge of turning the tables Ruby was able to resist for a record amount of time, and almost fooled herself into believing she could resist completely. But ultimately the pleasure just became too much and one sudden hard thrust had her moaning loudly in pure pleasure.

"Oh yeah, moan for me Ruby, moan for me." Daisy teased, "Moan like the bottom you are."

Which of course made Ruby fume with rage and want to snap at Daisy, but that's exactly what the other woman wanted, as every time Ruby had talked back in the past while getting her ass fucked had led to her moaning uncontrollably in between her words, diffusing everything she said and making her blush, and Daisy grin in triumph.

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