What If...Ruby Enlisted at SHIELD

BY : TheChemist
Category: Marvel Verse TV > Agents of S.H.I.E.L.D.
Dragon prints: 2673
Disclaimer: I do not own not have anything to do with any Marvel property (including Marvel’s Agents of SHIELD), nor any of the characters, especially Ruby Hale, Daisy Johnson & Grant Ward. I make no profit from this fictional story


This is not the universe you are used to. That is Earth-616. On that Earth, Ruby Hale was enlisted in Hydra by her mother. Ruby, at the tender age of 20, is a killer. She was cold-blooded, fairly psychotic, and deadly with a circular throwing disc. She was also gorgeous, with flawless skin, big juicy lips, and a body that was unbelievably curvy for someone so young and petite.

 

However, this is not that universe. On this Earth, which is one of an infinite amount within the multiverse, Ruby never joined Hydra, nor was she genetically modified by Hydra leader Daniel Whitehall. Luckily her physical attributes were unaltered. However, instead of joining the ‘bad guys’, Ruby was recruited by SHIELD, where she raised through the ranks expertly. 

 

“Ruby. I word please,” the Director, or Dean, of the SHIELD Academy called out in the cafeteria.

 

“Someone’s in trouble,” one of Ruby’s classmates jested as the gorgeous blonde stood from the table.

 

“Eat me, Tobias,” Ruby said coldly.

 

“Been there, done that,” the cocky boy shot back, earning a high five from his friends. “So have a lot of us.”

 

“I’m sure I wasn’t hearing anyone slut shame a young woman for being sex positive, am I?” Daisy Johnson said to the group of boys, making them all jump in surprise.

 

“No, Director Johnson,” the boys all replied in unison. 

 

“Good. Ruby, with me.”

 

“If this is about what I saw last night then I am so, so sorry.” Ruby immediately spoke as they stepped out into an empty hallway.

 

* * *

Last Night

 

Ruby Hale didn’t know what to wear when she was to meet tonight with the Director of SHIELD’s Academy, who had invited her to her private residence a week previous to go over an assignment. In fact, she was on the 44th straight minute of trying things on and taking them off, which was an impressive amount of time considering how small her wardrobe was. In the end, running tight on time, she decided on the school’s uniform, consisting of a short-sleeve white blouse and grey kilt with knee-high white socks and black boots with a 3 inch heel. 

 

Everyone knew where the Director lived on campus, as Daisy Johnson had an open door policy. She, much like everyone else on staff, lived in their own section of the small campus. Hers was the last townhouse on the block. While not huge, it had a privacy hedge on either side with a nice pool in the backyard. Ruby slipped through the side of the house and entered into the backyard as Daisy had instructed in a text message to her. 

 

“Mhmm...ahhh...yes!” 

 

As Ruby made her way down the side of the house, the sounds of moaning grew louder and louder. Quieting her walk and advancing in the shadows, the well-trained teenager continued into the backyard and was soon able to confirm that the voice that sounded much like the Director of SHIELD’s Academy was in fact belonging to Daisy Johnson.

 

“Yes Ward! Fuck me!” Daisy cooed.

 

As Ruby rounded the corner she averted her eyes up to the source of the screams. Sure enough, up on the second floor balcony was her Dean and mentor, Daisy Johnson. Unlike ever before, Ruby was looking at her mentor completely in the nude, bent over so her ass was pushed back and hands rested on the balcony as she was fucked from behind by her long-time boyfriend Agent Grant Ward.

 

While Ward too was naked and gorgeous in his own right, with all the whole tall dark and handsome thing working for him, Ruby couldn’t take her eyes off Daisy. While anyone with eyes knew that Daisy Johnson, aka Quake, was drop-dead gorgeous, seeing her completely naked and getting plowed from behind made Ruby so...wet. In fact, as she continued watching the half-Asian Director taking it from behind, causing her small perky tits to bounce gleefully in front of her, Ruby kept creeping forward, out of the shadows.

 

“I think we have company,” Ward mentioned after another handful of hard thrusts into his girlfriend.

 

“You know the plan,” Daisy replied, a smile growing on her face.

 

Ruby couldn’t tell that the couple were chatting, nor was she aware that her hands were moving on her own body. Subconsciously her left hand had roamed up her taut stomach in order to rub one of her massive C cup tits, while the right was rubbing her snatch through her underwear under the kilt. However, her heart rate soon raced as Ward looked down at her before giving her a smirk.

 

Ruby couldn’t help but stare up into his handsome face and return the smile. She let the eye contact linger for several seconds, locking eyes with the Special agent as he fucked the beautiful Daisy Johnson, before Ruby regained some composure. With a small shake of her head to break the trance, Ruby turned on her heels and exited the backyard promptly, returning home where she would masturbate twice to the image of a naked Quake getting fucked from behind. In fact, Ruby couldn’t stop thinking about what she saw 12 hours ago.

 

* * *

 

“It is about last night but no, you’re not in trouble. Nothing like that,” Daisy calmed her worry.

 

“Okay good because I swear I wasn’t spying or…”

 

“I know your a much better spy than that,” the Half-Asian woman replied with a laugh. “Listen, are you free tonight?”

 

“Yes I am.”

 

“Good. In that case I have an extra assignment for you...but of course you are free to pass. Grant and I are getting together again tonight at 21:00. Here is the key to my house. If you choose to accept, then I’ll see you then. Understood?”

 

“Yes, Director Johnson,” Ruby replied with a salute.

 

“When it's just us, no saluting and just call me Daisy,” the gorgeous former hacker corrected.

 

“Yes, Dir...Daisy.”

 

“Good girl,” Daisy smiled. “Oh, and wear your sexy schoolgirl uniform tonight. If you do come, that is.”

 

* * *

 

Though it wasn’t the easiest decision of Ruby Hale’s life, that distinction went to accepting SHIELD’s invitation to attend their academy and learn under Quake, this wasn’t a hard call to make either. Leaving her dorm room early, the blonde teenager dressed once more in a white blouse, schoolgirl kilt and knee-high socks, Ruby moved quickly and unseen across campus before using the key Daisy had given her to enter inside. Just like last time the sounds of moaning guide her way, this time leading her up the stairs towards the master bedroom.

 

As Ruby stood outside the door, she steadied her breathing a calmed her nerves. She knew exactly what they wanted when Daisy invited her over tonight, and Ruby wanted it more than ever. Ruby was far from a virgin, in fact it wouldn’t surprise her if she learnt she was the most sexually active student on campus. However, fucking around with teenage boys and girls was a whole lot different than sex with a pair as experienced and sexy as Grant Ward and Daisy Johnson. 

 

KNOCK KNOCK

 

“Gllk...gllkk...come on in,” Daisy’s voice called out from inside.

 

Ruby eased open the door, trying not to seem to eager and found the happy couple had already started without her. Laying flat on his back was the ruggedly handsome Special Agent Grant Ward, and laying on her stomach between his spread legs was the gorgeous Quake. In her hands rested Ward’s rock hard cock, which judging by the glistening coating on it had just recently been sucked on by Daisy. It was also worth noting that the SHIELD Director was already stripped naked with her amazing large booty splitting Ruby’s attention.

 

Ruby couldn't deny that watching her drop dead gorgeous SHIELD Director making out with the equally attractive man had her smiling, and frankly made her horny. And why wouldn't she be? Agent Daisy Johnson was as sexy as women could be. Her body type was both similar and different to Ruby’s own; while both women shared rock-hard body developed from hours in the gym, Ruby was much more top-heavy due to her large C cup tits while Daisy’s main asset was her awe-striking thick wide ass.

 

“Don’t be shy,” Daisy spoke, looking at Ruby with her big soft brown eyes. “Come help me out.”

 

Once Ruby had knocked on the door she had told herself she’d be game with anything that happened inside the bedroom therefore she didn’t hesitate once Daisy instructed her. As the shorter blonde walked towards the bed, Daisy turned her attention back to her boyfriend’s cock, giving the underbelly of his dick a long lick from base to tip. 

 

“Do you like the look of Agent Ward’s cock?” Daisy asked before swirling her tongue along his head.

 

“Mhmm,” Ruby agreed.

 

“How big it is,” Daisy asked, opening her mouth and bobbing along the first half of his dick, which equated to 4 of the 8 inches. 

 

“Uh-huh,” the teen nodded.

 

Pulling her pouty lips from his dick, Daisy locked eyes once more with her student, who was standing right beside the bed now. “Do you wanna taste it now?”

 

“Yes. So much.” Ruby replied without delay.

 

Daisy quickly got to her feet and pulled Grant up by the hand so all three were standing. Ruby didn’t stay upright for long though as Quake’s hands on her shoulders prompted the blonde girl to drop to her knees. No sooner did Ruby kneel before the much older man did Grant offer his dick to her lips, which were so plump they were made to suck cock. Flashing her green eyes up to meet his, Ruby parted her lips and took the first several inches of veiny dick onto her tongue.

 

2 sets of hands descended onto Ruby’s head and encouraged her blowjob. Cupping the back of her head was her mentor Quake, who kneeled beside her while the man twice her age clutched the top of her golden head and gently pulled and pushed her face towards his cock. Not that Ruby needed the help in how to give a blowjob, nonetheless Ruby loved that she had both of Daisy and Ward’s attention on her and her alone.

 

“God it’s sexy watching that cock so in and out of your mouth,” Daisy cooed into her ear.

 

“She knows exactly what to do,” Grant grunted, looking down and watching as his girlfriend helped the teenage stunner suck his cock.

 

Ruby was the veteran of hundreds of blowjobs so she was more than confident on her knees. Wanting to show the handsome man that she wasn’t some inexperienced girl, Ruby really bobbed her head in and out of his lap. Not afraid to gag herself, Ruby pushed her nose towards his groin until his head poked the back of her head, making her spit up some more saliva. With more spit came a faster blowjob as she dick-sucking lips glided even easier along his veiny member.

 

“I think you’re forgetting about something,” Grant commented. “Or rather a pair of somethings.”

 

Ruby smiled up at him from around his dick before pulling her lips off him. Daisy reached over and gripped her boyfriend’s manhood, angling it upwards and out of the way to better expose his hanging sack. Daisy slowly stroked the bearded man to keep him hard while affording him a brief reprieve to regain stamina as Ruby bent lower on her knees in order to run her extended tongue along each nut in turn. 

 

Not content to just lightly batting her wet tongue against each of his cylindrical balls, Ruby opened her mouth and swallowed his left one first. After several slow sucks on the sensitive nut, Ruby spat the left one from her mouth only to replace it with his right ball a moment later, giving it the same treatment as well.

 

As her half-Asian teacher tilted his cock towards her, Ruby didn't think, she only acted. Opening her mouth wide she inhaled half his length in one go before closing her lips around his manhood and bobbing backwards. As the blonde-haired teen began blowing him with better speed, Daisy loosened Ruby’s hair, letting it down so she could ball it in her fist and encourage her promising student to blow him harder, faster and deeper.

 

“Wanna share with me?” Daisy asked after Ruby eventually pulled Ward from around her plump lips.

 

“It would honestly be such a pleasure to suck cock with the legendary Quake,” Ruby said, admiration in her eyes. 

 

Seeing the gorgeous, youth girl sitting on her knees, a cock in hand with spit strings still connecting her mouth to Grant’s cock, Daisy felt such lust for Ruby. So before the young blonde could go back to sucking on the lucky Agent, Daisy Johnson grabbed the promising student firmly with a hand on either side of her youthful face so she could pull Ruby towards her. 

 

To say that the kiss they shared was explosive wouldn't do it enough justice. Both Ruby and Daisy poured every ounce of lust and desire that they had shared for each other since the first time they met into the tongue-filled kiss. It was raw and sloppy, but neither cared that their face was occasionally licked and that they were swapping large amounts of spit. The pair had chemistry and now they were finally experienced that built-up passion.

 

“Don’t think we forgot about you, stud,” Daisy said, eventually breaking the sloppy makeout session with her student. 

 

Ruby missed having the older woman’s tongue filling her mouth but she was more than happy to please the two top Agents at the academy. Once more, Daisy allowed the younger blonde to have the first turn since Ruby was the special guest after all, and Ruby didn't hesitate to seize the chance. Opening her mouth wide, she easily inhaled the first half of Grant’s length again before pulling her back up to the tip. 

 

"A real go-getter," Daisy mused as she watched the teenage girl energetically bob along his length.

 

Daisy waited a short time until Ruby slowed, then she took her chance. Lowering her gorgeous face down lower, she licked the portion of Ward’s cock not currently filling Ruby's mouth. Daisy kept moving her licking up, catching the other girl's lips from time to time until she'd forced Ruby off his cock altogether so that Daisy could get her mouth on his dick.

 

Ever since Grant started tutoring the gorgeous teen last year in fighting, the Special Agent couldn’t get the thought of fucking her out of his mind, despite the large age gap. And the only thing that made it all the better was the fact that his long-term and extremely sex-positive girlfriend was sharing the bedroom with them, especially since Daisy would be the perfect teacher for the still raw teenager.

 

"Awhhh...I've died and gone to heaven," Ward groaned with a smile as Daisy passed him back to Ruby.

 

The differences in their technique were obvious even for the most inexperienced of observers. Daisy had refined her oral technique over years of trial and error until she was an efficient machine. She took her time, not going too slow or too fast, but instead that perfect speed where she used her lips and mouth to caress the lucky bastard, always being sure to use a lot of eye contact as well.

 

Conversely, Ruby was all carnal passion and unrefined energy. She had no strategy or higher thinking other than to wrap her lips around Agent Ward’s manhood and bob her head all the way down past her gullet and into her throat, only stopping when her nose was pressed firmly against his pubic region. Her face reddened with the exertion but her eyes were screaming that she couldn't be happier pleasing this much older man.

 

“Isn’t she so pretty,” Daisy cooed up at her boyfriend.

 

“Especially with a cock in her mouth,” Grant agreed as Ruby seemed to suck harder while receiving such kind words.

 

"Mhmm...you suck that cock so good," Daisy complimented. “But now I want him to fuck you.”

 

“Yes please,” Ruby replied with a smile that couldn’t contain her unbridled glee.

 

“Good. Now let’s take your clothes off,” the older woman said.

 

Daisy didn’t want to take anymore time than required, such was her level of horniness at the current time. Therefore, she reached to the front of her pupil’s blouse in order to interlace her fingers through the button holes. With a sudden jerk of her arms she had the buttons popped from the shirt front. Meanwhile, as Daisy was pulling the blouse from Ruby’s shoulders before starting on her bra, Ruby was unzipping the slit in the side of her kilt so that when she got to her feet, she only had her white knee high socks since she didn’t bother wearing panties to tonight’s festivities.

 

“Oh dear Lord,” Ward practically gasped at the sight of the near nude student.

 

While Ruby’s stature was petite, seeing as she was barely 5’2 in height and weighed no more than 110 pounds. However, the girl was all soft edges and curves. Her time in the gym while at the SHIELD Academy was obvious to observe as she possessed thick but feminine thighs and booty while her stomach was flat. However, the asset Warm gasped in response to seeing was clearly her very large tits, a full C cup in size, which were made to look all the bigger and more spectacular given her slim frame and how they were so perky despite their immense heaviness.

 

“Yeah, I get that a lot,” Ruby said with a proud grin in regards to the older man’s expression. Turning to look at Daisy, the shorter blonde asked. “Can I fuck him now?”

 

“Yes. Let’s get his thick cock in that tight little pussy of yours,” Daisy replied before reaching out to grab Ruby’s arm before she could climb onto the bed. “But know that you will do whatever we say.”

 

Ruby didn’t really need much time to think of the correct answer that her superiors wanted to hear. Though she did have some slight apprehension about doing whatever these extremely horny and well experienced, she was nonetheless more excited about the threesome than actually nervous. She’d had more than enough sexual trysts of her own to be comfortable with almost anything this pair could throw at her, after all. 

 

“Yes, Director Johnson,” Ruby said with a mischievous grin.

 

Daisy reached out and pulled her man towards her, bringing him in for a kiss while still holding Ruby's hand beside her. The kiss was only brief as Daisy moved out of the way and pulled Ruby to take her spot, aided by Ward who was now standing naked chest-to-chest with the horny blonde. Ruby and the Special Agent kissed deeply and passionately, her erect nipples pressing against his solid chest as his cock was wedged against her flat tummy, all while the girl who was a Hydra agent on a different Earth found her pussy was an inferno, her arousal beading from her pink folds and down her inner thigh. 

 

Of course, Ruby’s excitement only grew as Daisy leaned into her side and kissed along her neck, up along her jaw. Within moments Ruby had 4 hands groping her very naked body as Daisy's set rubbed her back and groped her truly magnificent breasts while the much larger pair belonging to Ward rubbed through her very wet snatch and pawed her firm ass simultaneously. While Ruby’s ass was considerably smaller than the ass he was normally massaging in Daisy, the slim blonde still possessed a thick peach of a tush.

 

"Oh God!" Ruby shrieked, feeling the man slide his finger in her folds and begin playing with her bare pussy.

 

At this point Grant had Ruby spin around with her pleasantly bubbly ass grinding against his raging boner while he kissed the woman known as Quake over her star student's shoulder. It was a tight fit but his hand was still able to stay with Ruby's sex, his two fingers now gliding effortlessly into the wet snatch while the two gorgeous women rekindled their passionate love affair with one another via a sensual and sloppy makeout session.

 

“Our girl’s ready,” Ward stated, his fingers coated in Ruby’s juices.

 

"Lay down," Daisy ordered the lucky man.

 

Ward got in position as specified, laying flat on his back in the center of the massive bed. Ruby deduced successfully that Daisy wanted her to have the honors so she followed the man down onto the bed, crawling on her hands and knees until her toned legs straddled his waist. However, Daisy wasn't permitting the slim blonde to sit down on his lap and take his cock, not right away anyway.

 

And that was because Daisy wanted to make sure her pupil was good and ready to take the healthy-sized cock. In truth, it may have had more to do with Daisy really wanting to eat out the flawless teen. Though Daisy was definitely more into cock, when a girl was positively sensational as Ruby Hale ended up in your bed, Daisy couldn’t help but want to devour her peach of a cunt.

 

"Oh dear Lord," Ruby screamed in delight as Daisy's skilled tongue rummaged through her pink folds. "Yes!"

 

Daisy couldn't help herself from eating out her star student, and she could now confirm that teenage pussy tasted delicious, or at least Ruby’s did. As Daisy continued wagging her tongue as deep into Ruby's snatch as possible, she found her to be a little sweeter tasting than most pussies she sampled. Even during her tongue lashing and savoring the sweet taste, Daisy didn't forget about the horny man beneath her. Daisy's fist making a fist around his shaft and stroking it fully as Ruby's firm ass cheeks pressed against her eye sockets.

 

As much as Daisy would have preferred to eat out the SHIELD trainee for hours on end, she knew it had to have a bookmark put in it. With her hand sliding all the way to hold Grant at the base of his manhood, Daisy used her free hand to position Ruby into arching her low back and pushing her little ass out, at least until their sexes touched. As Ward felt the tip of his cock against her slippery folds, the Special Agent placed hands on Ruby's narrow hips and pulled her down after lining up her hole with his pecker.

 

“Put it all inside your pussy,” Daisy instructed.

 

"Mhmm...yes," Ruby cooed as she was entered. “It’s deep in me.”

 

Grant may as well have been a professional given the high level of skill he possessed in all matters of sex. Rather than thrust wildly up into the horny girl, Ward slowly pushed his hips up off the mattress then lowered back down, starting with half his length at first until now his entire 8 inches of cock was gliding into Ruby. 

 

"Yes. Fuck me." Ruby moaned, finding that she was craving his cock now.

 

The blonde teen began a constant stream of moans coming his way with each time her superior officer lifted his hips and drilled his cock into her waiting pussy.With each passing thrust Ward got faster, gaining speed as he really fucked Ruby. As was with all SHIELD trained soldiers, both the horny teen and older man seemingly endless amounts of strength and energy, but it was Ward being the one who was providing all the action in the initial volley so all Ruby had to do was keep herself propped up and let the man her father’s age fuck her relentlessly.

 

After a few minutes of this ultra fast fucking, which no longer surprised Daisy since she had first-hand knowledge of Ward’s prowess in the sack, the muscular man slowed his thrusting down. They went a little slower now, more at a regular pace with Ruby taking some control, lowering her hips down to his lap and letting him feel her pussy as it molded it's velvety folds to fit his veiny shaft as it slid all the way to his base, rolling her hips at the bottom to draw an extra grunt of pleasure from the man.

 

"Fuck I am so turned on," Daisy commented as her eyes remained glued on the fucking couple while her own hand rubbed her snatch.

 

Snapping out of her gawking behavior, Daisy stopped being just a viewer and got back into participating. Getting closer so that she was between the two sets of legs, the Superhero known as Quake opened her mouth wide and took the slightly swaying balls into her mouth, sucking on one nut first between switching to the other. It was a tougher feat simply because Ruby kept thundering her firm ass down onto the side of her face, reddening both her cheek and Ruby's own ass.

 

"God damn," Grant swore, barely able to handle the extra stimulus without painting Ruby's womb in his seed.

 

"Not exactly what they meant by having you sit on my face," Daisy mused before realizing that it wasn't a bad idea.

 

Though Ward and Ruby were in a really good rhythm and it was extremely sexy to see a confident and sexually experienced teenager as hot as Ruby Hale in action, grinding her hips and riding the muscular man, Daisy wanted another taste. Therefore the half-Asian beauty wrapped her fist around the base of Ward's cock, giving Ruby less shaft to ride. With each bounce upward by the blonde student, Daisy lifted her fist up until finally Ruby ran out of cock and her pussy was no longer stuff.

 

Daisy was swiftly onto his cock with her mouth, essentially throwing her face down on his lap. To say that it was her most enthusiastic blowjob in her entire lengthy sexual life would not have been a lie. Ward's cock coated in Ruby’s juices made Daisy hunger to suck harder, deeper and faster in order to taste as much of the teen’s nectar.

 

"Fuck Daisy...you're gonna suck the cum straight from my balls like that," Grant groaned as he slightly thrust his hips upwards into her mouth.

 

Though she had placed herself on the sidelines so that Ruby cold have a god fucking, Daisy was now edging into a starring role with the threesome. Before shoving her boyfriend back inside Ruby, Daisy gave her star student's pussy another dig inside with her tongue. Instead of simply watching Ruby bounce her amazingly fit body up and down, Daisy kept her head between the two sets of legs but this time with a different target in mind.

 

Daisy Johnson got into anal sex around 18 years of age, but it wasn't until she graduated from SHIELD’s espinoge training academy that she gained a true appreciation for the difficult but very rewarding craft. Therefore, the half Asian beauty showed no hesitation in using her hands to separate Ruby's tight little butt cheeks, extend her tongue and plant a long slow lick right over the blonde teen’s puckered rosebud.

 

"Ahhh! Oh my God!" Ruby screamed, tousling her hair as she nearly came like a freight time in record time.

 

With Daisy rimming her star student, Ward had to once more do most of the work by thrusting his hips skywards, not that he minded. After all, he was the meat in a sandwich of two extremely beautiful women. 

 

While Ruby stayed propped up on her knees, she was being fucked and rimmed towards an epically powerful orgasm. Feeling a wet skilled tongue like Quake’s as it licked, poked and prodded against her very responsive asshole was bliss, all while a wide cock spread her pussy and repeated filled her.

 

"Well this will either make it or break it," Daisy thought as she prepared to push Ruby to an orgasm.

 

Being sure to leave a large glob of saliva right on the middle of Ruby's asshole, Daisy pulled her tongue back and gave some breathing room for the teen to work with. As the blonde girl began riding Ward with more power, Daisy reached down and made short, fast circular motions with the pads of her fingers. When that only seemed to spur Ruby on even more, Daisy slowed her hand so she could push first one, then a second digit as deep into Ruby’s asshole as she physically could.

 

"Jesus!" Ruby screamed, barely able to suppress her genetically engineered abilities as she sat up straight, arched her back, threw her head back and came harder than ever before in her short life.

 

"Mhmm...let me taste it," Daisy pleaded, her fingers still lightly pumping into Ruby's asshole.

 

As Ruby rose her little booty up off of Ward's lap there was a whirl of motion as the party took up new places. Ruby moved the least as she was still positioned on her knees, only this time with her head resting along the bed and her tight little ass up in the air. Daisy too was relatively unchanged as she used her place beside the fucking pair to first suck all of the teenager’s cum from his cock before turning her tongue to the source of the extra sweet orgasmic juice. Meanwhile Ward had slid out from underneath the superhero-in-training and was now kneeling behind her, cock still rock hard and looking for more action.

 

"Grant has been excellent so far so let's give him the reward he's come to expect from me," Daisy said, still stretching out Ruby’s butthole with her fingers. "Ward, would you like to fuck this gorgeous teenager in her adorable asshole?"

 

"It would be an honor," the horny man replied, his one hand stroking likely on his dick and the other coming to stroke Ruby's deliciously curved backside.

 

"Yes! Please get that beautiful dick in my caboose," the far-from-innocent Ruby stated firmly, surprising both her older lovers.

 

Though craving and demanding anal sex seemed completely out of place for a girl as young and innocent looking as Ruby, what Ward and Daisy didn't understand was how her genetic modification at the hands of HYDRA had made her. The evil organization had made her the perfect spy, in all ways from being quieter on her feet, easier to learn new languages, and most importantly for tonight was that her asshole had actual pleasure centers, similar to her pussy. Though they didn't react as strongly to stimulus, Ruby was able to derive a good deal of pleasure from anal sex.

 

"Yeah? Wanna feel that big cock in your ass?" Daisy asked rhetorically after regaining her composure.

 

"Yes. Please fuck my ass," Ruby agreed.

 

Grant was impressed when the gorgeous blonde with huge tits for someone her age didn't so much as flinch as Daisy placed his cock against the entrance of her asshole. Despite Daisy warning him to go slow, Ward was betting that Ruby wanted anything but, however he'd respect the order. Needless to say, when Ward pushed his hips forward and felt the first half of his length engulfed within Ruby Hale’s rectum, she didn't grunt or curse, but rather released a low moan of satisfaction.

 

"Mhmm yes! Look at that booty taking it," Daisy cooed, helping by using her hands to pull Ruby's cheeks as far apart as possible.

 

The slow and steady approach was adopted until Ward had planted his entire length into Ruby's firm booty. It took a little over a minute for him to penetrate as deep into her colon as he could, at which point he stroked several times with his whole shaft. When Ruby only responded with moans, Ward picked up the pace little by little until he was fucking her just as hard as he did when filling her pussy. 

 

"My God! It's like an iron vice," Grant groaned as his dick repeatedly entered Ruby's asshole.

 

"More like steel," Daisy commented, bringing a small giggle from both women and earning her another passionate kiss from her student.

 

Daisy had been fucking Ward regularly ever since she joined SHIELD more than 5 years ago, so could tell when his endurance was waning. The hero known as Quake recognized those signs now, but Daisy didn't want to finish her tryst with Ruby yet. Needing to slow him down, the dark-haired beauty had Ward slow and shorten his thrusting until his dick popped free and Daisy was left holding him in her fist.

 

Ruby remained on her hands and knees but instantly felt shockingly empty as Ward was pulled out. Meanwhile both Daisy and Grant were rendered silent and still as they each looked down and appreciated the massive gape in what was normally a tightly constricted asshole belonging to Ruby Hale, staring straight down into the dark abyss of her asshole hanging wide open.

 

With a shake of her head to break the trance, Daisy sprang to motion, taking no time at all to lean forward and open her mouth wide. If Grant was surprised to find his regular hookup take his cock, which moments before had been lodge deeply in this gorgeous teenager's ass, and engulf the first several inches in her mouth in a repeated bobbing motion then he held his composure well.

 

"Of course your ass would taste insanely yummy," Daisy moaned, being sure she transferred a lot of extra spit for Ruby's benefit. "Now let's get this cock back in your hungry ass."

 

Once accustomed to the degrading act of tasting her star pupil's asshole straight from the man's cock, it was becoming a commonplace event, aided in large part to teenage assholes tasting pleasant. After every dozen or so thrusts forward by Ward he'd back far enough away from Ruby so the dick plopped from her backdoor with a wet sucking noise. Daisy would be ready and waiting, clutching the hard pole in her hand and devouring as much as she could fit in her mouth. For the portion that couldn't get between her plump lips, Daisy would extend her tongue and run it along the length of his cock, tasting Ruby's filth all the while.

 

"Like tasting my ass?" Ruby asked with a smile as she threw herself backwards, her firm cheeks rippling with the contact.

 

"So much," Daisy cooed, licking his balls until Grant backed further away from Ruby once more. "But I prefer eating from the source when possible."

 

Since Ward had only just left her asshole, Ruby's sphincter was still wide open. Daisy took advantage of the insanely large gape, especially given Ruby's narrow butt. Using her hands to pull apart Ruby's cheeks as much as possible Daisy dove forward with tongue out, burying the wet muscle a good inch inside her best student’s ass, the dirtiness of the backdoor coating her taste buds while simultaneously causing Ruby to scream in pleasure.

 

"Yes! God, yes! Keep fucking my ass! Keep rubbing my clit," Ruby all but shrieked.

 

With that, Daisy got her head out of the way and allowed Ward to literally slam his cock back into the loosened asshole. He didn't slow until his hips smacked against Ruby's smooth cheeks, causing them to ripple from the contact. Meanwhile as Grant started to ruthlessly fuck the teen’s backdoor with speed and power, Daisy listened to Ruby and reached under her, finding her bald pink cunt and rubbing through the slit with her fingers.

 

"Yeah? You gonna cum, you big titty slut?" Daisy asked rhetorically. "Cum on that big cock stretching your ass?"

 

"Gonna cum so hard," Ruby agreed. "Just don't stop!"

 

Up until this point Ward was handling the threesome extremely well. Both girls were talented with their mouths and both of Ruby's holes were tight and very pleasurable. As he began to sodomize the teen, who obviously very much enjoyed anal, he reached into his bag of tricks to delay his orgasm as long as he could. He thought of his grandmother, the entire line-up of his favorite football team and every other unsexual thought possible. However, Ruby on the verge of cumming from his ass-fucking was a different circumstance altogether.

 

"Yes! Uhhh! Uhhh! YYEEESSSS!" Ruby screamed, cumming once again for the second time in less than 15 minutes.

 

Shockwaves of pleasure shot up Ruby's spine as the waves rippled throughout her entire body. As if Daisy and Ward were unaware of Ruby cumming once more, her toes curling and body going coiled like a spring before relaxing without a hint of muscle tone were the visual signs. Once again, Daisy marvelled at the teen’s insane body. Sure, the intense training they put them through meant that they all had flat stomachs, toned legs and a firm ass, but Daisy moreso meant Ruby’s perfect and large tits - a full C cup that swayed with every convulsive jerk her body did as her brain was exploding like fireworks from the orgasm.

 

And that was the final straw for Ward as well. There was only so much he could take, and feeling Ruby's asshole quivering and randomly spasming on his already-close cock was simply too much to handle.

 

"Getting...almost...I'm close," Grant managed to eventually get out, his normally cool and calm demeanor displaced due to the intense, otherworldly pleasure her was experiencing. "Really soon!" Ward added more urgently.

 

"Not inside. You're gonna cum on her," Daisy said before lowering her voice so only Ruby could hear her. "I want to see Ruby's adorable face covered in cum."

 

"Yes please! Paint my face in your jizz," Ruby practically begged while still in the midst of an orgasmic stupor.

 

Though most girls her age, or any age, found a face full of cum to be rather degrading, Ruby loved the feel of a man spewing on her skin. The thought was interrupted though as the teen felt a sudden unstuffing of her backdoor. Though he was exhausted, Grant still moved relatively quickly as he pulled out of Ruby's asshole and flipped her over onto her back. He was beside the large breasted girl in a flash with his cock in his hand with her wide-eyed face staring up at him, or rather looking directly at his purple head which was milliseconds away from exploding.

 

Grant barely had to finish his first stroke before the familiar bubbling sensation started in his balls which preceded his orgasm. A heartbeat later the first strand of jizz was flying from his cock at Ruby, who out of reflex closed her eyes, opened her mouth and stuck out her tongue. Daisy couldn’t help but watch on with her pussy flooded out of excitement as she viewed her star student getting painted by her long-term boyfriend.

 

"Ugh! Fucking hell!" Ward grunted as streak after streak of cum shot from him and onto his target.

 

As Ruby felt the first stream of warm jizz coat her face in a line from her forehead on a downward angle down to her right ear she realized that she'd never been came on. As the second streak landed over the bridge of her nose and right eye, Ruby basked in the glory of having Grant Ward cover her face while his big assed girlfriend watched. The third streak landed on her bottom lip and adorable chin before several smaller shots were aimed into her mouth, which she dutifully swallowed in one mouthful.

 

"Let me grab you a tissue," Ward said, reaching to his right to grab the box on his nightstand.

 

As he was reaching, Ruby also decided to grab something, with her target being his slowly deflating cock. It stiffened slightly at her touch, drawing a small moan from the man. As she leaned her cum-splattered face closer, she opened her mouth and began sucking gently on the well-used dick, making Ward moan louder and shutter with each of her bobbing motions.

 

"By the way Daisy, you were totally right," Ruby cooed, taking another soft suck on Ward's cock before pulling away with an audible pop.

 

"That getting fucked was exactly what you needed," the dark-haired girl responded with a smug, satisfied look on her face.

 

"That...and also that I do taste really delicious," Ruby smiled before taking a long slow lick of the underbelly of Ward's cock, being sure to taste her asshole on his manhood.

 

"I've created a monster." Daisy stated excitedly.

 

“Not created, only finally discovered,” Ruby corrected with a cum-glazed grin.



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