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Skye's Anal Quest	By : TheChemist Category: Marvel Verse TV > Agents of S.H.I.E.L.D. Views: 7532 -:- Recommendations : 0 -:- Currently Reading : 0
Disclaimer: I do not own nor have any connection with Marvel's Agent of SHIELD or any property of the MCU or any of its characters, specifically Skye, Black Widow, Fitz, Simmons, Maria Hill, Garrett, Tripp & Ward. I make no money from this story

Chapter List
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"Skye, what's going on," Maria Hill asked. "You're unfocused and it is showing in your performance."
Now that the latest mission was complete, the team aboard the Bus headed by Agent Phil Coulson was called back to the SHIELD headquarters. The Bus needed some minor repairs, Phil needed to do some debriefing and prep for the next several missions, not to mention hand over some sensitive material that the team had collected lately.
It also allowed for the team to have some rest and relaxation...well SHIELD's version of that. Fitz and Simmons headed out to meet up with some friends they attended the Academy with and still stayed in touch with. Ward and May stayed more or less confined to the base though Ward would go out on occasion.
"It's nothing Maria, not really," Skye answered, taking another swing at the punching gloves the gorgeous brunette wore.
For Skye, she had meetings with Maria Hill, the second highest-ranking Agent within SHIELD, and the right hand of Commander Nick Fury. Based on Coulson's evaluations and her own opinion, Maria had taken a special kinship with the genius hacker and was fast tracking her to being a top field agent. Ward may be her regular Supervising Officer, but Maria Hill was going to oversee her development just as much.
"Oh? Let me put it to you like this. If you don't spill the beans we'll move along to grappling practice and we'll see how well you do with a clouded mind," Maria threatened, though it was lessened when she gave the hacker her warmest smile.
"Well...man trouble," Skye admitted. "I'm not sure if you know about..."
"You and Ward. Yeah, I know," the leggy agent cut her off.
"What? How?"
"I'm a top SHIELD Intelligence officer, second only to Nick Fury himself. Don't insult me with such a question," Maria answered. "Now explain."
"Ok well we've been together for a little while but you already know that. Anyway, I stumbled across a thumb drive that had him fucking all these different women in the ass," Skye blurted out.
"Yes, he has a reputation for being a lady slayer and very much into ass play. Hell, Romanoff said that he made her cum so hard from sodomizing her," the SHIELD agent shared.
"Oh I saw the evidence," the hacker commented. "And normally I wouldn't care about his past but some were after we started hooking up...including one with May."
"Yet you still have feelings for the cheating bastard and feel like it's partly your fault for you never taking it up the ass," Maria summarized.
"Yeah, like I forced him to go looking elsewhere," she added. "I just don't know what to do. I have one idea, chiefly getting revenge but don't know how."
"Well as a SHIELD operative I would say that if this is going to affect your relationship on the team then I have to move one of you to a new assignment so move on about it. As your close personal friend who cares about you, nail the bastard to the wall first," Maria spelled out for her.
"I knew we were friends for a reason," Skye smiled brightly. "Any ideas."
"One. Meet me tonight in my quarters. Let's say 9 pm sharp," Maria told her.
* * *
The rest of the day and early evening went by well enough for Skye. She didn't have any interactions with Ward, or anyone else from the Bus other then when she bumped into Simmons and chatted with the brilliant scientist for a brief time. Maria and her finished up their physical training before another agent led her through some simulations to train her mind as well.
She had just enough time to go the hall and eat a balanced meal that was optimal for her demands. She ate quickly enough though she got caught in a conversation with the enjoyable Clint Barnes, better known as Hawkeye. He was handsome and a flirt and she entertained the idea of fucking him to get back at Ward, but before she knew it the moment had passed as he got called away.
Remembering she had to be somewhere, she headed back to her room and grabbed a shower. She got dressed and locked the door behind her before she took off to go see her superior officer in her bunk.
"Come in agent," Maria said having heard the knock on her door.
"Thanks," Skye said, closing the door behind her. "Sweet digs."
"Thanks. Here, have a drink. It'll help," Maria said, handing the girl a scotch before sipping her own.
"The best plans always start with having to have a stiff drink, don't they," the hacker joked before downing her glass in one sip.
"My idea is to make your own video of you getting ass fucked by another man then let him see it," Maria revealed.
"But I'm not really into anal...like at all," Skye confessed. "That was the whole crux of the original problem."
"I know and that's why I invited you here tonight. Let me help you with that."
"What do you mean..."
Skye only had to wait for her answer as Maria moved aside the top sheet covering her bed and exposed several different phallic shaped objects. Skye was no stranger to sex toys, she had used some in her 22 years of life, but she had never been shown so many in one place...that place belonging to her boss no less.
"It's just like anything, it requires training. Most people jump right into anal without any prep. Those are the girls who hate it because it hurts so damn much. No one would jump into a marathon or bike race without getting ready for it before hand or else they will be in such pain and hate the experience," Maria explained as she took turns fondling each toy.
"That does make a lot of sense," Skye answered, thinking back to her own failed attempts, not to mention the tales some girlfriends would give about their own anal nightmares.
"Anal really isn't that hard but it can be done wrong and then you have horror stories," Maria started. "The first tip is loads upon loads of lube."
Maria closed her hand around the only green toy of the lot of them. Skye eyed the butt plug and noted it's every detail. The whole toy was only 4 inches long and only an inch and half thick at its widest portion right at the base meanwhile the tip was a manageable half-inch thickness. By comparing it to the other toys at Maria's disposable on the bed, this was an entry level one.
Skye watched as Maria popped the top of the bottle and smeared a healthy amount of the clear liquid onto the toy. She passed the dildo to Skye, who after hesitating for a moment started to work the lube all over the lengthy shaft for her friend. Meanwhile Maria put another dollop of lube onto her fingers before reaching back and spreading it around by rubbing it around her asshole to add more lubrication.
Maria extended her arm and took the slippery toy back from her apprentice as she got in position. Going onto her hands and knees, she lowered her small but perky chest down so it was pressed against the mattress while the hand with the butt plug stretched back behind her and butted the tip against her hole.
"Does it help being relaxed? I saw Black Widow rubbing herself constantly," Skye asked.
"You definitely. Being calm and relaxed is just as paramount as lube," the dark-haired beauty assured.
Maria ran her free hand out from under her body and between her legs to find her clit. She rubbed it slowly as her other arm flexed, Skye noting the muscles bulging. It took very little effort for the SHIELD operative's willpower to win as the green plug pushed past her anal sphincter and inserted itself in her own ass.
"Mhmm...and there you go," Maria said, looking back at Skye from over her shoulder.
"Holy shit," Skye gasped in amazement, looking down from only a foot away and seeing the leggy woman's anus expand to take the dildo inside.
Skye couldn't believe she was simply sitting beside her closest friend at SHIELD as she willingly showed her how to take something in her ass. Paying detailed attention, the hacker watched as Maria moved the toy methodically with the right amount of speed and smoothness. She would stroke another inch into her, watching as almost the entire length was inside the agent then withdrew it so only the very tip remained inside.
"The more you do it, the easier it gets," Maria said as she moved the green toy in and out of her asshole.
"And that feels good," Skye questioned.
"Mmhmmm," the brunette moaned in response.
"To be honest, it looks good from over here," she commented, no more than a foot away from Maria's rear
"See...it's not so bad at all," SHIELD's second-in-command told her rookie agent.
Maria smiled to herself with the knowledge that she was slowly getting Skye over her fear of anal sex...and that she was enjoying the scenes as well. Though the hacker was only consenting to this to get back at Graham Ward, Maria was hoping that she could get the girl curious enough in hooking up with the leggy goddess at another point in time.
"Do you think you're ready to give it a try," Maria asked, pulling the toy from her ass.
"Yeah, I mean...I think so," Skye answered with a smile that portrayed excitement with a little worry.
"Great. Get on all fours. Actually rest your shoulders on the bed so your arms are free," the SHIELD operative instructed. "Just the way I was."
Skye did as she was told and flipped over and got into position. She turned her head to the left in order to see her commanding officer that had already selected the toy to make the journey into Skye's ass. It was a tapered glass cylinder that had a small rounded head but got gradually wider along its smooth shaft.
"Okay so we have tons of lube on here and we'll get you to play with your clit to relax. Now do you want to do it, or would you rather I make the maiden voyage in your dirt road," Maria asked.
"I think you should do it," the rookie answered.
Maria agreed with the choice that the other girl made and was already in position directly behind the younger agent. The toy glistened in lube, as did Skye's asshole after Maria spread more of the liquid around her ring. Knowing that now was as good a time as any, Maria brought the two to its target, resting the tip butted up against Skye's asshole
"Just go slow...first time and all," Skye warned.
"I know babe. Know relax, rub that beautiful pussy and let me work my magic," Maria comforted.
With that Maria watched as the SHIELD agent took a deep breath and sighed it out. Taking that as the perfect time, the brunette flexed her arm muscles and started pushing the toy in. She kept up steady pressure until the slim toy entered past her restrictive barrier and passed into the girl's ass.
"Ugh," Skye winced in pain.
For having her backdoor breached for the first time since her horribly failed anal sex night a few year back, it really wasn't bad. In fact, if it wasn't for the negative feelings towards something going up her ass, the hacker doubted she would have grunted at all.
"It looks so pretty," Maria celebrated. "Now I'm going to keep going. Remember to play with yourself."
The whole toy was only 4 inches long and only an inch and half thick at its widest portion right at the base so Maria was determined to fit it all in Skye's booty. The combination of the lube and the hacker playing with her clit was having the desired effect, as Maria was able to push and pull the toy into her ass.
"So how does it feel," the more senior SHIELD agent asked.
"Weird. Not bad...just weird. I guess since I'm not use to it yet," Skye answered.
She never went to fast but kept a steady rhythm of going in and out, always leaving the tip inside her sphincter and always making more of the plug disappear inside Skye. It was only a minute or two later when she was threatening to get the last of the toy lodged in her rookie. To get her over the hump, Maria thought that a new distraction technique should be employed.
"Finger yourself now," she ordered.
Skye had already forgotten the discomfort of having her asshole expanded further then it had ever been, so she did as her mentor asked and immediately worked two fingers into her snatch. The superior officer continued to watch and wait for the perfect time to shove the last remaining bit of the butt plug inside, but for now she was enthralled by the wet slapping noises as Skye blasted her digits routinely into her pussy.
"You can feel the toy on the other side, can't you," Maria asked
"Feels so good...and slutty," Skye replied, her fingers gliding along the toy in her arse via the thin membrane separating them.
Seeing the look of pure pleasure etched on her rookie agent's gorgeous face, Maria chose then to smoothly guide the rest of the toy inside. Rather then yelp in pain like before, this time the half-Asian woman only bit down on her lower lip as her asshole expanded to take the widest portion of the toy until it was all in and it relaxed around the thinner neck.
"There. That's the whole thing," Maria told her. "That was the hardest part but we're a natural and opened right up."
"Really?!"
"4 inches of a decently thick fake cock is in your ass," Maria stated proudly.
"Wow...I guess I was nervous over nothing," Skye remarked. "It's really not bad at all."
"Good, now play around. Pull and twist it, play with your twat more. Have some fun," Maria told her.
As if still surprised that she had something lodged in her bum, Skye's free hand reached backwards in search of the toy in her behind. Maria moved her fingers away from the base and let Skye close her fingers lightly around the edges of it. As if testing it out, the talented tech expert slowly spun the glass toy, noting how her rectum could feel the lubed up metal rotating painlessly inside her.
Getting a little braver since it felt so comfortable, Skye began moving it up and down. Again, no pain followed so she pulled it side to side and stimulated more of her bowels with the fairly skinny tapered toy. Looking down between her legs she couldn't see it embedded, only viewing her shaved, pink pussy then Maria Hill's face with eyes fixated at her sex.
Skye was aware that there was no longer the other woman playing with the toy in her ass so she stretched back both arms and roamed herself. It felt so weird to feel where the end of the dildo was sticking out of her previously untouched rectum, even weirder when considering that it kinda felt good.
She was about to say something to Maria when she felt some small waves along the mattress. Looking to her left, the half-Asian agent saw that all the helping had gotten the leggy second-in-command worked up. Taking it like a real pro, Maria was easily plunging her own butt plug in and out of her ass with a torrid pace.
"Got jealous watching...mhmmm...needed to have some fun time too," Maria explained.
Skye's only exploration with the toy in her ass stopped as she watched her mentor masturbate with the butt plug she had used earlier. Without seeing her add anything other then spit, Maria was moving the toy like a green blur in and out of her butthole. Her toy was longer, maybe 6 inches, and a little thicker but to the dark-haired woman she treated it like it was nothing.
"Holy...crap," Skye gasped in awe.
"Sorry...needed a little something after watching you have all the fun," Maria finally spoke after a few more minutes.
"That was so hot," Skye thought.
"Okay I think you're ready for a big toy," Maria commented.
"You think so," Skye asked.
The younger agent felt a familiar grip placed around the wide base of the plug shoveled in her ass and knew what was coming. Hand returning to her clit, the half-Asian rubbed her clit and calmed herself as she felt pressure building against her sphincter until finally Maria was able to slowly slide the toy out of her freshly used asshole.
Rather then just set the butt plug aside, Maria Hill was too tempted to have a taste. Opening her mouth she raised the toy until it slid between her lips and glided along her tongue. She moved it in and out, twisting it clockwise in order to get every flavor that transferred from deep within Skye's backdoor.
"Wow...was not expecting that," Skye commented after seeing Maria taste test her ass.
"Don't knock it until you try it young one," the woman only a few years older then Skye told her.
"Sorry but doesn't that taste gross," the hacker asked, face scrunched up.
"Not at all. It has an earthy flavor to it but it's very pleasant. You can try it off this guy when I'm done with you," the SHIELD operative said, showing Skye the next toy.
"Holy crap," Skye exclaimed, seeing the next size up.
"You can handle it. Have faith in me," Maria agreed.
The two women weren't wrong in the least. In fact, as Skye sized it up nervously, she believed that the bulbous metal plug was thicker then her boyfriend's cock. That was enough to make the computer hacker nervous and knocked her down a peg when it came to her confidence at the moment.
"It's fucking huge," she swore.
"Then we add more lube," the brunette offered, placing a healthy dollop on both the toy and Skye's slightly gaped asshole.
Skye shook her head to get rid of the negative thoughts and get back to her positive attitude. She felt the cool liquid seeping into her opened bottom while her superior officer worked the toy to spread the lube around. This butt plug was different then the last one as Skye got a good look at it now.
Clutched in Maria's fist was a metallic toy that looked like a small bonnet pepper. It was 5 inches long, with one end tapered to a blunt point before expanding out to roughly 2.5 inches in width. From there it narrowed again to a small cylinder that went to the other end, a jewel-encrusted base that was several inches wide as to make sure the toy didn't get completely stuck into the user's backdoor.
"Spread your cheeks for me," Maria Hill ordered.
Once she thought it had enough on it to lubricate it for its passage up her rookie agent's dirt road, Maria pressed the tip back against her used asshole. She flexed her arm but this time the toy almost double the last one's size simple stayed in place, unable to breach the small opening. Easing off for a moment, Maria reminded her to relaxed herself further, before using her free hand to snake under Skye and find her pussy before trying to push inside again.
This toy was proving to be more of a challenge for Skye and even with fingers pleasuring her pussy it was still being denied by her stubborn arse. Thinking quickly, the more senior agent knew what might work so she got off the low bed and kneeled on the floor directly behind the dark-haired girl.
With this new position Maria was able to have her mouth much closer to the other woman's pussy and she was more then prepared to use that advantage. Opening her mouth, the second-in-command at SHIELD latched her lips around Skye's pink folds, started applying suction and darted her tongue out to flick her clit.
"Oh God...don't stop...ever," Skye moaned.
Maria had no intention of stopping any time soon and even put aside her quest to get the big toy into Skye's ass. She instead focused her attention on eating out the star SHIELD pupil, spreading her labia with her fingers so her tongue had an even easier time of batting at her sensitive nub.
Skye continued to scream loudly into the soundproof room but Maria was starting to change her approach. Rather then using all her energy at her clit, the brunette moved her tongue down to slither through the writhing girl's folds, getting a better taste of her juices. It was at this point with Skye so thoroughly relaxed that Maria's hand still on the base of the butt plug pushed in and succeeded where she had failed before.
"You did it babe," Maria celebrated.
"Fuckkkkk," Skye yelped. "That's massive!"
"And your tight little butt ate it up all the same," the brunette commented.
Skye had already forgotten the discomfort of having her asshole expanded further then it had ever been, aided in large part to pussy licking she had received from her mentor. The half-Asian rookie agent continued holding her ass apart as she could hear wet slurping noises as Maria's mouth continued eating her twat, routinely thrusting deep into her pussy to collect more of her juices while the massive bulbous toy rested in her bum.
"Fuck yourself while I eat you out," Maria ordered.
Using her mentor's oral skills to relax herself, Skye thought now was the optimum time to pull the jewel-encrusted toy from herself. Gripping tightly onto the pretty base, Skye used all the strength in her slender arm to apply steady pressure on the end and yank it from her dirt road. It was a real struggle, taking twice as long as it took to go in, but finally it came free with an audible pop.
Maria took a brief break in licking her pupil's snatch to poke her head higher and was greeted to the sight of the dark-haired hacker's gaped asshole. She got right overtop her arse so that she was able to look deep into her backdoor for a better look then after the first time, noting how the muscular ring's purple color transitioned to a flesher red with grooves noted embedded in the walls.
"Beautiful asshole Skye," Maria commented.
"Mhmmmm...shittttt....ugghhh," Skye groaned as the toy was shoved back in. "Thanks Agent Hill."
Maria gave her asshole a deep lick, causing Skye to cry out in a different but still positive moan before returning to her folds. The SHIELD agent was a bisexual so knew her way around a pussy and Skye was finding out just how well. The brunette had moved back to her clit, wrapping her lips around the nub.
Maria smiled inwardly as Skye stiffened like a log when she sucked on her clit, but was even happier to feel Skye lining the butt plus back up with her hole. As Maria batted her little pearl the hacker pushed the first portion of the toy into her ass, causing her to cry out in pleasure as a result.
"Someone likes having their ass played with, don't you," Maria asked.
"I really doooooo....God!"
Skye's reply was cut off as Maria made the cramp space around her ass and pussy more full. This time she broke the suction on her slit and instead just swiped at it with her tongue, which was still pleasing for the other woman. With her free hand, the brunette agent brought her two slender fingers together and pushed them into Skye's tight twat.
"Oh my God," Skye screamed, the digits hitting her reactive G spot.
The computer hacker rode out the shudder as waves of pleasure rocked her lithe body before reversing course with the toy in her ass. With the aide of Maria's fingers and tongue, Skye was able to push the toy further into her bowels, albeit slower than the rate the SHIELD operative was blasting her pussy.
"You are totally gonna cum, you big whore," Maria said with astonishment.
Maria was sensing that the rookie agent was getting closer even without Skye answering her question. Going for the kill, Maria continued her relentless assault on the other woman's clit with more rapid-fire approach. She also added a third finger into her filled cunt but her torrid pace did not diminish, and every thrust continued to hit her G spot.
"Oh God it's so good," Skye screamed again.
"Come on Agent! More! Fuck yourself! Oh yeah. Just like that," she was cheered on.
"Oh shit! Ohhhh....shhhhitttt," Skye screamed as she soaked Maria's fingers.
After her insanely loud and powerful orgasm, Skye went limp, barely keeping a grip on the toy resting halfway inside her backdoor. As her mental fog cleared, the tech expert slowly withdrew the metal butt plug until she felt the undesirable feeling of emptiness. Maria was right there, extending her hand to take the bulbous toy from Skye, returning it to the bedside table to be cleaned later.
"You see silly girl, anal isn't that hard," Maria said as both women came back to sit on the edge of the bed.
"After I warmed up it felt really good," Skye confessed.
"Obviously," Maria replied, holding up her cum-soaked fingers.
"So what's the next step," Skye asked her.
"I'm working that out now. I'll keep you posted but I my involvement is over."
"What? Why? You were a perfect teacher," Skye sulked.
"Because your team goes wheels up tomorrow morning, remember. But don't worry, I'll continue helping."
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Skye's Anal Quest