Disclaimer: I make no money from this. Must be 18 years old to read. I do not own or have anything to do with Arrow, Flash or Legends of Tomorrow, nor its characters especially Felicity Smoak, Oliver Queen, Maxwell Lord, Vandal Savage, Damien Darhk and Malcolm Merlyn.
Pairings: Felicity Smoak/Maxwell Lord/Vandal Savage/Damien Darhk/Malcolm Merlyn
Codes: M+F, Anal, DP, Oral, Orgy, Rough
Arrow: Alternative Timeline Part 9 - Bargaining Chip
by The Chemist
"So this is Russia," Felicity commented as she stepped onto the runway and looked around at her surroundings.
"Indeed it is Felicity," Oliver smiled over at his adorable and dorky assistant.
The pair had traveled together on a private jet from Starling City to this resort Russian city known for its scenic views. However, it was even more known for the big business deals, both legitimate and illegal that commonly took place here. That was actually what brought Oliver to the city, as he was representing Queen Consolidated so naturally he brought along Felicity.
Though the pair were regular fuck buddies since Oliver literally bought and paid for her ass, they were actually a great team from a business standpoint. Though Oliver was lazy and looked for the easy way out, he was well educated and gaining more experience by the day. However, it was Felicity who was helping to show his parents he was a worthy heir to the business, as her genius level intellect and undying loyalty to Oliver made her a perfect assistant.
"So the itinerary that we drafted up doesn't have any business taking place tonight," Felicity informed him as she thumbed through her smartphone.
"Not official business, however I do have a meeting with some fellow entrepreneurs," Oliver informed her.
"Really," she questioned.
Oliver explained to her that these type of dealings typically brought out the same people. Over the years he had grown to know some of them, all of whom Felicity would describe as shady...and that was if she was being as nice as possible. Some were friends from business only, while others he had known for a lot longer.
"Yes really. Now let's take the limo to the hotel and get some rest for tonight," Oliver told her as they walked towards the car waiting for them.
"Rest or rest," Felicity asked, her eyebrows lifting to get across her meaning.
"My good you have quite the hunger," he laughed as he held the door of the car for her. "We are jet lagged and the festivities tonight will require a sharp mind...so I'll grab a BJ in the car then we need sleep."
* * *
Felicity was happy that she remembered to brush her teeth before crawling into her bed and passing out for a couple hours after getting to the hotel. As much as she loved drinking and tasting cum, Oliver's in particular, it still left a really odd film in her mouth after a rest. Feeling like she combatted the jet lag well, she got dressed in a tight dress Oli told her to wear tonight and went and knocked on his door.
"Come in Felicity," his deep voice invited.
"Wow...you look rather nice," Felicity commented, seeing him in a tailor made suit.
"I should say the same to you," he smiled back. "Let's head down to the lobby. We are meeting some acquaintances."
The pair chatted casually as they passed down the hall and into the lift. A minute later they were spit out in the main lobby where the couple walked to the back lounge into a dimly lit bar. At a table in the back, surrounded by hulking figures, sat 4 men that Felicity all recognized from one way or another.
To the far left, where Oliver was headed towards sat a man Felicity had seen often throughout Starling City; Malcolm Merlyn. He was the CEO of Merlyn Global Group, the father to Oliver's best friend and a pretty sleazy man who always seemed to have a secret. Beside him sat a massive blond man that Felicity knew as Damien Darhk.
"Felicity, come sit," Oliver offered before introducing her to the group.
"A pleasure to meet you my love," an Egyptian accented man greeted.
"Thank you...Mr Savage," she said to the long-haired man who seemed to have a permanent sneer etched on his face.
"Leave it to Oliver Queen to bring a gorgeous girl to a private function," the man Felicity easily identified as Maxwell Lord, CEO of Lord Technologies.
"No offense, I would rather look at a beautiful woman's face every now and then rather then be stuck staring at your mugs the whole time," Oliver joked.
The group of 5 men shared a few laughs and stories as they got familiar with one another. They seemed to only meet like this once, maybe twice a year and Oliver was still the newest in the party. As the vodka flowed the conversation slowly started to turn from personal towards the political and finally to why they were all there.
"Men, just because we are here for business doesn't mean we can't have some fun," Malcolm said to the small group.
"What do you purpose," Vandal Savage asked.
"Just some cards, share a drink, wager a few hundred thousand dollars. You know, basic stuff," Malcolm answered.
"I suppose I could make myself available," Damien Darhk answered.
"I'm free as well tonight," the Egyptian agreed.
"Sounds great Mr. Merlyn. How's 9pm," Oliver Queen answered.
"9 it is. I'm on the top floor. Let's say a purse of $250,000 each," Merlyn added before the group went their separate ways.
* * *
The men had gathered in the impressive hotel suite just after their agreed upon time and after some socializing they broke out a deck of cards. Rather, the professional dealer they had bought did that as each of the dates the men brought made them a beverage at the expansive wet bar in the room. Naturally Felicity was Oliver's arm candy who stayed at the bar and interacted with the other girls who were all barely able to do basic math.
After awhile Felicity looked at her watch and found that it was nearly 1am. She'd been following the poker game with interested as she was known to play and win during her time at MIT. Oliver was doing very well, but he wasn't the chip leader, that honor fell to Damien Darhk. The three other men were floundering, a large gap opening up between them and the leading pack.
"Come on Oli, win this. You have business early tomorrow," Felicity thought, wearing her personal assistant hat and thinking of Queen Consolidated.
"Okay...I'm all in," Oliver announced as if reading Felicity's mind.
Oliver was hoping to win the hand and have Damien fold, which would have eaten into the larger man's considerable chip lead. However, the blonde man simply smiled at him like a wolf stumbling upon his crippled prey. Oliver wasn't bluffing so he wasn't too worried if the man stayed in, but the way the cards were falling for Damien he became nervous.
"Call," his opponent retorted.
"And the final card is...a Queen of Hearts," the dealer announced.
"Shit. I just nailed this," Oliver thought immediately.
Oliver had the better hand, it was impossible for him not to win in fact. He flopped a straight flush, a royal flush at that. However, he wasn't chip leader and based on the way Damien Darhk played, Oliver knew the taller man was either cheating or using some kind of magic. However, that wouldn't help him now and Oliver knew he needed to dagger the man now.
"Mr. Darhk, how would you like to make things interesting," Oliver asked.
"I'm listening," the smug man replied.
"Let's have a showdown, right here, right now," he proposed. "Winner take all."
"Now why on Earth would I do that? As it is, if I win this hand I take you out," Damien explained. "What could you possibly offer me that would make you think I'd go straight up for the win?"
"Let me put it like this," Oli started. "I beat you, I win your chips and you're on the sidelines. You beat me, you eliminate me and...you take my assistant for the evening. I see the way you look at her."
"She is very attractive," Damien agreed, looking over Oliver's shoulder to spy the blonde at the bar. "But I don't like unnecessary risk. I'll agree to your wager on one condition. No matter who wins the hand, I get the girl. And make it tomorrow night, I have business early in the morning and I won't be finished with her that swiftly."
"Actually gentlemen, as you can see you are not the only players at the table. For myself to agree to this, I would like an evening with the lovely girl as well," the formal speaking Vandal Savage interjected.
"Seconded," Malcolm Merlyn voiced.
"Agreed," Maxwell Lord added.
"So there it is pretty boy. Your chance to win the pot and the game and all it will cost you is losing that fine personal assistant of yours for a night. Do we have a deal," Damien summed up.
Oliver looked over his shoulder and motioned for the beauty to come to him. Doing as he wanted, Felicity allowed him to beacon her over. The group watched as Oliver whispered into her ear and she did a good job to keep her face neutral throughout the explanation. Only the trained observer, which everyone at the table was, saw her eyes bulge at one point. Her eyes made a quick scan of the men at the table before she whispered back to Oliver then sauntered away, every man's eyes on her fantastic backside.
"Deal," Oliver agreed, shaking each of the men's hands.
Even though he knew he had the hand won, Oliver was still starting to sweat. Damien wasn't natural, he could sense it. Standing up, the two gentleman squared up before the taller man flipped over his cards first. Exposing a pair of aces to go with the two that were in the community left Damien with one of the strongest hands in poker.
"Mr. Darhk shows four aces," the dealer announced, met by whistles by the two other players.
"Great hand," Oliver congratulated.
"Better luck next time kid," Damien smirked as he reached for the chips.
"But a royal flush is bit better," he countered, showing his cards.
"Holy crap," Malcolm swore, looking at Oliver's hand.
"The Straight Flush of Hearts wins the pot," the dealer announced.
Felicity looked around and saw the stunned look on all the players faces. Seeing a Royal Flush was a rare event, but seeing the best hand in poker beat the second best was akin to snorting cocaine with Jesus. The odds of it happening were nearly impossible...and that was even in the presence of an MIT grad.
"Well Mr. Queen, truly well met," Damien congratulated after his grimace wore off.
"My luck held up," the man in the green tie explained modestly.
"Our luck as well," Maxwell Lord added. "After all, we all get the lovely Ms. Smoak to share."
"I agree with my fellow businessman. Although the thought of taking turns isn't very appealing, I would hate myself if I passed on the chance to savagely fuck that adorable girl," Malcolm added, his words growing more passionate.
"Agreed. But it's quite late and we all have business with Stellmoor International in the morning. I recommend we part before we meet again tomorrow night," Vandal Savage reasoned.
"Well Oliver, though I'm disappointed about losing, at least I'm not leaving empty-handed," the taller Darhk said to Oli. "I hope Felicity is up for what I have planned."
Oliver didn't get the chance to reply to the smug yet crusty older man as he immediately started to walk away. Oliver grimaced as the words sunk in and he felt sympathy for his cute yet adorable assistant, who he found at his side. He looked over at her and saw too that the consequences of their bet had also washed over her, though her face was a mask.
"Let's go get some sleep," he told her, leading her by the hand back to their rooms.
* * *
Luckily the lateness of the hour they returned to their rooms and the fact she was still jet lagged meant Felicity didn't lose too much sleep thinking about what was to come. Before long she was getting dressed in her business attire and preparing for the busy day of meetings and negotiations that they needed to do.
It was 4pm when she and Oliver finally returned to their room, ordering room service and having a late lunch. The CEO of Stellmoor International was a woman named Isabel Rochev, and though she was extremely beautiful she was also a ruthless negotiator. Queen Consolidated didn't get as good of terms as they were hoping, however the deal did get complete despite the bigger amount of compromise they needed to allow.
"Hello. I'm here to collect Ms. Smoak," a servant to Damien Darhk announced as Oli opened the hotel room door.
"Are you 100% sure about this," Oliver asked the younger girl.
"Yeah, it's no big deal," Felicity shrugged off.
"Wrong, it's a very big deal," he corrected. "These men are...they may seem elegant and regal but they are bad men. All of them."
Oliver wasn't trying to scare her, only inform her of the situation she was placing herself into. All of Vandal Savage, Damien Darhk, Malcolm Merlyn and Maxwell Lord were criminals, thieves and murderers. They had assured Oliver that if Felicity needed to stop they would, but if they deemed it a rouse to end the festivities early then Oliver would be the one to pay.
"Listen Oli, ever since we first got together you awoke something...primal in me. I know not only look forward to sex but crave it. I want to keep testing my boundaries and this is just another opportunity," Felicity confessed.
Oliver looked at her stunned at the monster he had created. Giving her a final kiss on the forehead, Oliver wished her luck before she walked off the well-dressed servant. It wasn't a very far walk for her as Damien had another of the penthouse suites in the same hotel. With a swipe of the keycard, the servant led Felicity inside before showing her to the bedroom.
"My master wishes you to select the lingerie you'd like from the options he laid out. When dressed, return to me here," he explained.
After having her acknowledge his words, the servant left and closed the door behind her. Felicity looked over the outfit on the bed and started to strip off her blouse and tight business pencil skirt. She removed her bra and put on the black one for her, which fit her perfectly. She didn't know how Damien Darhk knew her size but she shrugged and switched into the matching thong.
"Nice boots, slutty, but I like," Felicity thought as she put on the black leather boots that went up to her knees.
"Excellent, I see it fits well," the servant commented as she left the bedroom.
"Umm...what you doing," Felicity asked.
Standing in one of the corners of the room, the servant had removed the chandelier from the ceiling and used the remaining fixture to thread a length of black rope through. Beaconing her over, Felicity walked apprehensively to the man who motioned for her to raise her arms. Doing so, Felicity found the man move with sudden quickness and before she knew what happened her wrists were bound together above her head.
"As per the Master's orders," he commented while stepping down from the ladder and walking behind Felicity. "As is this blindfold."
The MIT grad found her world go dark as the servant tied a thick piece of black material over her eyes. She had no experience with bondage or S&M, but she could kinda see the appeal of it. She had no control right now, this little man could do anything to her...and she kinda liked it. Her concentration was broken when she heard the lid of a bottle be popped followed by the sound of liquid being squeezed out.
"What's that," Felicity asked, a hint of panic in her tone.
"The last instruction I have. Now stay relaxed," he told her before bending down and moving her thong out of her massive canyon between her cheeks, a slicked up toy in hand.
* * *
"My oh my, what do we have here," Vandal Savage said in his Egyptian accent.
Off in the corner of the large room they saw Oliver Queen's very adorable personal assistant. She looked much different than last night, her ultra tight dress and high heels replaced by a pair of barely there black bra and panties as well as knee-high leather boots. Other differences were of course the blindfold covering her eyes as well as the fact she was tied with a rope to the ceiling above.
Maxwell Lord was the first to reach her, never breaking from his controlled walk. Running a hand down from her neck, his fingertip traced down her throat and between her tits, not overly large but clearly perky and perfect for her thin frame. He continued his descent over her flat stomach then hooked his finger into her panties only so he could pull them away before letting them snap back against her skin.
"Mmhmm...we are going to have fun tonight," Felicity heard Max speak.
Maxwell stepped back and his spot in front of the 22-year old was filled by Malcolm Merlyn. Ever since he saw Felicity back in Starling City always around Oliver he was taken by the gorgeous girl, especially her ass. Spinning her around to get a good look at the junk in her trunk, he was greeted to the sight of the thick ass in a tiny black thong. However, it was a large round object poking out from either side of the small strand of fabric that got his attention
"Well I see someone is prepared for tonight," Malcolm commented.
Pulling her thong to the side so everyone could have a good look at the three inch long black base of a toy resting over her asshole. Following Maxwell's example he snapped the thong back into place, this time the panties smacking the butt plug rather than skin. For added measure he cocked his hand back and gave each of her insanely large ass cheeks a hearty slap.
To show that she was a good sport and up to the challenge, not only did Felicity not whimper from the heavy blows but she actually wiggled her ass. Malcolm indulged her what she wanted to proceeded to give her 2 more spankings, much to her delight.
"I think we can remove this from the proceedings," Vandal spoke, taking Merlyn's spot.
Felicity felt the clasp of her bra become undone before Savage slid the garment up her arms. Felicity used her limited wrist motion to twist and hold the bra out of the way before feeling the eternal being reach out and clutch both her nipples in between his thumb and finger. He increased his pressure until the hardened nipples were painful, at which point he released them with a grin plastered on his face.
"Oliver Queen explained to you the situation," Damien Darhk asked, stepping in front of the tied up girl. "You may speak."
"Yes," she replied.
Damien adopted a pleasant grin on his face before his face contorted into a look that would have terrified the girl if she wasn't blindfolded. Reaching his arm to her, he took her neck in his hands and began to tighten, cutting off her airway. Felicity had been briefed that he did like to dominate his women so was prepared, her face a mask for the 10 seconds he choked her before he released his grip.
Felicity felt so vulnerable in her restrained position, but it was still turning her on. She felt Damien's hands back on her but not on her throat. With one hand resting on her hips, he closed his free hand around the monstrous butt plug currently filling her. He looked up and saw her mouth open wide but silently as he began pulling, but the toy was large and not coming out without a fight. Finally his strength conquered the tightness of her backdoor and the toy that was over 2 inches wide at the base popped free.
"Oh we are going to have so much fun," Malcolm smiled while seeing her asshole stay gaping open for several seconds.
Rather than put the toy aside or place it back in her, Damien stood up and spun the girl to face him and the rest of the group. Her lips were still parted and when she felt the rubber butt plug touch them she got the hint and opened wider. The tip was only an inch thick but as Damien continued to push more of the toy inside, Felicity had to open to the point of unhinging her jaw.
"How does that dirty plug taste," Vandal Savage asked, a bulge already formed in his pants. "You like the taste of your asshole?"
"Based on the sheer size of her asshole and who she came to Russia with, I'm willing to say she's tasted and enjoys her own shitter," Damien Darhk answered, bringing smiles to everyone's faces.
As the tall blonde man was making Felicity flavor her own asshole, Maxwell Lord rounded the bound girl and finished removing her thong. He took a sniff and found out Felicity was very aroused, which gave him an idea. As Damien removed the butt plug from between her lips, he took the chance and stuffed her wet panties into her mouth, making her taste that hole too.
"Yes, suck on them," Malcolm Merlyn instructed.
"I assume none of you mind if I have the first offering," Damien Darhk announced. "After all, it was my positioning that got us this rendez vous."
His words were met with 3 nods, not that the man who possessed deadly magic actually cared what the fellow billionaires thought. Stepping behind Felicity once more, Damien bent her down a little more so her huge ass pushed back to him. His pants were gone in an instant and with his erect cock in hand he didn't hesitate in stuffing half his length into her snatch.
"Mmmphhff....ffmmmph," Felicity moaned against her soiled panties.
After withdrawing once, he slammed back in but this time with his full length. As his hips slammed against her ass, her mighty cheeks rippled from the blow. Loving the view of it, Damien did so repeatedly with both hands on her tapered waist so he could pull her back as he speared forward.
"He is relentless," Vandal watched on in admiration.
Felicity most definitely agreed with the immortal Egyptian's assessment of her fuck buddy's style. Damien had the size and strength of a linebacker and he wasn't shy about using it to dominate the bound girl. Over and over his huge cock, which she guessed stood close to a foot in length and with impressive girth slammed into her at a speed that a normal man would have cum within minutes, yet he seemed undisturbed.
Damien didn't know it but his fierce fucking was pushing the horny girl to an orgasm that he didn't think was possible. Felicity felt it well up in her suddenly, pleased that the huge man could bring her to climax so fast. Then she released seconds before cumming that this would be no normal orgasm.
"SSHHHHHIITTTT! I'm cumming," Felicity screamed, her thong spat from her mouth.
The three businessmen watched on as Felicity squeezed her thighs tightly around the cock in her pussy right as Damien pulled out of her. He sensed she was a squirter only a second before and the drive to see her gush fluid was too strong. The second he pulled out of her snatch it erupted as a large stream of clear fluid jetted out and splashed on the marble floor beneath.
The men practically gasped in amazement and stroked themselves, getting harder watching the innocent looking girl drench the floor from squirting. Damien slapped her on the ass for her good work before letting his fingers soak in the fluid beneath. As she stood bent over at the waist, resting against her bounds in the ceiling, he flicked the fluid at her, her juices landing on her pretty face.
"So slutty," Vandal sneered though very aroused.
Seeing that the other men were all pantless with erect cocks, Damien Darhk was more than happy to have a breather as his poker friends had their turn. With a wave of his hand while muttering something inaudible, the rope bounding Felicity's hands undid and was tossed aside. The MIT grad felt knots in her shoulders from the awkward position she was held in for hours but the orgasm that just rocked through her body was making her ignore that.
"Good...now crawl over here," Malcolm insisted from his spot on the sofa.
Felicity turned to face her group of men here for her and soaked in the scene. Damien who had just fucked her raw was off by the bar having a drink as he caught his breath while the other three men were seated around the sofa. Finding the man from Starling directly ahead of her, Felicity sank to her knees and moved on all fours until she was kneeling in front of Merlyn.
"I like what I found," Felicity said in her sultry tone as she grabbed his stiff 8-inch member. "What do you want me to do with it?"
"Suck it babe," he told the fellow Starling inhabitant.
With a wicked grin on her face, Felicity glided his cock towards her face before engulfing his bulbous head between her lips. Malcolm couldn't help but let an audible moan as her hot wet mouth worked the first half of his cock over. The horny man was lucky that he had already entertained a pair of former Russian ballerinas the night previous or else he'd be dangerously close to popping his load in her mouth once she started inhaling his whole cock into her mouth with each stroke.
"Mmmmm," the woman in only leather boots moaned as she noisily slobbered on his meat stick.
"Oh yeah suck that cock," Malcolm groaned, his hands tightening on the back of her head.
He pleaded with her to keep going through body language alone by applying downward pressure on the top of her head to convey his message. Felicity got the hint as she was use to Oliver enjoying face fucking her as well. Relaxing her throat, she opened her mouth wide and allowed her technique to go out the window so the man old enough to be her father could thrust her all the way to the base of his cock.
"GGLLKKK...cllllhhhh," Felicity choked.
Seeing her face turning a few shades of red, Malcolm released her from his tight grip and allowed her to swallow in fresh air. In the process Felicity had spat up a lot of saliva to make his cock covered, which helped lubricate her throat as he pulled her back down.
However, rather than being upset at him for choking her with his mighty cock, she opened her mouth to take him once more into her mouth as opposed to curse at the asshole. Of course Malcolm didn't delay for a millisecond as he pushed his hips forward until his cock slammed back down her throat. He watched as her eyes nearly bulged out of her face as her gag reflex was narrowly avoided being tripped, small tears forming and rolling over her model-esque cheekbones out of reflex. His hips were now raising off the sofa as he opted to actually fuck her rather than the pull and hold technique he first employed.
Not content to simply sit and watch the girl choke on a fat cock, Vandal wanted action. Though his immortality taught him patience, the Egyptian high priest would show none of that now as his lust for the thick-bottomed girl was too great. Standing from his seat, he rounded the kneeling girl so he could squat behind her. Spitting into his hand and rubbing it around the head of his cock.
"Owwwhhh," Felicity whelped as her backdoor was thrust open by the Egyptian.
Her shriek was more from surprise than actual pain as her eyes and focus had been spent on Malcolm in his attempt to make her swallow his cock. She was getting good at guessing the size of manhood just from simply being inside her, so she estimated Vandal was rocking a long yet skinny dick, which was perfect for anal.
With the work the massive butt plug had done to loosen up her back passage, Vandal found that he was able to stroke his entire 10 inch cock into her phat ass. A crazed look was etched on his face as he held onto her wide hips to hold her steady as he squatted above her and pounded down into her booty.
"Fuck me, fuck me, fuck me," Felicity encouraged, her face flushed from being fucked in her face at the same time.
"You heard her Savage, give that bitch what she wants," Maxwell Lord said.
Vandal gave the horny girl what she wanted and really started to stroke into her tight ass. Even with how well-used her asshole had become in the previous months, the thickness of his cock and the tightness of her sphincter meant that he was not able to plow into her as fast as he would like, not yet anyway. It did however mean that her rectum hugged him so constricting that he didn't care that he couldn't pound her to oblivion as it felt better then almost any other woman he'd been with, which was saying something.
Sex was becoming like a drug for Felicity in the terms that she craved it and once she had a taste for it she couldn't stop. Even now, the thick-bottomed girl was just closing her eyes and letting go of herself, all the good and bad things in her life so she could just be lost in the amazing feeling of a hard cock driving deep inside her, even if it was a mass murderer in her ass.
"How's her ass, Savage?"
"Amazing," the immortal killer answered.
"Then why don't you take a break and share with the group," Maxwell asked.
Felicity was a reader of fantasy books and had a learned a few things from them that applied to her current situation. In a sword fight, much like in an orgy, when you were 1 against a group, the best strategy was to take out your enemies one at a time. However, with the men pumping her then trading off before getting too close to their orgasm she knew it would be a long, long time and much abuse before getting any of them to pop.
Not one to complain, the MIT grad rolled with the punches and got to her feet after feeling Vandal pull out of her exquisite ass. She wasn't free for long as she felt Maxwell Lord's hand close around her hourglass waist and spin her around so she was facing away from him. Knowing what he wanted, Felicity bent forward and sank into his lap, aiming his cock up with her wet pussy.
"Actually I had another hole in mind," the National City billionaire corrected.
Not really caring since her bowels were sufficiently loosened by the massive butt plug first then Vandal Savage, Felicity tilted his member back slightly then squatted down. She bit her bottom lip as he first pushed open her sphincter but once that unpleasant part was done she settled into a rhythm.
Maxwell Lord was in pure joy at this point. Always having a thing for fit chicks, after all he was dating Agent Danvers back in his hometown, he was even more excited to be sodomizing an ass as fine as Felicity's. Showing off her surprisingly athletic side despite looking like the hottest librarian he'd ever met, the thick-bottomed girl was bent over so much her hands rested on the ground as she lifted her ass up before crashing it back down on his lap.
"Here, open and swallow," the Egyptian demanded.
Felicity though nothing of the request and di as she was told, like was expected of their sex slave. As his dick glided along her tongue and his tip poked against the back of her throat, she kept concentration enough to continue to ride her asshole up and down Maxwell Lord's thick cock. What she lost in speed, Maxwell more than made up for by spiking his hips off the sofa and thrusting deep into her bowels.
"Tell me where that dick came from," Vandal Savage asked knowingly.
"My ass," Felicity answered timely.
"That's right. Can you taste your shitty asshole all over my cock," he further prodded, seeking to humiliate the younger girl.
"Yes," she admitted, knowing it was what he wanted to hear.
"Let her lean back," Malcolm Merlyn piped up, back on his feet.
Savage reluctantly pulled his slick cock from her mouth and allowed the curvy girl to indulge Merlyn's whim. With Felicity now resting her back on Lord's chest, she had a harder time generating enough lift from his lap so instead she focused on taking him balls deep in her rectum and grinding on him, which apparently was working for him.
When Merlyn stepped between Felicity's wide spread legs he knew he had surprised her from the look she gave him. Releasing what he planned on doing, the personal assistant did her best to stay calm and remind herself that she had survived and even enjoyed a similar experience with the well-hung Diggle brothers.
"Shit...now it's a party," Felicity groaned as Malcolm pushed inside her free pussy.
Not her first time getting double penetrated, fucked by two cocks at the very same time, it was still something she wasn't very used to. Trying to stay relaxed as she rested on Maxwell, the two businessman did all the work as they thrust into their respective hole they occupied on alternating rhythm.
Felicity felt like the night was passing by quickly but still none of the four businessman had spent their seed. She had no idea how long Malcolm and Maxwell spent see-sawing into her while Damien Darhk and Vandal Savage watched on, stroking their cocks. However, it had been enough time that now the two men on the outside looking in had grown restless and wanted back in on the action.
"I believe it's my turn again," Damien Darhk commented, his menacing figure shading the trio on the sofa.
Maxwell Lord may not have been a physical match for Damien, but Malcolm was more than capable of holding his own in a fight with the former League of Assassin member. However, there was something mystical about the hulking blonde that had been different when they were at Nanda Parbat together.
As soon as Malcolm stepped back, freeing Felicity's snatch, the MIT grad was pushed off the National City businessman as well. It felt odd for Felicity to go from being stuffed with nearly a foot of cocks in both holes to being completely empty. Damien Darhk was going to change that and in a hurry as he pulled the blonde onto his lap immediately.
Felicity knew exactly what to do as she got each of her juicy legs on either side of him to straddle above his dick. Having already fucked her pussy raw earlier, Felicity assumed correctly that he'd want to sample her other hole so as she sat she angled him backwards and plunged the 3rd different cock in an hour towards her asshole.
"My Lord you're huge," the nerdy girl groaned as she sat on his meat.
"And you are still somehow tight," the blonde man replied.
Felicity smiled at the compliment as she rode up and down and whole cock, which was the second biggest she'd taken next to John Diggle. Despite the fact that a lengthy amount of time had passed, Felicity was still rocketing her great ass up and down. She was tiring and covered in a layer of sweat that made her sunkissed skin glisten in the lighting but she refused to let it show.
"I have seen billion of girls in all my years walking this Earth and truly yours is one of the all-time greats," Vandal Savage said from behind her, palming each of her fantastic cheeks.
Damien was a powerfully built man so barely registered as Felicity's chest came to rest against his as he was still so focused on pumping his lengthy pole into the sexy woman's butt. He was unaware that it was Vandal who initiated her to lean on him but he would soon learn why. For the Egyptian's plan to work, he needed to allow the girl to be loosened up as much as possible, so for the next minute he simply waited and stroked his cock while the former League of Assassin member used his club-sized pole to batter her asshole..
Finally Vandal felt like he had waited long enough for Felicity to be widened out as much as she ever would. His cock was still dripping wet in the sexy woman's saliva from when he face-fucked her not long before, which would be of paramount importance to what was to come.
"Is he about to do what I think he's going to do," Maxwell Lord asked, his hand going to his cock and stroking it even harder
"Shit. I think he is," Malcolm grinned while doing likewise.
Vandal stepped up behind her milk-colored cheeks before exchanging a knowing glance with Damien. The hulking blonde man did a toothy grin then slowed his thrusting down so that Felicity was laying flat on top of him, her meaty legs wide open for the standing killer. Her pussy was underneath Damien and thus unreachable but that didn't matter to him as he placed his cock's tip neared the entrance to the girl's asshole, which of course was already occupied.
"Ummm...awwhhh...guys...I don't know if you'll both fit," Felicity discouraged while still moaning.
"You don't give yourself enough credit baby. This booty will totally stretch for us," Savage commented to calm her fears.
The girl continued to impress them with her resolute attitude and willingness to experiment sexually as rather than squirm to escape the situation, Felicity decided to help her masters. The MIT grad did her best to relax for the eager men to accomplish their goal as they focused on causing her as little pain as possible. Her helping was found to be working right away as Felicity could feel her anus slowly expanding to let a second dickhead have access.
"Bloody hell...fuuu...shhhhh...iiitttt," Felicity swore.
Though the beautiful girl was clearly in discomfort, the immortal being had no intention of stopping his progress. Vandal continued to push into her filled backdoor, determined not to stop until both he and his fellow businessman and killer were both balls deep in her asshole. Maxwell and Malcolm watched on in amazement, stroking their lengths as the two men took turns pushing into her expanding asshole, both of them half way into her booty at this point.
After the initial pain of having two cocks fill the same hole, especially that hole being her tight ass with two lengthy poles, Felicity found herself accepting the situation. No longer feeling like her backdoor was on the verge of ripping, she was actually enjoying the sensation. Her constant crazing to push her sexually was a large driving factor as was the fact being so horny made the double anal penetration surprisingly liberating.
"Oh God...need to cum," Damien said through gritted teeth.
Vandal Savage wasn't paying attention as he finally met his goal of cramming his entire cock into Felicity's asshole at the same time as Damien. With his final goal met, the Egyptian felt his own orgasm approaching like a flash of lightning. As if they had coordinated it before hand and executed it perfectly, both men gave in and groaned in delight as two loads of hot jizz rocketed from the tips of their penis deep into her bowels.
The two men slumped their heads in pure exhaustion as their nearly two-hour long fuck session was over. Vandal was the first to pull out of the equally tired woman before walking back and slumping down into the chair opposite where he and Damien had been simultaneously sodomizing Felicity. Meanwhile, Damien had enough strength left in him to roll the blonde from his lap, his cock spilling out from her wide gaping dirt road, and spilling her onto the sofa beside him.
"Don't mind if I do," Maxwell eagerly commented.
Wasting no time at all, the National City businessman shot between her legs and instantly had his cock plunging into her pussy. Felicity moaned and cooed but not with the same vigor as before, the night's festivities of being used and abused clearly having caught up to her. Maxwell paid that no mind while going balls deep into her well plowed snatch, pumping his entire frame into each thrust.
"Shit...can't...hold out...any longer," Maxwell groaned while filling her pussy in.
"I figured you're stamina would improve with you fucking that Danvers chick regularly," Malcolm mused.
"Cum for me baby," Felicity told him, her fingers reaching down to caress his full balls.
Her slut words, not too mention her hand playing with his nuts, still tight pussy and 2 hours of fucking her finally added up. With one last good thrust deep inside Felicity and holding himself there, Maxwell finally let go and allowed himself to finally cum. With a final grunt, he emptied his load into her hot wet cunt.
"And then their was one," Malcolm grinned, being the last man standing.
Having watched the beautiful assistant for whom he had seen countless times around Starling City being stuffed 8 ways from Sunday in truly the sluttiest display of depraved sexual desire, Malcolm was ready to burst. The former League of Assassin member had always enjoyed watching others fuck and tonight was no exception.
Felicity may have been out on her feet but she still had the wherewithal to know when she saw a man on the verge of cumming. Sliding off the comfortable confines of the sofa after Maxwell Lord had moved out from between her juicy legs, the MIT grad got to her knees no more than a foot from Malcolm's throbbing dick.
Looking down and seeing the cute yet adorable girl waiting for him to paint her face with mouth open wide and tongue sticking out, Malcolm did just that. With that imaged fixed in his mind, the businessman felt his legs grow weak as his semen bubbled up from his balls and shot from his tip.
"Awww," Felicity cooed once she felt his warm fluid start to ooze out onto her pretty face.
Malcolm stepped closer so that he could shoot the rest of his load with more force onto the girl, coating the rest of her face. After several streams had landed on Felicity, he smirked as he enjoyed the look of her with cum splattered on her forehead, nose, cheeks and lips. Felicity actually enjoyed the feel of his warm jizz on her skin, and the smile she flashed the businessman before shoveling it between her lips showed that.
"Miss Smoak, you aren't done yet," an exhausted Damien Darhk informed her.
"You guys all came, hard might I add," Felicity told him. "As per the deal."
"Yes, but you left a mess," the tall blonde explained. "Clean it up...with your mouth."
Based on the glare in his eye, Felicity counted herself lucky that she didn't turn to stone on the spot. Knowing that arguing would be the worst idea possible, Felicity nodded her head in acceptance. The cum that the three men had shot into each of her perfect holes had plenty of time to leak out and puddle on the floor beneath her as she took the double facial.
Crouching down, the MIT grad turned personal whore lowered her gorgeous face to the marble floor beneath where her hips were resting over. Hoping that the maid service in Russia were good at their job, Felicity pressed her plump lips to the ground and began slurping up the cum that had dripped out of her pussy and asshole. She could taste subtle differences depending upon which hole he liquefied load had come from.
"Well...I think we can all agree Oliver truly has a filthy whore on his hands," Malcolm commented as Felicity finished drinking up the three loads of jizz.
"And now, not to be an ungracious host, but I have business to attend to here in Russia tomorrow and need my sleep," Damien explained.
Felicity was the first to gather her clothes, which were still sitting folded on the guest room bed, slip into a white robe and exit the suite. She still was in disbelief that she had just slept with four different men all at the same time, but she had. She went straight to her room, drank a few mini-bottles of tequila before showering away some of the shame before falling asleep the second her head hit the pillow.
* * *
When there was no replied and he couldn't even hear any rattling, Oliver used his card key and opened Felicity's door. Walking into the room, he passed by a stack of clothes he remembered her wearing the previous night. In front of the bathroom door laid a hotel robe and as he looked to the bed he found Felicity passed out, not bothering to have put on any clothes before doing so.
"Hi sweetie," Oliver spoke while lightly rubbing her back as he sat beside her prone form.
"Mhmm," she grumbled. "Coffee...please."
Though it paled in comparison to the java from Jitters, the grounds the hotel provided in the room would do in a pinch. Oliver didn't get her to talk as he went about making the coffee as Felicity slowly perked up enough to throw on a shirt and a pair of panties.
"Any chance we can delay flying home by a day or 5," Felicity asked with a grimace on her face.
"Still sore," Oliver smirked.
"I doubt I can sit for a very long time," Felicity shared. "At one point there were two different penises in my butt."
"Wow! Double anal. Impressive Miss Smoak," he told the assistant. "Didn't think you had it in you."
"Oh I certainly did," she smiled before wincing in pain as she strode too much. "And I'll remember it for awhile."