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,or Supergirl, nor its characters especially Felicity Smoak, Slade Wilson, Isabel Rochev, Maxwell Lord, Oliver Queen and Alex Danvers.
Summary: To extract revenge on Maxwell Lord, Oliver sends Felicity to make a deal with ISabel Rochev with the intention of Lord catching wind and hijacking it. However, while his favorite mistress is away, Oliver seduces the other Danvers sister who's in town for business.
Pairings: Felicity/Slade Wilson (Brief), Alex Danvers/Oliver Queen
Codes: MF, Anal, Voyeur
Arrow/Supergirl: Business and Betrayal
by The Chemist
"You're sending me...ME...back to Russia!"
Felicity was well aware that she just screamed at her boss, her very rich and powerful boss at that, but she didn't care at all in the moment. She didn't care that the man was drop dead gorgeous and that she was his one number mistress. She didn't care either that he ran a company worth billions.
She didn't care about any of that when he brought up that short sentence. Russia was where she accompanied him for negotiations between Queen Consolidated and the company owned by Isabel Rochev. And in order to close the deal, he sold her off to 5 other businessmen who had their way with her for hours. In every hole...sometimes two of them at once in the same orifice.
"Felicity...you have every right to be upset but please hear me out on this," Oliver tried to calm her.
Felicity was fired up and pacing the ground of his office. As per usual, the Diggle Brothers stood outside the glass-walled room, acting as always as Oliver's personal bodyguards. She didn't hear what Oliver had just said but snapped back to reality as he approached her and clutched her arms to hold her steady.
"Listen to me Felicity. I need you. You are one of the few people I trust with such a sensitive matter," the bearded man told her.
"Really? I can't just be swapped out for one of your other whores? Aren't we all interchangeable to you anyway," she replied, getting defensive. "Or you can't risk their prestine holes so may as well send the ruined Felicity."
"Stop Felicity. I trust you...and I've given up the other women. Except for Helena," Oliver soothed.
Felicity was not expecting to hear this from the renown playboy. For as long as the tech expert turned personal assistant had known Oliver, he was always one to play the field. Even his engagement to Helena Bertinelli was only to link two great families and Starling businesses, much like in days of old.
But for Oliver to have sworn off all other women except to her was a massive deal. It was essentially the bearded man choosing to be with Felicity exclusively since his arrangement with the Bertinelli was only on the surface. He harboured no love for the woman and she didn't for him either, in fact she was a pure lesbian.
"So why does it have to be me," Felicity asked, the anger gone. "I thought you said Isabel's company was dirty and corrupt?"
"Oh it is, which is why this is all a ruse," he informed her. "The company is bad, rotten. And this is why I'm going to pretend to get a secret deal done to purchase it..."
"Which is why you would send your personal assistant who is brilliant and whom everyone thinks you are grooming to become the new CFO when you take over for your parents..." Felicity filled in.
"But it will get leaked through a fake mole," Oliver finished.
"Who are you screwing here?"
"Lord Technology," the man with an emerald tie answered with a wide grin.
Maxwell Lord, the founder and CEO of his own company, was one of the 5 men who did horrible things to Felicity that ill-fated night on her last and only trip to Russia. Of course Felicity allowed it to happen, but Maxwell was a huge asshole about it. Of course, he was also a dick to Oliver on his last visit to National City, but Felicity didn't have to know that was also a factor.
"Perfect! I'm in," Felicity agreed readily.
"Thought you might be. So it'll leak I've sent you to do a deal, he'll act and likely pay WAY over the odds. That'll cripple him in future dealings then I give the SCC some less than law-abiding info on Isabel's company and kill two dirty birds with one stone," Oliver finished explaining.
"Will it be dangerous," Felicity asked.
"Potentially...but I have a plan for that. You'll have protection," the Queen heir answered.
"Better," he grinned. "Let me worry about that, you need to go home and pack immediately. Private jet has wheels up in 2 hours."
"It's a covert deal. It needs to happen quickly or else too many red flags then Lord won't hijack it. So stop worrying and go get ready," he said, shooing her from the office.
Felicity gave a big smile of excitement and hurried out of the office. Oliver couldn't help but chuckle when she came rushing back in seconds later to pick up her purse she left behind before scampering out to the elevators once again. He'd have one of the Diggles drive her home and to the airport with all the documents.
However, his job wasn't done yet. He needed Maxwell Lord to catch wind of the set-up or else this was all for not. Luckily he knew someone in National City that was well connected and had just as big of an axe to grind against the fellow billionaire. Picking up his cell phone, he scrolled his contacts to the K section and selected the 3 number.
"Kara Danvers! How are you," he spoke to the Katco employee.
"Oliver! I'm really good. Planning another trip my way," the dorky girl asked excitedly.
"Sadly not...but I have something good for you. Still have aspirations of becoming a reporter?"
Oliver and Kara talked for the next ten minutes about how the National City resident could both help him and screw Maxwell Lord, the asshole who was secretly making her city a worse place to live. Of course Oliver didn't know she was Supergirl, nor did Kara volunteer that information. But the chance to legally take out the villain was too good to pass up.
* * *
"God I hate this place," Felicity said."
Only 6 weeks earlier, the quarky yet brilliant personal assistant had been standing at the same location, at the top of the staircase exiting Queen Consolidated private jet. Though there were more reasons than this to hate the ex-Soviet state, Felicity had her own personal reasons to lump in.
"Ms Smoak. I am Boris, your driver," a man with a thick Russian accent said to her.
As per her arrangement with Oliver, she had the driver show him the specific encoded message that the handsome man sent to Boris to make sure everything was secure. Safe with that knowledge, the perky blonde climbed into the back of the limo, however she was not alone. Sitting in the back with her was a large, burly man...who also happened to be ruggedly good looking despite the eye-patch covering his left eye.
"Oh...hello," Felicity greeted, instantly nervous.
"No need to be concerned Ms. Smoak. My name is Slade Wilson and I'm Isabel's business partner," he said with an Aussie accent of all things.
Felicity couldn't but be helped to admire the physical perfection of the man sitting across from her. She instantly recognized his name as she was the type that knew every detail when it came to business. But she had no idea that Slade would resemble a Greek God or some type of fictional superhero...or antihero for that matter.
"Yes I know...and you know me...yay," Felicity cheered, trying to take the awkwardness out of her first comment but only managing to make it more cringe-worthy.
"Have you been to Russia before," he asked as they pulled onto the road.
"Once...left a bad taste in my mind," she responded.
"Well that is truly a shame. A lovely woman like yourself should never have an experience that isn't pleasurable," he commented, placing a hand on her bare knee.
It all hit Felicity at once that the older gentleman was flirting with her...and not to subtly at that. Thinking back at all her lessons with Queen Consolidated, there was always a sexual tone during meetings as it served to unsettle and disarm their opponent. And now Felicity understood that it worked 100%.
So lost in her own thought process, Felicity was barely aware that Slade had gotten out of his seat and slide into the one directly beside her. She snapped out of it as she felt his large hand start to rub along the flesh of her inner leg. To have such a great looking man stroking her tender flesh made her excited, but she cursed herself for wearing a short skirt with her business suit.
"Oh well I guess there was some pleasure...yeah actually, definitely some...but altogether sore. Like I'm talking for weeks...like barely able to sit..."
Felicity's rambling, which she did routinely when nervous, was cut short by the Aussie. This time it wasn't his right hand on her thigh that got her attention focused back on him, but rather his free hand as it came up to cup her face.
"I'm going to kiss you now," Slade told her.
Felicity was so shocked that she didn't reply to the burly man. Instead she watched him approach her until less than a foot away from her face, at which point she shut her eyes and stopped talking. The kiss was soft as his lips pressed against her's, holding them there for several second before pulling away.
He pulled back just far enough to see her eyes were still closed and she wore an expression of satisfaction before leaning back in. This time his kiss had hunger that the first one lacked, as he pressed against her for a short time before going back in repeatedly. Not to become predictable, the dark-haired man moved his mouth down to start kissing the side of her very sensitive neck.
"Mhmm...we shouldn't," Felicity moaned, trying to remain faithful to Oliver.
"You come on Felicity. This is clearly what you want," his lips said before returning to kiss her neck. "And I've always believed bedmates make for better business."
As if to clarify his point about her wanting it, Slade traveled his hand up her juicy thigh and under her skirt. Sure enough, the patch of panties laying directly in front of her pussy was soaked through, her excitement for their perspective tryst apparent.
"No...I can't," she said with more conviction.
This time Felicity gripped his forearm with both her smaller hands and pushed him away. Never one to take advantage of a woman, Slade pulled his hand away from her skirt and followed his momentum back to where he originally started, on the other side of the limo.
"No problem. I must apologize, I read the situation wrong," Slade back tracked.
"It's fine," Felicity answered honestly.
"I don't know who this man is that you are saving yourself for, but I hope he's worth it," the Aussie stated.
"He is," the brainy girl thought with a smile.
* * *
"Alex, it's me," Kara said into her phone. "I've arrived in Russia safe and sound."
"Okay well be careful," her protective older step-sister demanded.
"I will...besides, I'm Supergirl. I can handle myself. Now tell mom that I'm sorry I'll be missing Sunday dinner," the Kryptonian added.
"She can't be pissed at you since I'm doing it as well," Alex shared. "I'm in Starling City to follow up on some possible alien involvement. It's a longshot but Director Lane wants me to check it out none the less."
"Well call if you need me. I should be able to fly back in about an hour...or less, who knows," Kara told her.
"Just do your job so Kat realizes how awesome you are and hires you as a full reporter," her older sister told her before they hung up.
* * *
"So far so good," Oliver asked.
"Yup. Met with Slade Wilson...nothing happened...and figured I'd come to the hotel, video chat with you then try to beat this jet lag with an early morning nap," Felicity spoke into her laptop.
"Okay perfect. There was a problem with the bodyguards I got for you but they'll be there by this afternoon," the bearded man replied.
"I miss you," Felicity moaned. "I know why you can't be here...but I still miss you."
"I miss you too. You'll be back from Russia as soon as we can manage it. Until then, stay calm, stay warm and know I...I love being with you," Oliver told her.
He had stopped himself short of saying I love you but the reaction from her lit up face was as if he had said those 3 little words. She was definitely in love with him and she was the closest a serial sex addict could come to feeling love and wanting to settle down with one person.
"Get some rest Felicity, you have a busy day planned. I'm gonna go to the gym and we'll talk later," the businessman said.
The pair said their final words before closing the application for good. Felicity's flight had gotten in sometime in the middle of the night, with her actually getting a few hours sleep during the voyage. Now she would get a few more hours and be ready for the busy work day which included a private party to celebrate the business transaction.
"Wait a second. He said he was going to the gym...but was in dress clothes...which means," Felicity's wheels were spinning now.
Opening back up her laptop, she opened an app that she had created herself. While it wasn't unique, it was highly effective for spying. This time she would use it for innocent albeit perverted purposes of using the spyware to activate Oli's computer's camera and watch him as he stripped down.
However, that wasn't what she saw right away. Instead, her heart plummeted in her chest and she felt like vomiting. On her screen, she was watching her muscular boss with a sexy short-haired brunette in his arms, kissing her passionately on the mouth.
"That son-of-a-bitch," Felicity cursed.
Deciding between closing the laptop in anger or continuing to watch, Felicity tapped a few buttons and activated the microphone on the laptop as well. She knew he would leave the laptop on his dresser, and he did it again with the positioning perfect to see both the bed and the space beside it where they currently stood and kissed.
"I'm still not sure the business that brought you to Starling, but I'm happy you let me take you to dinner Alex," Oliver said in between kisses.
Launching another application, this time it was a facial recognition one. After a few seconds, she broadened her search pattern to include state-wide agencies, then federal instead of her quicker yet narrow city-wide scope. Less than a dozen seconds later, the profile of one Alex Danvers of National City popped up on her screen.
* * *
For Kara, her trip to Russia felt great. The DEO had been trying to push Supergirl more and more so the prospective of a 5,000 mile trip excited them. Kara was eager for the trip as well, for several other reasons as well. The chance to prove herself as a reporter to Kat Grant, her mentor and boss was at the forefront of those.
She caught the jet stream and arrived well before Felicity Smoak's jet, borrowed from Queen Consolidated just as Oliver told her. She took a few pictures of Felicity getting into the limo and even one with the hot blonde with Slade Wilson in the car as well. She flew overhead and monitored the pair with X-ray vision, but it was uneventful other than some light kissing.
"Well Oli sure likes surrounding himself with beautiful women," Supergirl thought as the limo pulled up outside a swanky hotel.
Oliver had messaged Kara and asked if she wouldn't mind watching over Felicity until the afternoon when she would have the protection he secured for her. Supergirl would have liked to got a better lay of the land but she agreed without delay so found herself periodically using her enhanced vision to look in on the brainy assistant from another rooftop.
"Hey, it's Oliver," the dorky girl said as she say the two chatting via their computers.
However, in a few minutes, she was going to be even more devastated than Oliver's personal assistant when they saw the handsome man making out with the brunette with an athletic build. That was because Kara recognized the gorgeous woman as Alexandra Danvers, her own adopted sister.
"Alex!? What!? Why," so many questions flooded her mind. Too broken hearted, the naive Kryptonian fly into the lightening Russian sky, needing some privacy to grieve.
* * *
"I totally get what Kara saw in him," Alex Danvers thought to herself.
She was home the night Kara and Oliver came bursting in, completely oblivious to the DEO agent laying on the sofa as they were lost in their passion. It was out of character for the Kryptonian who was raised as her sister, as it was just as much out of Alex's character to be doing the same thing. But Oliver was charming, clearly handsome and simply irresistible.
And maybe then all the physical reasons that drew Alex to Oliver was the fact that her sister got him first. Her sister, who could fly, was bulletproof and had a morality compass that only pointed North. Her sister who was perfect and destined for greatness. So when her business brought her into contact randomly with Oliver Queen and he actually flirted with her, it sealed the deal...she needed to have him.
"Get these clothes off," Oliver said with visceral desire.
Alex had no complaints with that request and helped him shrug the form-fitting leather jacket off her shoulder and to the floor. She was dressed down, or rather as dressed down as DEO agents got, so her skinny jeans went next. Having bent down to peel them off her athletic legs, Oliver was now eye level with her delightful ass in only a blue thong, so he bent further forward and lightly bit the soft flesh.
"Woahh," Alex screamed with a smile on her face.
Oliver followed it up with a slap to the other cheek as well, leaving two equally red but very different marks of her fit booty. Needing to feel him once more, Alex practically pulled him to his feet before she pulled his head towards her and brought him in for a kiss. It started with just lips pressing together but quickly morphed into tongues battling for supremacy as they kiss passionately.
Not content with merely having the physically fit woman bottomless, Oliver finished the job by pulling her V-neck shirt over her head before they resumed kissing. Alex reached around behind her and unclasped her bra, having no reservations of sharing her medium-sized tits with him, which Oliver graciously scooped up with each hand.
"Bigger boobs than her sister," Oliver thought, unable to not compare the adoptive sisters.
Of course that wasn't the only difference Oliver noted between the two Danvers girls. For one, Alex was a lot more aggressive than the dorky girl in glasses. Case in point was how the short-haired brunette had whipped off Oli's shirt, pushed him roughly to the bed then made just as short of work with his pants.
"Very nice Mr. Queen. I can work with this," Alex commented, referring to his erect cock, which her hand was already lightly stroking.
"I'm glad to hear," the businessman replied as she bent down and took his tip between her plump lips. "God that's good."
The woman in her mid-to-late 20s by Oli's reckoning was resting on her knees and elbows between his outstretched legs while he laid on his back with his head in the pillows. Her hand worked the bottom section of his cock while her mouth expertly bobbed on better than two-thirds of his fleshy tool. What made the blowjob that much better was that her big, brown eyes never broke eye contact, despite how much of his veiny cock she shoved into her throat.
Once again, Oliver's mind compared the two sisters and once again Alex came out on top. He had no idea that she was bring her A-level stuff to this tryst since she was well aware that the Starling City billionaire had fucked her sister, but the fact remained she was giving one hell of a blowjob. Up and down her head continuously bobbed, alternating between going fast and slow as well as sometimes swallowing the majority of his dick while other times only his tip.
"You seem like a man who would like this," Alex said before sinking even lower towards the mattress.
Oliver must have had a small blackout while lost in his inner thoughts, because the next instant Alex's lips were no longer wrapped around his pole. Instead, the DEO agent was playing with his balls with her tongue. Of course Alex didn't forget about his dick, as she continued to stroke him with the build-up of her spit from her messy blowjob being excellent lubricant. Her talented tongue felt great as she took turns taking one of his large testicles in her mouth at a time.
"I think you like doing it as much as I like having my nuts sucked," Oliver retorted though he doubted she could enjoy the sensation as much as he was.
Alex was thrilled that her varied technique was having the desired effect on the Starling City playboy. She doubted that Kara would've shown such a take-charge attitude or been confident enough to do more than a well-intentioned but ultimately inexperienced blowjob. Putting Supergirl to the back of her mind for now, the naked woman moved up and took the tip in her mouth once more, gladly slurping up the clear pre-cum that she milked from him.
"Trust me, you haven't felt anything yet," Alex proclaimed with a smile as she immediately shoved half his length back into her mouth.
Using her mouth and hand in unison, the woman who hunted aliens as her day job started giving Oliver a sloppy blowjob, making sure she kept eye contact and made loud sucking noises. The muscular man was like every other guy she'd gone down on, as he loved looking into her puppy-dog eyes, but couldn't help but tilt his head back every now and moan a swear word.
"I see your reputation is well earned in terms of size and your great stamina," the brunette told him before licking up the underbelly of his cock all the way to the belly.
"Stick around and find out more," Oliver replied with a cocky but well-earned grin.
Truth be told, Oliver was also impressed with himself for withstanding her oral assault for the past 10 minutes. While he fucked more times in a month then 99% did in a year if not more, he hadn't had sex in a number of days. And if he didn't stop the eager woman soon it would be too late...and there was no chance he wasn't going to do dirty things to the more sexually confident Danvers.
As much as Oliver was enjoying Alex's well-versed fellatio ability, his resistance to spewing a healthy amount of jizz down her throat was ebbing away. Nowhere near done with her for the night, he knew that he had to break the perky brunette's skilled oral attack. Acting quickly before his mind got washed away in the pleasure the lithe girl was doling out, he rolled to the side just enough so his dick popped free of her talented mouth.
The DEO agent started to say before she was cut off by the billionaire's hasty and decisive movement. Flexing forward as if doing one of his daily sit-ups, the tall man hooked his hands under Alex's arms, feeling her bouncy tits against his palms in the process, then pulled her up the bed. He placed her face in the pillows beside him then shuffled quickly down the bed so that he was now between her prone legs.
It didn't take a rocket scientist to realize the position that Oliver wanted her in. Grinning because of his take-charge attitude, Alex planted her palms against the soft mattress and pressed herself up. This move rewarded the tall man with the brunette's little bubble butt being drawn up to be almost directly in front of his smiling face.
"Fuck subtlety," Oliver thought to himself.
Not holding back at all, Oliver bent forward and his tongue instantly contacted her pink folds that his fingers had already plunged the depths of. Licking up from her nub, the successful man dragged his tongue skyward until reaching her tight hole. Pushing his head even further against her, Oliver felt her ass cheeks against his closed eye sockets as his tongue buried deep in her twat.
"Oh God yes," Alex shouted uninhibitedly.
As good as being eaten out felt, and Oliver was actually quite good at it, it paled in comparison to a good dicking. Wanting him inside her on the double, this time it was Alex who showed off her elusiveness. Normally that was reserved for fighting aliens, but today it was so that she could roll to the side and flip the much large man back onto his ass.
"Frisky," Oliver smiled brightly as the smaller woman swung a leg over his powerful torso.
During his brief time licking her twat, Oliver knew for a fact that the brunette was gushing wet, yet she still eased her down on his girthy member slowly. As his tip and several inches disappeared inside her, he realized why. Despite being a couple years older than Kara and seemingly more experienced, this Danvers girl was equally as superhumanly tight.
However, she was a quick study and after bouncing slowly with only a quarter of his tool filling her out, she started going faster and deeper. She was wrapped up in her passion to not get Oli to throw on a condom, which suited him just fine. Instead she was focused on extracting every last drop of pleasure from their hook-up, as she rapidly ascend then descended on his fully erect member.
"Fuck...your dick feels so good filling me out," Alex moaned.
Opening his eyes as wide as he could, Oliver imprinted that moment into his brain forever. Her naked skin seemed to glow in the scant light that dimly filled the room. Alex's perky tits were bouncing in front of her with each bounce downward, that was until his large hands went and corralled each. They filled his paw perfectly, much like Kara's did, but Alex's twins had a bit more overflow,Her long legs, not as long or awe-inspiring as her adopted sister's though, were propelling her intense riding, while the view in the mirror behind her afforded Oliver the luxury of watching her meaty ass clap down onto his lap.
They were both fueled by lust and passion so taking it slow or easy never factored into their tryst, nor was the fact their was a little green dot glowing on the top of his computer which was usually not there. It was clear to each other that they were simply using the other for sure sexual gratification but they were adults and perfectly okay with that.
"God you feel so good," Oliver groaned while biting his lip.
Over and over Alex used her seemingly endless energy to ride to the top of his pole only to collapse back down as soon as she got there. Not just laying around, Oliver helped feed more of his dick into her greedy pussy by thrusting up just as she got to the end of his pecker, driving deeper into the horny girl.
Alex ran a hand through her shoulder-length dark hair as she continued to ride his full length. Though he was feeling guiltier than usual for somewhat cheating on Felicity when he gave her the idea they were exclusive, he was still a stud in the sack and was hitting all the right spots. It was because of this that she didn't mind doing all the work, especially since she was being pounded towards her long awaited orgasm.
"Yesss...just like that," Alex cooed. "Keep fucking my tight pussy with your big cock."
His large hands felt so good squeezing her small but perky tits, the palm of his hand feeling great as it rubbed her erect nipples. To help push herself over the edge and cum for him, Alex took one her hands that were being used to help propel herself up his rod and moved it between her legs. As she began rubbing her sensitive nub her riding slowed from the frantic pace she initially set, but the slower style suited them both. Oliver's dick had more time to properly probe her twat, plus it insured he would last longer and not cum before her.
"Cum for me," he demanding, sensing her orgasm drawing ever closer.
Though Oliver had known the girl for less than a day he had a lifetime of sex with beautiful woman so he had a good sense when one was on the verge of cumming. He drove his meat pole into her tight twat repeatedly with hands now at her tits to tweak both her nipples, a move that always seemed to help Felicity cream all over his dick. The maneuver seemed to work for Alex as it drew more moans and screams from the DEO agent. Finally after a few more minutes of the intense fucking, Alex earned her just rewards.
"Oh yes...I'm cumming...ughhh...awwhhhh...yes," Alex screamed at the top of her lungs as she came.
The physically fit woman fell to the bottom of his cock and stayed there as she rode out the amazing orgasm. Clearly exhausted from the massive energy drain, Alex tipped forward until her perky boobs were pressed against Oliver's naked chest. Her flexibility allowed for her to stay so fully flexed while the man's cock remained buried in her dripping pussy.
"Tell me Oliver...do you like when dates let you fuck them in the ass," Alex said seductively as she pressed back to a seated position.
"These sisters are as different as night and day," Oliver thought before keeping his tone level as he replied. "You could say I'm a big fan of anal."
"You look like you're having a stroke," Alex jested, her chest still heaving from the massive amount of energy she burned from the ride and orgasm.
"No, it's just that...I'm shocked. "You? You tiny little girl take anal! You cease to amaze me," Oliver shared while reaching for his bottle of lube in his bedside drawer.
"What can I say, I'm a butt slut," she replied with a grin. "Now let's stop talking about plugging my asshole and let's actually do something about it."
Oliver let the surprise wash over him, pulling the brunette back down to kiss her on the mouth once again. Alex kissed him back then felt his strong hands on her body, exciting her even more. Not solely touching her for the sake of it, Oliver manhandled the second Danvers girl he'd fucked in the last few weeks so that he rolled them onto their sides, her back pressing against his muscular chest, her plump ass nestled in his lap.
Behind her, she could feel Oliver's hand that was on her shoulder move down to grab his cock. He moved around to get his hips lined up perfectly so that his dick was slightly lower then his target; her clenched asshole. His top arm still rested across their hips, holding her still. She knew it was time to go when the familiar feel of a cock head pressed against her backdoor and came to a rest.
"Time to fuck me in the ass," Alex asked sweetly but rhetorically, looking back over her shoulder.
Words once again could not explain how horny the girl he had just met was making him. She completed her tease by wiggling her hips, simultaneously sensually rubbing his tip with her crinkled entrance while leaning back against his spear to add pressure.
Oliver snapped out of the lust spell that the little brunette had placed him under and finally reacted. Squeezing her womanly hips with more intensity, he pulled her backwards while also pressing his hips in towards her. He didn't want to be too forceful to start so it took a good 10 seconds until he felt Alex's forbidden hole yield, accepting the first inch of his cock in the process.
"Mhmm...ughh," Alex gasped with mouth wide.
Oliver also groaned, but he made a conscious effort to temper the volume of his, not wanting the experienced girl to think it was first time penetrating an asshole before. In reality, Oliver had fucked almost every girlfriend he ever had up the ass since being a sophomore in high school.
Being on their sides was perfect for the pair. In the beginning it allowed for the horny man to be in control while also allowing him to feel her smooth curvy butt cheeks on his hips and lower leg, not to mention the access to her tits. Oliver would have preferred greatly to be seeing her perky globes bouncing around freely in front of Alex while he continuously worked his most of his pecker into her rump, but he'd have to be satisfied at the moment for merely groping them.
"God you're super tight," Oliver groaned, realizing that being sodomize wasn't something she'd done lately.
The position was also useful for Alex as well. Being on their side give him control but also tempered as deep he could go unless she wanted more. This time though, that wasn't an issue as Oliver was proving himself to be an excellent anal lover, both gentle and considerate while also firm and enjoyable. She continued to encourage his thrusting deep into her bowels by rocking her hips back at him as he thrust his cock forward, causing her shapely ass to jiggle on contact.
"Oh shit...you're huge," Alex moaned in response. "You feel so good in my tiny ass."
"Starting to like National City more and more. Maybe time to set up an office there," Oliver thought as he rested with his entire 9-inch cock impaled in the older Danvers' rectum.
Oliver allowed himself the selfish pleasure of just resting a few moments while balls-deep within her sensational ass. Once he came to terms with the sensation of having his cock deep inside Alex's bowels he proceeded onwards. He placed one hand on her firm boob to grope while the other went to grab tightly onto her hip that was facing up.
Now with them both adapted and ready to actually fuck, Oliver retracted his hips until only his tip was left inside. As soon as he felt her muscular ring clamp down on his sensitive patch of skin at the crown of his tool, the billionaire playboy drove forward while simultaneously dragging her back into him. His entire cock slid into her anus in a flash. The feeling was beyond words for the adulterous man as he continued to slowly push and pull his lengthy tool into the willing female.
"Fuck this feels good," Oliver grunted while now continuously pumping into the sexy girl.
"Oh yeah! Go all the way! Deeper, deeper, deeper," she screamed encouragement.
Alex wasn't only encouraging him with her words, but with her actions as well. The man was turning out to be a great anal lover as he was taking things moderately slow, but still being firm and enjoyable. To help spur him along, the sexy DEO agent wiggled her hips and pushed back against him as he thrust forward, causing her shapely ass to jiggle as he plowed deeper into her butthole.
The pair were now really finding their stride as they continued to fuck each other hard. Oliver was driving into her faster by the passing minute but Alex seemed not only up to the task but was thriving. She was screaming in delight, which was an extraordinary feat considering how tight she was and how insanely big he was.
"Fuck you're so tight," he groaned, his orgasm pushing closer with each thrust into her bowels.
"Cum for me baby," Alex cooed, thrusting herself backwards onto his erection with all the force she could garner.
With his pending orgasm close, Oliver seemed to lose control of his passion as he was fueled by excitement. While still pile driving his cock into her asshole with as much force as he could muster, the adulterous male was pulling straight out of her rectum before slamming her sphincter back open as he went balls deep back inside her. He didn't think about how each time he did so it caused her hole to begin to close so when he sawed back in it could have caused her great pain, which it luckily didn't. The copious amounts of her own pussy juices still lining her hole was helping with his forceful re-entry.
"Oh God...keep giving me that cock...just like that," the horny girl cried.
"Almost there," Oliver grunted through gritted teeth, amazed with himself that he held out this long.
"Oh Fuck. Need to cum," Oliver said, orgasm seconds away.
"Ugh...yes...cum in my ass," Alex answered as their sweat covered bodies continued to slam into each other.
No sooner had the words been out of her mouth before Alex felt the first squirt of hot jizz shot deep into her bowels, coating them. All Oliver could do was tightly clench the athletically fit woman's hips and quickly stroke his cock into her asshole for the last few seconds. The muscular man continued to erratically thrust his hip sideways into her now still body as stream after stream of his thick fluid came flowing out into anal canal.
Tossing his head back, the cheating billionaire buried himself in Alex for the last time as the last few streams of thick warm cum into her rectum. He held himself still in the depths of her bowels until his love gun had emptied completely. Exhausted he rolled over onto his back and panted.
"My God," the big man groaned.
Alex looked over her shoulder and saw his facial expression relaxed into one of serenity, his iron-like grip on her various curvy body parts relented and his hip thrusting stopped, replaced with the mere light twitching of his sensitive dick still invested in the comfortable clamp she called an asshole. Using her legs one last time, the innocent-faced brunette slid forward before rolling onto her stomach beside the exhausted man.
"By the way, you've met my sister before right? Kara, Kara Danvers," Alex asked, looking as the handsome billionaire.
"Yeah, on my last trip to National City," he explained, rolling on his side to face her. "Why do you ask?"
"Let's just keep this little...coming together between us," the dark-haired girl replied.
"My lips are sealed," Oliver answered as neither of them noticed the light on top of his laptop wink out of existence.