Disclaimer: I do not own or have anything to do with the show Arrow nor its characters, specifically Oliver Queen and Felicity Smoak. I make no money from this act of fiction
Summary: Alternative world to the one set in Arrow where Oliver never left on the Queen's Gambit and stays to work at Queen Consolidated. Felicity is Oliver's personal assistant and asks for a raise.
Pairing: Felicity Smoak/Oliver Queen
Codes: MF, Anal, Blackmail, Oral
Arrow: Alternative Timeline - Olicity
by The Chemist
Oliver Queen was many things...Green Arrow was not one of them. Not in this Earth anyway. Back on Earth-One he was the vigilante who took up the bow after 5 years where he was assumed dead. However this Oliver Queen, in his tightly fitted Italian suit never got on the Queen's Gambit, thus continued in his life of privilege.
Without the experiences on the mysterious island of Lian Yu, Oliver continued on his path, just like his Earth-One counterpart would have done if not for the years spent there. Therefore, this Oliver Queen had ascended the ranks of Queen Consolidated through mostly nepotism rather than merit, though he had picked up many lessons in decept and underhanded dealings.
He was currently occupying the second highest position in the company, only reporting to his mother who he was slowly edging out of her own company. However, for now he was content with his corner office, little amount of work he actually had to do and his sexy personal assistant who he was currently scoping out her amazing ass as she did whatever she did.
"Hey Oliver I just have to get this," Felicity Smoak said after seeing the caller ID on her ringing phone.
"Mmm," he nonchalantly replied, busy in his own world.
Leaving her boss alone in his more secluded workstation that was attached to his main office, Felicity went through the door and back into the glass-walled room. It was her landlord on the phone and it wasn't a conversation she wanted Oliver to really overhear.
"Hi sir...yes I'm aware it's just that money is really tight...I know that but I also couldn't help that my mom got sick and I needed to send her all my spare money...yes I'll get the rest of your rent money...yes I do have a job, a good one in fact," Felicity spoke with her landlord.
Felicity knew that this conversation was coming, she just wasn't looking forward to it. The last few months she had been tardy getting her rent money to her landlord but a third month in a row was pushing it now. Despite being the personal assistant to the heir of the Queen fortune didn't come with a fat pay cheque, a situation Felicity was all too aware of.
"No I'm not going to quit this job and find one with more money. The Queen family are good-ish people and I've been with them for nearing one year. Listen I'll get your money so just stop. I have to go, bye."
"Felicity, did you make that reservation for me and Helena," Oliver asked as she entered the closed-off work area.
"Yes sir, 8pm like you asked at Adriano's," Felicity replied, back to business mode.
"My favorite booth?"
"Of course sir," she smiled before summoning all her courage. "Can I...um...talk to you about something?"
"What's up," the billionaire's son asked.
"Well as you know I've been your personal assistant for almost a year now...and I think I've been doing a pretty good job. So I was wondering if I could have a raise," she asked, blurting out the last sentence all at once.
"A raise? For what? Doing a pretty good job? I expect everyone at this company to do their jobs with some level of competence or else they are out on their ass, collecting food stamps while living in the Glades," Oliver scoffed at her question.
Oliver was now on his feet and standing on the same side of his heavy oak desk as Felicity, mere feet away from her. He had drawn himself up to his full size which was an impressive 6'2 inch tall and almost as wide across the shoulders. Even as he began lecturing the timid assistant, Felicity couldn't help but note how extremely handsome the man was.
"I'm sorry for asking..."
"Do you know how many people want your job? To say they work intimately for the future CEO of this storied company? And then you come, asking for more money then we already fairly compensate you for," Oliver continued to berate.
"I know and I'm super sorry. It's just that my mom got sick so I'm paying a lot of her medical and drug bills. I could just really use the extra money that the raise would allow for so I could get my landlord off my ass," Felicity justified.
At the mention of her ass and her sad story, the wheels in Oliver's head started to churn Desperation was a very powerful motivating factor and as a business man, the Queen heir knew it was something to always take advantage of. Also, the mention of ass reminded Oliver of Felicity's backside, which was far and away the biggest, thickest and best one he'd ever seen in his nearly 30 years and he loved the fact he got to stare at it all day while she wore her collection of super tight wardrobe.
As Oliver glanced up and down his personal assistant, he noted that today was no different then any other in terms of her attire. Felicity looked stunning in a pinstripe dress that sadly didn't show much in terms of cleavage, however it checked the boxes in terms of showcasing her best assets. The shortness of the dress showed off her thick yet very feminine legs while it was as tight as ever to make her ass stand out as always.
"Okay so since you are only doing a 'pretty good job' and you're not up for a job evaluation for another 8 months then the only way to give you a raise is if you perform more work for me," Oliver suggested, his mood and posture a complete reversal then what it was one at the beginning of their conversation.
"Sounds completely fair, sir," Felicity said excitedly.
Felicity could feel his eyes on her as they once again worked their way down her fantastically fit body all the way to her black high heels then back up her matching stocking-clad legs. She hadn't gleamed his motives yet as he began walking around her body to now settle behind the slightly younger woman.
However, as the heir to the Starling City business pressed his chest against her back and inhaled a deep breath through his nose to sniff the scent of her hair, the situation dawned on her. As if to prove she was correct, his arms wrapped around her body and his large hands instantly clutched her medium sized tits, squeezing them firmly.
"Wow...Mr. Queen. This is super inappropriate," Felicity said while pulling his hands from her, though he could tell her heart wasn't 100% in it. "And you have a girlfriend, Helena."
"I do indeed," he grinned.
Felicity let his one hand fall from her grip as he moved it to her flat stomach this time, however it didn't remain there for long. Drawing it down her tummy, he scooped under her short dress and found her mound through her panties. She was already wet just from his touch seconds before and was instantly moaning as he rubbed the damp patch.
"And I don't care," he whispered in her ear while she felt his finger friction her slit.
Her other hand had stopped pulling him away from her body so Oliver once again took up his firm grip of her breast. Not the largest set in the world, they did fit Felicity perfectly both in terms of size and perkiness as they matched her personality in that regard.
"You want the money don't you?"
"I do," Felicity said, her face going serious before his finger rubbed her clit once more.
"How does an extra...$1200 a month sound," Oliver asked while groping her boob.
"Amazing," her face contorting in a mixture of shock and pleasure.
With her answer, Oliver took his hand out from under her skirt and off her tit in order to find the concealed zipper on her back. He tugged it down and the dress fell from her shoulders to bunch around her feet. This time when his hands went back to her body it was on skin, sends jolts of electricity coursing throughout her excited body.
"Just to reiterate, you are now my little whore. Understood," he asked while kneading her bra-clad breasts.
Grabbing her firmly by her upper arm, Oliver spun the thick-bottomed girl back around so her perky tits pressed against his solid chest. He tilted her head upwards before devouring her mouth with his lips, his tongue slicing into her's immediately with the blonde giving up no resistance.
As Oliver's large hands closed around her phat ass and began pawing it, Felicity felt a wealth of emotions. She was essentially lowering herself to being a personal prostitute to this man, though she had crushed on him for 3 years, ever since she was hired to the company's IT division.
"Come on, up on the desk," Oliver instructed.
Felicity had gotten lost in the kissing, ass kneading and her own thoughts that she needed his words to prompt her to climb up on the desk. He had cleared the wood surface with a swipe of the arm already so as he helped her get to her knees there was no mess. A hand between the shoulder blades with some pressure told her all she needed to know about what he wanted.
"Like the view," Felicity said coolly after glancing over her shoulder to see her boss staring at her ass once more.
Oliver didn't answer right away instead he used the chance to run his hands over the smooth, rounded surface of her perfect ass. It was insanely large for such a skinny white girl to possess, but there was still one, very small obstacle in his way. Peeling away her thong left him with the view he was after, that of her pink pussy and tightly puckered asshole flanked on either side by a heavy cheek.
"Ever since I hired you I told everyone how good you asshole must taste," he said before parting her cheeks before leaning in and licking from her pussy, over her taint and finally on her ass. "And like always, I was right."
Despite the fact her snatch tasted sweet and flavorful on his first pass, he only had eyes for one hole. Pressing his face deep into the crevice her awesome ass made, the privileged man repeated lapped at the crinkled surface of her asshole.
"Oh...sweet baby Jesus that's good," Felicity moaned in response to each of his tongue's lashings.
For the first time in minutes Oliver finally surfaced and allowed both of them to catch their breath once more. The CEO's son bit her large cheeks playfully while the horny girl kept wiggling and pushing her ass back towards him to get more of his oral assault.
She got just that as she felt his tongue press back against her asshole, but only for a moment. Continuing up, Oliver licked up her crack and along her spine, moving over to her flanks to kiss her flesh there as she straightened up against him. With a hand on each of her hips he rolled her over, the blonde spinning under his lead until she was seated on the edge.
"Nice tits," he commented after Felicity flung the black bra aside.
Their lips found each other's once more with more of their electric chemistry before Oli broke away and leaned forward. Her boobs were perfect for her slender upper body, each capped with a small pink nipple that stood at attention even before his lips closed around them.
"Mhmm...yes," the glasses wearing assistant screamed.
His mouth and hand worked in unison so while he sucked and smacked his lips on one of her boobs he was pawing at the other. Felicity would give a sharp cry every time he pinched her erect nipple, but he had the sense it was from surprise not pain. Finally he broke away from her perky twins and leaned her back down to the desk and spread her legs.
"Let's see how good you taste here," Oliver said, staring into her blue eyes while swiping his tongue threw her puffy slit.
Felicity's head instantly started swimming as she layed on her gorgeous boss' desk as he ate her out with expert precision. His tongue was well versed in the act as it lapped deep within her hole one instant then would repeatedly flick her clit while his lips formed an air-tight seal around it.
Oliver had bedded hundreds upon hundreds of women in his short 28 years so he had his routine down pat, especially for what he wanted with his bought for whore. First using two fingers in her twat, Oliver blasted her pink hole while swiping her sensitive nub. As she got lost in his effort he pulled her legs further apart and slid one of his pussy juice-lathered fingers and placed it against her well-licked asshole.
"Just relax okay," he told her. It wasn't a question but a statement to the younger woman as he pushed his finger into her backdoor which yielded without much effort.
"Rub this," Oliver demanded as he placed her hand at her clit.
Instantly Felicity heeded his suggestion and did as her boss told her, flicking at her bean like she had done countless times when she masturbated, many times while fantasizing about the very man currently fingering her asshole.
"I...keep going," Felicity begged.
She was probably confused when he slowed down his thrusting but it was for a reason. Pulling out so only his tip remained keeping her backdoor open, Oliver pressed a second meaty digit against the first then pushed forward. It wasn't as easy with two but they fit and she was soon moaning once more as his tongue dipped deep in her cunt.
"Oh fuck," Felicity surprised both herself and Oliver by screaming in pleasure.
"She's totally gonna cum," Oliver thought while he picked up the pace with his fingers as her rather tight sphincter pushed open to accommodate.
As if to confirm his suspicion, Oliver looked up at Felicity and she flashed him her devilish grin that he had never seen from her before. He pulled his mouth away and watched her face as she continued moaning with her plump lips in a wide O. Felicity's hand kept up her rapid diddling of her clit while Oliver was nearly matching her pace with his finger thrusting in her booty.
"I think...ohh...that I'm...awwhhh...cuuummmmiiinnngggg!"
Oliver had made enough girls climax in his time to know that Felicity was about to even without her fragmented warning. Doing exactly what he was, his fingers continued to push and pull inside her as her own hand was a blur. Finally Oliver felt her dumper clamp down on his fingers and he stopped blasting her backdoor to not cause her pain.
"Oh my God...no boyfriend has ever done this before," Felicity told him as she basked in her post-orgasm bliss.
"And you obviously like it," he asked knowingly.
"Honestly...I've never felt anything so strong before," the blonde answered.
As soon as Felicity felt his two digits leave her butt she lifted herself off the desk to sit at the edge and bring him in for a kiss again. His passion was running strong as he dragged her off the desk by holding his hands on her head. The pair continued to kiss as Oli stepped backwards, bringing the IT genius in step with him.
"Ever wonder why I had this sofa added to the private office," Oli asked her as they stood in front of it.
He kissed her before she could reply, this time it was her tongue which entered his mouth first. However, as she pressed the advantage on the making out, he took her hand and placed it on the bulge in his pants. She took his hint squeezed around his cock through the fancy material, outlining it to be 7 inches long and it didn't even feel fully hard yet.
"I had a good idea," Felicity answered as she dropped to her knees. "After all, I've probably cleaned a good liter of cum from the leather already."
"My aim isn't always perfect," he grinned while Felicity continued to massage his hardening cock through his pants.
"This is so wrong," she said but with a wry smile. "Helena would kill me if she knew."
"You have no idea," he smirked as she withdrew his cock from his pants.
"Wow! Like seriously. Wow," Felicity said, staring at the largest cock she'd ever seen.
Her hand automatically picked it up and began to stroke it gently as she observed it more closely. His smooth shaft was decorated with some small veins, while his cut manhood with exposed pink head looked so inviting to suck on. He was also both longer and bigger then anyone she had ever been with, measuring a full 10 inches when at full size.
With a wicked grin on her face that she couldn't hide, Felicity licked her lips before guiding his cock towards her face before engulfing his bulbous head between her lips. The muscular man couldn't help but let an audible moan as her hot wet mouth worked the first half of his cock over. Oliver had been with a lot of women however the young blonde on her knees with her adorable glasses still on could handle herself against the best of them he thought as she started inhaling his whole cock into her mouth with each stroke.
"Yes. Suck it," he moaned in delight towards the skilled cocksucker.
"Mmmmm," she moaned as she noisily slobbered on his meat stick.
"Fuck. So good with your little mouth. I bet my little whore loves swallowing cocks and guzzling cum," Oli commented, holding her hair as he bucked his hips.
"Didn't know I was that easy to read," Felicity bantered back as she licked the side of his pole.
"With those dick sucking lips and naughty librarian glasses, it's my experience they need a good fucking the most. But don't worry, I won't be cumming for a long time," he bragged.
Unfortunately she had to pull her mouth off his manhood to get return his dirty talk, but he welcomed the break even if it only lasted a moment. The second after giving her replied the lips of the horny girl were wrapped back around his glistening cock, already dripping wet in her copious amount of saliva.
Felicity parted her plush red lips and brushed her long hair behind her ears then took him into her mouth again. Just like before Oliver moaned audibly as she started sucking him off while he was left with his head tilted back and fingertip digging into the top of her head. She enjoyed the affect she was having on him, but shifted all her focus on building momentum as she bobbed her head up and down his towering pole, taking more of him inside her each time.
"Mhm...shit," the billionaire heir groaned. "Definitely worth the money so far."
"Right. Thanks," Felicity replied, strand of spit connecting her lips to his cock still.
Oliver loved the fact the girl seemed to love giving head based off her very enthusiastic performance thus far. He wasn't sure if buying a personal prostitute via extortion would mean she'd half-arse it, but quite the opposite. And now he would get to experience her divine oral skills whenever he wished, plus more.
For Felicity, it was business as usual as she had grown use to life on her knees from her time with ex-boyfriends and the odd random one night stands. However this time she wanted to give Oliver a great blowjob for two reasons. The first reason was for the fact he found her hot enough to give her an unscheduled raise so he could fuck her. And other reason was because she had always found the pampered heir attractive and now was her chance to display herself.
The blonde pulled her mouth from his dick, now slick with her saliva and used her hand to feverishly beat his meat. She did this so that she could use her tongue to help corral his heavy sack to bring it into her mouth.
"Oh God...so good," Oliver grunted, gripping her head tighter.
Felicity took turns taking each nut into her mouth and giving it proper attention before she moved back to something more solid. She moved half of his pole between her lips while stroking the other half. Using her free hand to massage his sack again, she could hear how much he appreciated what she was doing.
"Thought you'd like that," she grinned.
Felicity found herself helped off her knees with her mouth making an audible popping noise as her lips broke the tight seal around his cock. After giving her a deep kiss, Oliver eased them down onto the sofa so his back was resting against the upright while Felicity's was pressed back against him.
"Um...are you gonna put a condom on," she asked, feeling his head rubbing through her folds.
"Absolutely not," he answered as he thrust inside her.
"Mhmm...ohhh...kay," Felicity moaned as he started pumping inside her.
He fucked her steadily but with an edge of gentleness since it was their first time together and she was remarkably tight for a 24 year old. Using half his length he pushed in and out of her gushing mound, feeling her pussy spreading and relenting with each passing thrust. Finally he felt his base get fully sheathed in her wetness with his abs pressed firmly against her amazingly huge ass.
Taking off the training wheels now, Oliver held little back. Rearing back before spearing into her at full force, both of them moaned in delight. The billionaire ran his top hand up from her smooth hips, over her flat tummy and finally to grab ahold of her bouncing tit while his mouth worked on kissing the nape of her neck.
"Fuck! You have such a great body," Oliver complimented as their sweaty bodies thudded against each other.
"Thanks boss," Felicity replied while moaning, the boob not held by the businessman jiggling about.
"Tell me. Tell me what you are," Oliver demanded.
"Mhmm...I'm your personal little whore," Felicity screamed, her large ass rippling with every thrust.
"Is my nasty slut gonna cum again for me," Oliver asked, his free hand strumming over her clit now.
"Pphhhh....uccckkk yes," the nerdy girl answered, nearing her climax by the second.
"Squirt all over my cock like a good girl," he added, his thrusting and rubbing reaching a fever pitch.
"Oh my God," Felicity said, running a hand through her golden hair with her eyes squeezed shut and breathing more ragged. "I'm cumming. Don't stop. YYEESSSSSSS!"
Oliver kept his pace going with both hips and hand until he was sure that the blonde girl had ridden out her second orgasm of the night. Just like the first she was a screamer and came hard, coating his cock in a thick layer of her juices in the process. He slowed his thrusting until he finally pulled free of her velvety grip, smoothly getting to his feet and rolling her onto her back.
After back to back orgasms, Oliver was willing to bet Felicity wouldn't get in more subdued mood then this, which would suit his future actions perfectly. With his strong arms he positioned her on the sofa with her thick booty barely hanging over the edge and her legs spread wide. As he pushed them backwards, Felicity had the wherewithal to clutch them so he had full access to her completely bare sex.
"To make sure you deserve your raise I'll need to check out your third hole as well," Oliver told the exhausted girl.
Felicity tried to remain calm but panic was threatening to overtake her. This wouldn't be the first time a man had successfully wormed his way into her ass, after all all men she'd ever been with had tried and succeed. However, none were the sheer size as Oliver, with his thickness a real issue for her as he continued rubbing his tip along her crinkled entrance.
"I don't think you'll fit back there," Felicity said with an edge of nervousness.
"Do you want that raise? Seriously, do you want it," he asked, his tip never leaving her crinkled surface.
"It's just that I haven't done...this...awhile," the blonde informed him, trying to think back to when she last had a boyfriend.
"Well let's hope it's like riding a bike. Now spread your ass for me," Oliver demanded.
Felicity didn't use words instead responded to his demand with action. Oli liked how subservient she was becoming to him in only a short amount of time, aided greatly by the fact she was in love with him. Running her arms through her spread legs, Felicity grabbed a handful of each of her large cheeks and pulled them apart, making her tight backdoor gape ever so slightly.
Oliver didn't hesitate further as he pushed forward firmly yet without malice. The combination of the wetness of his shaft, relaxed attitude of his personal assistant and how he had loosened her with his fingers earlier had helped significantly. Felicity still grunted as his tip disappeared into her dirt road, but it was minimal with all things considered.
"Oh God. It's so big," she grimaced.
This not being his first time sodomizing someone, Oli knew the proper thing to do was wait for Felicity to make the next move, which happened in short order. No sooner had he penetrated her bowels was when the girl several years his junior rocked her fit body side to side in a gesture for him to take the reins.
With her seal of approval achieved, the billionaire took control back. With two hands now holding onto her hips to still her motion, the muscular man began making more progress into the depths of her anus. Though it was slow he didn't mind as his small strokes kept getting more of his fat cock inside her.
"Fucking tight," he grunted.
Always thinking of more, Oliver started to push more inside and go faster almost at the same time. This caused the curvy blonde to groan more and he noted the tendons of the back of her hands tighten. He figured that it may be too much too sooner so he slowed his thrusting down but kept it so that it was three-quarters of his length sliding in and out of her ass.
"This how you like it in your bum," he asked confidently.
"Yeah...just like that," she replied in a soft tone. "I like that."
"You like my big cock in your tiny asshole," he asked, testing the water by going faster once more.
"I actually do," Felicity answered, surprising them both with the honesty.
Even with 6 inches of his shaft continuously knifing into her ass, the personal assistant-turned-prostitute continued to voice her satisfaction which became muffled when she began biting her plump lower lip. Over and over again her expansive asshole stretched to what had to be her limit in order to accommodate his eager probing. The smile on her face and the way she looked up at him while he drilled into her only helped to elevate the lust he felt for the submissive girl.
If she was in pain from the relentless ass fucking he was doling out to her, Oliver could never have known it. With each time the full length of his cock slid out of her bowels only to pierce them once more until he was balls deep, she moaned. In fact, when she wasn't biting her lip the blonde demandingly urged him to keep fucking her ass.
As he held steadfast onto the curves of her hips where her narrow waist bellowed out to create the modest curves, she wiggled her booty enticingly for him. He took up the invitation each time by rearing back before spiking her on his spear in her rectum without fail.
"Holy crap! You are so wet," Danny said as he reached down to rub her snatch.
"I really love this," she replied while moaning.
Felicity was under him and loving every passing second of the sodomy. She had learnt the secrets of pain-free anal sex so was happy to offer her cute butt up to any man she wanted, Oliver being no exception. Though his thrusts were getting harder, they were not painful to her, especially with his two fingers probing her cunt at the same time.
"Roll over. I need to see that big ass shaking as a fuck your tight little dumper," Oliver so elegantly stated.
The personal assistant only smiled as he withdrew from her well-used asshole. He was far from the first man obsessed with her mighty ass, nor would he be the last. It defied logic how large it was given her petite frame, yet was extremely firm instead of flabby, making it the idle booty for anyone's tastes.
As Felicity flipped over and rose up onto her hands and knees Oliver was compelled to raise his hand then crash it down hard against her phat ass, watching the thick muscle ripple and redden. He didn't get too slap happy as the way her booty was presented to him made him need to get back inside her.
"Ffuucckkkk," the billionaire hissed as he pushed back into her ass.
This time Oliver didn't need to start slow since they had already loosened her up from their first round. Picking it back up where they left off, Oliver was stroking his entire length into her boundless ass within seconds. Over and over her ass rippled as his hips smacked against the curvy muscle, pitching the former secretary forward only for his strong arms to rear her back simultaneously.
"Yes Oliver. Go for you," she implored, her asshole being used for his pleasure.
"Gonna...cum...soon," Oliver warned between thrusts, each one stronger and feeling more penetrative than the last.
"Mhmm...oh...cum right on my ass," Felicity begged, feeling him becoming more erratic which signalled his imminent orgasm.
"No...in your ass," he groaned, not able to withstand any more of her vice-like booty.
Rearing back one last time Oliver plunged as deep into her rectum as he possibly could. Holding himself pressed inside her, the billionaire released his seed, pumping his thick cum against the deepest walls of her bowels.
Felicity felt the last stab of his cock and knew what was coming. She could actually feel his load splashing inside her anus, coating her with the oddly warm fluid. The sensation alone was almost enough to bring her to a third orgasm, but she was too exhausted from their lengthy romp to climax once more.
"Wow," Felicity moaned as Oliver pulled his deflating cock from her ass for the last time.
"Right back at you," Oliver replied as he tracked down his clothes and began getting dressed.
"So any chance I could get the first month of the raise in advance," the adorable assistant asked once she was back in her own clothes as well.
"I suppose so. Well, I think a blowjob as I write it would suffice, don't you," he asked with a wicked grin.
"Yes sir," Felicity agreed, the realization of her new life finally dawning on her.
Oliver Queen straightened up his clothes and looked himself over in the mirror. He looked good and not even a hint that he had just fucked his personal assistant, a woman who until that point had morals. Now she was corrupted, preyed upon due to her desperation. Oliver didn't care, after all he had just bought himself his very own anal whore that he could play with as often as he wanted.