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: The Diggle Brothers are the personal security to Oliver. After a mishap in the club, John steps in to fight off two men while Andrew hunts down the photographer to destroy any proof. As a reward, Oliver gives them Felicity for the evening.
Pairings: Felicity/Oliver, Felicity/John Diggle/Andrew Diggle
Codes: MF, MMF, Anal, DP, Oral
Arrow: Alternative Timeline 2 - Felicity Meets The Diggles
by The Chemist
The Diggle Brothers has just entered the glass walled office of their boss Oliver Queen right on time. They were both ex-military that were recruited to work as Oliver's bodyguards so they had a firm understanding about punctuality. However, the blonde billionaire had yet to arrive so the two men sat in the chairs opposite his fancy desk to wait.
The ex-military men did not have to wait long though. After only several minutes, the heir to the Queen fortune strode out of his inner office with the gorgeous Felicity Smoak, his personal assistant in tow. Oliver wasn't surprised to find the two goons present, though the look on Felicity's pretty face was that of surprise and embarrassment.
"Gentlemen, no need to stand," Oliver greeted them as they stood to attention the second their boss came into view. "And Ms. Smoak thank you for your help with me again on that special project."
"Oh...umm...of course Mr. Queen," Felicity flushed, still mortified that the Diggles likely knew that they were dumping uglies in the secluded inner chamber.
"Shit, forgot to change into my other shoes. Just one minute guys," Oli stated before disappearing once more.
"My God...that is one damn fine booty," Andrew Diggle groaned to his brother as they watched Felicity leave without their boss around.
"Best decision Oliver ever made was hiring Felicity," John agreed. "How that fit white girl has an ass that phat is beyond my reasoning."
"Alright, let's head out," Oliver said as he re-emerged.
The plan was a fairly simple one for the evening. Oliver's best friend Tommy was the owner and operator of the hottest club in Starling City and tonight was going to be the location that Oliver took Helena too. If his money wasn't enough, being close with the owner meant the pair would have the very best the club had to offer.
As always the Diggle Brothers drove the fancy car, well the older brother John did the driving as Andrew sat beside him. Tonight Oliver's date was simply meeting him at the club so they didn't have to worry about making any pit stops. They pulled up to the back of the club where staff was waiting for important guests, Oli being among them.
"Fuck this club is awesome," Andrew stated as the brothers took up their post at the entrance to the VIP.
"Mhmm," John grunted his agreement.
However, that was really when the night took an unexpected turn. Oliver and Helena had been there for roughly an hour, dancing on the floor and making out in their secluded booth. On their last foray to the dance floor in their VIP section, a man who clearly had too much to drink bumped into the pair.
"Watch it asshole," Oliver yelled as he nearly tossed the drunk halfway across the floor.
"Big mistake," replied one of the three massive men headed his way.
Oliver hadn't known it at the time but the drunk man who danced into him was actually Ray Palmer, another rich boy who owned a company though he was an actual tech genius, not some trust fund baby. As Ray's bodyguards closed the short distance between them and Oli, the billionaire braced for a beating he knew was unavoidable.
Oliver watched the center man rear his arm back to deliver a powerful blow to his face but the punch never came. Sensing the danger, John and Andrew swung into motion. The bigger of the two ,John, intercepted the more aggressive goon and laid him out with a kick to the front of his knee, causing him to pitch forward before a right cross knocked him down for the count.
Flanking the trio from the right side, Andrew spun the closest goon towards him. The smaller man was wiry and fast so he ducked the wild swing by Ray's bodyguard and came back swinging with a few body shots of his own. As the goon dropped his hands to protect his battered ribs and kidneys, Andrew took the opportunity to blast the man with a tight uppercut, knocking him off his feet and to the ground.
"Go Helena," Oliver said, shooing her away from the danger.
As Oliver spun to handle the third man, he found that task was already being handled for him by his hired help. After disposing of his first attacker easily, John Diggle was ready for more, though this third fellow seemed a tougher test. John took a few hits but none too damaging before he was able get behind the fighter and apply a chokehold that proved too much for Ray's man.
With both Ray and his three hired thugs all on the floor, Oliver could have left and let that be that but it wasn't his style. Running over the sprawled billionaire, Oli didn't break stride as he sent a kick directly into his rival's ribs. Ray grunted and flopped onto his back, barely able to breath before several more kicks were delivered.
"We have to go Oliver! Papperazzi are here," John shouted as he pulled the muscular businessman away.
"Fucking asshole," Oli spat at Ray before allowing the big black man to steer him away.
"I'll take care of the lone cameraman," Andrew shouted at his retreating brother.
The crowd at the club started to flock to the action but John and Oli were already navigating the throng of people before anyone got a close look at what had happened. By the time they exited the club at the rear entrance and loaded the rich man into the limo, Andrew had caught up with them, showing them both the camera off the man who had recorded Oli's attack of a defenseless man.
"You two were amazing. Like fucking...superheroes," Oliver exclaimed once back in the safety of the limo.
"It was nothing," John answered from behind the wheel.
"All in a night's work," Andrew added.
Oliver was still playing out the details in his head of what had transpired, specifically his part in it. He didn't blame himself for starting it, but things would have been very different if not for the two men seated in the front of the car. He needed to show his appreciation for there good work that went above and beyond what was required of them.
"Listen guys, how about you let me show my thanks to you," Oliver offered.
"You compensate us very nicely already Mr. Queen," the shorter of the brothers remarked.
"I meant in a different matter. I see the way you stare at Ms. Smoak, hoping that either your vision will turn to x-rays so you can see that great ass of hers. What if I...give her to you guys for the evening," the billionaire shared.
"You mean like a prostitute," John asked.
"Not quite. She and I have an arrangement for lack of a better word," Oli answered.
"That arrangement sounds a lot like a pimp and his ho," Andrew jumped in, drawing smiles from all three of them.
"Listen. It's completely your call. You want her tonight at the Ostrander Hotel tomorrow night, then it's yours. I'm gonna call them right now and book a room, tell you two the number and if you show up then that's up to you," he spelled it out. "Either way she'll be there and ready to...well, she's game for anything. Anything."
The two brothers remained silent as they drove the expensive car through town to get Mr. Queen back home. Before he got on his phone to make the call to Starling City's best hotel he text the ever-willing Felicity to meet him at his mansion for a little late night booty call. With those items all done he picked up the conversation in progress in the front seat between the two men.
"She is really hot with that whole naughty librarian thing going on," Andrew stated to his older brother.
"And that ass," John added with a grin.
"That ass is right," the shorter man agreed. "But would we split her? Like I get the first hour then you take over?"
"You go first? Are you crazy? I'm older, bigger and brought you into this operation in the first place," John disagreed.
"If I may," Oliver jumped in. When his two enforcers didn't rebuke him, he continued. "You guys are brothers. Brothers share...if you catch my drift."
The two men exchanged a look at each other that bordered on them having a telepathic conversation that can only happen between two people who spend that much time together. Oli told them no decision was needed tonight and for one, both or neither of them to show up at the room tomorrow night was fine.
By the time he was dropped off at the front door of his parent's manor that he had an entire wing to himself for, Felicity was standing in his room waiting. She was dressed in some lingerie that she had bought at his request, an all black number consisting of a bra, thong, garter and stockings.
"Before we get started, I have need for you tomorrow night," Oli told her as she dropped to her knees like the submissive whore he had made her. "You will be at the Ostrander Hotel tomorrow night at 9pm sharp. Pick up something new for the occasion."
"Yes sir," Felicity obeyed as she started undoing his trousers. "Fancy place."
"Indeed it is," he agreed as her lips wrapped around his cock. "But it won't be me that you'll be entertaining. The Diggle Brothers did me a great service tonight and you will be there prize."
"Oh," Felicity said, pulling her head back so her lips broke contact with his lengthy pole.
"Is that a problem? Because if it is a could find someone else to do that...as well as run my day-to-day life," the billionaire asked, clearly threatening to terminate her if she declined.
"No. No problem," Felicity answered though in a ton that indicated her mind was already thinking about the repercussions of her actions and what that would make her.
"Excellent. So make with the blowjob then your driver will take you home. Oh and that taste is Helena's dried pussy juice, fucked her about an hour ago," he shared.
With her original grin wiped clean from her face, Felicity glided his cock towards her face before engulfing his bulbous head between her lips. The dirty blonde-haired man couldn't help but let an audible moan as her hot wet mouth worked the first half of his cock over.
"Yes. Suck it babe," he moaned in delight towards the talented cocksucker.
"Mmmmm," Felicity moaned as she noisily slobbered on his meat stick.
Her time for being stunned by his request was not for right now, after all she'd have almost 20 hours to think about it. With that in mind, she blocked the appointment from her thoughts and focused back on giving her boss, who sexually bought her 10 days ago. Felicity knew she could be a lot of things with her keen intellect, but the personal fuck toy for one of the most influential men in Starling City never was one she imagined.
"So you want me to do what I do to you...but with them," Felicity couldn't help but ask mid-blowjob.
"That's right," Oli answered.
Oliver showed his bought whore that he was interested in fielding anymore of her inquiries right then by bunching up her long blonde hair and holding it behind her head. With it out of the way and now able to cup the back of her skull, the rich man pulled the lingerie-clad personal assistant back towards his cock.
Unfortunately she had to pull her mouth off his manhood to ask the question, but he welcomed the break even if it only lasted a moment. The second after feeling him take control, the lips of the horny girl were wrapped back around his glistening cock, already dripping wet in her copious amount of saliva.
"Much better," Oliver groaned as the blonde bobbed her head along most of his length now.
Felicity wasn't done thinking about what he was intending her to do tomorrow but she had to ignore it for now or else it would consume her totally. Instead she banished the thoughts as best she could for now and began building momentum as she bobbed her head up and down his towering pole, taking more of him inside her each time. After a good minute of the more intense blowjob, she slowed her pace back down then pulled off his spit-covered cock altogether.
"So they would get to do whatever they wanted? Would it be one at a time or...how would it worked," she asked looking up at time.
"Okay here is the last answer you will get from me before I blow all over your adorable face and glasses. I don't know if they will take turns pounding you flat into the mattress with their monster cocks or whether they'll throw caution to the wind and cram your once tight asshole at the exact same time. But whatever kinky, degrading shit they have in store for you, you will care out. Understand?"
Felicity knew he was really mad now and that was something she knew was a very bad thing. Knowing she needed her A-game for the rest of her time on her knees, she took his cock that was 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.
The personal assistant 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.
"Mmm...much better," Oliver grunted in satisfaction as Felicity had finally regained her focus.
It helped that after he had fucked her every day since they came to their arrangment that Felicity had picked up on what he liked and what would get him off quickly. It wasn't her initial goal to make him cum hastily, but after upsetting him to the point of yelling at her she was just giving Oli the best blowjob she could.
With a combination of her mouth and hand massaging his entire 10-inches of cock, Oliver was clearly loving what the lingerie-clad nerdy girl was doing. It helped greatly that her free hand was pleasurably rolling his nuts with her fingers, plus he got an extra perverse thrill in looking down into her face and find Felicity staring right back up at him.
"Sllrrrppp....ggrrrggglll....ssllllrrrpp," Felicity noisily continued her sucking, using lots of spit since she was taking him so deep repeatedly.
"That's it. Be my good little slut and finish me off," Oli implored.
Felicity knew it wouldn't be long now so she put every ounce of energy she had into accomplishing her goal. Her head was a blur as she constantly pushed into him that backed up off, her lips dragging along his veiny shaft in the process. Her hand went from massaging his full sack to rubbing the spot right where his shaft met the rest of his ripped body, a particular sensitive spot for the young Queen man.
"Yes! Cum for me," Felicity begged when Oliver pulled his dick free of her relentless oral assault.
"Fuuccckkk," Oliver swore as he came.
With her glasses on Felicity didn't need to close her eyes for fear of getting salty cum in her eyes but they did so out of reflex. Stream after white stream populated the brainy girl's face, including several streaks that splattered over her librarian-like glasses. Once he was all done, Oliver looked down to find 5 solid lines of ropey cum decorating Felicity, the girl who was truly his cum whore.
"Still so much jizz even after being with Helena," Felicity stated as she removed her glasses and tracked down some tissues.
"Well you may be in for a shower of semen if the Diggles have their way tomorrow night. Anyway, get dressed, go home and I'll see you at the office tomorrow morning," Oliver instructed before disappearing into the shower without so much as a goodbye.
* * *
Despite the bombshell that Oliver dropped on her last night, the next day at work was like any other. The pair worked together seamlessly to accomplish all that Robert and Miora Queen asked of their son to perform at the company he would one day become CEO of. That meant that there was also an afternoon delight session where Oli bent the attractive personal assistant over his desk, but that too was the new normal.
"Okay we are all done here. I have a golf game with Curtis in an hour so why don't you knock off early and go do a little shopping. Get something the Diggles would like," Oliver told her.
It was the first time that the evenings plans were mentioned. For awhile Felicity was hoping that last night was a weird dream and that her boss, who she pimped herself out to sexually to make rent, didn't offer her out like a common street whore to his work friends. However, his parting words left no doubt about that.
"Oliver, listen. I've been thinking about tonight..."
"I'm hoping you're not going to say what I fear you may. Depending on how the next sentence you speak goes, I have had a pleasure working with you here at Queen Consolidated and I wish you luck in your future endeavors," Oliver stated flatly.
A few seconds went by as Felicity stood there stunned in front of her gorgeous boss. Finally she spoke. "No. I was just going to ask when I...ummm...should arrive and...ahhh...expect my guests?"
"Awh. Wise choice," Oliver smiled brightly. "For one, here is a company car that you can use for the foreseeable future," he answered, passing her the keys to a $30,000 brand new vehicle. "You can go anytime, the reservation is under Shadow Wilson, an alias I commonly use. The boys were informed to be there at 9pm and you know how they are for timings."
"Oliver...the car...are you sure," Felicity gaped.
"Of course. You are a valued employee of our company and this is how I show it. With uncalled-for raises and beautiful cars," he smiled at his sex slave. "Oh and use the spa at the hotel if you wish. I just recommend a colonic, you never know what weird shit guys are into."
* * *
"I could quit. I don't need to subject myself to this," Felicity thought, wrestling with her choices.
In fact, she had been having the same conversation inside her head ever since the news was broken by Oliver that he was pimping her out to his two thugs. Sure, John and Andrew were nice guys and very attractive if she was being honest with herself, hell she could even see herself going for them in real life. However, this wasn't her choice.
"So I'd lose my job with the company that has employed me since graduating and I doubt Oli would jump at the chance to write me a favorable reference letter. After all he's the same guy that blackballed a former researcher for spilling coffee on his laptop that had ever file backed up anyway."
As much as Felicity didn't want to look for another job, she actually liked the job she had. Sure the hours could be long at times, especially with their new arrangement, but Oli took like 15 weeks of vacation which she was paid for. Plus there was her ridiculous salary she was on now, double that of any other personal assistant she knew plus now a company car.
Felicity may have been troubled by the order from her boss but as soon as she was done shopping at the lingerie store, which she was becoming a regular patron of, she found herself parked at the hotel. It was a grand hotel, the best in Starling by a country mile and as she checked in she noticed a prominent model and famous movie director in the entrance as well.
* * *
"So do we set up ground rules," Andrew asked his older brother while the lift took them up to the penthouse.
Although they both had some apprehensions about their decision, they were not willing to sacrifice first turn with Felicity. That meant they would share her at the same time, something they hadn't done since their first tour overseas with some very horny soldier.
"Same as before. No crossing swords," John replied.
The elevator came to a stop before the doors opened up to an elegent hallway. The two men strode out and went to the second of only three rooms on the whole floor and used their card key in the door. When it flashed green John pushed the heavy door open and the brothers stepped into the room.
"Damn," Andrew exclaimed at the sight of the personal assistant.
"Perfect body, adorable face. Wow," John added with more description.
Their compliments and astonishment was well deserved for the sight that greeted them in the large room. Standing in front of the king-sized bed was Felicity who had done away with her business attire and had donned her newly purchased lingerie.
Felicity's sunkissed skin was in contrast to the black undergarments gracing her perfect body. Only a bra covered her upper body, see-through and hugged their modest chests tightly, pushing up their tits to show off massive amounts of cleavage. Meanwhile her pussy was covered only by a barely-there matching thong wile a garter belt, stockings and high heels rounded out the drool-worthy outfit.
"Now how can I ever repay your boys' compliments," the blonde girl said with a mischievous grin.
As the men had walked into the room, Felicity was able to reach out and use each of her hands to target the groin region of her two suitors. As they took up the space on either side of her, they were both sporting half erections at just the sight of her in her sexy outfit so with the friction from her hand they both were now throbbing against their denim prisons.
The personal assistant turned her head to kiss John deeply, requiring the much larger to bend down to embrace her despite the heels that helped prop up her height. Andrew didn't mind because as she locked lips with his older brother, he was left with using his mouth to suck on her perky tits after undoing her bra, instantly making the nipples erect.
"You wanna suck this fat dick," John asked with her hand already rubbing over his groin.
"Mhmm yes...that's what I'm here for," Felicity retorted. "You too Andrew."
Both men regrettably pulled their mouths away from the blonde, who was showing none of the internal dilemma she struggled with much of the day. They watched the very attractive girl lower herself to the carpeted ground to get onto her knees in between them as they both sought undoing their pants. By the time she had gotten into position between the two men they had undid their pants and slid them down their legs, standing naked from the waist down. Standing side-by-side with their erect cocks, the former MIT grad looked on and couldn't help but salivate at the sight.
"That's a whole lot of penis," Felicity said out loud, forgetting that the thought should have been part of her internal monologue.
Sizing them up, Andrew's cock reminded her of Oliver's in a way. It was a perfectly proportioned cock that was neither too short or long, too thin or thick. It was idle, measuring a good 8 inches of ebony meat that looked good enough to devour without thought.
John meanwhile was a different beast. Much like his outward appearance, his cock was simply massive. At full mast he was nearing a foot long from base to tip but even more alarming was the thickness. Felicity reached up to circle his pole and couldn't even clasp her forefinger and thumb together!
"It's not gonna bite you baby," Andrew said looking down at the gawking female. "Go ahead and suck that dick."
Caught being in awe of both of their massive cocks, the personal assistant turned corporate prostitute snapped out of her worshipping state and into action. With a black cock equipped in the palm of both hands and stroked them both with the friction of her hand on their smooth shafts.
"Mmhm...awwhh," the men groaned in unison.
Being no stranger to finding herself on her knees and in front of a pantless boy, all that changes this time was the number of guys. Choosing to orally please John Diggle first, she opened her mouth and mimicked the action of French kissing someone except this time it was with the tip of a cock. Her lips were just able to completely engulf his dickhead while her tongue went about licking the entire surface of his sensitive skin.
Wanting to get more of his dick wet with her saliva, Felicity freed his tip from her mouth. Extending her tongue she ran it's moistened surface down one side of his baseball bat-thick member until she reached his base. The thick bottomed girl was able to do this while still stroking the other man's cock with her free hand, getting grunts of approval from him. With her hands and mouth working at the same time, she licked down and took turns open-mouth kissing John's equally large nuts before returning to the base and licking up the other side of his member.
"Fuck you're good," the larger Diggle told her.
"And the only thing better than sucking one cock is sucking two cocks," Andrew added as she shifted her mouth towards his dick. "Ain't that right slut."
"Mmhmm," Felicity moaned around his tool affirmatively.
"Don't worry Andrew, I didn't forget about you," she said with her adorable smile.