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, nor its characters especially Felicity Smoak, Donna Smoak, and Oliver Queen.
Pairings: Felicity Smoak/Oliver Queen, Felicity Smoak/Donna Smoak/Oliver Queen
Codes: MFF, FF, MF, Anal, Incest, Oral
Arrow: Alternative Timeline Part 8 - Smoak Family Fun
by The Chemist
"Baby are you sure I can swing by tonight and pick up a pair of shoes," Donna asked her daughter over the phone.
"Of course mom! You may be slow in returning but you always take care of my stuff," Felicity replied. "Oh, one thing though. I have a man coming by at some point but we'll be tucked in the bedroom so feel free to root around in the closet."
"I'll be as quiet as a mouse," Donna told her daughter. "A man huh? Is he handsome?"
"Dreamy," she answered. "Anyway I have to get ready. Just drop by after work, no problem."
The mother and daughter hung up and continued on with their day. Felicity sent Oliver a text that part one of their plan was a go tonight, which would mark the first time Oliver fucked her in her own apartment. She understood why, secrecy was a big deal for the future heir to the Queen fortune, especially when he was engaged to one of the biggest families in Starling as well.
While Felicity went about cleaning the rest of the house and making sure that her bedroom was arranged in the best way possible, Donna went back to work as a cocktail waitress. Not quite 40 years old, the blonde was still blessed with a great body that was just as tight as when she was Felicity's age.
Nearly 6 hours later, Donna was done work for the evening. She got into her car and made the short trip across Starling to where her daughter lived. Felicity had given her mother a key last week since she was constantly stopping by anyway so Donna unlocked the door and slowly opened it. There were the remains of a fancy dinner on the table but no people in sight.
"That's my girl," Donna thought, hearing the faint moans of a woman she instantly recognized as belonging to her daughter.
The older Smoak woman made short work of her objective. The closet barely creaked as she opened the door and when no changes were observed from the direction of the bedroom, Donna carried on. She tried on several heels before deciding on taking two of her favorite pairs with her. As quietly as she entered the apartment she left, locking up behind her as she went.
Donna was headed back to her car but she stopped at the entrance of the building. Felicity's apartment was on the first floor and she knew that the bedroom had a window in it. She knew she shouldn't be snooping and prying into her daughter's love life, but it was so rare that the brainy girl ever talked about a man. Deciding, she walked away from her car and snuck close to Felicity's window.
"Oh my God!"
She could barely comprehend what she was seeing. She was prepared to look in on her daughter in the middle of sex, which she was, but she never would have guessed she was sleeping with Oliver Queen. Her Oliver Queen. The same guy who had fucked her less than a week ago and now here he was with her daughter.
Donna had no idea how long the couple had been going at it, either for their current sex session or the length of time they had been seeing each other. The elder Smoak was so flabbergasted she couldn't think or even move, instead staying out in the open so that if either her daughter or Oliver turned towards the window they would clearly see her.
"Don't react but your mother finally showed," Oliver whispered as he sank down against Felicity's body.
"She was never known for her punctuality," the curvy blonde responded.
For the couple, Donna's tardiness wasn't a bad thing by any stretch, in fact it just meant that Oli was able to fuck his assistant for longer. However, it did come at quite the cost, that being mainly his stamina. He wasn't even worried about anyone walking by the window other than their target, a Diggle brother was placed on either side to prevent the average peeping Tom from stumbling upon the steamy action.
"I'm glad that I can actually really fuck you now," Oliver told her, spiking his hips sharply between her legs to accentuate his point.
That was only a type of the iceberg from the hulking figure. Rearing his hips back again, Oliver unleashed a torrent of hammering thrusts deep into Felicity. The brainy assistant was just as pleased to have her man fucking her in earnest now, spreading her legs wider from her position on her back to allow him unrestricted movement.
Felicity had chosen to kept her nightie on, the black lingerie bunched up on her fit stomach and still concealing her perky tits. She didn't want to throw too much stimulation at her mom in order to give her less reason to be creeped out and leave, blowing her opportunity to have a threesome with her and Oliver. Seeing her only daughter being fucked by the man who recently banged her was on thing, no need to see her tits as well.
"Mhmm...well sorry...awwhhh...fucking me for almost...uhhhh...two hours was torture," Felicity spoke there her moans of pleasure.
"I'm sure you'll find a way to make it up to me," Oliver smirked without breaking stride.
Donna couldn't peel her gaze around from the scene before her. She knew she should walk away, after all she had plenty of reason to. For one, that was her daughter, her only child in the middle of having sex. However, Donna had always treated her more like a younger sister than as a kid and now she had something in common with her. Felicity always came across a little prudish, especially in the man department so seeing this side of her was shocking.
"Where...ughh...do you want it," Oliver asked impatiently.
Felicity thought for a brief moment while Oli's strokes into her cunt became more and more erratic. "Let's give mommy dearest a show. Cum on my face."
"Expose Donna to the true slut her daughter is, I like it," he grinned.
Donna was surprised that she didn't want the action on the other side of the window to end, but she had seen enough men in the final throws of pleasure to know when an orgasm was coming. She watched as the ripped man did a few last hard thrusts deep into her exhausted 23-year old daughter then pulled out of her twat and crawled the bed.
The marathon sex session had depleted him too much and now that he knew Donna had caught them in action, the last of his determination was gone. Oliver stroked his cock a final time before taking aim at Felicity's pretty face as the cum erupted from his tip. 6 streaks of jizz shot out of his tool and plastered across the witty girl's face, coating her forehead, nose and cheeks mostly, with small dribbles running on her chin and lips as well.
"I keep forgetting you cum like a geyser," Felicity mused while whipping a glob of cum from her eye socket.
"It's why I include hazard pay into your salary," Oliver laughed as he flopped back in bed. "She's gone by the way."
After seeing Oliver paint her daughter's face in cum, just like he had done to her when they fucked in his hotel's shower, Donna got out of sight. She didn't want to be discovered by Felicity now, after watching her get fucked by the hunky man. Even though it was her own flesh and blood, Donna couldn't help but feel so unbelievably turned on at the sight of Oliver's massive cock slicing into Felicity then erupting onto her face.
"Momma needs a cold shower," Donna said to herself as she made her way back to her vehicle.
* * *
The next day, Donna looked down as her phone began to vibrate on the table beside her. The image of her daughter Felicity came up on the screen and instantly she was back thinking to what she saw last night. Her legs spread wide as Oliver's cock slammed into her twat. Her perky chest bouncing with every thrust still trapped inside her nightie. And of course her pretty face absolutely doused in the businessman's cum.
"Hi mom! How did the shoes work," Felicity asked.
"Oh hi baby," Donna replied, focusing back on the present. "The shoes? Right, the shoes! They were great, date was great."
"You okay? Seem distracted," Felicity asked with a smile, knowing exactly what was going through her mind.
"Yes I'm fine. A little distracted is all but I'm here with you baby," she said, trying to give her daughter her full attention.
"Anyways, wanted to see about dinner tonight. There's this great little Greek place at 4th and Waterdown," Felicity offered, the location less than a mile from Oliver's off-the-books condo.
"Perfect Felicity. I can meet you there at 7:30pm," they agreed before hanging up.
* * *
"How's your slovakia," Felicity asked her mother.
"Oh it's fine baby," she replied, remembering to take a bite of the spiced meat.
"Ok mom, spill the beans. What's up," Felicity prodded.
"Fine, I'll just come right out and say it. I saw you with Oliver last night. I came to get the shoes, heard noises then went out back and spied on you," her mother admitted. "I know it was a huge invasion of your privacy...I just couldn't help myself. You are always this proper, innocent girl and so the one time you aren't I had to see who brought it out in you."
"Oh he brings it out in me alright," Felicity confessed.
"What do you mean? This wasn't just you sleeping with your boss one time," Donna asked as her face showed curiosity and excitement.
"Honestly...it's been months of him and I...and sometimes his friends and other women hooking up," she revealed. "Even after I found you slipping out of his house last week...I kinda slept with him like an hour later."
Felicity studied her mother's face for some emotion but surprisingly the easy-to-read Donna wore an expressionless mask. It was a lot of information she just shared with her mom and she knew that when she found out about Oli with Donna it rattled Felicity more than she let on. And now she did the same to her mother with even more news.
"And there's more. Oliver has it firmly in his brain that he wants to share a bed with you...and me. Together," Felicity went on. "Ideally tonight."
This time her words got a reaction from Donna finally. She straightened up and looked as though she was told a nuclear war was starting throughout the world crossed with someone having slapped her in the face. Felicity knew that the first part was a big amount to digest but wanting to fuck mother and daughter at the same time would be a bridge too far for any sane person.
"Oh My God! This is so amazing," Donna shrieked in excitement.
"Wait, what? You don't find it weird," Felicity asked her mom, honestly surprised.
"What? No of course not! It's like we are sorority sisters, sharing men like this," the older woman disclaimed. "It's so fun and exciting, makes me feel like I'm in college again."
"Wow! It took me quite a bit of time to get my own mind wrapped around this I thought you would need it too," the younger girl added.
"The surprising thing is you being into this. You always seemed so sexually naive and innocent and now you want to have a threesome with your boyfriend, who we've been sharing, and your mother," Donna countered. "You have no idea how excited I was to find how wrong I was when I spied you with Oli."
"I honestly didn't see this coming," Felicity admitted. "Oliver did but I thought it would freak you right out."
"Babe! I thought by now you knew I was the cool mom. Your best friend even," Donna told her, added by rubbing her forearm. "So is Oliver waiting for us like right now," she asked excitedly.
"Yeah, in his condo around the corner," the brainy girl replied.
"So what are we waiting for? Let's go," Donna all but screamed.
Felicity couldn't help but smile at her mother's excitement and care-free attitude when it came to sex. She was a free spirit, so much so that she was willing to fuck the same man at the same time she was going to do so. It was still so crazy to Felicity, but somehow Oliver had talked hr into it, like he always managed to do.
After receiving the sex and settling the bill, the two Smoak women left the restaurant and drove the incredibly short distance to Oliver's condo that he kept private for this very reason. His engagement to Helena Bertinelli was like an old school joining of two big families of Starling City, a marriage that would forever link the mob and all their connections to the legitimate yet shady business of Queen Consolidated.
"You have your own parking spot here," she asked her daughter.
"We use this place very often," Felicity answered, leaving her mother wondering how much of Oliver's semen her daughter had been filled by.
A short walk to the elevator and journey up 15 floors arrived the pair outside Oliver's condo door. Felicity used her key to unlock the bolt before the mother and daughter entered. Oliver had light music playing and had dimmed a majority of the lights to help set the mood. High heels clicked on the floor as they walked into the bedroom and found Oliver waiting for them.
"Well done Felicity," he told his assistant. "Always had faith. You accomplish whatever you set that brilliant mind to."
"Hi Oliver," Donna practically gawked at the shirtless man, studying each of his ripped muscles.
"Hello Donna, a pleasure to see you again," the smooth-talker replied, kissing her hand in the process. "Felicity, why don't you go change in the washroom."
Felicity smiled at her boss, gave a sideways look to her mother who only had eyes for Oliver before disappearing into the marble-tiled bathroom. Like he always did, the handsome man had laid out a sexy outfit consisting of only a bra, stockings and garter belt, this time being pure white.
As Felicity changed, she was absorbed in her own thoughts and not for the first time started to have second thoughts about what she was doing. Standing pantie-less in lingerie, she was about to go join a threesome...with her mother! It was incest, which was wrong. Oliver and his silver tongue had distracted her but now outside of his influence she was all but determined to march back out and tell them she couldn't go through with it.
Felicity's words were cut off abruptly as she exited the washroom and found her mother already between Oliver's legs with his inhumanly thick cock in her mouth. The rich man was flat on his cock with hands behind his head as he watched the older woman stroke her plump lips down his hog, getting about half of it in her warm mouth before retreating back up.
In her mind she tried to form words to speak, wanting to say that this was all too much for her. That it wasn't what she wanted anymore. There was a problem though as her lips and tongue didn't form the sentences. Her body and mind were in strict combat against each other and right now her lust was winning.
"Hope you wouldn't mind, started without you," Donna said to her daughter while using her hand to rub along his spit-slick cock.
Not trusting herself to speak, Felicity instead shook her head to answer. Donna smiled at her and immediately went back to blowing Oliver, her Oliver, her boss and regular fuck buddy for the past several months. After watching her mother and Oliver going at each other, Felicity found herself getting turned on. She was watching with no more scorn or disgust in her crystal blue eyes, as that was replaced with the fog of lust, which was becoming thicker by the second.
"Why don't you come join us," Oliver proposed.
"Yeah, come on down here sweetie," Donna encouraged her daughter.
When Felicity stayed rooted to the floor no more then 2 feet away from the edge of the bed, Oli knew that she was teetering. Knowing he kneeded to act quickly, he moved Donna out of the way and got to his feet, his naked body rounding behind Felicity. The lovely blonde felt his hard cock, wet in her mother's spit, press against her huge ass as Oliver kneaded her tits through the bra.
"You won't regret this," he whispered in her ear before kissing the nape of her neck.
"But...mhmmm...it's my mom," she replied, her argument sounding weak again.
"You need to break out of your close-minded shell baby! It will be amazing," Donna told her, kneeling at the edge and facing her daughter.
"I don't know," Felicity countered, her knees feeling weak from the kisses.
"My god Donna, look at her ass," Oliver said, turning Felicity so the older blonde could see her from the side.
"So hot! Come on sweetie," her mom said again, this time reaching out and grabbing her hand.
With her mom folding one hand, Oliver clutched the wrist of her free arm and brought it backwards. Even while in the middle of such inner turmoil, Felicity still didn't hesitate to close her fingers over his enormous cock and start to stroke him.
"I really hope I don't regret this," Felicity finally said.
Oliver didn't give her a chance to rethink her choice, stepping around in front of her and pushing her down by her shoulders. Felicity didn't resist and let her boss force her to her knees where she rubbed her hand down his dick one last time before opening wide and inhaling his cock. The very same cock her mom had been blowing no more than 2 minutes earlier.
She couldn't think about that right now so she closed her eyes to block out the external world and thought only about blowing Oliver. His cock was thick but her mouth had grown use to spreading wide, her lips gliding halfway down his 8 inch length before his tip hit the back of her throat. She held him there for a few seconds to spit up some spit, coating his cock richly in her saliva before repeating the process a few dozen times.
"Felicity...don't you think you should be a more gracious host," Oliver lectured.
"I can't believe I'm actually saying this but mother, why don't you come down here and suck this cock with me," the brainy girl asked her mom.
Donna was kneeling on the ground beside her daughter in the blink of an eye. With the energy of any girl half her age, the fit mother opened wide and steered Oli's cock back into her mouth, showing none of the apprehension that Felicity had done when realizing her lips were bobbing one a dick lubricated in her daughter's spit.
Felicity couldn't help but turn her eyes to the right and watch her mother in what was clearly her natural element. Her whole body swayed towards Oli as she gobbled down ? of his shaft then leaned away to let him ride along her lips. After a minute of Donna's enthusiastic blowing, Oliver pulled back and angled his member back at Felicity, who was glad to take back the reins.
"I like this side of you Felicity," Donna cooed from beside her kneeling daughter.
"The side with a dick in my mouth as you watch," Felicity asked after Oliver took his cock and placed it back in Donna's mouth.
Oliver was loving the oral attention of the two gorgeous women but he couldn't help but want more. Unlike their threesome with Sara Lance a month ago, the billionaire noted that there was no teamwork between the mother and the daughter. Deciding to change that, he placed a hand on the top of each of their heads to control them.
"That's it, help her suck," Oliver encouraged.
Felicity was slightly hesitant but trusted Oliver and eventually allowed him to place her lips on his shaft. While her mother worked an inch away sucking on his tip, the brainy girl rode down his tool, running her tongue and plump lips up and down. With each pass back up, Felicity felt Oliver's hand pulling her further towards his head until the mother and daughter were touching.
"That's it...now kiss," he demanded.
Donna had no problem with the request, to actually make out with her own daughter. Pulling her lips away from sucking him off, she wagged her tongue at his pee slit. Felicity could feel her licking her plump lips as she did so, then gave in as well. Spilling her own tongue out, she did likewise, starting at the crown of his cock then moving up until they were licking each other more then him.
Oliver knew it was a risk getting Felicity to kiss her mom though she wasn't 100% committed, but looking down and seeing the gorgeous relatives with their lips pressed against each other was the reward he sought. He felt his dick somehow grow harder, the strain almost painful as mother and daughter engaged in a full-fledged make-out session.
"Now I'm going to fuck your mother Felicity," Oliver explained, pulling the slender older woman to her feet.
"Is that okay with you baby," Donna asked.
Felicity looked up from her knees in time to see the hulking man pull her mother's tight fitting blue dress up and over her head. Donna stood before her in a matching set of bra and panties, her large and still perky C-cup tits looking fantastic. Her thong showcased how fit her ass was, meanwhile her mother had not an ounce of fat on her stomach or hips. A true physical specimen even though pushing 40 years of age.
Oliver had her thrown to the bed and scooped her into position before yanking off her panties in one smooth motion. Just like her daughter, Donna was completely bare above her sex, making her pink pussy glistening with moisture stand out even more. Gripping his cock, Oliver spread Donna's legs wide with his free hand before stroking his entire length into her pussy.
"Oh My God! He's so much bigger than your father," Donna blurted out as Oliver made slow, long strokes into her pussy.
"Mother! Too much information," Felicity scolded.
Felicity was on her feet once more, standing beside Oliver. Even though she still wore her high heels, the MIT grad was still a good half-a-head shorter than the businessman. Showing off his multitasking skills no doubt honed from countless threesomes, Oli kissed Felicity deeply while starting to thrust harder into Donna's wet twat.
Then Oliver became truly amazed by Felicity. Apparently totally accepting of the situation, the brainy assistant knelt on the bed without ever breaking her lip lock with her boss. Just to the side of her mother, she was able to make out with Oliver but now reached an arm down and started to rub her mother's clit as he stroked his entire tool inside her.
"Yes baby! That feels so good," Donna cooed.
The screams of pleasure that were spewing forth from the older woman were loud and plentiful. Her mouth remained open in a permanent O as her daughter frictioned her sensitive clit and Oli's cock hit all the right places. Her tits had spilled over the top of her blue bra as well, Felicity getting a chance to see her mom's perfect natural tits as they swayed with each thrust Oli did into her.
Felicity could sense that her mom was already close to cumming even though it had only been minutes. Still leaving her hand in place, she moved away from Oli and hovered over her mother's head. Donna looked up and reached for her daughter, their tongues first contacting before their lips pressed tightly. Unlike their first kiss, this one was full of unbridled passion, their tongues spilling out as they hungrily locked lips.
"Come on mom, cum for me," Felicity said, staring deep into her mother's eyes.
Donna felt her daughter's fingers leave her clit but before she could protest she felt the small hands roaming her perfectly round tits. Felicity kneaded her soft flesh, squishing them together before teasingly pulling on her erect nipples. Oliver took up the reins of diddling her sensitive bean and in no time the overload of stimulation was too much for her.
"Yes Felicity! I'm cumming!"
"Did you like fucking my mom," Felicity asked, turning her attention back to Oliver.
"I think we both know that answer," he smiled before pulling his throbbing cock from her wetness. "Suck me Felicity."
The demand was met with the last of Felicity's apprehension, apparently the act of sucking his dick covered in her mother's juices still seemed taboo to her. However, Felicity had always been resilient and this time was no different. Leaning over her mom's exhausted figure, the personal assistant opened her mouth and caught his tip between her lips. She started slow, only bobbing on his head but after awhile she was over her reluctance and began devouring his shaft, still richly coated in her mother's cum.
"Do you taste me on his big cock," Donna asked.
"Yes," Felicity answered before sticking out her tongue and running it along the underbelly of his manhood. "And it's so tasty."
"That's it, now have some straight from the source," Oliver dictated.
This time Felicity didn't hesitate, she only reacted to his wish. Lowering herself the extra few inches, she allowed Oliver's cock to spill from her mouth, his slobbery tip tracing over her cheek until right in front of her mother's warm snatch. Diving right in she placed her lips against her mound and Felicity eat her out.
"Oh God Felicity! Feels so good with your tongue inside me," Donna screamed as her still sensitive gash was munched by her daughter.
Oliver looked down and watched as the eager 23-year old stuck her tongue deep within her mother. Her lesbian lessons with first Sara then Sara and Nyssa had clearly paid off her the girl in glasses as it really looked like she knew what she was doing. Needing to fuck someone right away, Oliver pulled up on Felicity's hair to yank her free before slamming his dick right back into Donna.
"So you've enjoyed fucking my daughter Oliver," Donna asked with a grin. "And you Felicity, I had no idea you had it in you. To keep this sex God satisfied is a tall order."
Still with her hair bunched in his fist, Oliver pulled her higher until he could capture her lips with his. Felicity actually enjoyed the mild pain of having her hair pulled, something she got across to Oliver with the depth and hunger of her kiss. He could still taste Donna's pussy juice on her lips and tongue, something that made him spike even harder into the older Smoak woman.
"Such a dirty boy, fucking my mom in front of me," Felicity told her lover.
"And now it's your turn," Oli declared.
Once Oli pulled out of Donna she started to roll out of the way but a hand on her chest by Felicity stopped her dead. Taking control of the threesome, her daughter leaned down to suck on Oliver again, tasting her mother's cunt in the process. Not forgetting about Donna, she used her hand to rubbed through her slit before finally pulling away from both.
As Donna moved to her hands and knees and crawled further up the bed, Felicity took the vacant spot in front of Oliver. Laying on her back with him between her meaty thighs, she looked like a carbon copy of her mother only 20 years younger. They resembled each other greatly in the face and in their fitness, but while Donna had the superior chest, Felicity held the huge advantage in the booty department.
"Yes," Felicity hissed as Oliver entered her. "Fuck me."
Oliver had no problem giving into her request, in fact he was going to do it anyway. With one of her juicy legs resting on the bed, he angled the other one up onto his shoulder. With his hands wrapped around her thigh, he had something to hold onto and pull back as he drove forward. The two knew each other so intimately that Oli knew the big-booty girl could handle the deep and rough penetration, tonight being no exception.
"Oh my! Your boyfriend certainly likes fucking you hard," Donna observed.
"You have...no idea," Felicity agreed through a series of moans.
For a short while Oliver held nothing back as he repeatedly slammed as hard and as fast as he could into the 23-year old blonde. Felicity's tits heaved inside her bra as she was tossed back and forth, her mouth held open so her screams could fill the room. Once he slowed down for a breath and to recoup some stamina was when Donna pulled her daughter's head back and kissed her from upside down, their noses pressing against the other's chin in the process.
"I know we fucked last night but boy did I miss this cunt," Oliver grunted while picking back up his thrusts.
Oliver kept fucking the screaming girl as he leaned over top her fit body so he could capture her mother's lips with his. Slipping his tongue into Donna's mouth, the pair kissed as Felicity kept taking Oliver's cock spiking deep into her womb. Every so often Oliver would break the kiss with her mom to lean down and lock lips with her, the second he pulled away the vacancy taking up by Donna as mother kissed daughter.
"Hey Oli, can I ask a favor," Felicity spoke, which was met by a nod from the horny man. "I really want to see you fuck her asshole."
"Wow! Felicity," Donna looked at her daughter in shock.
Oliver couldn't help but smile like a proud father seeing his child reach her full potential. Felicity was strong willed and becoming more and more sexually liberated, two great qualities he adored about her, but he thought a motherly threesome would be almost impossible. Yet here she was with his cock buried in her twat and asking him to sodomize her mom.
"Don't worry, he's great," Felicity told her mom.
Oliver pulled out and beaconed Donna over to him. She had no problem with this though she was still stunned from the declaration from her daughter. Regaining some composure, the older Smoak opened her mouth wide and sucked on Oli once more, this time with the added treat of tasting Felicity's juices all over his rod.
Meanwhile Felicity could all but feel his eyes on her ass as she crawled back behind her mom, who had propped herself up on hands and knees to blow Oli. She used her little hands to pull apart Donna's slim but curvy cheeks and give her better access to the blonde's bald pussy. It was quite a sight for her as her folds were so pink and already moist, the daughter even found herself subconsciously licking her lips before dipping her head forward and running her tongue through her slit.
"Umm God that's good honey," Donna groaned as her child tasted her pussy.
Remembering why she had gone behind Donna in the first place, Felicity got to work. She flashed the man at the other end of the bed a quick glance, seeing a look of pure elation on his face as his thick cock pushed into her mom's talented mouth then focused on the matter at hand. Felicity extended her tongue again but this time as she dipped her head back towards her mom's backside.
Her wet tongue glided over the sealed crinkled entrance to her back door in a broad contact several times, transferring a good amount of spit in the process. She knew that Donna would need it to take Oli's massive cock back there, and she was more than happy to help out. Narrowing her tongue now she placed it right in the very center of her asshole then crammed it inside, able to taste her mom now more thoroughly, and liking what she had to offer.
"Hey," Felicity mock protested as Oliver swung her mother around 180 degrees.
"It was your idea to do this," he told the younger girl.
With no more arguing with Felicity, Oliver gave all his attention to Donna and more importantly her butt. Between Felicity tossing her salad and the older woman's blowjob, his cock was more than lubricated for the passage into her ass. Testing his theory, he placed his tip at her entrance, waited for Donna to relax then pushed in. Though her asshole looked tight, it yielded with little effort and allowed Oli to get almost half his member before he stopped and reversed course.
"Shit...he really is huge," Donna exclaimed, him feeling even larger in her smaller hole.
Oliver appreciated the compliment but it was nothing he hadn't heard before. Focusing on fucking the 40-year old, the hulking man made thrusts with the majority of his cock and slowly added an inch every few times. It took barely a few minutes until his ripped abs were bouncing against her tight backside, making her round cheeks jiggle from the contact.
"Come lay baby," Oliver beaconed to Felicity.
The sexually liberated girl had been at her mother's head, kissing her deeply whenever Donna wasn't using her mouth to moan in pleasure. Worming her way under the thin woman, Felicity positioned her head right overtop of her mom's bald pussy and had the best view in the room to watch as the entirety of Oliver's cock hammered into her backdoor.
Knowing how big a challenge it was to be sodomized by the Queen man, Felicity sought to ease some tension for her mother. She was completely liberal with showing sexual affection towards Donna now which showed as she didn't think twice in sticking out her tongue and using it to swipe through her wet pussy lips and clit. As she approached her pink hole, Felicity dipped her tongue inside to taste her juices and could actually feel as Oli's dick pushed in and out just a thin barrier away from her.
"Oh My God! Yes! Lick my pussy! Fuck my ass," Donna screamed.
Oliver was thoroughly enjoying himself as he too was looking down to partake in the view. It aroused him greatly to see such a small, firm ass taking his monster cock deep into her bowels. It had the extra thrill of just being able to make out Felicity's pretty face as she licked at her mom's pussy. Thinking he could use more lube to help Donna, Oliver pulled out and realized Felicity had the same idea.
"Hope this is for me," Felicity commented as she angled his cock downward and engulfed his shaft, tasting her mother's ass on him.
"I can't believe you and my innocent little daughter are so filthy," Donna exclaimed, watching Felicity suck him straight from her ass.
"Wanna see deep inside your mom's ass," Oliver asked, already knowing Felicity's answer.
Sure enough, Felicity squirmed out from underneath her MILF and knelt beside the tall man. She knew exactly what he expected of her, she reached and and took hold of her mother's cheeks and pulled them as far apart as possible. Oliver aimed at the center of her small gape and poke right into it, not stopping until he was balls deep in her ass. He held himself in her for a few seconds then pulled out slowly and showed Donna's daughter how wide her asshole could get.
"Oh wow mom! You are gaping so much," Felicity observed.
Oliver didn't mind slowing things down for a little bit. He didn't know how long the threesome had been going at it but he was feeling the strain on his stamina. Buying himself more time with this slice of heaven, he pumped inside Donna's ass for several strokes as Felicity watched before pulling out and turning to the kneeling girl.
The first time Felicity wrapped her hand around his shaft to hold him steady while flashing her eyes up with a look of mischief. Knowing her role, the big bottomed girl opened her mouth and once again took her boss' cock straight from her mother's ass into her mouth. After bobbing several times she released him and watched as he used the saliva-slick tool to rail her mom for a spell before she got another turn sucking him off.
"Your turn to show your mommy how you take it in the ass," Oliver grinned wickedly.
"Mhmm," Felicity nodded. "Thought you'd never say so."
As if their movements were coordinated, Oliver crawled onto the bed as Donna rolled to the side. Flopping over onto his back so his erection stood straight up in the air, Felicity was there in a heartbeat to straddle his lap. It was her mom who had his cock in her hand, stroking him a few times before positioning his ready-to-go member against her daughter's backside.
Anal for Felicity was fast becoming his favorite action with his favorite fuck buddy. Her ass was meant to be plowed deep and hard, two things that Oli was more than capable of doing. Using her body weight and gravity, Felicity showed her mom had commonplace the act had become for her by riding his pole all the way to the base before she rocked her curvy hips.
"You like getting fucked in the ass you dirty girl," Donna asked her daughter, her fingers rubbing through her daughter's slit.
Felicity responded with action rather than words, continuing to ride her boss all the way down so he was balls deep in her ass before reversing course so only his tip remained in her puckered hole. Donna was actually amazed by the speed at which her 23-year old daughter threw herself down on the thick cock, feeling more proud of Felicity now than ever before.
"Yes Felicity...ride that dick," Oli encouraged before reddening each massive cheek with a firm slap.
"I'm gonna feel that cock through your pussy," Donna told her, sliding a digit into her cunt.
Felicity couldn't even equate how much pleasure she was currently experiencing. With her mother's two slender fingers pumping into her cunt as she took Oliver's cock deep in her ass repeatedly, it was like heaven. Anal had become so common between them that it had no pain with it and the feel of her holes being stretched at the same time was too much for Felicity after such a sensual night already.
"Yes! I'm cumming," the youngest of the three thundered.
Oliver noted how Felicity had slowed right down, choosing to stay resting deep on his lap with his dick buried completely in her ass. He didn't mind the break as he rode out her orgasm, able to feel her tight backdoor quiver against his manhood. He let her rest another 30 seconds before he lifted her up with his strong arms high enough until his cock sprang free and thudded against his abs.
"Look at the size of her gape," Donna observed.
"Like mother like daughter," Oliver grinned, able to assume that Felicity's asshole hung even wider open then Donna's.
With quickness that seemed unlikely to come from such a big man, Oliver sprang into action. He knew he didn't have a lot left in the tank but he would make every second count. Leaving Felicity on the bed resting on knees and her modest chest, he grabbed her slender mom and lifted her up so that when he lowered her she was resting her pillowy tits on Felicity's back.
With the Smoak women stacked on top of one another, Oliver had the pick of all four holes. Rather than choosing just one, he rotated between all four, starting with Felicity's freshly creamed pussy. A throbbing cock suddenly thrust inside her woke her up, even more after he withdrew and crammed her asshole full of his cock. After a few lightning fast pumps he went higher up and fucked both of Donna's inviting holes as well.
"Won't last much longer," Oliver stated, still going for one Smoak woman to the other.
"I want it," Felicity pleaded. "I want it all over my face," she begged.
Oliver was going to be more than happy to give his personal assistant who he made his own whore whatever she wanted as long as he could cum. Pulling out of Donna he straightened up, still standing tall on top the bed. Mother rolled off daughter and both Smoaks got to their knees in front of their man.
"Promise to share with your mom," Oliver asked.
"Yes. Just give it to me," she demanded.
The businessman twisted his strong frame more to the right in order to have his tip perfectly aligned with Felicity's youthful face. As he stroked his nearly foot-long length in front of her, Donna decided to not to pout about missing the facial and help him along the way. She did so by ducking her head down low beneath his beating hand and taking his balls into her mouth.
Oliver stroked his member for another few seconds until the first strand of white cum came bursting out. Felicity heard his familiar grunt, his telltale sign of his orgasm before she felt the first streak of cum splatter against the back of her palate. Holding steady, she kept her mouth open wide and tongue out as she proceeded to collect his entire salty load in her mouth. Finally after what felt like her mouth couldn't hold anymore, Oliver slumped forward completely spent.
"Oh my. That's a lot of cum," Donna commented. "Let me taste some."
Knowing what she wanted and having already agreed to share, Felicity propped herself higher up onto her knees while her mom sank lower onto her's. Once Donna's mouth opened wide, Felicity held her hair back and slowly drizzle the cum mixed with her spit into her waiting gullet. She stopped when her mom had swallowed about half the load then pulled Donna towards her for an open-mouthed kiss where the pushed the jizz between their tongues until it was either smeared on their lips or drank down.
"That was one of the hottest things I've ever seen," the exhausted billionaire commented.
"Well one Smoak girl has been known to blow minds so you never stood a chance with the might of two serving you," Donna replied, bringing a giggle from her daughter.
"Now we are going to go wash up," Felicity commented, grabbing her mom's hand and heading back for a tandem shower.