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Nov 21, 2023

As Fate Would Have It | DILF!Anakin Skywalker

Anakin Skywalker gets a new secretary, who also happens to be his favorite OnlyFans performer.

this is part one of my new series based off of this blurb.

rating: explicit | pairing: anakin skywalker x afab!reader | wc: 3.7k | read on ao3 warnings: modern!au, undisclosed age gap, SMUT [use of toys (dildo and fleshlight), mutual masturbation, squirting, watching of pornography]

After midnight is Anakin’s favorite time of the day. His kids have been asleep since 8:30 pm— their weekday curfew— and he’s finally stopped working on the project he brought home from work. It kept him from watching 101 Dalmatians with Luke and Leia but “it needed to be done.”

He completed it well after the twins went to sleep, his neck was aching, and he needed to unwind. Now, he’s settled on the left side of his king bed, back propped against the headboard and his tablet waiting for him on the nightstand. He’s been thinking about this all day. Ever since he got the notification at 1:48 p.m. that HoneySuckle uploaded a new video.

While he was at work. On a very busy day, he might add. As much as he wanted to get away to watch it immediately, he couldn’t. But now he has uninterrupted time to enjoy himself and the woman he’s about to watch.

Anakin watches HoneySuckle exclusively. For over three years now, he has been subscribed to her page for $7.99 a month, which is an absolute disgrace to the quality of content she puts out. That’s why he tips her at least $200 for each video. It’s a number that hardly means a thing to Anakin. But to HoneySuckle, it is everything. It’s a cushion for incidentals. For the flat tire on her Mini Cooper. The vet bill for her orange tabby, Panini. She has expressed her thanks to him in their private messages, but it never seems to be enough.

Their casual conversations are never enough.

It comes as a great surprise to Anakin to see that her newest video is dedicated to him. Him— Anakin Skywalker AKA skyguy81. AKA HoneySuckle’s biggest fan and number one supporter.

Squirting for Sky 🖤

He’s never clicked on anything faster in his life. The edges of his brain are beginning to fog. The mere thought of Honey getting off to the thought of him makes goosebumps prickle along his skin and his cock begin to swell. But then he sees what she’s wearing. Or, not wearing for that matter. Usually, she’ll begin videos with a full set on. Whether it’s a lacy bra and panties, a teddy, or a babydoll, teasingly taking off her lingerie is part of her brand.

Not in this video, though. In this new 23 minute video, she is wearing a black garter and thong with roses embroidered in the mesh along her hip bones. Sheer black stockings are pulled up to her thighs and as she spreads her legs— dear God— Anakin sees that her panties are crotchless.

Every video is expertly angled so only the bottom half of her face is on camera. She’s mentioned to Anakin in the past that this is not her full time job and therefore some anonymity is important. He doesn’t need to see her whole face to know she is beautiful.

“I bought this just for you,” Honey says directly to Anakin. “You said you liked black. I hope you like this.” She goes to grab the vibrator next to the pink dildo on her bed.

“I love it,” Anakin mumbles. Running her hand over one of her bare breasts, she turns on the vibrator. The familiar hum of the toy reminds Anakin to put on his headphones. Just in case.

Now with that taken care of, Anakin can begin taking care of himself. It doesn’t take long for the guy to get hard when he’s watching Honey. Hell, he can just think about her and he’ll be horny. The melodic cadence to her voice, the angelic sounds she makes when she cums, the lustful desire to bury himself in her cunt. She is the only woman he has desired since his wife and he doesn’t even know her name. But he knows the curves of her body as if he’s felt them with his own two hands. God, how he wishes he could touch her, kiss her, pleasure her.

It’s pathetic. He is pathetic for wanting the impossible. Anakin Skywalker is a smart man. A genius in many regards. Yet he’s delusional enough to think her messages might mean something. That this video dedicated to him means something.

Of course, it doesn’t. Everything about his conversations with Honey is transactional. It’s part of her job. That’s it. Nothing more. You’re not special.

But fuck, does it make his cock hard thinking this is all for him. Well, this is for him. The title of the video says so. With her legs spread nice and wide, Anakin can see how wet she has become from the vibrator on her clit.

Stiff and dribbling precum on his belly, Anakin wraps his long fingers around his equally long shaft. He swipes his palm over the tip to lubricate the rest of his dick. Honey has now turned off the vibrator and grabs the dildo. Despite its playful color, it’s a formidable size. A similar 7 inches to Anakin’s cock, she opens her mouth and the tip disappears. Then a little bit more… and a little more… until she’s gagging. She pulls it out of her mouth with a loud gasp. Messy strings of saliva fall on her chin and chest.

“Fuck,” she breathes. “I love choking on your cock. Feeling it so deep in my throat until I can’t breathe.”

This sends a jolt through Anakin’s whole body. His cock lurches in his hand and he knows all too well that his hand will simply not suffice tonight. He pauses Honey’s video and reluctantly gets off of bed to retrieve his Fleshlight from his hidden stash in the closet. Usually, his hand does just fine. He’s used to it by now. Being a single dad in his early forties and the CEO of his own company, he doesn’t have time to go on dates. He has one woman on his rolodex of hookup numbers and even then, he doesn’t contact her often. Usually it’s her who needs him. He prefers it that way, anyway.

Anakin returns to his bed with the barely used Fleshlight in hand and immediately resumes the video. Honey continues to give the dildo a blowjob, making Anakin ache for it to be his cock in her mouth. He can only imagine how warm it is. How he’d make her relax so he can shove his entire length down her throat. How she’d sound choking on his dick and not some pink toy.

Again, she holds it in her mouth until her lungs are screaming for air. Anakin ruts his hips up into his fist. He’s waiting to use the Fleshlight until she puts the toy in her cunt.

Which is right now. She lines the tip of it to her opening, pushing the head in teasingly before removing it and dragging it along her folds.

“Have you been good today? Do you deserve to fuck me?” The seductive nature of Honey’s voice is so familiar to Anakin, yet every time dirty talk drips from her lips, his spine tingles.

“Please, Honey,” Anakin whispers, hovering the opening of the Fleshlight over his cock. “Put it in, baby.”

As if obeying his command, Honey pushes the toy into her hole. At the same time, Anakin lowers his own toy onto himself. The tight Fleshlight sucks in his dick and it damn near has Anakin’s eyes rolling to the back of his head. He’d forgotten what it feels like… how similar yet different it is to real pussy. Fuck, what he would do to have his cock in Honey’s actual cunt. The best he can do is use his overactive imagination.

Honey is thrusting the dildo in and out of her and soft moans fill Anakin’s ears. He yanks the Fleshlight up and down—a lazy way of using it, he knows— but it does the job. “That’s it…” he breathes. His heartbeat is racing impossibly fast, chasing down an orgasm that is going to arrive far too soon. “I fuck you so well, don’t I, Honey?”

“Mm…” she whimpers, pushing the toy deeper and further into her. “Your cock’s so big… fills me up so well. Feels so good!”

“You have no idea how good I could make you feel,” Anakin growls. In his mind she’s on her back, just as she is now. Her knees are pushed up to her ears and Anakin is thrusting into her tight hole to no end. He’s so deep, he can see himself in her stomach. He kisses her, finally tasting her on his own lips. Their tongues are doing a dance, his fingers are on her clit for maximum pleasure. And she’s screaming his name. She can’t believe how good he fucks. How he, at 42 years old, can last as long as he has. “I’m not fucking geriatric,” he’d say. He’d make her cum at least twice before he does, just to prove a point.

Honey then takes the dildo out of her cunt and brings it back up to her mouth. Anakin removes the Fleshlight. She hollows her cheeks around it whilst reaching for the vibrator. She turns it back on and returns it to her clit. Her toes curl at the sensation and a moan is muffled by the cock in her mouth.

“Let me hear you,” Anakin encourages, no matter how silly and pointless it is to do so. “Please, Honey. I love hearing you moan.”

She takes the dildo out of her mouth to announce that she’s going to cum. “Oh, fuck. Fuck!”

She’s squirming on the bed, mouth shaped in that glorious ‘O’. As her orgasm rattles through her body, she keeps the vibrator on her swollen numb and returns the dildo to her pussy. Anakin follows suit and sheathes his cock once again, thrusting his hips up to the speed Honey is fucking herself.

“I hope you…fuck, that feels good,” she is interrupted by her own pleasure. It’s her authenticity that Anakin adores and enjoys the most. It never feels like she’s performing. “I hope you’re making yourself feel as good as I feel. Are you fucking your hand? Your mattress? A pillow? I bet you wish you were in my tight cunt. Don’t you?”

“Yes,” Anakin breathes. He is on fire now. He’s not sure the coil in his belly could get any tighter. He’s going to cum soon and Honey hasn’t even squirted yet. There’s five minutes left of the video. “You wouldn’t believe—ah, fucking hell— wouldn’t believe how badly I want to fuck you.”

“I’m gonna squirt! Oh my God…please cum for me. Cum while I squirt for you!” Honey removes the dildo as the clear liquid sprays from her cunt. Anakin abandons the Fleshlight and takes over with his tried and true hand. He’s pumping quickly, he’s mesmerized by Honey and how she squirts a little more each time she puts the dildo back inside of her and pulls it back out. Her back is arching off of the bed as she drops both toys and cums one last time.

Anakin is cumming now, too. His sack twitches up toward him while he releases his load on his belly. He stuffs a fist into his mouth to silence his moan. He bites down on his own hand with fervor, and it hurts. He isn’t completely finished when he hears her utter the words ‘last video.’

Wait, what?

He needs to go back. Surely, he didn’t hear her correctly.

“I hope you all enjoyed yourselves while watching. I know I did. This is a bit of a last hurrah for me. I’m starting a new job next week and I just don’t think I’ll have the time to upload, so this might be my last video. Thank you for all of the support over the last three years. I had a great time. Kisses, HoneySuckle.”

And that’s the end of it. Anakin is stunned. He watches her video again. And then once more. There's a lilt to her voice that makes Anakin think she is happy to be done with this. He should be happy for her. But he hangs onto the word ‘might’.

Honey said this might be her last video. Anakin shouldn’t feel so fucking relieved that his favorite OnlyFans performer might still upload videos. What is wrong with him? He has no real connection to her whatsoever yet he feels disappointed by the idea of not having her videos in his life anymore.

Fuck it. He sends her a $500 tip, a little message and goes to wash up.

Panini is pressed against your side, purring contentedly while you stroke his back absently. You’re wrapped in a sherpa cozy in bed while watching The Great British Bake Off. It’s your bedtime show. You’ve probably seen every series at least 3 times, simply because it’s the show you put on to go to sleep. But most of the time, you end up staying up to watch it as if you’ve never seen it before.

Your phone lights up with a notification. You glance at it but immediately do a double take. You grab your phone off of your nightstand and stare at the screen with your jaw dropped.

Skyguy81 sent you a tip!

$500

You pause in the middle of Prue Leith giving her thoughts on someone’s Showstopper. You swipe right to open the message.

That was spectacular, Honey. From the lingerie to the beautiful way you cum. You certainly know how to put on a show. I must admit, I was a bit disappointed to hear that it might be your last video. You are the only performer I watch. I will miss you. I wish you the best of luck with your new endeavor.

And I know what you are going to say. “It’s too much.” It is not. Please accept the tip as a token of my appreciation. You helped me feel less lonely on the days I needed someone the most. - Sky

Why do you feel like you’re about to cry? Sky has been your top supporter since you began uploading videos during COVID. It was just supposed to be a way to make ends meet. To pay off the student loans and any other financials that came up. The tips started off relatively small. $50 here, $75 there. He was the first to give you a $100 tip.

Then, after about a year, he upped it to $200 after each video. Your thank you messages to him turned into conversations. Short ones, never deep or personal, yet you feel like you know him. You feel like…no, it’s silly. You feel like he could be a friend. If you both weren’t hiding behind a screen and fake names, maybe you actually could be.

You begin typing a response.

Sky- I am going to say it anyway. THAT IS WAY TOO MUCH!!! You have been far too generous to me over the years. I don’t deserve it.

He replies in a matter of seconds.

I have to disagree, Honey. I wish I could do more for you.

Like what?

I would take you out to a nice dinner. Perhaps share a bottle of wine while we get to know each other.

Would you take me home after?

Whose home?

Whichever you’d like.

I’d take you back to your house and leave you with a goodnight kiss.

That’s all?

You would like more?

What the hell are you doing? Are you actually flirting with this man? He could be 60 years old and bald! Not that there’s anything wrong with being 60 or bald, but come on. You’re in your 2os. You have to have some limit. You stare at his username. Skyguy81. Maybe 81 is his birth year? So, that would put him at 42. 42 isn’t too bad…

Oh, what the hell. It’s not like you’re actually gonna meet this guy, right?

Well, I might wear something special underneath my dress. Something that I paid for with the money you’ve given me. Wouldn’t you want to see it?

Yes. I would.

What would you do if you took me home?

When you don’t hear back from Sky after thirty minutes, you assume he fell asleep. It is nearly 1 a.m. on a Thursday night. Or is it early Friday morning? Regardless, he probably has work in the morning.

With a rather loud yawn, you decide it’s time for you to go to sleep, too.

Luke and Leia barge into Anakin’s room at 7:30, dressed and ready to go to school while their dad is still fast asleep. He must have slept through his alarm. Luke is poking him in the side and urging him to wake up.

“Alright, I’m up,” he grumbles, scrubbing his hands down his face. “Have you two eaten?”

Leia nods. “Eggos and orange juice.”

“I wanted a Toaster Strudel,” Luke says.

“And I told him we don’t have any Toaster Strudels,” replies his twin sister.

“Yes we do! You just didn’t look hard enough.”

Anakin pinches the bridge of his nose. He feels a headache coming on. He didn’t drink last night, so why does he feel hungover? “Ahsoka ate the last one when she was here on Tuesday, remember?”

“Oh yeah,” Luke recalls.

“Dad, we’re gonna be late for school if you don’t get out of bed,” Leia says.

Anakin checks the time on his phone. Your message from last night is at the bottom of his notifications. He already has five work emails to answer. His calendar pings with reminders about meetings and his assistant’s retirement party. “Bring your things to the front door. I’ll be down in a few minutes.”

In the rush of getting himself dressed, not only does he put on two different pairs of socks but two different pairs of shoes, too. He doesn’t realize this until after he enters the office and Dorothy, attentive as ever, points it out as he’s walking past her desk and into his office.

Dorothy is 74 years old, a widow, and owl fanatic. She has been Anakin’s assistant since he started the company 20 years ago. “Did you get dressed in the dark, Mr. Skywalker?”

Even after two decades of Anakin’s insistence on calling him by his first name, Dorothy continues to defy him. “I overslept,” Anakin answers. “I was rushing to get ready because you know how Leia gets when she’s late to anything.”

Dorothy nods. “Yes, she is the most punctual 9 year old I know. I presume you did not eat breakfast.”

“No, I didn’t.” Anakin opens his emails.

“Why don’t I get you an egg sandwich from Dexter’s after I retrieve a matching pair to one of your shoes.”

“I didn’t ask you to do that.”

“You didn’t have to.”

Anakin cracks a smile. Dorothy has always been two steps ahead of Anakin. She’s been somewhat of a mother figure to him over the years. She believed in him when no one else did. How many people are going to put their faith in a cocky 22 year old with wild engineering innovations? Dorothy was there when his wife passed away and nannied the twins off and on for a few years while Anakin regained his bearings. His heart contracts. He is truly going to miss her. “Do you have to retire, Dorothy?”

“I’m afraid so,” Dorothy replies with a bittersweet smile. “You will be just fine. And I trust my successor will attend to your needs just as well as I have. I picked her myself. I know exactly what you need in an assistant, Mr. Skywalker.”

Did Dorothy just wink at Anakin before leaving his office? What the hell does she have up her sleeve?

Gold and brown leaves dance across the concrete in the courtyard of Skywalker Enterprises. The autumn air bites at your cheeks and you’re thankful you decided to wear a beanie along with your plaid pea coat.

You notice Dorothy’s silver hair before the rest of her as she walks toward you with two cups of something hot in her hands. “Good morning, Y/N.” she hands you the cup.

“Good morning, Dorothy,” you reply with a smile. You lift off the lid to smell the contents. The steam tickles your nose before recognizing the warm spices of Chai. “You remembered my drink order?”

“Of course.” Dorothy sits across from you. “I trust you went over the files I sent you regarding Mr. Skywalker? How are you feeling about the job?”

You take a meager sip of your Chai latte. It’s still too hot to drink. “I read all of them at least three times. He doesn’t seem too high maintenance.”

“Far from it,” Dorothy replies.

“But…” you begin, wondering if you should even mention it.

“What is it, dear?”

“I just find it a little strange that I haven’t met him. I would’ve assumed he’d be part of the hiring process. Isn’t it important we get along?”

“Oh, don’t worry about that. Anakin gets along with everyone! He’s a charmer,” Dorothy sips on her drink. “He entrusted me with finding a replacement for myself because I know him better than anyone. I know his needs better than he knows them. And you, my dear, have shown you are more than capable to take over. Your references spoke very highly of you.”

Right. Your references— one of which was your best friend who pretended to be a famous influencer who you “assisted” for 2 years after college. The other was a family you nannied for for only 2 weeks while the wife was out of town and the dad thought he could pull off some fantasy of fucking the nanny. The only good thing that came out of it was him telling you he’d give you a stellar reference for your next job. Turns out he wasn’t lying.

“So, I’ll start on Monday? By myself? No shadowing or anything?”

Dorothy nods. “I will officially be retired by 5 p.m. today. After which, Mr. Skywalker is yours.”

Don’t you wish. You’ve seen photos of him in Forbes. It’s an understatement to say he’s handsome. And it would be a lie to say you didn’t apply for the job because of his looks. By some miracle you were chosen out of hundreds of applicants and hired. You’ve signed the papers already. You’re officially on the Skywalker Enterprises payroll. Of course, you’ll be on probation for 90 days but Dorothy seems confident you’ll be a good fit.

Hopefully you will live up to Anakin Skywalker’s expectations.