#maybe dilf!Ari x his babysitter!!! | Explore Tumblr Posts and Blogs

worksby-d · 2 years

Text

Pairing: dilf!Andy Barber x babysitter!Reader

Summary: Andy offers to drive you to a halloween party after babysitting for him, but you get distracted before you can get there.

Warnings: Age gap (Reader is in her 20s), Andy’s imaginary younger kid that I made up to make the plot work, car sex, blowjob, fingering, creampie, 18+

Word count: ~2,000

a/n: Changed this prompt to be for Andy at the last minute because I miss him soooo much 😣💕 I’m sorry to the Ari girlies. I’ll make it up to you, I promise 🫶

Part Two

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Skipping down the steps, you're in your own world as you quickly gather your jacket and shove the rest of your clothes into your bag, heading toward the kitchen to wait patiently for Andy and Jacob to get home.

Andy had texted you earlier today, asking a last minute favor of you to watch his youngest daughter while he and Jacob had a father-son evening. It wasn't like the Barbers to have not asked weeks in advance, but they're like a second family to you at this point, so you couldn't say no. But you do have plans to get to once those two are finally back.

Sending Andy a quick text, politely asking for an ETA since he wasn't sure before, you jump hearing his phone ding from just a couple feet away.

“Never mind,” you chuckle, walking into the room and seeing them both standing there already. “Sorry, I didn't hear you guys come in.”

“That's alright,” he laughs. If you aren't mistaken, you swear he does a double take after his eyes land on you. And you kind of hope that’s the case for a different reason, but he's probably just trying to decipher your costume. “We just got back. Figured you were putting the princess to bed, but maybe you were playing dress up..?”

“Oh, no,” you giggle. You know he's joking as he gestures to your outfit – a white skirt, white cropped tank top with thigh high tights, white heels, and a halo on your head to match. “I have a Halloween party to get to, so I was getting ready since she fell asleep early.”

“I didn't know you had plans tonight, I'm sorry–”

“No, it's okay.” You can’t let him apologize. He didn't force you to say yes. “I'm always happy to help out. I have a friend coming to pick me up though, so I'm just gonna hang out a while longer if that’s okay. This is kind of out of their way.”

“Well… Tell them they're off the hook.” Your confusion must be evident. “I can give you a ride,” he explains. “Yeah, Jacob’s here now, so I can leave for a bit, no problem.”

“You don't have to–”

“It's the least I can do.”

. * ✦ . ◍ ∘ . * ✦ ‧ ∘ ⊹

It's a quiet ride at first. You spend the first couple minutes trying to come up with some small talk. You've always talked to his wife more than you have to him, so you're not coming up with much.

As if he can read your mind, he takes it upon himself to break the silence.

“Laurie and I separated.”

Is this his idea of small talk?

You have kind of been wondering though since it was Andy who contacted you for once and since she wasn't at the house when you got there. Plus, you wouldn't admit it to anyone else, but you noticed his missing wedding ring.

“Just felt like I owed you an explanation for the last minute need for a babysitter today. It's my weekend with the kids, but I didn't want to let Jake down, so…”

Glancing at him beside you, there's a sadness in his eyes–very clear as they're lit up under each street light you pass–and you wish there was something you could do for him.

You're not sure what to say honestly. Your initial reaction is scoffing an astonished, “her loss,” but you figure that's probably the wrong thing.

“Oh…” You let your solemn tone fill the quiet for a second. “I'm sorry to hear that.”

You don't leave it at that though, instead punctuating your words with a daring hand resting on his leg.

His heart races the same as yours at the contact – But while yours does so out of nerves awaiting his reaction, his is a result of not having felt such a gentle touch in so long.

As your touch lingers, he has to resist his impulse to drop a hand from the wheel and take yours in his.

For fear of misreading your movement, he just grips the steering wheel tighter, trying his best to not dwell on what’s probably nothing.

You watch as he shifts slightly in his seat, gauging his reaction to your subtle advance. When he doesn't pull completely away or ask what you're doing, you assume you're in the clear.

Seeing how far he'll let you go, you slowly move your hand higher up his leg, gently brushing your fingers along his inner thigh.

He's trying to keep his composure, but you hear the hitch in his breathing as your touch gets closer to where he's secretly wishing it would go.

In an instant, he’s slowing the car down, and you smirk to yourself as he veers to pull over on the side of the road.

It's a dark one, nearly silent save the rustling of what's left for leaves on the trees as a few gusts of wind blow by.

He lets out a deep sigh when you take your hand away from him, finally looking toward you to search for any signs that he's gotten the wrong idea. But you're unbuckling your seat belt and leaning over to undo his too.

“You look so sad,” you whisper. “I can make you feel better.”

Your eyes meet his as you move closer to him–as close as the center console separating you will allow anyway.

“Yeah?” His voice is low as he watches you kneel on your seat, putting a hand back on his leg to hold yourself up.

“Uh-huh,” you hum, putting an end to his anticipation as your hand slides over the crotch of his jeans, palming against his cock. “If it's okay with you…”

His head falls back against his seat, a groan escaping his lips, when your fingers work to undo his belt and move his pants out of the way, ghosting over his hard dick.

“Go ahead and show me, pretty girl.”

He moves his seat farther back so you can comfortably take up the space between himself and the wheel. You can't contain yourself, eagerly replacing your hand with your mouth, taking as much of him as you can before softly gagging.

“Oh, fuck.” A breath gets caught in his throat. One of his hands gathers any hair from falling on your face, while the other rests on your upper back to keep you down. “You're good at that.”

Lifting your head, you let out a small laugh before sinking your mouth back down on him. Hearing him pant above you, you can't help but squeeze your thighs together in attempt of some sort of relief, no room to slip your own hand between your legs.

Andy catches on though, his leather seat squeaking each time you squirm. His hand on your back glides down to your ass, finding that your skirt is conveniently short enough to just flip up and pull your thong aside.

Deft fingers expertly find your clit, already slick from your dripping arousal.

He tsks, “All this just from sucking my cock, babygirl?”

Your whimper quickly turns into a moan as he pushes a finger into your sopping pussy, legs already trembling from the sudden intrusion.

“You're a sensitive one,” he chuckles.

You have to come up for air for a second, resting your cheek against his body while your hand takes over, slowly stroking his hard cock.

“Andy–” Your voice trails off, all words forgotten as he continues thrusting a second finger into you.

“Keep going, angel. I've got you.”

Taking him back in your mouth, nothing but lewd noises fill the car. An involuntary thrust of his hips makes you gag again.

With tears threatening to spill from your eyes, you have to push off of him for a breath again. And as tempting as it is for him to fill your pretty mouth, he doesn't force you back down this time.

He pulls his hand from between your legs, eliciting a whine from you as he kindly smoothes your skirt back into place.

You have to sit up slowly, but once you're steady, you swiftly clamber into his lap, straddling your legs on either side of his.

“Woah, eager,” he teases, putting his hands on your hips to support you. He has to reach up to remove the halo from your head though so it doesn't get ruined pressed against the roof of the car. “I usually take my time with people I like.”

Attempting to ignore the heat that flushes across your face following his words, you let out a shy laugh. He can't help but notice how breathtaking you look – the glittery makeup on your eyelids and cheeks reflecting the bright moonlight peeking into the dark vehicle.

“My friends will wonder where I am.”

“So…” He smirks. “Another time then?”

“Another time,” you nod, breathless again as you lift up and begin sinking down on his cock.

“Shit–”

“Andy–”

You sigh in unison.

Feeling a breeze across your damp forehead, you’re reminded of the windows you kept cracked for air. You drop your face to his neck to muffle your moans, afraid of being too loud.

It doesn't take long for you both to teeter on the edge of your highs after working each other up. He can feel your legs quivering against his own as you continue to ride him.

“Can feel you're close,” he grunts, gripping your hips to help you move.

You cry out, quickly grazing your teeth against his neck to quiet yourself as he fucks you deeper, clit bumping against his pelvis each time you come down.

“Fuck, sweetheart. Give it to me. I wanna feel you cum.”

He's got you in the palm of his hand at this point, you'd do anything for him. Your orgasm washes over you as an intense heat flooding your body. It leaves you trembling in his arms, biting down where his neck meets his shoulder to keep yourself from screaming his name.

“That’s it,” he breathes, working you through it as he chases his own release now. “Good girl. ‘m right there with you. Gonna leave you full of me for the–for the rest of the night.” He stumbles over his words. “No one will suspect a thing from the girl dressed like an a–angel.”

“Please,” you choke out, wanting, needing, to feel him. “Andy–”

Your pleas are cut off by a low growl in your ear and his arms tightening around you to keep you still as his cock twitches, release spilling deep inside you.

Letting out a shuddering breath, your body goes lax against him. The rise and fall of his chest as he works to steady his breathing is the only thing you can feel for a few moments.

“You with me, Y/N?” He chuckles, albeit still a little out of breath, as he checks on you.

“I think so,” you laugh and let out a sigh before finally lifting yourself off of him.

You instantly feel his cum dripping out of you, but he's a man who sticks to his word–quick to push it back in with two fingers before adjusting your panties back into place.

Your cheeks burn and you avert your eyes from his, whimpering at the obscene act. But your eyes fall on his neck, littered with evident bite marks outlined by your shimmery lip gloss.

“There's glitter everywhere,” you giggle, bringing your thumb up to try to wipe some off of his skin and his t-shirt. “I'm sorry.”

“Hey, don't worry about it.” He shrugs, but tries to get some that's misplaced off your face too though. “Let's get you to that party, sweetheart.”

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