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shewrites444 · 2 days ago

Text

pretty [ art donaldson x babysitter/age gap! reader smut ]

[ Hiii me popping up on here for the first time in forever lmao. I've been on a Challengers kick lately, let me know if I should write more on Art perhaps. :D ]

WC - 3.5k (unedited story, so apologies for any errors)

[ Summary - The reader and Art have been having an affair for the past few months after she became the Donaldsons' occasional babysitter. A lot of porn with a slight plot. ]

[ Warnings - Age gap (reader is college-aged, art is in his like mid-thirties), cursing, cheating/affair, oral (m&f receiving), dirty talk, tiny breeding kink mention, unprotected sex ]

It's not like it mattered to Tashi, well, anymore, what her husband did in his free time. A year or so ago, when Art found out about Tashi and Patrick's on-going affair at their challenger, he felt crushed, defeated, sickened, all emotions jumbled into one component, knowing what his wife was doing behind closed doors since they were teenagers. No amount of "I love you's" could make her drawn closer to him, no amount of care, compassion.. nothing. I mean, it would only make sense that an affair that lasted over ten years, especially with his former best friend and teammate, would fundamentally fuck up their marriage.

Tashi tried to fix it, she really did, by cutting off all connections to Patrick, promising Art she'd be better for not only him, but their daughter, Lily, and the careers and finances they shared together. She knew all the logic behind an affair was unjustifiable, and it made sense to fix a marriage with someone who genuinely cared for her and the family, careers, and finances they created together.

Art stopped playing tennis that year, and like they had promised each other months before, decided to work on the foundation full time, and with newer responsibilities, came the need for a sitter that wasn't only one of their parents when Art had a game or two.

That's where you came into the picture.

You were an undergraduate student at NYU, about to graduate in the spring with a heavy need for any sort of finances to help you afford your rent the rest of the semester. Knowing that your niece was in class with Art and Tashi Donaldson's daughter, that set up a fairly easy connection to a potential babysitting gig. They were millionaires, hell, maybe even billionaires at this point, so you'd be bound to get a pretty solid paycheck.

You were in luck. They needed an occasional sitter on the weekends, and a handful of nights during the week, and given that they both knew your sister, you were already trusted. Easy money.

You got along with Lily pretty well, too. Not to mention the Donaldsons were kind to you as well, and the amount of money they gave you for watching their one daughter, who was pretty self-sufficient other than needing to have a bedtime story or two read to her each night, was fucking ridiculous. Not like you were rolling in dough, but they surely overpaid you. Not like that was a problem for either parties, though.

Overtime, you talked more to Art when Tashi was starting to have more meetings, interviews, and other miscellaneous tasks that required her attention as they expanded connections to the foundation. At first, it was a bit awkward, given that when babysitting, usually the dad was a bit more absent, or quiet, but he warmed up to you after a few nights. He'd ask you about how Lily was, even ask you about school, or what you wanted to do after graduation, pay you, and that was really it. It was simple, really, until it wasn't.

And here you were, months later, standing at the small kitchen island in your apartment, which was, frankly, a bit inhumane in size for an inhabitant, but it's New York City, and it's what you could afford, even on the Donaldson's payroll. You had a small salad bowl in front of you, sliding the grape tomatoes off the cutting board in your hand into the mixture, as no other than Art Donaldson stood next to you, the tongs in his hand as you handed him the bowl.

Playing house with a married 35-year-old man wasn't on your list of things to do this year, but it's not like you were complaining.

From an outside perspective, it felt wrong, but to you, it felt just right. It was cliche, and well, bad, being apart of an affair for a multi-millionaire last name, and a man that was married, with a whole family, but you tried not to think about it.

Did you love him? You had never been in love, so you didn't really know, but probably not, at least not yet. Did he love you? You didn't think so, but he definitely favored you more than his own wife, and you weren't even thinking that because of the situation, you genuinely knew he preferred you.

"You want me to put a show on?" Art asked softly, glancing down at you as you walked over to the kitchen, rinsing off the cutting board. His eyes averted to your ass, glancing at the sweat shorts that hugged your figure, before looking up to meet your eyes when you turned around.

You knew he checked you out, it's not like that came to a surprise. Art was sweet, really, but it's not like he wasn't a sexual man because he was older. If anything, that made his sex drive higher. You shrugged, sliding past him to open the fridge and grab the salad dressing. "Eh, I'm good with whatever."

You can hear him set the bowl down, and his free hand travel to the side of your waist, over the thick cotton of your sweatshirt, as you grin to yourself, shaking your head while you set the dressing on the counter. "Shouldn't we eat first?"

"Just missed you today." Art muttered, lightly turning you around to face him before giving your forehead a light peck. "Haven't seen you all week, pretty."

Your cheeks redden, and the familiar pit in your stomach follows directly after. Fuck. Art was older than you, yes, but an emotional man at the fact of it, but he was so fucking needy. He'd come see you, not even two or three days between, and act like it had been two months without contact. He'd lay his head on your chest, play with your fingers, tell you how much he missed you, all because you hadn't seen him in not even a week. From the outside, that probably looked pathetic, a married man, who had a wife and child at home, coming to a college-aged girl's apartment, not even the size of his bedroom, cuddling her like he was a teenager. It was fucking toxic, actually, but again, you tried not to think about that part of it.

"Well, why don't we eat, and then you can show me that you missed me later, hm? That okay?" You step back slightly to look up to him, reaching forward to cup his rose-tinted, pale cheeks. You lean up to kiss him, pulling away to slide out of his embrace, your eyes following the meal you had just made together.

Art was pouting, basically, as he frowned at the corner of his mouth, walking towards the other side of you and gently taking the tongs out of your hand. "I'd rather show you now. You can't tell me you don't want me to fuck you right here, sweetheart."

"Art." You purse your lips together, shooting him a glare. You could pretend to be annoyed all you want, but he knew you weren't aggravated with him. It's not like you didn't enjoy him fucking the shit out of you on your kitchen counter, or anywhere, matter of fact. He'd fuck you right in your car when he walked you out of his house after babysitting, he didn't give a fuck. He liked you a lot, way more than he should, even in the given scenario of an affair.

"What?" He tilted his head, looking down at you with that stupid cheeky-ass grin he'd always give you when he knew you were fibbing. You wanted him, obviously. Sometimes, he didn't know why you even pretended to act like you didn't want it right then and there.

Art really wasn't even the most dominating guy, but if that's what you wanted, he'd put on a fucking show. He'd bend you over and fuck the shit out of you if that's what you wanted him to do. He'd make it hurt, if that's what you wanted him to do. But again, he liked you, so he'd never actually hurt you.

You glance down between you, the obviously erection in his sweatpants pointing right at you. You look back up to him, that look of pure want on his face so obvious. You glance to your bedroom. You don't have to speak, he already knows, and he listens so fucking easily.

The chemistry between the two of you was a fucking pain sometimes. You'd be so wet when he'd do as much as touch your back, it would piss you off sometimes, and you would think that after fucking him for a few months now, that feeling of freshness would go away, but it didn't.

You'd do more than just fuck, too. If he wasn't such a public figure, he'd take you out on real date, probably try to pursue you in some way if he wasn't married, and just a more normal-status guy, but that wasn't the case. He would make efforts though, buy you flowers sometimes when he'd come over, order the two of you something to eat, whether it was Chinese takeout or a 5-star review restaurant steak, he didn't care. He just wanted to please you, the best he could. All the time.

Right now, his definition of pleasing you was gesturing for you to lay down on your twin-sized bed, and plant his face between your legs, eating your pussy until you were begging him to fuck you with something other than his tongue.

You wiggled yourself out of your shorts and underwear in one, Art assisting you by pulling them off your ankles and onto the wooden floor. He spread your knees apart, kneeling on the hard ground before his hot breath was planting kisses between your thighs, his eyes never leaving yours.

You gulp, averting your attention to his mouth. You watch him get closer, and you can only gasp when he latches onto your clit. You feel him move his hand onto your thighs, wrapping around them from the back and holding your sides, his pale, calloused hands digging into your skin. It didn't hurt though, not at all.

"Oh my god." Leaves your mouth without a single thought. Art knew exactly how to please you. "Art, you're gonna make me cum before you even fuck me."

He looked up to you, lips still pressed against your pussy, his eyes locked with yours for a moment, before he focused his attention to your body again. He didn't care. Guess that was the point.

You shake your head in disbelief, your back naturally arching as he pressed his tongue harder against you. God, you couldn't even imagine what it was going to be like when his cock was inside you, even though you'd slept together plenty of times before.

His tongue kept pace on your clit, as he moved one of his hands off your thigh and closer to your pussy, gently pushing his middle finger through your folds. Fucking hell, as if he couldn't make you more turned on.

"Art." His name rolled off your tongue. "You're gonna make me cum. I wanna finish with you."

He listened to you, and he obliged, despite how much he wanted you to cum now. Art slowly pulled his finger out of you, and his mouth away from you. He leaned up, motioning himself on top of you, before you moved your hands to lightly push him off.

"What's wrong?" He asked, almost immediately, his eyes dropping, almost disappointed. You knew his cock was aching to be inside you.

You lean up, your hands traveling to rest against the sides of his broad shoulders. "Here. Lay down."

Art wasn't going to fight that. He eagerly nodded at your request, your positions switching in seconds as he laid down on your bed. Your hands began to pull at the waistband on his sweats, and his underwear, sliding them off his body in one.

You weren't one for sucking cock, but with Art, you fucking adored it. You liked to watch him fall apart at just your mouth, knowing that he'd crumble once he fucked your pussy. You liked edging him to the point he was whining, begging, pleading to fuck you, or you to fuck him. Just depended on the day.

"You gonna suck my cock, pretty girl?" Art asked you, softly, a half-smile on his pink lips as he moved one of his hands to cup your cheek, his elbow propping his body up slightly. "Gonna let me fuck your mouth?"

"Mhm." You murmur, nodding as you move down to spit on his cock, wetting the tip before you peck a few kisses against his tip, glancing up at him as you laid on your stomach towards the end of your bed, front of your body aligned with his middle. "Gonna let you fuck my throat, Art."

Art's grin followed the rest of his lips, his cheeks dark red as his mouth hung open. He watched you lean down, his cock enveloped by your mouth. You had pretty, plump lips. Pretty and full lashes you'd bat when he fucked your throat. He could watch you suck him off all day. He could just be with you all day.

"You're so beautiful, [Y/N]. My pretty girl." He praised you, his hand still glued to your cheek, bits of spit against his thumb as you bobbed your head, his cock hard and full in your mouth. "Gonna let me fill your mouth up, hm? Or should I fill your pussy instead? What do you want, baby?"

It's not like you could answer the question. You keep sucking him off, looking up to his blue eyes, before you force him down your throat, muffling any sort of gag that your body desperately wanted to let out. You wanted him to know you could take his cock.

"God." He moaned, his eyes never leaving yours. He rubbed your cheek. "Your mouth feel so good, but I really wanna fuck you. Please, baby. I wanna cum in you. That pretty pussy, please."

It didn't take you much convincing to slide his cock out of your mouth and lay down on your bed. It made you feel embarrassed, desperate even, with how eager you were to have him stuff his cock inside you. Not like he judged you for that at all, just internal thoughts you'd have occasionally.

He sat up, his cock hard and straight, as his knees dug into the mattress. He took his shirt off in one pull, tossing it into the pile of your combined clothes before he moved you more towards the middle of the bed. He aimed his cock at your pussy, your legs spread wide for him, before he leaned forward, slowly pushing himself inside you, the both of you moaning at the raw feeling.

Art could be rough if you wanted him to, and you'd do the same for him, but typically, he savored the moment he entered you each and every time. He'd told you several times, that you were no where near in comparison to any woman he'd been with. No competition. You were it. In every way. Part of him wished he had met you earlier, maybe at Stanford or even grade-school. God, he would've worshipped you back then, all the way to now, and the future. You checked off all his boxes, physically, emotionally, sexually, everything. In a different narrative, he would've married you and had a life with you. Fuck tennis. Fuck everything. He'd rather whatever life he could've had with you.

"You feel so good, pretty. You always do." Art leaned down to press a hard kiss against your lips. He pecked your cheek, his lips moving to your ear. "I'm gonna fill that pussy. Gonna make you mine, baby, my sweet girl.. You want that? You like that?"

You nod, your mouth open as you moan, rather loudly as he picked his pace up the more he talked to you. "Y-Yes, baby, fuck yes, fill me up. You're so fucking sexy.. You fuck me so good, Art."

Art groaned at your response, moving his head back to align above yours, his overgrown curls bouncing with his movements, the bed squeaking underneath you. He'd let his hair grow out a bit more lately since you complemented it awhile back.

"Gonna fill this pussy, pretty girl. Gonna give you my cum." He muttered, almost to himself, as he looked between your bodies at what he could see, watching himself fill your hole. It was obvious you were fucking a former pro-athlete. He could fuck you for hours if he wanted to with the amount of stamina he had, regardless of his age. It was fucking hot, how much, and how long, he could fuck you.

You could feel your orgasm increasing the more he penetrated you, the more he pulled his cock nearly out of you and forcing it back inside you, sending jolts through your body. You were already overstimulated enough from just slower sex, him fucking you like a bunny was almost too much for you to take. Not like that was a bad thing though.

"Come on." You talk to him, watching between the two of you, too. "Make me cum, baby. I wanna finish with you, Art. Please, baby. Fuck me so good."

He nods, his body rocking against yours, your legs moving up to wrap around his hips, keeping him closer, and more inside you. You wanted him to fill all of you, not missing a drop of his cum. You wanted him to make you ache when you woke up tomorrow morning.

"Fuck." He groaned, moaning into your mouth as he kissed you, his tongue sliding against yours as he came inside you.

You felt your body jolt, finishing at the same time, as he filled your pussy up. It felt so good to be on the same level, the same energy, as him. So fucking good.

He gave it a few seconds before he pulled out of you, sitting back up, making sure he fucked your right. He rolled to the side before he pulled you closer to him, his hand running through your frizzy hair, kissing the side of your forehead.

You smirked, looking up to him, a small laugh leaving your lips. "What? You can't be shocked, we've had sex so many times I can't even count it at this point."

"I'm not shocked." Art laughed, playing with your hair as he looked up to the ceiling. "It just feels so different with you. You know how much I like you, [Y/N]. Just feels good is all."

"Hm." You watch him look up. You wanted to bring something else up, more emotional topics, but, as much as you knew he did fancy you, you didn't want to fuck up the moment. "Feels good to me, too." Is all you say in return.

Art looks down at you after a moment. "Yeah?" He grins, moving closer to you as he kisses your lips. "Good."

"Yeah." You return his kiss, slightly leaning up as you look to the door. "You wanna eat now? Got your energy out?"

Art shrugs, sitting up. He pecks your bare shoulder. "Maybe not. Maybe can let the rest of it out later."

"God, you're hornier than me." You scoff, pushing him off with a red face, laughing to yourself at the man before you. "Let's eat. I'm starving."

"What you say." He smirks, clearly teasing you, before stepping out of the bed, grabbing his clothes and tossing yours to you.

And that was what was odd about you and Art. It was casual, but not in a hookup sense. Casual in the way that you could sit down and eat with him, make a meal with him, watch shows and movies together, like a normal couple. It drove you insane sometimes. He felt the same way, but how the hell could he tell you that, when he could never actually be with you? He'd have to mask it some type of way, and usually that was through sex. Not like he didn't enjoy it solely for sexual reasons, because, god, he enjoyed fucking you, but he also enjoyed you.

He watched you finish your plate as you sat on the sofa together. You were gorgeous, the perfect picture of the woman he'd want to be with for more than just this. But that was something you'd have to figure out later.