#ceo!gray

It was a regular, run of the mill Youtuber party—one Grayson almost didn’t go to as he and his twin only uploaded on the platform once or twice every other month. Their almost-departure from the platform wasn’t intentional, but their production company kept them plenty busy. While Y/N was fairly consistent in terms of uploading content, she hardly ever went to Youtuber parties. She was usually working. On occasion, if she decided she wanted to have sex, she’d pick someone up at a bar, get herself taken care of, and go back to work. That particular night, though, her closest friend convinced her to go. At the very least to be a wingman for when she decided to get with the host of the party.

So Y/N went to the party and that was how she ended up sitting on the host’s balcony to smoke, so she’d be away from everyone, as she decided where to go at that point. The feeling in the pit of her stomach told her she needed release, and the friction from rubbing her thighs wasn’t doing it anymore. In the entire hour she’d been at the party, she hadn’t met anyone—man or woman—that she wanted to take home. The cigarette helped ease her while she figured out if she wanted to go to a bar, or if she’d handle it solo that night.

I want to get fucked, she thought to herself.

Once deciding what she wanted to do, she searched through her phone, reading reviews of the bars nearest to her, occasionally taking a drag of her cigarette as she scrolled through Yelp.

“Mind if I bum one?” A deep voice asked, making Y/N tear her attention from her phone. She looked the man up and down, an eyebrow raising involuntarily. He was big. In almost every sense of the word: tall, muscular, and from the slight imprint she could see on his pants, he was well endowed.

“Not at all,” she stated, taking her pack of spirits from her purse, offering it to him. He took one gingerly, placing it to his lips. Before he could ask, Y/N was already standing up, flicking her lighter to light him up.

He smiled sheepishly, “thanks.” She nodded, waving him off before taking a seat again, gesturing for him to sit with her. After a moment of taking in the beautiful, and intimidating, stranger in front of him, he took the seat next to her. “I’m Grayson, by the way,” he introduced himself, reaching his free hand out for her to shake.

She raised an eyebrow in question for a moment, “I know who you are.” It was Grayson’s turn to raise a brow in question. Instead of continuing the sentiment, she introduced herself, taking his hand in hers, “Y/N. Nice to meet you, Grayson.”

She held the handshake for a beat longer than necessary, the action not going unnoticed by Grayson. “So, how come you’re up here smoking, instead of downstairs in the backyard with actual people?”

“I could ask you the same question, couldn’t I?”

Grayson chuckled, “You could.” The tension was so thick you could cut it with a knife. Grayson desperately wanted to fill it, Y/N desperately wanted to know how much longer they had to make small talk before she could slyly ask him to take her home. “Truthfully, I saw a beautiful woman and I wanted to talk to her. So I asked to bum one, even though I don’t even smoke.”

Y/N wasn’t sure what she was expecting in terms of an answer, but that wasn’t it. Despite that, his candor made a real laugh escape from through her lips. “I commend the honesty, but you could’ve just talked to me, it would’ve probably been borderline creepy either way, though,” she smirked as a blush formed on the apples of his cheeks. “Cute,” she commented, making his blush deepen.

The goofy smile on Grayson’s face made her almost not want to take him home. He was too sweet. “Shut up. C’mon, I told you my reason, what’s yours?”

Y/N looked at him for a moment, wondering if she really wanted to take Grayson home. One glance at his bulging biceps and the way his pants started stirring by just her gaze, she decided almost instantaneously that even if he didn’t come home with her, she’d be playing with herself while picturing him that night. Might as well have the real thing. “I was deciding what bar to go to to pick someone up.” He visibly gulped, making Y/N want to bend over in that same second for him. “I’m not sure that’s necessary anymore, what do you think?” Her eyes didn’t leave his, and she watched as his hazel orbs darkened in desire, any trace of the sweet and almost vulnerable man she’d seen just seconds ago was washed away.

Knowing his bulge was evident through his striped pants, he turned his body to face Y/N. After flicking his cigarette onto the ground he leaned in a little closer, leaving their faces just inches from each other. Y/N could tell she was already soaked by the mere look he was giving her. She copied Grayson in tossing the cigarette, leaning even closer. “I think…” he started, placing a gentle hand on her hip, rubbing circles into it with his thumb before continuing, “I think that’d be a waste of a few trips and gas—wouldn’t be very environmentally conscious of you, would it?”

She nodded, “You’re absolutely right, how inconsiderate of me.” Her lips were just a hair away from his now. Her core was aching in waves to the rhythm of the circles Grayson traced on her jeans. “Thanks for keeping me environmentally friendly,” she practically whispered before colliding her lips to his. Her arms wrapped around his neck as he lifted her off her chair with ease. She caressed the stubble on his face as he walked her into the bedroom connected to the balcony. He dropped her gently onto the bed before pulling his shirt off over his head, leaning down to attack her neck with his lips. He kissed, licked and sucked gently, careful to not leave any marks as she unbuckled his belt and unbuttoned his pants, pulling them down hastily. Grayson chuckled at her eagerness before clasping his hand around her neck firmly, pushing her into the bed, “Don’t be so hasty, babygirl, or I won’t fuck you the way you want me to.”

She groaned at the nickname, her pussy was aching to be touched by him, but as much as she wanted him, she wanted to be in charge more. Looking him right in the eyes, she wrapped her jean clad legs around his torso and with all the strength she could muster, she used his surprise to her advantage and flipped him over to be under her. Grayson was shocked as she straddled him, wrapping her smaller hand around his throat, squeezing the sides of it as she leaned down to kiss him passionately. She ground into his boxer clad boner, moaning as she straightened back up, hand still around his throat, “It’s ma to you, honey.”

If it were possible to be more turned on, Grayson would be. Women didn’t generally fight for dominance with him. Defiantly, he ripped her crop top into two pieces of fabric, revealing the lacy black bra underneath, which he easily unclasped, immediately taking one of her nipples into his mouth, sucking on it greedily as he unbuttoned her jeans. The moan that escaped her lips that time was so loud, he wondered if she was a screamer. Deciding he didn’t want to wait to find out, he easily grabbed her hips and flipped her back under him. Grayson pulled her jeans off in record time, standing up to admire her body for a moment.

Y/N groaned in anticipation, throwing her legs up to pull him down. She pushed his shoulders down with her legs until he was on his knees on the bedside. He got the message clearly, tearing her panties apart. “Are you kidding me?” Y/N asked, laughing breathlessly.

“I’ll buy you new ones—and a new shirt.” He smirked. She wanted to wipe that right off his face. The only way she could think to do so was to shove his face between her legs.

Grayson happily and eagerly licked between her folds, making Y/N arch her back in anticipation. Grayson wanted to taste her, pleasure her, slowly build her into orgasm—but Y/N wanted to get fucked. “Baby boy, this is sweet,” she started as he pushed in a finger carefully, licking circles around her clit, “But foreplay is for lovers, suck on my clit and then fuck me already.”

Grayson didn’t need to be asked twice, he went down on her until she was bucking her hips, nearing her orgasm. She grabbed his hair in fistfuls, “Don’t stop, Grayson. Fuck, baby, please!” He lifted her hips, never letting up on her clit, and looking up into her face, relishing in the stoic woman becoming putty in his hands. Her groans and moans grew louder, Grayson was sure her orgasm was going to attract attention downstairs, which only pushed him to get her to scream. Grayson wrapped an arm around her wide hips to keep them up as he pushed two fingers inside of her, walking them on her g-spot. This sent Y/N over an edge, screaming his name so loud, he wondered if she remembered where they were or if she simply didn’t care. She breathed heavily as she began to grind herself on his face, coming down from her high.

Before she could fully compose herself, Grayson flipped her onto her stomach, eliciting a gasp from the woman he needed to be inside of. He hadn’t ever needed someone like that in his life, but looking at her glistening pussy made him so eager, he didn’t even try to ease himself in—he bottomed out immediately. Y/N gasped loudly as she felt him in her stomach, “Fuck, a little warning would’ve been appreciated, baby boy.” Grayson barely heard her, though, as he felt his body tense up. She felt so good. He slowly pulled himself back out, making them both moan lowly, “Grayson—“

He stopped his movements, he was only halfway out when he leaned forward, grabbing a fistful of her hair, “I’ve put up with your lip, but if you want me to fuck you, we’re going to do it at my pace.” She groaned, she usually wasn’t this turned on by being a bottom, but he’d brought her to such an intense orgasm that she let it slide, wanting nothing more than another one, she turned her head back to look at him, “I’m sorry, sir.”

“That’s right, ma,” Grayson said, kissing her softly, making her stomach flutter at the stark difference that kiss was to the way he was pulling her hair. Without warning, he was pounding into her roughly, one fist in her hair, the other on her hip, smacking her ass roughly every now and then. He fucked her so roughly, practically tossing her into different positions like a rag doll that she stopped thinking altogether, just enjoying being fucked by a man.

At some point he flipped her onto her back, his face in the crook of her neck as he pounded in and out of her slick, tight pussy. “Grayson,” she moaned. He was getting closer to cumming, wishing he didn’t have to just yet. Y/N felt the exact same, wanting it to never end. The familiar feeling was building in the pit of her stomach, causing her moans to increase in volume again. She opened her eyes to see Grayson looking at her, beginning to slow his hips. She shook her head frantically, “Don’t slow down, baby, I'm so close.”

He nodded, his eyes never leaving hers, “Me too, but I don’t wanna—“

“We can go back to mine after if you want, just please let me cum.” With that, he picked up his pace, groaning loudly and closing his eyes as he came closer to release. She grabbed his jaw in her hand roughly, holding him in place and looking him in the eyes as she bucked her hips against him, making his jaw drop slightly, “You gonna cum for me, baby?” She asked lowly; he nodded in response. “Look me in the eyes when you do.” His groans and her moans filled the room as they came together, their eye contact increasing the intimacy and intensity. Grayson half-collapsed on her, getting no protest from Y/N as she kissed his forehead. “That was fucking amazing,” he whispered, his head landing in the crook of her neck.

“You still wanna go to my place?” She asked. He nodded eagerly and bolted upright to get his clothes on. Y/N giggled at his eagerness as she put on what was left of her ensemble, rolling her eyes as she was half naked. Grayson laughed at the stern look on her face. She rolled her eyes as she picked her purse off the floor, leading the way out. Grayson followed her out, reaching for her hand. She raised an eyebrow at him, “Hand holding?” Grayson shrugged, tightening his hold on her as they walked out of the influencer’s house. Y/N was catching stares from her sudden toplessness, but she shrugged them off as she led Grayson out.

“Did you uber here?” She asked. Grayson nodded as she led them to her car. She tossed him the keys, “You alright to drive?” He nodded again, smiling softly, seeing her eyes were getting heavier once they were seated. Y/N put the address into the car’s GPS and the ride was silent aside from the music playing on the radio. She wasn’t sure if it was the way his jaw clenched as he drove, or if she was trying to wake herself up a little more because she really didn’t want the night to end, but she moved to take her seatbelt off, sat on her knees, and turned to Grayson.

“W-what are you doing?” Grayson knew exactly what she was doing.

“Returning a favor,” was all Y/N said before unzipping his pants and tugging at their waistband and the waistband of his boxers simultaneously. Grayson went back and forth between looking at her and the road, his palms sweating as he lifted his hips for her to have access to him. His dick popped out from the cotton that kept it captive and bobbed up towards his stomach, making Y/N moan at the sight. She knew he was big, she felt him in her stomach but seeing it? It made her core tingle in anticipation for what they were going to do back at her house.

She spit into her hand and wrapped her fingers around his dick, stroking it a few times before taking the tip into her mouth. Making Grayson moan and tighten his hands on the wheel.

“Jesus Christ,” he hissed. She’s a fucking psychopath, he thought briefly as she took more and more of him in her mouth. Slowly but surely she got his entire member inside her mouth, loving the feel of it in the back of her throat. She picked up speed, making Grayson’s hips buck in surprise, tingling at the vibrations from her moans. He peeked down at her and saw she was bobbing her head on him, while also playing with her clit. The sight had him groaning, wishing she was sitting on his face and that he wasn’t driving.

“Fuck,” he whispered as his balls began to tighten. Y/N pulled her hand from inside her pants and lightly grazed her nails against his balls, slowly tracing shapes into them. Grayson wished he could’ve held out to see what she would’ve done next, but suddenly he was slamming on the brakes, groaning out a loud obscenity, and bracing Y/N’s head before it hit the steering wheel.

As quickly as she started the act, she pulled herself back and into her seat, licking her lips in the process. “Your cum tastes really good,” she commented in surprise.

Grayson looked at her with wide eyes, putting his pants back on. Nodding his thanks, he couldn’t help himself when he grabbed her face and kissed her passionately. She returned the sentiment, giggling as he said, “You’re fucking crazy.”

The rest of the drive was filled with laughter and light jokes as they decided to get to know each other throughout the rest of the 40 minute drive. By the time they pulled into her driveway, they knew each other’s family member’s names, tidbits about their high school years, and quite a bit about work—both being devoted to what they work in.

“Ethan and I really want to take on a new… project, I guess you could call it. It’s more of a second business. We’re just worried that we won’t be able to put in as much of ourselves into it as we’d like. The production company takes a lot of manpower to keep running,” Grayson said as they walked through Y/N’s front door.

Y/N nodded, processing it as she pulled out a couple of wine glasses, pouring some rosé, her favorite. “I don’t think it should be as complicated as you’re making it, Grayson,” She began, handing him the second glass. “If it’s important to you and your brother, then make it a priority while its a seedling. Your company’s expanding pretty rapidly, right?”

“Yeah, sort of, its been kind of overwhelming honestly.”

“Then expand a little bit in terms of employees. Add in a couple of people to oversee projects for you and Ethan. You guys could be proper CEOs. Working on budgets and expansion, and dipping into the creative aspect now and then after this other project gets on its feet.”

“What if we’re too small to be adding any additional roles? What if it sinks us?”

Y/N hesitated for a moment before offering her help, “I’m sure it won’t, but in any case, I can take a look at it for you with some of my team, see what route is best for you guys.” She’d never even held a full conversation outside of sex with a one night stand before, let alone practically asked to see them again in the light of day. Grayson seemed very genuine though, she’d taken a bit of a liking to him. She could see him almost being a friend of some sort. Maybe one with benefits.

“You’d do that?” Grayson asked in surprise.

Y/N shrugged before making her way to the kitchen, making a breakfast shake and some toast. After placing the two smoothies, and a large plate of avocado toast on the coffee table, she turned the tv on loudly, taking a quick bite of her toast, sitting back and watching as Grayson sat up, startled by the loud music from whatever show she’d chosen off of Netflix.

Grayson looked around the room in a confused state before his eyes landed on a smirking Y/N. She turned the tv to a normal volume and gestured towards the food. “Made you breakfast as a thank you.” Grayson’s eyebrows shot up at the gesture, his chest warming at how kind it was. She wasn’t as cold as she made herself out to be. “A thank you? Also, is that smoothie dairy free?” He asked sheepishly.

She looked at him strangely, “No, it’s almond milk—the only dairy consumed in this household is cheese. I didn’t think that’d compliment the fruits very well, though, but if you want some—“

Grayson pecked her lips, effectively cutting her sarcasm off, “This was really nice of you…ma.”

For the first time, in what felt like maybe ever, Y/N blushed. Grayson noticed, but didn’t comment, he simply smiled triumphantly. “Why’d you sleep on the couch?” She asked, sipping on her smoothie. Grayson shrugged, “something told me you weren’t the type to cuddle.” He wanted to seem nonchalant, but his heart couldn’t help but stutter at the thought that maybe she wanted him to cuddle her.

“I’m not.” Or not, he thought.

“Then good thing I didn’t stay in your bed then, huh?” Grayson mocked her, a smirk finding its way onto his face despite the slight disappointment he felt. Y/N made a face, nodding a bit, continuing her breakfast. They watched the show in a comfortable silence, finishing their respective meals. Once they did, Y/N watched as Grayson gathered their dishes and made his way to the kitchen to wash them. She followed suit, sitting on the countertop by the sink as he cleaned up.

“Thank you,” she muttered as he finished. He leaned his hip against the sink, facing her, his signature goofy smile on his face as he said, “You made breakfast, it was only right. About last night—“

“I’d like to do it again, if you’re interested,” she stated. No use in beating around the bush, not when she wanted something. Grayson’s eyebrows shot up, his heart racing as he moved to stand between her legs. He placed his large hands on her thighs, “I think something could be arranged,” he muttered. Grayson softly rubbed up her thigh, his thumbs only an inch from her core, before he pushed them back down to her knees, rubbing circles into them, a smirk on his face.

He leaned in closely, his breath tickling her neck before he began to place small, fluttering kisses on it. Y/N chuckled as he made his way down, making Grayson’s heart skip a beat as he continued kissing down her chest and breasts through the fabric of her shirt, a small smile playing at the corner of his lips. Her laughter stopped when he pressed his lips to her hastily; his tongue swiping against her bottom lip for the entrance she decided against, pushing him backwards instead. Grayson groaned as the pretty, red painted smirk he knew he’d grow to be very fond of, took its rightful place on Y/N’s face as she said, “Not quite yet.”

Those three words ignited a flame that neither of the two would quite know how to extinguish. They met up almost everyday for three months, creating an unspoken, but strict, routine: on Sundays, Grayson helped Y/N film and edit her videos. He’d sleep over on Saturday nights. Most of those Saturdays consisted of Thai takeout and a movie followed by long makeout sessions and sometimes fast and rough sex, sometimes it’d be a nightlong 50 Shades ordeal, and sometimes they wouldn’t have sex at all—they’d just hold each other and talk, something neither of them could bring themselves to do with anyone else. The next morning Y/N would make breakfast while Grayson set up her equipment. At some point, he became her unofficial cameraman and would spend the evening helping her edit.

During work on weekdays, they’d spend hours on FaceTime. Helping each other through the lull that paperwork brought, and Grayson especially loved when Y/N began a new project and took him into meetings. Her eyes would sparkle as she ran through ideas with her team, her phone propped up so he could see her, and she always kept at least one AirPod in so he could hear her too. She had to learn how to acknowledge Grayson’s commentary while staying as professional as possible; she spent a long time earning the respect she had, she wouldn’t want to damage that.

A couple time’s a month, Y/N returned the weekly favor Grayson did on Sundays and would help the Dolan twins with their videos. She’d help them film sometimes when they needed more than one cameraman, and she’d helped them plan a few videos as well. They’d truly become best friends; Y/N knew Grayson almost as well as his own twin did and Grayson knew her better than anyone else did.

To Y/N, it was all perfect. She had someone she could call her best friend: someone who could make her laugh until she wheezed, make her scream in orgasm, someone who knew her Thai order without asking, and bought her tampons and groceries whenever he was able to—their dynamic was perfect. There was no drama, no distraction from work, no—

“I think we should stop,” Grayson said one Saturday at Y/N’s door. He’d gotten there a lot earlier than he usually did, but Y/N had a tendency to wear lingerie as loungewear so she was never not ready to be taken by him. He’d knocked so loudly, she imagined the scenario going very differently as she was already untying the red silk robe while opening the door. Her manicured fingers fell from the robe as he spoke.

While their friendship and all its factors meant more than a great deal to Y/N, Grayson was beginning to see that there was no future in what they were doing. No matter how close they became, no matter how happy they were, no matter how familiar they’d become to each other…Y/N was never going to see him as more than a friend. He’d come to terms with this reality. This didn’t mean that it didn’t hurt him, but it did mean that he’d asked a girl he’d met, and had a rather lengthy conversation with at a coffee shop that morning, out on a date. He liked Nancy enough. She was kind and soft-spoken. She reminded Grayson of sunshine, except on legs. He knew that if they were to go out, it was more than likely that he’d fall in love with her.

But she wasn’t anything like the fiery, intimidating, and blunt woman he’d grown to love. He wasn’t sure that anyone like Y/N existed, he highly doubted it—but at the very least she’d stay his friend.

“Stop what, baby boy?” Y/N asked as she furrowed her brows, not bothering to cover herself back up, her red lacy bra and underwear on full display as she left the door open for him to walk through. She took a seat on her couch and patted the space next to her, concern in her eyes. He seemed nervous and reluctant. She knew what he meant, but she didn’t understand where it’d come from. They were fine last night before he left to go back home to hang out with Ethan, what had happened in less than 24 hours that would have him wanting to leave her?

What did I do wrong? She asked herself, suddenly wanting to kick him out so she’d be in control of the situation. So maybe the sting of losing someone she’d become so close to wouldn’t hurt as much.

Grayson ignored the stirring in his pants at both the sight of her and the pet name. He’d never been one to be submissive, or enjoy it at the very least, but having Y/N dom him, made him change his mind. Judging by the color she was wearing, that’s what he would’ve been in for had he not said anything. He wanted to take it back as he took her in, his mind briefly imagining her tying him up and making him beg for her—but he pushed the thoughts down. He needed to move on.

“Stop the sex part of our relationship.” He clarified. There was a brief pause before he continued, “I met someone.” He was hoping to elicit some type of reaction. A part of him, the selfish part, hoped that she would realize his feelings if she felt him slipping away. That if she watched him begin to fall for someone else, that it’d change her mind about relationships, about commitment.

Grayson’s life wasn’t like the romcoms he binged with Y/N on Saturday nights, though. He’d always found it ironic that romantic comedies were her favorite, when commitment was something she couldn’t fathom. He was disappointed when a wide smile, one he didn’t think he’d ever seen before, made its way onto her face, “Really? That’s great, Gray! Tell me about her?”

It took him a moment to gather his disappointed pieces and shove them in a box but once he did, he told her about Nancy.

The pair sat together on the couch, discussing Grayson’s potential love interest, both doing their best to ignore the tension it brought between them as they both figured it was a figment of their own imaginations. Y/N didn’t want to let what they had go; she knew a relationship would take him away from her in big ways—not just sexual but also their weekend routines, or even just hanging out in general. He’d met someone, though. She knew what that meant to him because he wasn’t like her. He wanted a family one day. She wasn’t the person to give that to him. And the way he described Nancy? He described her as some kind of goddess living amongst them, and it was something she could never amount to even in her wildest dreams. Even if she was the ‘settle-down-start-a-family’ type, he wouldn’t love her. She was too much of the opposite of what he wanted.

What felt like hours later, but was really only half of one, Grayson checked his watch to see he had to get going or else he’d be late for the date. “She’s gonna love you,. Who wouldn’t?” Y/N smiled, fixing his hair a bit after walking him back to her front door. She knew she was doing the right thing, letting him go. It didn’t hurt her any less, though. Grayson’s eyes softened, silently begging her to ask him to stay.

But Grayson knew his best friend better than anyone. She either wouldn’t notice his silent pleas, or she’d ignore them. So instead of making any other embarrassing attempts to get her to ask him to cancel the date, he kissed her forehead swiftly and grinned, “I’ll let you know how it goes.”

She nodded, closing the door behind him. Y/N slid down her door, ignoring the startled feeling the cold tiles brought as they met her warm, exposed skin. She brought her knees up under her chin and tried to calm her breathing as her chest began to ache and tearless sobs racked her body. She didn’t want to cry, but the second the thought of Grayson no longer being in her life crossed her mind, the tears fell freely.

If he didn’t stick around for the sex, it was only a matter of time before the friendship aspect of their relationship deteriorated too.