A Challenge

By Bre (dust2dust34)

Disclaimer: I don't own anything related to Arrow.
Rating: Explicit
Author's Notes: Part of my Heartbeats Olicity smutlet collection.

Summary: Smut Drabble Prompt: ladymalfoi – "Is that a challenge Mr. Queen?"

"Is that a challenge, Mr. Queen?"

"I do believe it is, Ms. Smoak." Oliver gave her a level look. "The entire day."

Felicity snorted. "Please. Easy schmeasy."

Oliver smirked at her boldness, pinching his lips to hide it from her. "Alright. Good. Tomorrow then."

"Tomorrow it is." She turned back to her tablet, and Oliver turned back to the TV. He flipped through a few channels, not seeing the shows, his attention on his periphery. He could practically see the wheels turning in her head. "Should we make it interesting?"

Oliver raised an eyebrow, looking at her as he hit the mute button. "I'm listening."

"If I win - which I will, so be prepared - you have to do everything I ask you to, for an entire night." The smile he gave her was slow and predatory and she returned it. "Including cleaning." His eyebrows hit his hairline, not expecting that. "And fixing the air conditioner. And alphabetizing the spices." He chuckled and she leaned over, tapping his lips, her voice growing husky as she said, "And showing me you know how to spell supercalifragilisticexpialidocious with your tongue."

Oliver inhaled sharply, narrowing his eyes and she just smiled at him.

"Okay. And if I win?"

She sighed, patting his chest. "You won't." He laughed. "But let's make it dealer's choice."

He stared at her for a long moment. She met his gaze boldly, far too self-assured, which was only going to make tomorrow so much more fun. He knew what he wanted, but he didn't say anything, watching her watch him before she made a slight face. And then she bit her plump bottom lip, before sucking it into her mouth as she fidgeted under his gaze. The sight sent a burst of arousal through him.

"Be nice," she warned.

Oliver only smiled before turning to face her where they laid in bed, his hand sliding across the comforter. He slid his finger under her camisole strap, slipping it down her shoulder. Goosebumps rose under his touch, and he watched with fascination as a light flush spread across her chest. They both stared at his hand as he slid her tank top down, exposing her breasts.

And then she swallowed and Oliver's cock hardened as he followed the delicate line of her throat up to her rosy cheeks.

"I get to do anything I want to you, Felicity," he said, his voice low, a soft growl from deep in his chest.

Felicity blinked, licking her lips, her eyes meeting his. "Anything?"

Oliver's eyes drilled into hers, his fingers dragging over her breast. They slipped over an already peaked nipple, and she gasped, arching into him, her eyes never leaving his.

"Anything."

He watched her pupils dilate at the promise in his voice, and her breath grew shallow as her mind worked overtime to capture everything that single word entailed.

"It's a deal then, Mr. Queen."

Oliver probably should have mentioned that he had planned this the second he found the butterfly vibrator in her nightstand.

He knew about her toy collection, and they had played with some of them a few times, but it didn't hold the appeal it had with other women.

He usually got far too distracted by Felicity herself to properly use any of the damn toys.

Until he spotted the butterfly.

The wireless remote butterfly.

She came after a mere minute the first time he turned it on.

They were alone, and they were going to be alone all day, something she had not known until they'd walked into QC and she noticed Diggle wasn't going upstairs with them. He said he had a few errands that were going to keep him busy, and all of Oliver's meetings had been bumped to later in the week.

The entire day was free and clear and only for them.

She had not been pleased.

"This is cheating, Oliver," she whispered, straightening out a pile of papers with more force than necessary at her desk.

Oliver smiled at her - the fact that she was whispering at all was adorable, considering it was just them. He fingered the remote in his pocket where he stood in the doorway of his office. "You didn't say there were rules, Felicity."

"I think it's a pretty obvious rule," she replied, her cheeks flushed from the first orgasm. "I didn't think you would-"

Oliver switched the vibrator on to its first setting, and Felicity's words ended in a choke as the little butterfly came to life against her. He'd personally checked the placement when they'd gotten into the office, something for which she'd smacked the back of his head for, so he knew it was strapped on just as they had planned.

As he had challenged her to.

"Wear it all day."

"All day?"

"All. Day."

She'd known his schedule, knew he had back-to-back meetings for most of the day, and that John was usually there… she had obviously thought it was going to be easy, that Oliver wouldn't toy with her like that in front of people, especially since the vibrator made quite the racket when it was at its highest setting.

The little butterfly was pressed against her nether lips, the head directly on her clit, the antennas artfully positioned so each side of her sensitive nubbin got stimulation. The wings were spread out in perfect position, enough to send vibrations across the lips, while the rest of the body was teasingly pushed against her tight hole.

He'd made sure of that, tightening the straps of the vibrator where they were wrapped around each thigh and one connecting strap around her waist to keep everything in place.

Oliver switched the remote up a level, increasing the vibrations and Felicity's mouth gaped open, her half-lidded eyes glazing over.

His mouth went dry as her hips arched towards the vibrator, her fingers turning white where she gripped her desk. She already had a light sheen from the quick orgasm he'd brought her to just a few minutes ago, and he watched with fascination, the sun highlighting her from behind, making her glow from the flush slipping across her skin.

God, she was beautiful.

He was already growing hard, just watching her, despite having her twice that morning, his body tensing with each passing second.

Just thinking about the words he'd whispered in bed were shoving heady doses of need through his veins when she'd said, "Again?"

"You think it's going to be easy for me to just sit there, doing nothing but making you come over and over again?" His half-hard cock slid against her and she gasped. "Not able to do anything but watch?"

This wasn't just a challenge for her.

Felicity moaned, the sound coming out in strangled pants, her hips rotating in her chair as she squeezed her thighs together, pressing the vibrator against herself hard. Oliver's finger nearly slipped on the damn remote when she fell back in her chair, her hips arching up, one hand landing on her thigh where she dug her nails in.

He shut it off.

Felicity let out a low, pained keen as she slumped in her chair.

She opened her eyes, glaring at him, her chest heaving.

He just smiled and headed back into his office.

He watched her as he sat down.

Her lips moved as she randomly adjusted things on her desk with shaky, uneven movements. A long moment passed where she finally started to calm down, and Oliver watched her the entire time, readjusting his hard cock in his pants, biting back the hiss when he cupped himself. He may have little self-control when it came to the gorgeous woman sitting out there, but he had some at least - he could wait, he would wait, no matter how long he had to watch her luscious hips rotate against the little vibrator, or her hands slowly tighten on her chair arms as she moaned his name…

Oliver groaned, shaking his head.

Damn it, at this rate, he wasn't going to last.

Felicity gave no indication that she was aware of his eyes glued to the back of her head, as she turned back to her work, looking like she was cooling off.

Oliver pulled the remote out, and ratcheted the vibrator up to its third setting.

Felicity froze, her body stiffening, her shoulders trembling. Her hips started rotating almost immediately, and she gripped the desk with one hand, the other keeping her chair still as she rode the vibrator.

Oliver hit the fourth level after a moment, and watched her come with a sharp shout, her back bowing as the orgasm rocketed through her. He felt his own flush coming on, his cock hardening to the point of pain as she ground against the chair, her head falling forward, sobs of pleasure echoing into his office.

With a quick flip, he slipped the vibrator up to the fifth level, flicking it between the two levels, making her come again before he slowly eased off, finally silencing it.

Felicity fell forward onto her desk, her forehead resting against the cool glass. He waited, his eyes on her, his breathing heavy and controlled.

She finally sat up, and he grinned when she made a point to not look in at him, turning back to her computer.

The third time was an hour later.

The fourth time was over lunch, when she purposefully scheduled a telephone conference.

She was in there with him, taking notes dutifully as he answered the questions appropriately, responding when necessary, listening to the Hong Kong office as they talked about a midnight emergency for something or other… alright, he wasn't really paying attention.

One of the men on the other side asked if he had seen the report they just emailed over, and Felicity nodded, having already printed it. She went to her desk, retrieving the paper, and the second she entered his office again, he turned the vibrator on high.

Felicity faltered, choking back a moan, her eyes slipping shut.

She came quick and hard, just like he wanted - his response to her scheduling the damn call in the first place - and she nearly fell from the force of her release, biting her lip to keep from crying out her pleasure as her entire body quaked.

Oliver had to give her points because she remained standing in those sexy stilettos, albeit extremely shakily, finally making her way to his desk, handing him the paper - the very crumpled paper she had clenched into a tight fist - as he said, "Yes, I've got the report right here."

He kept the vibrator on a low setting for a while after that, teasing and tormenting her, and Oliver watched her sit at her desk, staring blankly at her computer, all her energy concentrated on the butterfly between her quivering thighs.

He could tell she was wavering with the fifth one, which he slowly - slowly - built towards, one that cascaded through her body like a gentle wave, judging by the way every inch of her reacted to it, and that she was getting unsteady with the sixth.

It was almost the end of the day when he gave her her seventh, sitting on one of the sofas in his office, and she came with a sharp groan that was bordering on painful when Oliver finally set the remote down.

He stared at her where she was sprawled across the cushions, her breathing labored, her body twitching with small aftershocks.

"I…" she started, her voice raspy and dry. "I win."

Oliver gave her prone body a smile. "Not yet. Come here."

Felicity barely had enough energy to lift her head as she looked at him. "What?"

He just cocked his finger at her in a 'get over here' motion.

With a breathy whine, Felicity stood, looking like a fawn learning how to walk again. Oliver gripped her waist, pulling her between his legs, forcing her thighs together, making her gasp, a sharp tremor jerking through her.

"You," Oliver said, his hands slipping down to the hem of her dress. He slid them up, pushing the material up as Felicity looked down at him through hooded eyes. "Are so fucking gorgeous when you come, Felicity."

Arousal darkened her eyes and her lips trembled as Oliver hooked his finger into her thong, pushing it down. It was soaked, and her juices smeared against her leg all the way down her inner legs where she dutifully stepped out of them.

He smiled up at her, letting his eyes drift down to her bare sex, a small patch of hair and the little purple butterfly still strapped in place her only ornaments. The flash of purple, the red, aroused tender skin, and the straps hooked around her - it was sexy as hell.

Oliver hooked her dress in the strap around her waist before he quickly undid his pants, letting his aching cock spring free. Felicity bit her lip, her eyes on him as his hard cock swayed between them, the head dark with need, the thick vein running up the side practically throbbing.

"Hard day?" she asked with a little chuckle and he narrowed his eyes, unable to stop the smile at her words, before he pulled her towards him. She lifted her legs, straddling him in his office chair, the vibrator still in place.

"You might say that," Oliver hissed as his cock slid against her soaking entrance. She was dripping, she was so wet, and Oliver slid his hands up her legs, his thumbs dipping down to slide across her inner thighs. His breath hitched when he felt the evidence of her multiple orgasms smeared everywhere.

He barely touched the vibrator and Felicity shuddered, her head falling back, pressing her chest against his face.

"You are so wet," Oliver whispered raggedly, his eyes on her sex and his cock slipping against her. The vibrator glistened, pressed between her puffy lips, her little clit hard and red against the butterfly head. "So beautiful."

"Oliver," Felicity whispered, her voice cracking, the exertions from the day stripping her of any ounce of self-consciousness that she usually showed when he took his time exploring every inch of her.

He gripped her hips and he lifted her, her thigh muscles clenching and his cock slid home, slipping into her with ease.

"Oh… god," Oliver groaned, the sensations of her slick walls rhythmically squeezing him pushing him further along than he wanted.

Felicity dug her nails into his shoulders, using him to help her lift her hips and thrust back down against him and Oliver gave her another guttural moan, already feeling his own release coming on way too fast as he watched himself slip out of her and then slide right back in, his cock spreading her already abused lips, pressing the butterfly up against her clit.

The sight of him spreading her like that, filling her completely, wearing a vibrator he had used on her all day… it was one of the most erotic things he'd ever seen.

She dropped particularly hard on him, and he slid in deeper, his pubic bone shoving the vibrator up against her clit, and she let out a needy moan.

Oliver blindly fumbled for the remote he'd left on his desk. When he found it, he gritted his teeth, flipping the switch to whatever random setting it landed on.

The vibrator roared to life, and Felicity yelped his name the same time he growled hers as the vibrations translated through her tender flesh and right into his. Oliver nearly dropped it as he grabbed her hips, lifting her up and down rapidly, the vibrations sending them both into overdrive.

"Oh god, oh god, oh god," Felicity babbled, unable to do anything but hold on as Oliver thrust her up and down on him. The chair squeaked under their ministrations, scraping against his desk as he pushed them higher. Felicity buried her head in his neck, and he pressed his face into her shoulder, his hands slamming her down harder and harder until Felicity came with a hoarse shout of his name in his ear.

The sound of her heavy panting, his name a litany on her lips, had the base of Oliver's spine tingling. He had enough state of mind for his thumb to find the remote and he shoved it up to its highest setting.

The loud buzzing sound of the vibrator echoed the wet sounds of her sex and the squeak of the chair as he grunted, "One more."

A plaintive cry was his response.

She lasted all of fifteen seconds.

"Oliver, I can't, I can't, please," she whimpered, the words tripping over her tongue.

Oliver shut the vibrator off instantly.

He dropped the remote and gripped her hard, shoving her down against him in three short thrusts that had him roaring his release as he came into her. He arched up into her, her sex milking him, shoving them away from his desk. The chair rolled back into the wall, the dull hit making them both groan.

Her walls rippled around him, and he groaned pitifully, matching the uneven keels Felicity was making.

They clung to each other, slowly coming down.

She was pure liquid in his arms. Oliver slowly slid them around her, hugging her close and she groaned.

"You okay?" he whispered, turning his face to press a kiss to the side of her neck.

Her only response was a discombobulated hum.

He grinned, pressing her closer so he could push his stubble against her sensitive skin.

"You know," he said. "I think I won."

"What?" she asked groggily, trying to lift her head as awareness set in.

He cupped the back of her neck, pulling her down so his lips were pressed to her ear. He kissed the shell softly and whispered, "I won, Felicity. You didn't last all day."

She huffed, trying to sit up before the little bit of strength she had managed to gather disappeared and she slumped against him.

"Damn."

He smiled, his hands sliding down her back and to her firm, beautiful ass. He felt himself hardening inside her at the thought of what he had in mind.

Oliver gripped her cheeks, pushing her against him, making her moan, and then he spread them wide, his finger slipping against her tiny puckered hole. She made a small sensual sound, and Oliver bit his tongue when she rotated her hips against him.

He massaged her lightly, testing the waters, and she moaned, a shudder making her body shake as he waited for her reaction.

Her answer was to lift her head with a lazy, sexy smile, her makeup smudged, hair wild, before giving him a wet, eager kiss.

The End

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