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Working out the Kinks

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Masquerade

It started on Halloween of their fourth year. Instead of having a free-for-all, Dean Pelton chose to theme the Halloween 2012 dance as a masquerade ball, transforming the Greendale cafeteria into a dark, dramatic, sexy lounge where, according to him, “Anything could happen.”

Jeff was usually not one to cover any part of his face, knowing it would be a crime to deny his adoring fans of his rugged good looks, but he supposed he could get on board with the whole masquerade thing. The masks provided at the door only covered the eyes, so his stubbled, chiselled jaw line was still well displayed.

The beauty of a masquerade ball was that Jeff could still wear an intentionally sexy outfit without getting flak for it from his friends... except for Britta, who once again missed the point entirely and arrived dressed as a raccoon wearing a black mask (“It’s called a mask-erade ball, Jeff... raccoons naturally have masks. Duh doi!”).

For Jeff’s part, he was decked out in a tux, sans tails, wearing a perfectly arranged bowtie around his neck. His dark suit was offset by a white Phantomesque mask—the only one like it on the entry table. If he wasn’t already pleased with the opportunity to dress to the nines for a party, he was as soon as he donned the slick, white mask.

Jeff hung back by the drink table as he surveyed the scene before him. In true Greendale fashion, the students had gone all out with their costumes. Several wore period outfits, complete with what he assumed had to be some very unpleasant and constricting undergarments. Not that he was complaining. Between the corsets and the push-up bras, the ladies of Greendale had never looked so good. Others flitted about in dazzling eveningwear, the likes one would never otherwise have a reason to wear to a Greendale function.

“Milord.” He heard her before he saw her. Annie sidled up next to him wearing something he never in his life would have expected to see her in. She wore a slim-strapped gown with a plunging neckline, and even deeper plunge in the back, showing off her delectable alabaster skin in places Jeff had never seen it before. The gown was a slim-fit to the floor, where the hem dusted the bottom of her heels. The skirt boasted an utterly scandalous slit that reached her upper left thigh, revealing the creamy skin that Jeff had only dreamed of.

The look was completed with a shimmering royal blue mask, that when placed next to her eyes gave them a mesmerizing, unearthly quality that made Jeff feel like he was drowning in them.

Jeff swallowed hard, raking his eyes over her body for longer than was even remotely appropriate. He was drawn from his trance when his eyes reached her face once more and found her smirking back at him.

“See something you like?” she teased.

This is what their relationship had become, ever since the end of the previous school year. The lines that were already blurred had nearly vanished entirely.

“I see a lot of things I like,” he said, finally finding his voice. He returned her smirk. “Isn’t there some kind of rule about only showing skin in one place at a time?”

“That rule doesn’t apply on Halloween, as I’m sure you well know.”

“Ahh, yes. It is truly the world’s greatest holiday,” he threw back, falling into their usual pattern despite a rocky start. He noticed then that a slow jazz song had begun to play and offered her his arm. “Dance, Milady?” She grinned and took the proffered arm, letting him lead her into the midst of other dancing couples.

Jeff pulled her in as close as he dared, splaying one hand across her bare lower back and taking her hand in his other. Easily, he began guiding them in a small, slow circles as her body sunk further into his. He let the thumb that rested on her back trace gently over her spine as he caught her eye.

“You look insanely hot.” His voice was gravelly, and he knew it betrayed the things she was making him feel, but at that moment he couldn’t be bothered to care. He had an armful of the sexiest version of Annie he could imagine, and he wanted her to know it.

Annie shivered underneath his touch and stare, her mouth parting slightly to draw in deeper breaths lest she drown in his scent. She watched him from under her eyelashes and her skin tingled beneath his hand on her lower back, pulling her against him insistently.

“You don’t look so bad yourself,” she responded breathlessly. “I always thought Christine belonged with the Phantom.” She noticed the bob of his adam’s apple as he swallowed, before ducking his head down so his lips were next to her ear.

“So did I,” he whispered dangerously. She felt a surge of arousal course through her from his breath on her ear.

“You want to get out of here?” she asked, a hint of a quiver in her voice. Jeff neglected to respond, he only pulled away and began guiding her away from the crowd with his hand still on her lower back, fingers slipping ever-so-slightly beneath the hem.

~~

Moments later, Jeff found himself against the closed door of a supply closet, Annie’s tongue deep in his mouth as his hands groped at the skin of her back, touching every scintillating inch of skin he could possibly get to. Annie moaned against his mouth and raised onto her tip-toes, their masks clinking together.

“We should take these masks off,” Jeff mumbled against her mouth, while simultaneously pulling her harder into his ever-growing erection. Annie shook her head, pulling her lips from his as she went to work on his bowtie.

“No,” she said breathlessly. “Let’s keep them on.”

The next few minutes were spent disentangling bowties and unbuttoning shirts and pants, and pushing blazers away from broad shoulders, leaving Jeff halfway naked before Annie. He tugged down the low front of her dress and pulled her breasts out, palming them roughly and thanking the Lord for the lack of bra potential that this particular breast allowed.

He lowered himself to his knees and dove in to fully take advantage of her breasts—her gorgeous breasts that he’d dreamed of far too often in the past. He held them each in a hand and pushed them together, alternating nipples in his mouth and teasing the other with his thumbs, groaning against her as he sucked her into his mouth and teased her with his tongue and teeth. Annie’s held his head to her chest, fingers clinging in his hair as she enjoyed his ministrations to their fullest extent.

Satisfied that he’d had enough of her breasts—for now—Jeff returned to his feet and reclaimed Annie’s lips in a hot, needing kiss while she pushed his underwear down to meet his pants at his ankles, taking rough hold of his cock and pumping him desperately in her hand. Jeff groaned into the kiss and pushed himself into her grip, desperate for the release that he’d needed ever since he first laid eyes on her in that ridiculous dress.

“Sit down,” Annie directed him, pushing him back against the door insistently. Jeff obeyed, watching her as she straddled his legs and pulled her dress open by the slit, revealing her centre to him, unencumbered by panties. Jeff groaned as she knelt down over him and in one quick dip, took him completely inside of her.

“Fuck, Annie,” Jeff moaned, immediately attaching his lips to her neck once she had settled onto him. He grabbed her by her hips and helped her set up a quick, desperate pace on top of him. He bent his knees and used the leverage to push up into her as she came down, the effort causing her exposed breasts to bounce freely in front of him, tempting and teasing him as he sought his release deep inside of her.

The quick build-up led to an even quicker conclusion that the two raced toward the finish, brows slick with sweat, chests heaving with laboured breaths. Jeff pulled Annie into him and devoured her breasts once again as he neared his end, desperate to have her come around him as soon as possible.

Annie took in the sight of Jeff feasting on her breasts as she fucked his cock with everything she had, and felt herself going rapidly over the edge as a result of the combination of sensations. She grabbed the back of his head, digging her nails into his scalp and held his mouth to her breasts as she rode out her orgasm, her moans coming out in sharp, quick gasps.

Jeff couldn’t help but come as she began convulsing around him, milking his cock and drawing out everything he had to give. He bit down into the flesh of her breast as he forced himself up into her hard and fast, groaning into the soft flesh of her chest and flicking her nipple desperately with his tongue.

Upon coming down, Jeff disengaged his mouth from her chest and dropped his head back against the door, looking up at her and finding her looking back at him under heavy lids, a small smile on her face, hair askew and makeup smudged. She looked completely and thoroughly fucked.

He really liked that look on her. 

Chapter Text

Parks and Recreation

It was mid-November and Jeff and Annie hadn’t so much as hinted about the events of the Halloween dance. For Jeff’s part, he was incredibly frustrated that he hadn’t been able to have a second (or third, or fourth) go with her. He was still recuperating from being thoroughly fucked on the floor of the storage closet at school, and he would have been completely okay with re-enacting the scene as many times as Annie wanted.

But she wasn’t even looking at him anymore. Each time he tried to meet her eye, she averted her gaze and struck up a conversation with someone—anyone—else. Seriously. At one point she’d chosen Garrett over him. It was intensely frustrating.

Or maybe it was all in his head. Maybe he was crazy and Annie was acting completely normal, because despite how incredibly awkward he now felt around her, the group seemed totally unfazed—even Abed, whose job it was to point out even the most minute changes in the group dynamic.

He was pulled from his ruminations by Troy loudly declaring it an outdoor study day, due to the unseasonably warm weather (he wasn’t sure he’d call it an Indian Summer, since it was only November, but the heat was incredibly out-of-the-ordinary for Colorado this time of year). The rest of the group was easily swayed, many of whom had been staring longingly out the window ever since their first class of the day.

All seven of them wandered away from Greendale to a nearby park, surrounded on three sides by woods filled with a winding array of hiking trails. It was one of Greendale’s more picturesque spots, and was one of Jeff’s favourite places to go running in the warmer months. He felt contentment overtake him as soon as he settled onto the warm, green grass with his friends.

“I still can’t believe how nice it is,” Troy exclaimed excitedly. “You know what this means, right?”

“Ultimate Hide and Seek?” Abed supplied. Troy grinned widely.

“Ultimate Hide and Seek!” The two shared their special handshake, leaving the rest of the group watching them confusedly.

“Umm, I thought we were here to study,” Annie complained.

“Boo!” Troy shot back. “Come on Annie. We can study any time. It’s never going to be this nice again!”

“That’s not true, it’s just not going to be this nice again this year,” she responded.

“It does sound kind of fun,” Britta interjected. The brunette’s eyes landed on her.

“Guys, we have our English final in three weeks, we have to start studying.” Jeff laid back on the grass and decided to let the group deal with her. He knew he would rather be playing Ultimate Hide and Seek (but what makes it ultimate?) than studying, but he also knew he wasn’t about to try and sway her. Things were still too awkward. He zoned out, staring up at the white, puffy clouds in the sky.

“Okay then, it’s settled,” he heard after what could have been a very long time, knowing his friends. “We’ll play for an hour, and then we’ll study,” Abed summarized. Jeff pushed himself back up.

“Not it,” he drawled out. The rest of the group looked at him confusedly. “Just making my intentions clear. Okay, so how do we play this game?”

“Jeff, Troy just explained the rules, two minutes ago,” Annie said. Jeff met her eye only briefly, before flitting over to Troy.

“Again, for those of us too awesome to listen the first time?” he asked. Troy launched into the explanation.

“Okay, two teams of two—except whichever team has Pierce, that team gets three—run into the forest while the third team tries to find them. If we make it back here to home base, we’re safe, if the seekers find us, we’re it. Simple as that.”

“What are the teams?” Jeff asked.

“I’ve devised a system by which each person is matched by athleticism and wits,” Abed explains. The group looked at him blankly. “Britta, Pierce and I are together due to the potential for hijincks, Troy and Shirley because they never have storylines together, and Annie and Jeff to increase our audience appeal.”

“Uuuhhhhmmm!” Annie said quickly. Jeff’s eyes shot wide and looked between her and Abed.

“Last to say “hot coffee from a proper copper coffee pot,” has to seek,” Abed finished.

“HOTCOFFEEFROMAPROPERCOPPERCOFFEEPOT!” Five voices screamed at once. Annie and Jeff continued to stare in dumbfounded silence. Did he know? Was he trying to force them together? WHAT WAS GOING ON?!

“Annie and Jeff are it. On your marks, get set, GO!”

Before the pair was able to fully realize what was going on, all of their friends abandoned them, disappearing into the woods.

Jeff and Annie looked at each other uncomfortably.

“Soooooooo,” Annie drawled out. Jeff jumped to his feet.

“Let’s seek. We’re seeking right? Let’s seek,” he said, quickly starting in the direction their friends had run.

“Wait, Jeff!” He stopped short and turned back to her. “We have to count to a hundred to give them time to hide,” she finished a little lamely. Jeff groaned and returned to where she was sitting and began pretending to count in his head.

They sat quietly for a moment, both sinking into the awkward tension between them. After what was easily more than a hundred count, Annie let out a sharp sigh.

“This is stupid,” she huffed.

“No kidding. I definitely could have said ‘hot coffee from a proper copper coffee pot’ faster than Britta.” She rolled her eyes.

“I’m talking about this, Jeff,” she said, waving her hand between them. “We don’t need to be like this, you know.” He let out a sigh and met her gaze.

“I know.”

“I don’t want to be.” She offered him a small smile. “I miss you.” He quirked a grin.

“Yea?” She nodded decisively.

“Yea. You’re one of my best friends. I don’t want to lose that just because we... you know.”

“We... had ridiculously hot faux anonymous sex on the floor of a supply closet?” he offered, a semblance of the Winger smirk on his lips. Annie flushed a bright red.

“Yes,” she said quietly. “Not that I’d put it that way.” He grinned a little wider.

“Oh, well how would you put it?”

“I wouldn’t put it any way... can we just... forget about it?” Jeff felt the grin slip off his features as his heart dropped in his chest.

“We uh... we should probably get to seeking,” he suggested. Annie took note of his sullen features, but nodded. They each got to their feet and headed toward the woods to find their friends.

~~

“Okay, there has to be some kind of rule about how long this can go on,” Annie complained after searching for what seemed like a very long time for their friends. Jeff shrugged. He hadn’t really said much of anything since they left the clearing, feeling dejected and unenthused after their conversation.

“Doubt it.” Annie sighed and looked at him out of the corner of her eye.

“Oh great, stuck in the middle of the woods with Monosyllabic Man.”

“You stole that from Gilmore Girls.”

“You know I stole that from Gilmore Girls.” Jeff felt himself flush lightly.

“Yea... they air reruns on Saturday afternoons.” Annie giggled lightly and Jeff felt himself respond to it in ways he desperately did not want to.

“I’m telling everyone,” she teased, poking his arm. He rolled his eyes, but couldn’t help the small grin the forced its way onto his lips.

“You do and I’ll tell everyone you went commando to the Halloween dance.”

“No you won’t—if you did, you’d have to tell them how you found out,” she countered. He stopped short.

“I’d be okay with that,” he shot back. She stopped and turned on him, a slight edge in her voice.

“Why can’t you just let it go?” He crossed his arms over his chest.

“Because I don’t want to let it go,” he said in a low voice. “And I kind of hoped you wouldn’t be in such a rush to let it go either.”

“Why not?!” she demanded, her voice slightly louder than intended. Jeff felt a pang of anger in his gut. He was irritated, and not ready to play nice with her after being completely dismissed.

“Because I liked it, okay?!” he spat, a little louder than intended. “And I would have liked to keep doing it, but you went and got all weird afterward, and I couldn’t even talk to you about it because you kept shutting me down whenever I tried to have a freaking conversation about it.” Annie frowned.

“I wasn’t trying to shut you down,” she said softly. His brow furrowed.

“Then what were you doing?” She looked down, toeing the dirt with her flat.

“I was just trying to put off having the “discretion” talk again. I figured if I acted like nothing happened then you wouldn’t freak out or feel the need to shut me out again.”  Jeff frowned.

“So you shut me out instead?” She raised her eyes to meet his, regret apparent in the deep blue pools.

“I thought I was making it easier for both of us. I guess I was wrong.” Jeff nodded.

“Yea, I guess so.” A silence passed between them for a long moment, until Annie stepped a little closer.

“So what are we going to do about it?” she asked. Jeff stepped into her, wrapping his arms around her waist.

“Well, Annie,” he said. “We’re adults. We can do whatever the hell we want.” He dipped his head so she could feel his breath falling across her lips.

“We, uh...” she stumbled over her words, flustered. “We should find the group.”

“They can wait,” Jeff said insistently, pushing forward and claiming her lips desperately. It had only been three weeks since he’d tasted her, but it had been three weeks too long. He needed her, and now she knew it beyond a shadow of a doubt.

Jeff manoeuvred them off the path and into the woods, pressing her back up against a large oak tree. He pushed his knee in between her legs, dragging her core over his upper thigh as she moaned into his mouth.

“We’re in public,” Annie mumbled against Jeff’s lips, not stopping her movements against his leg. Jeff pushed her harder against the tree and moved his mouth to her neck.

“We’re in the woods,” he corrected. Annie moaned as he found a particularly pleasurable spot on her neck and began to suck on it. She held his mouth to her as she increased her pace against him.

“The group could be anywhere,” she protested meekly. Jeff pulled back, removing his leg from between hers, starving her of his contact.

“Do you want to stop?” he asked, slightly out of breath. She looked up at him, heavy lidded, and shook her head decisively.

“Come back.” She grabbed him by the collar and dragged his lips back to hers, kissing him deeply and with purpose. Jeff hoisted her up so she could wrap her legs around his waist and pushed her back into the tree, grinding himself into her, relishing in the relief offered by the friction. The two moved together hard and fast, desperate for some form of release.

“Fuck, Annie,” Jeff moaned into her mouth. “This is all I’ve been able to think about for three fucking weeks. I want to be inside of you.” Annie moaned at his words and ground hard against him once more before dropping her feet to the ground.

“Then what’s stopping you?” she questioned. Quickly, she popped the button on his jeans, pushing the zipper down and pulling his cock out through the hole in his underwear. Jeff pulled her back up and she wrapped her legs around him once again, allowing him to shove her underwear out of the way before entering her quickly.

Annie cried out at the sudden invasion, but her sounds quickly turned into moans and pleas for more as he set up a punishing pace inside of her, weeks of tension falling out with each desperate thrust. Jeff’s mouth reattached to her neck as he plunged in and out of her over and over again.

“Fuck. So good,” Jeff mumbled against her neck, increasing his pace inside of her. Annie moved her hips against him, meeting his each thrust with one of her own, needing him more and more as the moments passed. It didn’t take long for her orgasm to creep up on her, the mix of teasing and the wait driving her insane with need.

“Ung, harder,” she demanded, wrapping her arms more tightly around his shoulders. Jeff tightened his grip on her hips and began pulling her back to him hard with each thrust. She cried out, becoming lost in the overwhelming sensation of climax. Jeff bit down on her neck, riding her through it, coming only as she came down from her height.

“Fuck, fuck, fuck,” he repeated as he thrust uncontrollably into her as he came. He buried his face in her neck as he lost his breath.

When finally he was spent, Jeff settled Annie back onto her feet and put his now spent cock away, before lowering himself down to the ground, leaning against the tree. Annie pulled her underwear back in place and slid down to join him, settling in between his legs and leaning against his hard chest.

“If I knew that was part of being ‘it’, I wouldn’t have been so opposed to the idea,” Jeff joked, dipping his face into her neck and placing a kiss there. Annie turned slightly to face him.

“What are we doing here, Jeff?” she asked tentatively.

“I don’t know,” he answered honestly.

“Are we going to keep doing it?” Jeff chuckled lightly.

“Do you want to?” Annie bit her lip.

“I might,” she said timidly. “Do you?” Jeff wrapped his arms around her, pulling her back against him.

“I could be persuaded,” he teased, pressing his lips just beneath ear. Annie got lost in the sensation for a moment, and then suddenly remembered what they were doing in the woods in the first place.

“Oh, crap!” she exclaimed, pulling away from him and up onto her feet. Jeff looked up at her confusedly.

“What’s wrong?”

“The group! We’re supposed to be “seeking” them. They’re going to start wondering where we are.” Jeff sighed deeply and pulled himself to his feet, brushing some leaves off of himself before starting to swat at her back.  “What are you doing?”

“Well, Annie, leaves you can probably explain away, but people are going to start asking questions if you show up with bark all over your back.” Annie giggled as Jeff removed the last pieces of evidence from her sweater and hair, before turning her to him, wrapping his arms around her waist.

“So...” she said softly.

“So,” he repeated. “You want to keep doing this?” She offered a small smile and nodded.

“That sounds good.” Jeff leaned in and left her with a small, innocent peck on the lips before grabbing her hand and directing them back to the path they’d abandoned, heading back to home base where they would almost certainly find their friends waiting for them. 

Chapter Text

Winner Takes All

It had been nearly four months since that day in the park. Four months since Jeff and Annie decided that the sex was just too damn good to stop doing it as often as possible. Initially, Jeff had been under the impression that this would lead to the inevitable ‘relationship’ talk, and that he would have to bite the bullet and actually commit to Annie (something he was surprisingly willing to do). His inclination thus far had been proven incorrect, however, as Annie had yet to mention anything to suggest she wanted something more out of him than just great sex.

And great sex it was. Not only great, but adventurous, sexy, kinky, and occasionally quite strange. Jeff figured out not long into his –whatever it was—with Annie that she was using him to try out all kinds of theories for how two people could get each other off. Jeff, being the accommodating guy he was, had no issues with working her through their various kinks—some of which he’d tried, but a surprising amount that he hadn’t.

It took about a month for Annie to feel comfortable enough to ask Jeff to try something a little bit out of the ordinary. Through November and most of December, they’d been firmly committed to the basics, testing one another’s limits and discovering the spots that made them squirm, moan, laugh, shudder and, of course, come instantly. It was near Christmas when Annie finally suggested something a little less ordinary for their often bi, tri and quadro-weekly sex sessions.

Her first kink had been one that Jeff was all too happy to help her out with. She had snuck into the Greendale Glee Club’s storage room and absconded with the slutty Santa outfit she’d worn the year earlier to entice Jeff to join them for the Christmas pageant. He didn’t even bother denying that she’d hit on one of his most favourite versions of Santa, and the two had enjoyed a thoroughly not-safe-for-work rendition of Santa Baby.

A few weeks later, Jeff finally decided Annie was ready to try out one of his kinks—namely, a rehash of her exceedingly scandalous attire from the second paintball war. Clad in a bosom enhancing corset and bloomers around her ankles, Jeff fucked her the way he’d been wanting to ever since he first laid eyes on her dressed in old-west style.

Since then, the kinks had become a more common part of their time together. They tried all kinds of things, including, but not limited to food play, car sex, anal sex (something Annie swore she would never do again), re-enacting scenes from porn, various role-play scenarios, and a variety of medium-risk voyeuristic endeavours that nearly got them caught by one or more of their friends on numerous occasions. 

Jeff wouldn’t necessarily call Annie a ‘fetishist;’ just curious. She was open to trying new things and sharing experiences, something he’d never really gotten to do much of in the past (one night stands tended to limit the potential for out-of-the-box ideas). He found he was learning just as much about his own sexual appetite as she seemed to be about hers.

This night in mid-February was not one of the crazier night’s they’d shared. In fact, it wasn’t really much of anything. Annie had come over for a movie night (with the unspoken assumption that it would lead to something more fun than watching Harry meet Sally for the billionth time), and naturally the two abandoned the movie halfway through in favour of making out like teenagers.

Annie laid out on top of Jeff on his couch, their mouths moving together unhurriedly, hands casually brushing over one another with no real destination in mind. Sure, Jeff was hard—it was impossible not to be with a gorgeous woman on top of him, every so often grinding against him and moaning into his mouth— but he didn’t feel any urgent need to take care of that issue. He was content to run his hands over her backside and up into her hair, tangling into the silky strands as their tongues moved together inside his mouth.

Annie ground her hips down into him and pulled away from his mouth with a small smirk.

“You want me,” she teased gently. Jeff grinned and put his hands on her backside, pushing her down onto his hardness.

“Where’d you get that idea?” She giggled and kissed him lightly. He caught her lips and drew her back in for a deeper kiss. “Mm,” he said softly against her mouth. “I think you want me too.” She withdrew and narrowed her eyes.

“You have no proof,” she joked. He raised an eyebrow and snuck his hand between her legs, running a finger over her underwear.

“You’re pretty wet for being completely unaffected,” he mused. She ground down into him again and they both groaned at the contact.

“I bet you want me more,” she taunted. She dipped her head down and placed her lips against the skin revealed by the v-neck of his sweater. He put his hands back on her ass and pushed up into her.

“I’m not so sure,” he shot back as she groaned. Her hips began a pace all on their own over him.

“No? I bet I could prove it.” She pushed herself up and let her knees fall to either side of him, straddling him and pushing herself back into his erection. He put his hands on her hips and helped her move on him.

“And how do you plan to do that?” She grinned and pushed down harder.

“By lasting longer than you do.” He raised an eyebrow.

“It’ll never happen.” He pushed up into her core and dragged her over his length. She braced her hands on his chest and ground over him in circles.

“What makes you so sure?” she asked. He reached up and pulled down the front of her tank top and bra, palming her breast.

“Because I can think of about fifteen ways of making you scream my name off the top of my head.” She groaned, putting her hand over his and pushing his palm more firmly into her breast.

“You sound pretty confident.” She moaned as he brushed her nipple with his thumb. “Sounds like we’re going to have to work this out the old fashioned way.”

“Oh yea? And what’s that?” He squeezed her nipple between his thumb and forefinger, making her squeak.

“Competition?” she suggested, swivelling her hips on him. He narrowed his eyes.

“What kind of competition?” She grabbed his hand from her breast and disentangled herself from him, falling back onto the far side of the couch. He sat up and looked at her confusedly.

“The kind where you don’t get to touch me,” she explained, taking her hard nipple in her own hand and squeezing it. Jeff made a face.

“I don’t think I like that rule.” She grinned and spread her legs, affording him a view up her skirt as she began to tease herself over her underwear.

“I think you’ll manage when you hear the rest of my idea.” Jeff watched her intently as she touched herself.

“If it involves more of that, I’m all ears,” he said, motioning toward her hand making lazy circles over her crotch. She grinned.

“Alright, here’s my idea. We each watch each other masturbate—like really masturbate, no half-assing it— and the first person who comes has to... I don’t know... buy the other dinner.” Jeff raised an eyebrow.

“Buy dinner? Careful, Annie—that almost sounds like a date.” She stopped her fingers on her body and looked at him stiffly.

“It’s not a date, it’s paying up—you in?” Jeff hesitated, wanting to push the ‘date’ thing, and more than a little disappointed that she’d shut it down so quickly. “Unless, of course, you’re afraid you’ll lose.” Her hand returned to her crotch and she resumed her ministrations there. Jeff silently cursed his competitive spirit (and his completely natural biological reaction to a hot woman touching herself three feet from him).

“Oh, don’t worry, Babe. I never lose. But when I win, I don’t want dinner.” Her brow furrowed.

“Then what do you want?” He smirked and began palming himself over his jeans.

“You’ll find out soon enough.”

The two shared a competitive smile before tearing off their clothes and getting down to work.

And that was how the two of them found themselves sitting on either end of the couch naked, avoiding all physical contact with one another as they worked themselves over to the sights of the other person pleasuring themselves.

For Annie’s part, she opted to spread her legs as wide as she could given her position on the couch, offering Jeff a clear view of her fingers slipping in and out of her wetness. With her other hand, she alternated between circling her clit and playing with her breasts, knowingly mimicking Jeff’s signature moves. It was difficult for her to maintain her composure given how built up she’d already been before they started, and it was made even worse by having to watch Jeff stroke himself as he watched her with a heavy-lidded stare, lips parted, breaths coming in slow, measured inhales and exhales. She considered avoiding her clit to win, but didn’t want to break the rules she’d come up with herself.

While Annie became intimately acquainted with every inch of her body, Jeff did his best to keep a tight hold on his cock without losing control and bringing himself to the finish. About midway through, he realized he was at a great disadvantage. Although he knew Annie was a big fan of his dick, it could only be so hot watching a dude jerk himself off. For him, though, it was like viewing the best live porn show he could imagine—Annie Edison finger fucking herself while groping her own breasts. It wasn’t at all a fair competition.

Jeff circled his hand over the tip of his cock, gathering and spreading his pre-cum over his erection to make it slicker. The motion almost derailed him, as he thrust the most sensitive part of himself up into his palm in search of more friction. He let out a low moan and reached down with his other hand to cup his balls. He knew it was counterintuitive, to try and bring himself up further while simultaneously wanting to last as long as possible, but the image of Annie a few feet away with three fingers rapidly plunging into her core made it nearly impossible not to. He either needed to give himself relief, or plunge into her wetness as soon as possible.

And he knew she was wet, because with each slip of her fingers, he could hear the wetness of her pussy, and he could see her fingers glistening.

He grabbed the head of his cock and fisted it tightly, jerking faster despite himself.

Annie could feel herself losing control as Jeff appeared to lose his, his hand moving faster, harder over his cock, his hips beginning a steady rhythm as he began to fuck his hand. She dipped two fingers into her mouth and brought them down to her clit, rubbing it in time to his thrusts, moving her hips in circles against her will, desperate for more friction, more relief, more of him, more, more, more. She felt herself begin to shudder, and in the back of her mind wanted to stop, but she couldn’t. She was so close, she felt so much pressure and she desperately needed to release it.

With her eyes trained on Jeff’s thrusting hips and hard cock, and her ears trained on his shuttered breaths and the occasional obscenity dropped from his lips, she began convulsing around her fingers, crying out his name and grinding against the two fingers attached to her clit.

Jeff watched her intently as she lost her battle against her climax, momentarily forgetting that it had ever been a contest in the first place, focusing only on the fact that this gorgeous woman had just fingered herself into oblivion in front of him, and wondering why the fuck he hadn’t buried his cock deep inside of her yet.

It was with the thought of being embedded deeply in her post-orgasmic wetness that Jeff lost complete control, coming hard, ejaculate covering his abdomen as he grunted with each glorious spasm of pleasure.

Annie watched Jeff under heavy lids as he came all over himself, partly disappointed that she’d lost, but mostly just completely enraptured by the look of pleasure on his face as he finally let himself go. She pulled her soaked hand from between her thighs and got up onto her knees, moving over to where he sat back watching her curiously. She extended her hand toward his mouth, rubbing one wet finger along his lower lip, and moaning as his tongue darted out to catch what she’d left for him. She moved to retract her hand, but Jeff grabbed her by the wrist and brought her fingers back to his lips, sucking them in deeply and cleaning each digit diligently.

Annie bit her lip and peered down at his come-covered midsection. With a sultry glance back up at him, she maintained eye contact as she lowered her lips to his abdomen and darted her tongue out, licking it up.

“Fuck, Annie,” Jeff moaned around her fingers, sucking a little harder. The two watched each other as they cleaned every bit of evidence of their competition away, swallowing it down.

Once Annie was finished, Jeff grabbed her upper arm and hauled her up to meet him, kissing her soundly, each tasting of one another and each finding that incredibly sexy.

“You win,” Annie mumbled against his mouth. Jeff pulled away with a little smirk.

“Yea, well, I warned you about that.” She rolled her eyes and manoeuvred so she was settled in between his legs, her back resting against his chest while his fingers gently smoothed over the skin of her stomach.

“So what do you want now that you’re the victor?” she asked.

“Oh, you’ll find out soon enough, Milady. Don’t you worry.” She made a face.

“Well, now I’m worried—I wasn’t before.” Jeff chuckled and put his lips against her neck, kissing the warm skin gently while refusing to divulge any information about how exactly she would be repaying him for her loss.

Annie only stayed a short while longer, not wanting to cause suspicion amongst her roommates. Abed and Troy were generally pretty good to believe that she was going to the library every night to study, but it got a little hairy when she arrived home hours after the library closed.

 “Oh!” Annie said, just as she reached the door. Jeff watched her curiously as she dug into her purse and extracted a piece of paper, handing it over to him.

“What’s this?” She bit her lip, looking a little nervous.

“Just something I want to try,” she explained. Quickly, she leaned up and gave him a peck on the lips before disappearing out the door, leaving Jeff contemplating the neatly folded piece of paper in his hand. He opened it up and regarded the title with no small amount of shock: “In which Jeff Dominates Annie.”

“Ho. Ly. Crap.”

Chapter Text

Elephant in the Room

 

In which Jeff Dominates Annie

Do’s

Restrain, handcuff, blindfold

Pull hair, choke, slap, spank (belt or hand), face f*ck

Call names, swear, yell, demean, humiliate

Come wherever you want

 

Don’ts

Anal

Hot wax

Clamps of any sort

Cause injury, scars or burns

Blood play

 

Safe Word

Elephant

 

~~

Annie answered the phone on the second ring.

“Are you sure about this?” he greeted.

“Yes, definitely. That is, if you’re okay with it.”

“I mean... yea, I am. I just want to make sure you’re absolutely certain this is what you want.”

“It is. It really is.” Jeff took a deep breath and looked back at the paper in his hand.

“This is a lot of... stuff, Annie.”

“I know. I just want to know what it’s like. I understand if you don’t want to do it though.”

“No, I’ll do it, as long as you’re sure. And if you promise to use the safe word the second it gets too much for you.”

“I promise.”

“I’m serious, Annie. Don’t let me, or anyone, do anything to you that you don’t want. You elephant the crap out of me if you need to.” She giggled on the other end, causing Jeff’s tension to release slightly.

“You have my word,” she assured him once again. Jeff let out a breath and acquiesced.

“Okay. Be here at 7:30.”

“Okay... what should I wear?” Jeff thought about this a moment.

“Something you’re not too attached to.”

 

~~

Jeff flitted around his apartment making final preparations. He was more than a little nervous about Annie’s kink. It wasn’t that he was necessarily uncomfortable with the stuff on that list (although most of it was well out of his normal repertoire), he just wasn’t 100% sure he could bring himself to insult and demean Annie the way she wanted him to, let alone actually hit her. He knew he could do it, but he still wasn’t sure he wanted to.

He figured he’d just see where the night took them.

Annie had made it pretty clear that she wasn’t into dom-lite. She wanted him to fully commit to owning her for the evening, something he knew he would do for her even if it gave him a slight case of the heebie-jeebies. It was just... how could he possibly look into those Disney eyes and call her anything other than Princess?

He looked at his watch. 7:28. He knew she would knock at precisely 7:30, so he was going to have to get over that particular hang-up real quick. He looked around his apartment and suddenly had a thought, bolting into his bedroom to retrieve a tie from his closet.

He jumped when a rapping came at the door. He checked his watch: 7:30 on-the-dot.

He tucked the tie into his back pocket and mentally shook away his lingering doubts. This would either be awesome or horrible; either way, it was an experiment. What’s the worst that could happen?

Okay, he didn’t want to think about the worst thing that could happen. He pushed it out of his mind and opened the door, wordlessly stepping aside so Annie could enter, and then shut the door behind her.

Time to put on a show.

Jeff grabbed Annie by the arm and twisted it behind her back with one hand and took a handful of hair in the other, shoving her into the door and holding her there with his body weight.

“You still sure about this?” he growled in her ear. He felt her shiver and tugged her hair a little harder, bringing her head back so he could see her large blue eyes.

“Yes,” she said breathily. He applied more weight against her, sufficiently squishing her front into the hard wood.

“No backing out?”

“No,” she said, a little firmer. He jerked her head to the side and ran his nose over her neck, breathing in her scent.

“What’s the safe word?” he asked.

“Elephant,” she answered immediately. He dropped her arm and unhanded her hair, giving her a shove against the door before backing off slightly. She remained facing away from him.

“Turn around,” he commanded in a low tone. Annie did so quickly. “I know your rules—now you get to hear mine. No talking, unless I ask you a specific question. You can call me Master, or Sir, but nothing else. Don’t look me in the eye, don’t move a muscle without permission, and above all else, don’t you dare come until I tell you to. Understood?” She nodded. “Answer me properly, slave.”

“Yes Master.” Her voice was low, airy, and Jeff could hear a slight quiver in it. He took that as a sign that he was doing well. He closed the gap between them, standing at full height in front of her. She stared straight ahead at his chest, heeding his rule of never looking him in the eye.

“Cute shirt,” he teased, reaching out to finger the buttons on her blouse. It was one she didn’t wear often—she’d heeded his advice to wear expendable clothing.

He grabbed both sides of the shirt and tore it apart, sending buttons flying. Annie jumped slightly at the rapidity of his movements, but kept her eyes downcast as he tore the bottom buttons before sliding the remnants of the shirt off her arms, leaving her in her bra and skirt.

He stood back and crossed his arms over his chest.

“Take off the rest of your clothes.” Annie started to look up, to question his pace, but quickly remembered the rules and silently set about following his order. She slid her skirt over her hips and let it fall to her feet, stepping out of it, before slipping off her flats. “Bra and panties, too,” he amended. Annie reached back and unclasped her bra, slipping it off before pushing her underwear down to her feet and stepping out of them as well.

Once she was fully naked, she let her arms hang limply at her sides as she awaited further instruction.

“You learn quickly—I guess I shouldn’t be surprised by that,” Jeff mused. He stepped forward and began making wide circles around her, inspecting her body. Annie flushed under his gaze.

“You like standing here like this, don’t you? Naked, cold, desperate to be fucked?” Annie bit her lip. “Answer me.”

“Yes Master,” she said softly, though it came out sounding much like a moan. It was incredible the effect he was having on her before he even touched her.

Jeff chuckled darkly behind her before coming back to stand in front of her.

“Spread your legs.” She did so. “Now touch yourself.” Her eyes shot up, forgetting the first rule on his list. “Eyes down, slut—do as your told.” Annie averted her eyes, but felt a surge of arousal course through her at his language. Anyone else and she would have been offended, but not Jeff. Jeff could pretty much say anything to her at that moment and she would dissolve in a quivering pile of goo.

Slowly, she reached one hand down between her legs and traced her finger over her slit, dipping it in to tease her clit. She gasped and closed her eyes, circling the small bundle of nerves before fingering it directly.

Jeff stood back and watched her tease herself, and couldn’t help but do the same. His hand shot to his crotch, rubbing the beginnings of his erection.

“Put your finger in your mouth—taste yourself.” Annie did so, sucking the finger all the way in before slowly dragging it halfway out and circling the tip with her tongue. Jeff closed the distance and grabbed her hand from her lips, placing it between his own. It was only slightly tinged with her taste at that point, but it was enough to bring a moan to his lips. He withdrew the finger and grabbed her by the waist, leaning down to murmur in her ear.

“You taste so fucking good.” She moaned at the gravelly tone in his voice. “It’s a shame I’m going to have to punish you for breaking the rules.” He could feel her shiver beneath his fingertips.

Jeff reached into his back pocket and withdrew the tie he’d collected earlier as he made his way behind her. Wordlessly, he placed the tie over her eyes, securing it tightly behind her head.

“Can you see?”

“No Master.”

“Good.” Jeff grabbed her by the arm and led her blindly through his apartment to the door of his bedroom where stage two awaited her. He pulled a pair of handcuffs from his dresser and attached one to one of her wrists, raising her arms well over her head to loop it over his pull-up bar, then attaching it to her other wrist. When he stepped back, he was pleased with the outcome. Annie was stretched as far as she could go, standing on her tippy-toes.

“Comfortable?” he teased. Annie shook her head. “Good—it’s about to become a whole lot less comfortable anyway.”

Jeff stepped back to admire the view of a naked Annie stretched to capacity in front of him. Her breasts were jiggling slightly as she fought to maintain her balance, and the skin of her stomach was pulled taught, making her look even more streamlined than usual. It was a bizarre thing that having such control over her actually made him hard, but he couldn’t deny that that was the case. She was sexy as fuck, and she was completely at his mercy. For a progressive, feminist man, this was weirdly erotic.

“Do you know why you’re up there?” he asked, undoing his belt loudly for her benefit. She swallowed visibly.

“Yes Master.”

“Why?” he pulled the belt from its loops.

“Because I disobeyed you Master.”

“And do you know what happens when you disobey me, Slave?” she shook her head. He looped the belt in his hand and reached it forward, dancing the loop through the valley between her breasts and downward over her stomach. “You get punished, until I decide you’ve paid your debt.”

He began to circle her with the belt, running it over her skin, watching her squirm and shiver as it tickled and taunted her. He brought it over her backside and flicked it quickly, making her cry out in surprise more than pain.

“Do you like that?” he asked.

“Yes Master,” she breathed out. Jeff quirked a small grin. This chick was fucking insane.

He pulled the belt back and connected it a little harder with her backside. She didn’t cry out, but rather let out a sexy little grunt. He put the belt in his right hand and reached out with his left, cupping one cheek roughly before pulling his hand back and slapping it with moderate force. Annie cried out again.

“Hand or belt?” he asked, genuinely curious.

“Whatever you want, Master.” His hand connected again.

“Pick one,” he demanded.

“Hand!” she cried out. “Hand, please. Master.” Jeff reached the belt up and put it to her lips.

“Open up.” She did so, and clamped her teeth over the leather once it was situated.

“Don’t drop it.” He pulled his hand back and connected it once again with her backside before rubbing over the red skin, soothing it before doing it again. Annie grunted with each slap, but didn’t cry out so as to avoid dropping the belt from between her teeth.

Jeff positioned himself flush behind her. He was still a good head taller than her even with her stretched out as she was.

“I like you like this,” he mumbled in her ear, reaching one hand around to palm her breast, the other going to the apex between her legs. He kicked her legs apart, causing her to lose her balance slightly and fall back against him. He began groping her breast and clit to the same beat. “You’re so vulnerable. Do you like being my slave?” He bit her ear and she nodded quickly, still holding the belt between her teeth.

“Do you think you’ve been punished enough?” She nodded. Jeff pushed his hips into her backside, making her moan. “Should I take you down and fuck you?” She nodded again. He chuckled darkly in her ear. “I’m not done with you yet.”

And then he was gone, and Annie did her best to regain her balance without him to support her. She was so wet she could feel herself beginning to drip. She clenched her legs together as best she could and tried to alleviate some of the need she felt, but it was difficult to do with such limited balance. She clenched her teeth tightly around the belt with frustration.

Jeff retrieved a dining chair and brought it to where she was chained, setting it a few feet away and taking a seat. He sat quietly for a few moments, making his plan of attack while he let her sweat it out. He watched as the strain of the position became more and more difficult for her, and forced himself to stay in his seat and not immediately set her loose. This was what she wanted—he would let her have it.

He watched her work her thighs together and couldn’t help but feel satisfied. Somehow this was working for her. He didn’t know how or why, but she was painfully aroused—he could smell it from where he was sitting.

“You a little uncomfortable?” he asked. She nodded “Want me to let you down?” She nodded again. “If I let you down, I expect you to show me how grateful you are to me—you understand that, don’t you?” She nodded again, and he got up from his chair and sauntered over to her, grabbing the key from his pocket and setting her loose. Annie nearly toppled over when she was finally down—Jeff caught her and righted her before handcuffing her wrists behind her back.

“Get on your knees,” he demanded. She quickly obliged. He yanked the blindfold from her eyes and tossed it aside, going to sit in his chair.

“Come over here.” She shuffled to where he sat on her knees, stopping in between his legs. He popped the button on his jeans and pulled his shirt over his head, casting it aside.

“Get the zipper,” he told her. It took her a moment to realize he meant her to do it with her teeth. He grabbed the belt from her mouth and rubbed it menacingly over her back as she mouthed his crotch to get the zipper down. “Back up,” he instructed her, before standing and pushing his pants and underwear off, finally naked before her.

She allowed her eyes to roam over his body as he settled back into the chair.

“Like what you see, Slave?” he teased. She nodded enthusiastically, a small smile on her features. Jeff fought not to grin. She was too fucking adorable sometimes.

“Lick it.” She leaned forward and licked his erection from base to tip a few times, before flicking her tongue around the tip. “Balls too.” She lowered her head and leaned in to provide some attention to his boys, alternating licking between them. “Good girl. Now put your mouth on it, and suck.”

Annie repositioned herself before working the tip of his cock into her mouth, taking it a little deeper with each push. Jeff put his hand on top of her head and forced her further down, making her gag. He chuckled a little, and did it again before settling back in the chair and letting her work her mouth over him, a slightly difficult feat without her hands for balance, but she was managing just fine. He tangled his hands in her hair, but let her guide the motion, enjoying her talents fully.

After a few moments, he decided it was time to get back on script. Without warning, he grabbed a handful of her hair and tugged her mouth away from him. He shot to his feet and pushed his cock back into her mouth, setting up a fast past, going deeper than she would generally allow, gagging her each time he hit the back of her throat. Both of his hands tangled in her hair as he fucked her face thoroughly, tears escaping her eyes as she gagged around him.

“Fucking suck on it,” he demanded. She attempted to gather herself enough to suck each time he withdrew, hollowing out her cheeks around him. He pulled his cock out and forced her head backward so she had nowhere to look but up at him.

“Do you like that?” he asked harshly. “Do you like when I fuck your mouth?”

“Yes Master,” she choked out. He released one hand from her hair and grabbed his cock.

“Open your mouth, stick your tongue out.” She obliged, and he began alternating between dipping his cock in and out, smacking it against the flat of her tongue, and slapping her face with it. After a few moments of this, he shoved his cock into her cheek and tapped the tip through her skin.  She moaned around him.

“Do you like when I slap you?” he asked. This had been his biggest concern, so her answer would decide just how far he would go for the rest of the evening. She swallowed back some dryness in her throat.

“Yes Master,” she responded. He tightened his hold in her hair, forcing eye-contact.

“Don’t lie to me, Annie. Only say yes if you mean it.” She met his eyes, and for a moment it was just Jeff and Annie, the way they always were.

“I mean it,” she said with a self-assuredness that he hadn’t heard much that evening. With a nod, he shoved his cock back into her mouth and regained his pace. She continued to suck and swallow around him, making him dizzy with desire.

He figured now was as good a time as any to pop that particular cherry. He withdrew his cock and in a quick swipe, brought his hand across her cheek, making her cry out. It wasn’t a hard slap—not enough to cause any real pain, but it did leave a pink shade where his hand had connected.

“Again?” he asked. She nodded and steadied herself for another swipe. He took it, and her cry sounded more like a moan than anything else. Jeff shook his head.

“You’re kind of insane, you know that?” Annie quirked a small smile and opened her mouth wide again, inviting him to retake her mouth. “You’re a good girl,” he praised. He shoved his cock in once more, hitting the back of her throat and holding her head down on him for several seconds, blocking her airway until she began to struggle. He withdrew, and she gasped a deep breath in, recovering and looking more than a little flushed. He did it twice more.

Finally satisfied that he couldn’t take anymore of her mouth on him without coming, Jeff fisted her hair tightly again and pulled her up to her feet by it, turning her around and pushing her through the doorway into his bedroom. He unhanded her hair and pushed her forward, sending her flying into the bed.

“Bend over and spread your legs,” he demanded. She obliged, resting her face against the mattress for balance, as her hands were still cuffed behind her back. Jeff wasted no time getting situated behind her and forcing two fingers into her dripping hole. She couldn’t help but cry out. He smacked her ass, hard, and then entered three. Annie forced herself to stay perfectly still as he fingered her hard and fast. She had already been built up so much since she’d arrived, it was almost impossible to maintain her composure now that he was finally, finally touching her the way she needed him to.

Jeff knelt down and leaned in to taste her drenched core, knowingly torturing her now to a point where she might inadvertently break the cardinal rule. In truth, he wanted her to break it. He wanted to see her come apart without any semblance of control.

But he also wanted to fuck her into oblivion, so he didn’t give it as good as he knew he could (although Annie’s moans and cries were enough to make him nearly come all over himself).

He soon retreated and returned to his feet.

“Do you want me to fuck you, Slave?”

“Yes Master.” Her voice was a moan. He grabbed her by the hair and pulled her up to him, groping her breasts and thrusting into her hands bound behind her back.

“Beg for it,” he growled in her ear. He felt her shiver against him.

“Please, Master. Please, please fuck me.”

“More,” he commanded, grasping her breasts and squeezing her nipples painfully. She cried out.

“Oh fuck,” she cried out. “Please fuck me. God, please, now,” she plead. Jeff unhanded her breasts and pushed her forward.

“Get up on the bed.” Annie raised her knees up onto the mattress with his help, resting her face back into the sheets and arching her back for him as he settled himself at her opening and pushed in, starting up a ruthless pace.

“Don’t just sit there,” he demanded, smacking her ass. “Fuck it.” She began pushing back into him, meeting him thrust for thrust as the two grunted and moaned and cried out together. Jeff reached forward and grabbed Annie by the shoulders, pulling her up against him and circling a hand around her neck as he plunged into her, biting and licking at her ear and neck while his spare hand raced to her clit, fingering it roughly.

Annie began to shiver beneath him as his finger sped over her clit and his cock took a punishing pace inside of her. She cried out, screaming his name over and over again. Jeff couldn’t be bothered with the ‘rules’ anymore—not when they were both so close.

“Ung, please let me come,” she cried out. He disengaged his hand from her neck and thrust her forward onto the bed, face against the sheets once again as he took hold of her arms behind her and used them as leverage to fuck her harder.

“Not yet,” he ground out, wanting to drag this out until the last possible second. Annie’s cries became louder and more insistent as she began to convulse around him beyond her own control.

“Fuck, Jeff, please,” she cried out.

“No!” he growled. He pulled out and picked her up easily, dropping her on her back on the mattress and spreading her legs, surging back in and dragging his thumb over her clit. He watched her face, mesmerized, as she tried desperately to keep from coming. Her breaths came in short, quick gasps as the muscles in her entire body seemed to clench and unclench uncontrollably. He leaned further over her and pounded in harder.

“Look at me,” he demanded, moving his hand to loosely circle her neck. Her eyes shot wide open as she fought a losing battle to maintain her composure. “Come.”

Instantly, his name began to leave her lips in a long string as she tightened around him, nearly taking him over the edge with her—but that’s not how he was going to go. Not this time. He continued to fuck her through her orgasm until she was a boneless pile on the bed, finally pulling out on the cusp of his own climax.

“Get on your knees,” he demanded, jerking himself rapidly as she got into position on the floor. “Open your mouth.” She did so, and he placed his tip on her bottom lip as his orgasm overtook him, squirting his come into her open, waiting mouth. He cried out her name as he came, desperate to feel her on him. He dipped his cock into her full mouth, having her suck the rest of his orgasm out of him until he was completely spent.

When finally he had no more to give, he pulled away and looked down at the open-mouthed women beneath him.

“Swallow,” he said darkly. She closed her mouth and forced the come down her throat before opening it up and assuring him that she had done so. He dipped his spent cock back into her mouth a few times, letting her suck him until he was completely flaccid and too sensitive to handle the contact any longer.

Annie stayed on the floor while Jeff got his bearings. Finally, after a moment, he retrieved the key to the handcuffs and set her loose, helping her to her feet, and manoeuvring them both into the bed and under the covers.

“Holy crap,” he mumbled to himself, exhausted and spent. Annie sunk her head into the pillows and watched him for a moment. He met her eye, a little shyly. “You okay?” She smiled and nodded.

“Better than,” she assured him. He relaxed a little, for the first time since he read her letter. She bit her lower lip.

“You look like you have something to say,” he said softly, searching her features for signs of discomfort. She shrugged.

“Not really... I just don’t know how we’re going to top this, that’s all.” Jeff laughed out loud and leaned forward, capturing her lips.

“I’m sure we’ll figure something out. We always do.”

Chapter Text

Internal Affairs

“Annie!” Jeff called, jogging to catch up to the younger woman in the hallway of Greendale Community College. It was now mid-March, several weeks after they’d delved into the world of domination and submission (something Jeff was still reeling from). She spun around just fast enough to avoid losing her balance as he grabbed her by the arm and pulled her into an empty classroom.

“What’s wrong?!” she asked, immediately concerned.

“Nothing’s wrong—everything is awesome,” he said with a Winger smirk permanently affixed to his lips.

“What are you talking about?”

“Do you remember our little competition a few weeks back?” he asked. Her brow furrowed. “Oh, who am I kidding—of course you remember. It was your idea.” Recognition became apparent on Annie’s features as she recalled the night in February that he was talking about.

“I remember,” she said a little breathlessly. “You still haven’t collected your winnings.” Jeff smiled a little wider and nodded.

“That’s true—and that’s about to change.” Annie’s eyes narrowed.

“Okay...” Jeff reached into his pants pocket and retrieved a small purple cylinder, holding it out for her to examine. “Umm, what is that?” Annie eyed the device nervously. Jeff smirked and rolled the small dome between his fingers.

“Well, Annie, it’s a vibrator.” She looked up at him with wide-eyes.

“A vibrator,” she repeated. He nodded with a conspiratorial grin.

“A bullet, to be precise.”

“Uh huh—and what is it doing here?”

“Oh, that’s the best part,” Jeff said. “You see, this isn’t just any vibrator—it’s all decked out. This baby has seven unique settings, so you never really know what it’s going to do to you, and ten speeds, so you don’t know how hard or fast it’s going to do it. And you want to know what makes it even better?” She glared at him, and he forged on. “It’s completely wireless, and it has a range of up to 100 feet. 100 feet! Can you believe that?”

“I really can’t,” she deadpanned. Jeff surged onward.

“And you know what’s so great about this? No, no, don’t guess, let me tell you. The great thing is, you can put it up in there and no one would ever suspect you had a vibrator knuckle deep inside of you. So if you were to stick this one up there, say, right now, you could spend the whole day getting zapped with this thing, and no one would be any the wiser—well, except for you, obviously. And me.” She looked at him, stone-faced.

“Jeff...”

“Wait, wait—there’s one more thing. The best best part. I know I said all of that other stuff was the best part, but this is actually the best part.” She sighed deeply, crossing her arms over her chest. “The best part, Annie, is that while you have this little guy shoved up your cooche, I’ve got this,” he pulled another small device from his pocket, holding it out for her to inspect.

“What the hell is that?” she asked, her facing going pale.

“That, Milady, is the remote control. The remote control that I’m going to be holding on to, and using to torture you all. day. long.” He finished with a wide, more-than-slightly evil grin.

“You’re out of your whole damn mind,” she said flatly. Jeff quirked a brow.

“Seriously? Because I think this might just be the best idea I’ve ever had.”

“You honestly think I’m going to stick that up there and let you do that to me all day?” Jeff shrugged.

“I don’t see why not.” She rolled her eyes.

“No. No way. Come up with something else.” Jeff sighed.

“Alright, fine, you can either take this option, or you can wait for my back-up plan.”

“I’ll take it.”

“Hold your horses—the kick is, you don’t get to know what the back-up plan is, when it’s going to happen, or whether or not it’s going to be worse than this one.” Annie worried her lower lip as she regarded the small plastic object in Jeff’s hand.

“Why can’t you just tell me what the alternative is?”

“Because that would defeat the purpose,” he said plainly. “So what’s it gonna be, Miss Edison. Do you run with the devil you know, or take what’s behind door number two?” Annie looked back at the device hesitantly.

“If I do this...” Jeff’s eyes lit up. “IF! I’m going to need some assurance that you’re not going to...abuse the privilege.” Jeff visibly deflated.

“But I won,” he argued.

“It’s my vagina!” she countered. He crossed his arms.

“You may have a point,” he conceded. She let out a breath.

“We need ground rules.”

“Okay, fine,” he said, noticeably less excited. “What are your rules.” Annie took a moment, thinking about all of the ways this could go badly for her.

“Okay... I have a test in my English class today. I need to focus.”

“Whatever, I’m not even in your English class.”

“100 foot radius?” Jeff nodded his understanding.

“I won’t do it unless I’m in the room, deal?” She nodded.

“Okay, good. Second, I’m giving a presentation in our History class, and it’s worth 40% of my grade.”

“No tests or presentations. Got it.”

“And at some point I’m going to have to go to the bathroom... I’m not leaving it in while I... you know.”

“Sanitary concerns. Check.”

“And just... you know... don’t be a jerk, okay?” He offered a “who, me?” look, and Annie glared at him.

“Ugh, fine. Anything else?” She thought about this for a moment, before reaching out an open palm. Jeff grinned and placed the device in her hand, watching her close her fingers around it.

“Don’t make me regret this,” she said finally. Jeff’s snarky grin dropped off his face for a moment.

“Hey, you trust me, right?” She regarded him sceptically. “Right?” She sighed.

“I guess.” He smiled and reached a hand out, resting it on her cheek.

“Good. Then let’s have some fun.”

Jeff walked Annie back to a table and reached up under her skirt, pulling her panties down and off before lifting her up onto it. He placed a kiss on her inner thigh as he spread her legs.

“You want to do it, or should I?” he asked, peering up at her. Annie regarded the device in her hand for a moment before relinquishing it to Jeff.

“I must be an idiot,” she mumbled, leaning back into the table. Jeff just grinned and popped the end of the device in his mouth, greasing it up with spit before placing it against her hole.

“Tell me when to stop.” He pushed, and watched the purple plastic disappear inside of her.

“There,” Annie said as she felt it reach her cervix. Jeff retracted his finger and brought it to his lips, tasting her. He stepped away and grabbed her underwear once more, slipping it over her feet and up her legs. Annie slipped off the desk and pulled it up the rest of the way, moving a little to get used to the feeling of the vibe inside of her.

“How’s it feel?” he asked.

“Umm... weird,” she admitted. “It’ll take some getting used to.” Jeff smirked and held up the remote in his hand, pressing a button. Annie felt the device begin to buzz inside of her and her breath came shakily as she reached out to grab Jeff’s arm to steady herself.

“This is going to be worth your while—I promise,” Jeff assured her, switching it off. She looked up at him sceptically.

“Yea, yea. We’ll see.” She turned to leave, but Jeff grabbed her arm, swiftly pulling her in for a quick kiss. When they broke, he offered his patented Winger smirk.

“Enjoy yourself,” he said with a wink. Annie rolled her eyes, but couldn’t hide a small grin. With that, she grabbed her bag and made her escape from the room. Jeff watched her go, and flicked the device on just as she rounded the corner. He grinned when he heard a small gasp from down the hall.

This would be fun.

~~

True to his word, Jeff abstained from abusing his power while Annie stood and presented to their History class. He also gave her a reprieve during most of her other classes, even though he was more than a little tempted to give her a jolt when he walked by her English classroom.

The rest of the time, she was entirely at his mercy. He watched her shiver slightly as soon as she sat down from her presentation. She shot him a glare, and he turned the power up just a little more, rocking her from the inside. He smirked at her white-knuckled grip on her desk, and turned it up once more before finally giving her relief by switching it off.

Lunch was an especially amusing time for him, as they and their friends surrounded a table in the crowded cafeteria. Because the room was so loud, he was able to turn it up to its highest setting and no one would be able to hear the buzzing—except for Annie, he assumed. From his spot across from her, he could see her fighting to maintain an impassive expression when he turned it onto a pulsating setting and left it on for a good five minutes. Annie shot him a glare, which garnered the attention of Abed.

“What’s going on?” he asked.

“Nothing!” Annie cried out, her voice tinted with a hint of hysteria.

“You look like you’re mad at Jeff,” Abed suggested.

“Nope! We’re good!” Annie said, attempting to be measurably more calm and failing. Jeff bit the inside of his lip to keep from laughing.

“We’re just having a disagreement about who was the best Star Trek captain,” Jeff supplied. Annie fixed him with a glare, willing him to turn off the device before she went completely insane.

“Annie doesn’t even watch Star Trek,” Troy interjected.

“Exactly, which is why she’s completely unqualified to partake in the discussion,” Jeff argued. He switched the mode back to a steady buzz, catching Annie off guard.

“Oh god!” she cried out. The group looked at her curiously, Jeff with a raised eyebrow. She looked around at the group. “I mean—could he be more condescending?” Jeff chuckled and switched off the device, watching as she visibly relaxed.

“Okay, Chandler Bing,” Jeff teased. Annie glared at him, a flush coming up her cheeks.

The group, however, seemed convinced, and returned to their previous conversations.

This went on for most of the day—whenever Jeff was close enough to make it happen. Annie would be walking down the hallway, and suddenly the bullet would come to life inside of her. Jeff chuckled out loud as he walked by her in the hallway.

“Looking a little flushed there, Annie. You feeling okay?” She bit her lip and leaned against the wall.

“Better than ever,” she came back in a biting tone. Jeff just laughed and walked away, turning up the intensity before flicking it off just before going out of range.

It was around 3 p.m. when Jeff found himself being hauled into a storage closet (their storage closet), and being, quite literally attacked.

Annie grabbed him by the back of the neck and kissed him furiously, following up with a swat on the arm as she broke away.

“You. Are. Evil!” she punctuated each work with another swat, which Jeff took with a grin. He dipped his hand into his pocket and turned the device on again. Annie went to swat him again, but instead grabbed him by his bicep, holding on tightly as he ramped the intensity up to 10. She let out a shuddered squeak and leaned her body heavily into his as her entire body was wracked with the vibrations.

“You were saying?” Jeff teased, circling his free arm around her to help her maintain her balance. He switched the mode to a continuous pulse.

“Fuuuuck,” Annie moaned into his chest, squeezing his bicep a little tighter.

“Such a potty mouth,” he admonished. She raised her eyes to him.

“I’ve played your little game all day,” she ground out. “I sat still in two of my classes while you tortured me with this thing, I played along with you’re stupid lie during lunch, I sat through study group with this thing going off every five minutes!” Jeff raised an eyebrow.

“So what’s your point?” She grabbed the hem of her skirt and panties, and pushed them both down, kicking them off.

“My point, Jeff, is that you’ve had me on edge all day, and if you don’t give me an orgasm right now, you will regret it.” Jeff smirked and changed the setting back to vibrating. She backed up, setting herself onto an abandoned desk and spreading her legs for him. Without a word, he crossed the room to where she was and dropped to his knees.

Quickly, he leaned in and swiped his tongue along the length of her slit, smoothing over her dripping hole and ending with a quick flick to her clit. Annie cried out and reached down, fisting her hands in Jeff’s hair, holding him against her as he dipped in again, this time worshipping her clit the way she’d been needing him to do so ever since he inserted the vibrator that morning.

Jeff placed both of his hands on her inner thighs, pushing them further apart and opening her even more fully for him. He reached into his pocket and changed the setting once again, causing Annie to moan loudly at the sudden change in sensation. He grinned against her, and went back to work, sucking, licking and nipping lightly at and around her clit. He did this for a while, bringing her up to the point where she was nearly ready to come, before pulling away and turning off the vibrator inside of her, chuckling each time she groaned in frustration.

Finally, Jeff decided he’d tortured her long enough—if an entire school day could be considered ‘long enough.’ He easily slid two fingers into her wet core and extracted the soaked device, before turning it back on and resting it against her clit. Annie cried out at the new sensation, and within seconds, was coming with all of the intensity of someone who had been deprived of her glorious climax for nearly six hours.

Jeff dipped his tongue inside of her as she came, lapping up what she let go of and soothing the sensitive nerve endings beneath his tongue. Annie’s entire body seemed to be wracked with shivers as she came down from her orgasm. She reached out and grabbed Jeff’s hand that held the vibrator flush with her clit, tearing it away, unable to stand the sensation any longer.

Jeff placed a kiss to the inside of her thigh before standing up between her wide-spread legs. He turned off the vibrator, fisting it in his hand as he leaned over her, kissing the overheated flesh of her neck and faced before settling on her lips. Annie kissing him back hungrily, grasping at his shirt collar to keep his body in contact with hers as she continued to shiver from the power of her orgasm. Jeff stayed over her, just kissing her for several moments, until she unhanded him. He gave her a hand, pulling her so she was sitting upright. Once she had regained her balance, Jeff recovered her panties and skirt, handing them back to her so she could re-dress.

“We, uh...” Annie seemed to think for a long moment about what to say. Jeff grinned, knowing it was because she was halfway to brain dead following her powerful orgasm.

“We...” he teased. She blinked a few times, looked around the room blindly for a moment before settling back on him.

“I dunno,” she finished lamely. Jeff chuckled and closed the gap once again. He tucked the device in his pocket, and wrapped his arms around her.

“Neither do I,” he said softly. He leaned down and kissed her fully, enjoying the way she melted into him. “You okay?” he asked softly as they broke apart. She offered an unfocused grin and nodded.

“Okay...” she drawled. He just laughed and helped her off the desk, offering an arm around her waist to help keep her upright, as her legs had begun to feel remarkably like Jell-O.

“Okay. Let’s get you home before someone thinks you have some kind of head injury,” he teased. Annie attempted to glare at him, but she was still a little hazy from the force of her orgasm.

“You’re trouble,” she managed. Jeff grinned and led her to the door.

“Yea, but you like it that way.” She just leaned further into him, letting him lead her out into the hallway and to his car.

Although she couldn’t quite verbalize it just yet, she had all kind of plans to show Jeff just how effective the bullet could be—and not just on her.

Chapter Text

Bowl of Fruit

“Stop laughing,” Jeff mumbled from his spot on the stool. He tried not to move as he said it, knowing he’d get a good telling-off if he ruined the perfect portrait position that Annie had put him in. She giggled a little more.

“I’m sorry! It’s not you,” she promised, though her giggles continued. Jeff rolled his eyes.

“If it’s not me, then what the hell is it?” She shook her head.

“I can’t say.”

“Why not?”

“Because if I do you’re going to want to look at it, and you’re not allowed to move.” Jeff huffed out a breath and tightened his grip on the strategically placed bowl of fruit in his lap.

“I can’t believe I’m doing this,” he groaned.

“No one other than my professor is going to see it, Jeff. It’s just for my Art final—we needed a human subject, and I felt awkward asking Abed.” Jeff jerked his head to look at her. “Don’t move!” He turned his head back.

“Why would you ask Abed anyway?” he asked, trying not to sound as jealous as he felt.

“Because Abed is a statue—I don’t know if you’ve noticed, but every time you breathe, that stupid banana moves a quarter-inch.” Jeff felt mildly relieved, but only temporarily, because as soon as he took another breath, Annie began giggling again.

“For God’s sake, would you tell me what the hell is so funny?” he demanded. Annie bit back her laughter, but couldn’t stop. “I swear to God, if you don’t stop laughing, I’m coming over there and you’re never going to get me and this bowl of fruit back this way again.”

“I’m sorry!” she exclaimed. “It’s not you, I promise. It’s the banana—it’s just the way it’s sticking up, it looks kind of... phallic.” She devolved into giggles again, and Jeff looked down, realizing for the first time that the banana was, in fact, sticking straight up. “Don’t move!” she exclaimed again, although she couldn’t even pretend to hide her amusement. Jeff just grinned and relaxed, facing forward.

Annie had asked him a few days earlier to be her model for her take-home Art exam. She was tasked with painting a nude model. The bowl of fruit had been her idea—she was willing to take an A- if it meant not attempting to paint Jeff’s penis.

“But you love my penis,” he had reminded her. “Why wouldn’t you want to immortalize it forever? You could hang it over your bed and remember all of the good times you’ve had with it.”

Nonetheless, Jeff was a little relieved when Annie had placed the bowl of fruit in his lap. As much as he would have enjoyed watching her squirm, he was kind of glad to not have to sit there and have her capture him in his altogether—well, at least not flaccid.

It was now only a few weeks from the end of the school year, and with it, graduation. Everyone was neck-deep in books as they studied for their finals, which allowed Jeff and Annie a little more time to spend with each other. As the school library extended its hours, Abed and Troy became less suspicious of Annie when she said she was going to be studying late into the night. She’d even managed to sleep over on one occasion, slipping out at 6 a.m., long before Troy or Abed would be awake.

As Jeff sat on the hard stool, attempting to stay completely still, he thought about what had happened over the past several months. He and Annie had gone from just friends, to friends with benefits, to this... two people who spent almost every evening together. Sure, they still fucked like bunny rabbits, and often attempted new and interesting kinks in the bedroom, but there was more to it. He’d noticed the shift ever since their foray into domination and submission. Annie came over more often, she kissed him hello and goodbye, and they even casually made-out sometimes without having sex.

If Jeff were to define it—something he had already done in his head—he’d say they were in a relationship. A very happy relationship.

Unfortunately, Annie didn’t seem to feel the same way. Sure, she was more affectionate than she used to be, but she still shied away at the mere suggestion of a non-sexual outing (read: date) with him. He wasn’t used to feeling like the needy person in his relationship with Annie, and it wasn’t a feeling he enjoyed. He wanted her to fawn over him, and stay the night, and call him her boyfriend, and maybe even one day tell him she loved him—but she didn’t seem to be on that road. The same road he’d been on since October.

He let out a breath and refocused on keeping his posture just right. Annie wanted him to look like some sort of Greek Adonis (something he’d teased it was impossible for him not to resemble), so he was intent on helping her achieve the look she was going for. If there was one thing Annie liked more than intensely erotic sex, it was getting good grades.

“Thanks for this, by the way,” Annie said softly, breaking the silence. Jeff offered a small smile without turning his head.

“Anytime, Milady.”

~~

The two stayed that way for another 45 minutes, Jeff’s butt becoming numb and his back aching from the position, Annie eyeing him critically and every so often muttering obscenities into her canvas. Finally, when he felt he could sit still no longer, Annie set down her paintbrush with a sigh.

“Well, I’m not exactly Michelangelo, but it’ll do.” Jeff let out a relieved breath.

“Can I move?”

“Yea. I just wish I could get the nose right—but it’s too late now. The paint is practically dry already.” Jeff creaked a little as he stood up from the stool. He set the bowl down and reached his arms over his head, stretching every which way to try and undo the kinks left by the position. “Sore?” Annie asked, sounding a little guilty. Jeff offered a one-shouldered shrug and crossed his living room to where she stood with her canvas, examining the picture.

“This is great,” Jeff said, pleasantly surprised. Sure, it didn’t look like him all that much, but he could see details that anyone else might have missed—like a small scar above his lip, and a birthmark on his side. In fact, she’d gotten more of the minute details right than the obvious ones. His nose was a little off, and his lips were slightly fuller. His eyes were a little larger in the painting than they should have been, and his ears were a little smaller.

But those details—they were so intimate. She’d noticed things about him that went beyond “hot Adonis body.”

“It’s really not that good,” Annie said with a grimace. Jeff offered a half smile and leaned down, kissing her softly.

“It is. Thanks, Babe.” Annie smiled up at him.

“You’re a liar,” she said softly. She looked down. “And you’re still naked.” He chuckled and turned toward her more fully, attempting to wrap her up in his arms, but finding resistance in his back. Annie noticed his grimace. “Come with me,” she said softly. She took hold of his hand and led him to the bedroom.

“We never discussed payment, but I guess this’ll do,” Jeff teased as Annie led him toward the bed. She rolled her eyes and gave him a little shove, urging him down.

“Lay on your stomach, Winger.” He offered a confused look.

“Uh, I don’t think that’s going to work very well.” She giggled and gave him another insistent shove.

“Just do it.” Jeff watched her curiously for another moment, but eventually obliged, settling himself on his stomach in the middle of the bed, his hands tucked under his pillow. Wordlessly, Annie climbed onto his lower back and started kneading the tense muscles in his shoulders. Jeff let out a groan.

“God, why haven’t we don’t this before?” he asked. Annie giggled.

“Because you’ve never had to sit still for two and a half hours for me before?” she supplied. She reached up and began rubbing his biceps before working her way back to his neck and shoulders. Eventually she shuffled lower, working over his lower back.

“You’re really good at that,” Jeff said drowsily, letting her hands work him into utter relaxation.

“I used to give my dad shoulder rubs whenever he got home late from work.” Jeff made a face and peered over his shoulder at her.

“What’d I say about comparing me with your dad?” She groaned.

“Eww, not like that, Jeff.” He chuckled and closed his eyes again, allowing himself to drift a bit as she took care of every crick her evil art project had left in his back.

A few moments later, she dipped her head down and placed a long, slow kiss in between his shoulder blades, and then another a little further up. Jeff sighed contentedly beneath her lips and turned himself around, allowing her to settle down on top of him, still fully clothed against his naked body. She rested her head against his chest and closed her eyes. He kissed her forehead lightly.

“Thanks Babe,” he said softly.

“Thanks for being my muse,” she whispered. She kissed his chest lightly before sliding her body down his, dropping her lips onto the soft skin of his sternum, diaphragm and abdomen, leaving warmth in each place she kissed. She swirled her tongue around one of his nipples, then flicked it lightly, causing Jeff to let out a small sound of appreciation.

As she worked her way down, Jeff closed his eyes, falling completely into the sensations of her mouth and hands on his body, calming, caressing. It was much sweeter than usual. He wasn’t accustomed to being cared for so gently.

Annie dropped her mouth into the dip between his hip bones as she took his flaccid penis in one hand, squeezing it gently in the warmth of her palm. Easily, she lowered her mouth over it, lips grazing the base as she took him in fully. Soft, though he was, Jeff knew that wouldn’t be the case for very long as Annie withdrew her mouth, sucking along him, tongue massaging him to life as she went.

As she pulled her mouth away, she began pumping the organ once more, pulling the foreskin back to reveal his head, and licking the underside of the newly revealed skin, causing Jeff to gasp in a small breath. The sensation was so sudden that it almost crossed the line from pleasure to discomfort, but she recovered it with her smooth tongue caressing his head in circles.

She gripped him tighter as he gradually became hard in her hands, his length growing more with each swipe of her tongue, each suck that hollowed out her cheeks, and each kiss placed to each individual part of him. She pulled her mouth from his cock and began pumping him faster in her hand as she dipped her face underneath and licked the small area where his balls met his base, sucking the skin there into her mouth before dipping lower and providing the same attention to each individual testicle.

Jeff groaned as Annie sucked each of his balls into her mouth, massaging them with her tongue, and then using her spare hand to push them in closer to his body once she released them, sending a surge of arousal straight through him, finally pushing his cock to its full potential. He kept his eyes closed, revelling in the sensations as she worshipped every part of him, creating a slow, but intense burn that started in his gut and worked its way through his entire body.

Suddenly, Annie pulled away from him completely, causing Jeff’s eyes to fly open. He regarded her confusedly as she moved to his bedside table.

“What are you looking for?”

“Just... something,” she said coyly, retrieving what she had been looking for and shutting the drawer. Whatever it was, she kept it guarded from his view as she quickly returned to where she’d left off. Jeff dropped his head back into the pillow and closed his eyes, opting to let her just do whatever she wanted.

Annie reclaimed her previous position and began pumping him again as she resumed licking and sucking on his balls. Suddenly, Jeff heard a strange buzzing sound from between his legs, and before he had a moment to consciously realize what it was, there was an intense vibrating sensation against perineum as Annie placed the bullet vibrator against it. Jeff groaned loudly at the sensation, spreading his legs wider to give her more access to the oft-forgotten bundle of nerves, providing the most intense pleasure as she returned her mouth to him, taking him in fully and sucking each time she withdrew.

It didn’t take long after she began doing this, hitting nearly every major erogenous zone at once, for Jeff to lose control. His hands clenched and unclenched in the sheets as he began to shudder from the inside out.

“Ung, Annie. Fuck. I’m gonna come,” he warned, fighting not to thrust his hips up into her mouth as she provided him with the most intense pleasure. In response, she began sucking him harder and faster. She pushed the bullet harder against his perineum, a movement which sent a powerful surge through him as she hit a particular spot within him that forced him apart.

Overtaken with pleasure, he began squirting come down her throat, his breaths coming in short, loud gasps as his body seized and shook uncontrollably. He could feel her swallowing around him, milking every drop from his overwrought cock, hand still palming him, pushing his balls up further, forcing even more intensity into his orgasm. She didn’t remove the vibe until he had completely exhausted himself in her mouth.

Once he was fully spent Annie continued to suck lightly on his now waning erection. The sensation was almost too much to handle as his head had become so incredibly sensitive. When finally he was flaccid once again, Annie dragged her lips from him. She placed a soft kiss on his inner thigh before working her way back up his body with kisses, retracing the path she’d taken downward in the first place.

Before finally laying out alongside his shivering body, Annie dropped the vibrator back on his bedside table and retrieved a blanket from the foot of his bed, covering them both and settling her head on his shoulder, placing a kiss there. Jeff wrapped her up in his arms tightly, unwilling to let her go. Still in a haze, he idly thought to himself that he’d never had as much of an appreciation for fine art as he did in that moment.

With a lazy hand making circles on her hip, the two finally drifted into a contented sleep. 

Chapter Text

Moonlight Sonata

It had been a long day. It started at 7 a.m. with a ringing telephone, followed by a high-pitched squeal on the other end that lasted for at least 45 seconds. Next up was coffee. Lots and lots and lots of coffee, and a few bites of cereal to ease a grumbling, nervous stomach. Following breakfast was a much needed shower and shaved, leading to blow dried and styled hair. A pressed suit was pulled from the closet and a choice made between a blue shirt, white shirt or black shirt. Blue shirt. And a dark blue tie.

At 8 a.m. he met a blond for a coffee. She wasn’t graduating—she had another two years left before she would complete her credits for a Psychology degree.

“I’m surprised you managed to get out of bed this early,” he’d teased.

“Cut the crap, Winger. You know I wouldn’t miss this.” He bit back a smile and sipped his coffee.

At 8:45 a.m. he met Annie, Abed, Troy and Shirley at the entrance to Greendale. Britta and Pierce had gone inside already to get good seats for the ceremony.

“I can’t believe we’re finally here,” said Annie with a watery smile. Troy, Abed and Shirley shared similar sentiments. Jeff just watched the young brunette with an odd feeling in his chest. When the other three started toward the building, he grabbed her hand and gave it a little squeeze.

“Thank you,” he said softly. She offered a confused smile. “For helping me get here. I couldn’t have done it without you.”

She squeezed his hand once before relinquishing it, following after their friends in flowing gowns.

~~

It was now 9 p.m. The day had gone smoothly. No one tripped walking across the stage. There were no last minute, “Sorry, you need one more credit,” disasters. The speeches were (mostly) painless, and the Dean managed to dress like a man for the entirety of the ceremony. Once all of the scrolls on parchment (or legal sized paper printed in the Dean’s office) had been passed out, the group once again reassembled outside the school for a final time, promising to meet at 7 p.m. for dinner at Mortie’s Steakhouse.

Over dinner they’d talked, laughed, joked, argued the appropriate amount, shared meaningful speeches (a Winger, Edison and Nadir speech), and waxed poetic about how their friendship would transcend college. At the door they’d shared hugs and promises of seeing each other the next day, or the following weekend, or a vague soon, and one by one each person had left. Shirley was going home to her boys, Britta home to feed her cats, Pierce home to bed, and Abed and Troy to wait in line for the midnight showing of the new Batman movie.

Jeff and Annie waited them all out, hugging, smiling, crying (Annie), and laughing off sentimentality (Jeff). Now it was just them, standing in the abandoned parking lot, looking at each other and each searching for the right words to define this moment.

“Come with me,” Jeff said after a long pause. Annie eyed him curiously, but accepted his outstretched hand that guided her to his car. They rode together in silence for a while, comfortable and completely at ease with one another. The high-stakes part of the day was over. Now it was just them.

“Where are we going?” Annie asked after a while. Jeff’s lips quirked up, but he didn’t answer. Annie seemed to accept this and rested her head on the cool glass of the window, watching the street lights fly by as they drove out of town.

~~

Annie became marginally more concerned with their whereabouts when they pulled off the highway and started down a long dirt road, surrounded by woods on either side, with only Jeff’s headlights illuminating the path.

“Is this the part where you kill me?” she joked, though her voice held a tone of uncertainty that made Jeff chuckle.

“It’s an important ritual sacrifice. They need virgin blood.” Annie grinned.

“You don’t think the Gods will remember all of our nights of debauchery?” Jeff slowed the car and took a second turn onto an even scarier looking path. “Seriously, where the Hell are we?”

“We’re almost there, just hold your horses.” Annie bit back a retort and squinted out the windshield, which was being brushed by unkempt tree branches as Jeff eased the down the narrow passageway.

It was only another moment before he reached a clearing. Annie gasped in a small breath as she took in the sight before her. It was a lake—a clear, gorgeous lake, surrounded on all sides by trees, save for the small sandy inlet in which they were parked. The full moon shone bright and blue overhead, casting a hazy glow over the entire area. She stepped out of the car and looked out onto the lake, inky black with tiny waves rolling up the shore.

It was cold by the water on this chilly May night, but it wasn’t the cold that caused her to shiver as Jeff approached her, coming to stand behind her with his hands around her waist. She sunk back into his large body.

“How do you even know about this place?” Annie asked, her voice barely above a whisper, not wanting to disrupt the complete and utter tranquility. Jeff leaned down and placed a soft kiss to her neck.

“Stumbled upon it a few years ago,” he vaguely explained.

“It’s beautiful.” She felt his lips curve upward against his neck.

“You’re beautiful,” he mumbled into her skin. There was that shiver again, working its way up and down her spine. She turned in his arms, slinging her arms around his neck.

“What are we doing here, Jeff?” He leaned down and kissed her softly.

“I’ve been saving this place for the right person,” he admitted. Annie felt her body heat up under the intensity of his gaze.

“And you settled for me?” she teased. Jeff could hear discomfort in her voice.

“You’re smarter than that, Annie.” Suddenly, he pulled away and headed back to his car, popping the trunk and digging around for a moment.

“What are you doing?” He slammed it shut and returned with a large towel.

We are going for a swim,” he said with a grin. Annie’s eyes widened.

“Umm, that water is going to be absolutely freezing, Jeff.” He shrugged, throwing the towel down on the sand.

“C’mon, Annie. Live dangerously.” She crossed her arms.

“Well, I would, but I didn’t bring a swimsuit.”

“Oh crap, neither did I,” he said with mock concern. Then, in dramatic fashion, he pulled his shirt over his head before fingering the sleeve of her dress. “I’ll show you mine if you show me yours.” Annie’s eyes narrowed.

Jeff,” she jokingly admonished. “Did you bring me here to go skinny dipping?” He quirked a grin and stepped forward, grabbing hold of the zipper on the back of her dress and pulling it slowly downward.

“You caught me,” he leaned down and placed his lips next to her ear. “Does that bother you?” He grinned when she shuddered beneath him and moved to unbutton his pants. Together, they proceeded to remove the rest of their clothes before tentatively making their way to the water’s edge. Annie toed it and jumped back.

“Ahh! Cold, cold cold!” she cried out. Jeff just laughed, and with reckless abandon ran full tilt into the lake, diving once the water reached his thighs and disappearing beneath the blackness. He emerged a few seconds later.

“Holy crap!” he yelled. Annie laughed out loud, but made no moves to enter the water. “Come on!” he called. She shook her head.

“No way!” He rolled his eyes.

“Come on! I did it!” his chattering teeth belied his confidence. She wrapped her goosebumped arms around her naked stomach and shook her head.

“You’re insane!” she called back. Jeff swam a little closer to shore, coming to stand where the water skimmed his hip-bones.

“Annie,” he said in a slightly menacing tone. “Don’t make me come get you.” Her eyes widened to Disney proportions.

“Don’t you dare!”

“Annie, I can guarantee whatever this water does to you, it’s doing a lot worse things to me.” Annie eyed him confusedly before trailing her eyes down to where his hips disappeared into the water. She giggled in recognition. “Hey, this is no laughing matter.” She just continued to laugh on shore, while Jeff waded up to where she stood. Without a word, he grabbed her and slung her over his shoulder in a fireman’s carry, ignoring her cries as he waded back out and dropped her into the water. She resurfaced with a gasp.

“Oh my God!” she cried out. Jeff crossed his arms and eyed her amusedly. She smacked his chest. “Jerk!”

“That’s what you get for mocking my freezing genitals.”  She rolled her eyes and slicked her hair back out of her face. Jeff admired her glistening body as she did so.

“Ugh, stop checking me out, perv,” she said, dipping herself into the water to get used to the temperature. Jeff just grinned and sunk into the water as well.

It took a few moments, but they both did eventually become accustomed to the cold water, finding it more pleasant than the breezy outside air. They swam together for a little while, poking, teasing, joking—falling into comfortable patterns that they’d perfected over the past six months. After a while, they swam a little closer, until they were sharing the same space, bodies moving together, tongues slipping against each other inside hot mouths.

“Jeff,” Annie said, breaking away with a conspiratorial grin. “Are you trying to seduce me?” He met her gaze with lust-darkened eyes, unable to fight the inherent effect her body had on him.

“Do you need to be seduced?” he asked softly. Her grin morphed into a genuine smile as she shook her head. Jeff pulled her closer, the cold water parting between them as her skin became flush with his. He kissed her gently, her lips tasting of gloss mixed with lake water.

She breathed into his mouth as she wrapped her legs around his waist, letting him hold her up in the slightly-too-deep water. Their lips worked together softly for a while, barely even kissing, just moving. Her tongue dipped out and tasted his lower lip, running along the outside of it, before she closed her lips around it and sucked on it lightly.

His hands trailed beneath the water over her back, down to cup her backside and pull her into him. Despite the cold water, he felt heat radiating between them, warming him from the inside out.

It was a slow burn as he slipped inside of her, breaths coming together, lips fused gently, hips rolling into one another as the moments wore on. Jeff broke away from her kiss and they just watched each other as his hips left hers and returned in long, slow thrusts. Her blue eyes were mesmerizing in the moonlight, to the point where Jeff couldn’t help but stare. She watched him back just as intently.

He began to shudder, and he knew it wasn’t from the cold. Her lips were moving in soundless prayers as she clenched around him, breaths leaving her throat in quick pants that fell across his face, warming his cheeks. Holding on with her tight and warm around him was a lost cause, and so he gave himself over to the sensation of being completely overtaken by her body, surrounded by her as his climax came and went.

Jeff hugged her tightly to him, his chin coming to rest on her shoulder, their bodies flush and panting as they relaxed into the embrace. His feet gave way on the sandy bottom and he allowed the water to take them deeper, floating together in the blackness where he treaded for them both.

The feel of her lips on his ear brought him back to the present. He turned his head and caught her lips in a soft kiss. She broke it with a small smile.

“Happy graduation day, Jeff,” she whispered, not wanting to disturb the utter tranquility of the abandoned lake. Jeff kissed her softly again, noticing for the first time that she had begun to shiver.

“Ready to go?” he asked. She nodded and reluctantly broke away from him so they could both swim to shore. Once there, Jeff picked up the towel and wrapped it around his back, opening it up so she could join him. She did so willingly, her slick body coming to rest against his, her head against his chest, as he closed the towel around her and held her tightly against him for several moments before they finally put their clothes back on and returned to his car.

“Where to, Milady?” he asked once they heater had been turned on full blast. She held her hands over the blower as one would a crackling campfire, soaking up the heat into her chilled bones.

“Home, Jeeves,” she teased, throwing a small grin over at him. It didn’t reach her eyes though—not in the way her smiles had earlier in the day. Jeff attributed it to the late hour and put the car into gear, directing them back the way they’d come.

~~

It was about a half hour later when they reached the front door of Annie, Troy and Abed’s apartment complex. Jeff put the car in park, and Annie quickly unbuckled. She sat still for a moment, toying with the damp ends of her hair. For some reason this silence felt different that the ones they usually shared. It was filled with something else; something heavy and unspoken.

“Thanks for tonight,” she said softly, not meeting his eyes. Jeff reached over and grabbed her hand. She let him, but was slightly stiff in his grasp.

“You okay?” She nodded, and raised her eyes to meet his.

“I’m good. Really good,” she said softly. She leaned over and placed a chaste kiss on his lips. “This was a good way to end things.”

Before Jeff had a chance to respond, or even fully contemplate the meaning of those words, Annie was gone, running toward the entrance of the apartment complex and away from him.

End things?

He sat back for a second, stunned, confused. And then in a moment of decisiveness, killed the engine and got out of the car, chasing after her. 

Chapter Text

Closing Statements

Annie had only just opened the lock on her door when she felt a hand grabbing her arm, pushing her through. She looked up at Jeff, wide-eyed as he slammed the door behind him.

“What the Hell was that?” he demanded. She stepped back away from him, slightly afraid having never seen him so angry before.

“What was what?” she asked, timidly.

“The end of things? What the Hell, Annie? Why would you end things?”

“I just thought it was implied that it was over,” she explained, genuinely surprised by his reaction.

“Why would you assume that?” he asked.

“Because without Greendale I don’t have any logical reason to meet you anymore—we’d have to at least tell Troy and Abed about it,” she explained, her voice raising slightly to become more even with his.

“So?” She rolled her eyes.

“Really, Jeff? There’s no way you’d want them to know.”

“Why not?”

“Because you thrive on secrecy. We both know that’s what made this so much fun for you.” He stepped back, literally taken aback at the suggestion.

“Why on earth would you even think that?” She rolled her eyes.

“Come on, Jeff. Literally the moment the group found out about you and Britta, the two of you ended... whatever it was you had going on. Why would this be any different?” Jeff crossed his arms, irritated.

“Annie, if I was actually concerned about secrecy, do you really think we would have done it in the Dreamatorium while Abed and Troy had a John Candy marathon?” Annie opened her mouth to respond, but Jeff continued, hammering through occasions. “Or how about when we fucked in my car during a group potluck? Or when you had a vibrator inside you for an entire school day? Or when you gave me a hand job while sitting on the inflatable sofa behind Troy and Abed?”

“What’s your point?” she demanded.

“My point, Annie, is that when I want to be discreet, I act discreet. You know why nobody knew about me and Britta? Because we were careful. You and me? We weren’t careful. We were practically begging to get caught.”

“Why the Hell would you want to get caught?”

“Because I love you, you idiot!” Annie stopped only briefly to consider those words, before ploughing onward.

“Wait a minute... you stole that from Gilmore Girls!” Jeff ground his teeth slightly.

“Yeah, well... you know I stole that from Gilmore Girls.” She rolled her eyes.

“Jeff, it’s not fair for you to just throw that out there whenever you don’t get your way!”

“Seriously?! Is that what you think this is?”

“Well what the Hell else am I supposed to think? We’ve been doing this for months, you could have said it any other time.”

“Like when?!”

“Oh, I don’t know, maybe in the lake tonight, or in the car. Or, you know, weeks or months ago!”

“What the Hell was I supposed to say? “Oh, hey Annie, I know you’ve made it exceedingly clear that you have no interest in a romantic relationship with me, but I just wanted to let you know that I’m in love with you. No pressure’.”

“When have I ever made it clear that I don’t want to be with you?”

“Umm, every fucking time I brought it up. One time you literally stuck your panties in my mouth when I suggested a date.” She crossed her arms with a huff.

“I didn’t hear you complaining when you had my panties in your mouth.”

“That’s because I had your panties in my mouth—that typically puts a stop to the thing saying!”

“You liked that!”

“Okay, you caught me! I like have your panties in my mouth. I like having your tongue in my mouth, and your earlobe in my mouth, and your finger in my mouth, and your tits in my mouth, and your clit in my mouth, and, fuck, I don’t know, you’re elbow in my mouth!”

“My elbow?!”

“Point missed, Annie. I like having you in my mouth. I’m a dude, you’re hot, you taste good, I like fucking you. Big fucking revelation!”

“So you don’t love me, you just like sleeping with me!”

“I didn’t say that!”

“Then what the Hell are you saying?!”

“I already said it!”

“Under duress!”

“Oh for fuck’s sake,” Jeff said in a huff. In a quick movement he closed the gap between them, pushing her hard into the wall. “You don’t like how I say it? Fine! I’ll fucking show you.” Annie didn’t have a moment to contemplate what was happening before Jeff’s lips were fused with hers, and her legs were hoisted around his waist by large, strong hands. Her body was shoved roughly against the wall and his erection pushed hard into her centre.

“Yea, ‘cause this is gonna prove you don’t just want me for sex,” Annie said in between kisses.

“Shut up and let me fuck you,” Jeff mumbled against her mouth.

Together, they fought against the wall, hands fisting in shirts and dress hems, pulling and kneading and ripping until every scrap of clothing had been torn from their bodies. Jeff wasted no time pushing three fingers into her, finding her wet and ready for him as she ground down into his hand, mewling and crying out at the suddenness of the invasion.

“You have any more complaints?” he asked, pumping his fingers into her roughly. She held on around his neck tighter, nails digging painfully into the skin of his back.

“Shut up and fuck me, Jeff,” she ground out. He met her gaze with one just as intense before ripping his fingers from her core and plunging his cock into her wetness, bottoming out on the first stroke. Annie cried out at the sensation, and immediately began moving her hips against his, desperate for more.

Jeff didn’t waste time. He had something to prove, and he knew it. He pulled out and in another swift thrust, pushed all the way back in, setting up a punishing pace. With each thrust, Annie hit the wall a little harder, but she couldn’t be bothered to care. All she could feel was the place where they were joined, and the incredible burn of his cock filling her rapidly.

After a few moments, Jeff readjusted, putting his arms under each of her legs, spreading her even wider for him and forcing her to hold on tighter to him, lest she tumble to the ground. In this position, he pumped in and out with even more fury, fucking away his frustrations as he pulled her hard against him. She began bouncing off of him with more athleticism than he was aware she was capable of, which only made him want to have her more.

There was still so much he didn’t know about her. He needed to know it all. He needed to know her inside and out. He needed to touch every part of her body and know how every part of her felt against him. He wanted to taste every inch of her skin, and then fuck it. He didn’t even care if it wasn’t a place one could traditionally fuck—he just wanted it. He wanted it all.

And if he couldn’t have it all, he would take everything he could possibly get out of this final moment between them.

Annie began shuddering against him and losing her grip on his neck as she quickly came undone. Jeff pushed her back flush against the wall and readjusted so he was once against holding her upright as he pounded into her, coming with a ferocity that he had only rarely felt. Every muscle in his body tensed as he filled her with staggered thrusts. His breaths came in loud, heavy gasps that forced him to refill his lungs quickly, lest he give in to the spots appearing before his eyes.

And when he came down, they shuddered together against the wall, a mess of sweat and sex hair and mixed bodily fluids seeping out of the space where they were still connected.

Jeff fell against Annie, breathing heavily into her neck as he fought to keep his balance. With a final jolt of energy, he pulled her from the wall and turned them around, sliding down the wall into a seated position as Annie’s knees came to rest on either side of his legs. She leaned forward, resting her forehead against his shoulder as she, too, caught her breath.

“I wasn’t going to do this tonight,” Annie mumbled into him after several moments. His brow furrowed.

“Wasn’t going to do what?” She pulled her head from him and sat up straight, her hands resting on her thighs.

“I wasn’t going to end things. I thought I’d give it a few more weeks... but then the whole lake think happened, and I just knew...” she let her voice trail off as tears sprung to her eyes. Jeff shot his hand out to capture the one rogue droplet that fell.

“You knew?”

“I knew I loved you,” she admitted softly. “And I tried not to. I tried not to let myself, because that’s not what this was. I was supposed to be a grown up and be able to separate and compartmentalize these things, but I can’t. I thought I could, but then tonight it didn’t feel like sex anymore, it felt like we were making love, and I just couldn’t keep trying to convince myself that I didn’t love you.” Jeff reached forward to cup her face in his hands.

“It felt different tonight because it was different, Annie,” he explained. “Maybe it wasn’t a conscious decision, but tonight I was making love to you. I’ve wanted to make love to you for so long, and it just happened.” He stopped a moment, taking a breath and looking off into the space behind Annie. “I’ve never wanted to make love with anyone before.”

“Then why me?” she asked quickly. His eyes shot back to hers.

“Why not you?” she bit her lip.

“After three years, I kind of got the impression you weren’t interested in loving me.”

“Truth?” he asked, forcing eye contact. She nodded hesitantly. “After 35 years, I wasn’t interested in loving anybody. But I love you, Annie. I need you to believe that.”

“I do,” she quietly said. Jeff quirked a small smile.

“You do?” she nodded.

“I guess I just needed to be convinced. I’m like that sometimes. Cynical.” He raised an eyebrow.

“Annie, you’re the least cynical person I know.” She huffed a small laugh.

“Maybe optimism is just my cover. It’s easier to pretend things are going to be okay than it is to sink into your genuine belief that they wont be.” Jeff dropped his hands to hers and held them both.

“Annie, I can’t promise you that I’m going to be good at this. God knows, my track record kind of speaks for itself. But I’m willing to try, if you are.” She waited a moment before her lips turned ever-so-slightly upward.

“Even if it means you occasionally watch Glee with me?” A look of abject horror donned on his features, causing Annie to break out laughing. “Maybe just Gilmore Girls, then.”

“Gilmore Girls I can do,” he amended, relaxing slightly. Annie bit her lip.

“Does this mean we’re going to tell the group? Make it official?”

“Facebook official, even,” Jeff teased. Annie laughed lightly and leaned forward, kissing him gently.

“Thanks for running me down like a madman,” she teased. He smiled widely.

“Well, geez, if I knew all I had to do to get you to be with me was attack you when you were alone in your apartment, I would have done it months ago.” Annie made a face.

“Okay, our love story is going to need some fine tuning.” Jeff laughed out loud and wrapped his arms around her, pulled her to him tightly.

“Just be sure to leave out the part about the vibrator when we tell my mom,” he teased. Annie giggled against him, sinking into his embrace. They stayed that way until the chill in the air reached their skin, and then parted only briefly enough to collect their clothes and retire to Annie’s bed. There would be time enough for discussion and details in the morning.

End