How did they get here? This thought resounds in Jeff’s head as he jolts at the sensation of Annie’s tongue lingering over the head of his cock.
He knows the what, where, when, and why, and heck, he figures he might even be able to describe the how. Nothing concrete, though, no single moment that switched their dynamic to Annie working him like a high-class escort. The memory of her hands caressing his inner thigh while Back to the Future 2 blared in her apartment comes to mind, how the tentativeness of her touch lit a smouldering fire in his lower stomach. Maybe it had been the increasing boldness of her fingers circling higher and higher while her eyes stayed glued to the screen, the rest of the group chittering away in the kitchen none the wiser. It could also have been the moment she stepped off that plane from her summer internship in Washington three months ago, her smile bright enough to rival the sunshine beaming from the windows overhead. She looked at him unflinchingly that day, and he pretended he was still breathing when she maintained the eye contact. A warmth flitted in his chest like somehow Abed, Shirley, Britta, and Troy were stagehands and bit parts and he and Annie the lead actors.
The ‘when’ happened somewhere between the airport and Back to the Future 2 . A group invite turned into just the two of them at some small hipster bar nestled in a cul de sac, complete with ten too many scotches for each of them, banter about his mid-life crisis around his renewed love of Rambo , and Annie riding his face twenty minutes later.
Whatever the ‘how’, Annie had grown in his heart like some orchid/weed hybrid, catching him off-guard at every smile over viral cat memes and subtle brush over her nipples in public. God, this girl-- woman --strumms his heart and penis with a harpist’s finesse, and he loves it.
The pop of her lips off his cock startles him back to reality. ‘Jeff,’ she whispers, cheeks flushed. ‘I have an idea.’
He stares down at her naked between his thighs and tries not to come at the sight. ‘Hmm?’
Her gaze falls to the floor. ‘Well, I’ve been doing some… research and wanted to try something I read about.’
He sits up at that. ‘I bet it was filthier than that bondage clip I caught you watching.’
‘No!’ Annie smacks his calf and crosses her arms, hiding her nipples from his view. Jeff pouts. ‘Not quite like that, though I wouldn’t mind trying that at some point...’
‘Go on. Little Jeff’s listening.’
‘What do you know about milking?’ she says, biting her lip.
That catches his attention. He coughs and shrugs. ‘I’ve heard of it but never done it. Haven’t met a woman curious or bold enough to try.’
Her doe eyes grow wide, and she shrinks back, loosening her grip on his cock. His throat constricts. ‘But I’ll try anything once.’
‘I knew you’d say yes. Lay back.’ She leans back towards him, a grin suspiciously close to a smirk splitting her face.
‘Hmm, I like when you take control. Have your way with me, mistress,’ he says, giving her a salute.
He ignores his heart leaping as she snorts. ‘He says with no sarcasm intended.’
He gasps when her lips wrap themselves over him again with no hesitation. Her tongue glides down his shaft while her hands cup his sac, gently massaging. Her pace quickens, the suction of her mouth tightening to the exact pressure she knows he loves, and even as he groans and hits the back of her throat, her gag reflex reacts little. God, she is a fucking fast learner, a vixen disguised by a kaleidoscope of cardigans and stuffed animals.
She chooses then to feel around for the lube on the side table but not before leaving a kiss on his glans glazed with pre-cum. His hips jerk towards her mouth. The iciness of the air around them begs him to shove himself back into the warmth of her throat, but the distance proves too great. He huffs, pouting as he watches her fiddle with the cap of the lube. She lets out an ‘uh-huh!’ when the thing comes off with a click. She squeezes its contents into the palm of her hand, the sound causing his erection to harden more than he cares to contemplate. Then just like that, she grips and strokes his shaft in her lube-free hand, the other trailing over his sac and perineum until she reaches the pucker of his ass. Her gaze catches his then, a silent question in her baby blues. He grants her a smile and nod despite the lump in his throat.
One of her fingers lathers a helping of lube to his entrance and gently probes in. The sensation has him knitting his brows--he doesn’t know if it feels uncomfortable or vaguely pleasant or some amalgamation of the two. All his thoughts flood away as she presses forward then out again. The discomfort dissipates as she pumps in and out in a sliding rhythm, pushing deeper each time. The sensation attracts his attention away from her hand fondling his shaft to the fullness he feels from her other. When she adds another lubed digit, that feeling grows, coaxing a half-moan, half-grunt from him.
She brushes a spot inside him, and his eyes shoot open.
‘ Fuck ,’ he hears himself say, blood rushing to his ears.
Annie stares up at him from where she’s sliding her tongue over the tip of his erection. There’s a smirk in her gaze that hits him, his breathing growing heavier as her fingers curl and brush against that same spot once more. Warmth spreads through his pelvis as she sucks his cock and circles her fingers in tandem, his jaw going slack. His mind blanks as the pressure builds behind his shaft and his brow furrows as his awareness hones in on the slickness of Annie’s tongue and her digits circling. A groan escapes him when a sudden wave of bliss courses through his limbs, only to be slammed with another much stronger. His hips strain off the couch, one hand curling into a fist beside him while the other entangles in Annie’s hair, guiding the path of her mouth over him. A few more strokes of her fingers and lips overwhelm him, his fingers tightening to a bruising strength in her tresses and a whine breaking free from him. Every hair on his body stands on end as he explodes at the back of her throat, euphoria radiating across his torso, creeping up over his shoulders and neck before sneaking down to the tips of his toes. It’s all he can do to keep his head on straight.
He continues to shake even as she withdraws her mouth from his deflating cock. A drop of his release hangs at the corner of her upper lip, and he watches intently as she licks it from there with a smirk.
‘Jesus, Annie, I should let you carry out your research on me more often.’ He runs a hand through his hair, struggling to catch his breath.
She shrugs with a tilt of her head, and his hand reaches out to tuck a lock of hair behind her ear. ‘See? I knew you’d enjoy it!’ She winks and lowers her voice to a conspiratorial whisper. ‘I think your neighbours know that now, too.’
‘And I should care why? I’m a card-carrying adult with sexual needs, perfectly natural since the dawn of humankind.’
‘I’m sure they don’t need the detail, though, Jeff.’
‘They’re probably living vicariously through hearing it, anyway. Don’t spoil their fun.’
Annie’s eyes light up the moment he says ‘fun’, and he waits for her suggestion.
‘Speaking of fun…’ she says seconds later, confirming his suspicions, ‘my research went a little bit further, and I want to try something else.’
‘Adventurous. I like. What’s your proposal?’
‘Pegging.’ She chews her lip, and he fumbles trying to place the word but comes up blank. ‘It’s basically where I give and you receive. Instead of my fingers, it’s a strap on.’
He struggles to keep his jaw from dropping open, choosing instead to lean forward with his hands clasped. ‘Well, that’s definitely a suggestion.’
Annie shifts almost imperceptibly back from him, staring at the ground. He watches her cheeks flush as his eyes rove over her form, and he conjures the image of her stroking a neat black cock between her legs, her gaze sharp, determined. A breath catches in his throat, his shaft twitching.
‘Damn, I’m visualising you wearing one, and it’s doing things to me,’ he says. ‘If it feels anything like what you just did, consider me your willing guinea pig.’
And just like that she perks up, beaming like she’s won the lottery ten times over. He can practically feel her holding herself back from clapping, the observation eliciting quirk of his lips to match hers.
‘Okay! Well, there’s so much we need to get, manuals I need to read… of course, my research was only cursory--’
He leans forward then to kiss her. ‘Just don’t start the fun without me,’ he says when he breaks away.
They agree on Greendale and the study room via text messages at 8 o’clock sharp, far enough outside school hours to avoid the group’s suspicion. (‘ Meet at the parking lot? ;)’ Annie messages him first thing, and he pretends the stomach flip it inspires is indigestion). A stone weighs on his shoulders the moment he jogs up the stairs at Greendale’s entrance, growing heavier with each tick of the stupid clocks in his classroom, office, and the teacher’s lounge. When lunch rolls around, he slips beside Annie while everyone else argues over the merits of sweet potatoes over their normal counterparts and which lunch lady dollops out the best serving size (Britta, of course, makes an impassioned statement that ‘lunch people’ is the correct and only term for these white collar workers). His fingers itch to hold Annie’s hand or caress her inner thigh but settle instead for resting a hand on her thigh under the table. She observes him, offering a knowing grin, and he stares at her lips, painted today a glossier shade of red than normal. He crosses his legs to hide his response from any curious onlookers, forcing him to swallow the conspicuous lump in his throat. They stay that way, his hand on leg, her gaze periodically returning to him with a conniving gleam, until she rises and meanders onto her last classes for the day.
She avoids him afterwards, ignoring his text to confirm they are still meeting. Some part of him recognises this as one piece of a masterplan, an entree of foreplay before the main course--and it’s working! Jeff Winger’s not one to wait or submit easily even in the face of Annie’s goddamn doe eyes. At least, this is what he tells himself on the drive home while struggling to keep his foot steady on the pedal and racing through one too many traffic lights.
He’s pulling up out the front of his apartment when his phone lights up. Annie’s name flashes on the screen with a notification reading ‘1 image attached’, and his chest constricts. He presses on it, waiting for his and Annie’s texts to appear. His mouth dries when the image materialises.
Annie. Clad in a lace bra, black and barely restraining her cleavage, with a strap-on to match.
Another text zooms onto the screen as his brain strains to catch up. This one? :) Or did you want to choose another…?
He breathes through his nose, one hand gripping tight to his steering wheel, the other on his cell. Gay, Winger , gay! echoes Pierce’s voice from the back of his head.
His thumbs freeze over his cell’s keyboard. He scopes over Annie’s form in the photo again, shifting in his seat, lingering over her cleavage and fake shaft, and shrugs. If him liking an adult woman with a makeshift cock makes him even slightly queer, then he’d take all of it. Besides, Pierce hardly represents the pinnacle of open-mindedness.
That one. No need for it to look like a unicorn , he types, then hits send. His fingers pause for a second before he continues.
You looking fucking incredible, btw. Pale skin with the black is working for you.
He waits a few seconds more, and her reply darts onto the screen.
You’re just saying that because you got a look at my cleavage.
He chuckles to himself. She’s entirely wrong, of course, but Jeff Winger is an honest-to-God boobs man.
Another text arrives a second after the last, and he stops chuckling.
But I don’t look nearly as incredible as you’ll feel.
High promises, high confidence. He sighs and flicks through another message. Let’s call it even, kiddo. I’m on my way.
He tucks his cell into the side compartment and fires up the engine, foot even on the pedal as he maneuvers back onto the street.
Annie tugs her jacket tighter around her, peering around the parking lot from behind a random tree she had chosen. No sign of his Lexus yet. She shifts her weight from one foot to the other, drawing her awareness to the tightness of the silicone shaft and harness against her hips. She stares at her feet, the breeze skimming her skirt over her upper thighs, while her fingers tap rhythmically on her forearm. Breathing in, she surveys the area between her and the entrance, half expecting to spot the one decent security still in Greendale’s employ.
A harsh flash of light blinds her then for a second. She raises a hand to block out the worst of it, enough to see an all-too-familiar Lexus, slick as a well-polished Louboutin. Her grip on her jacket tightens further as she watches him slip out and click the door into the lock behind him, the sound barely breaking the night’s silence. He turns and spots her there, whistling as he strolls over.
‘You have the audacity to look like a bunny in headlights after those messages?’ he says when he’s a few feet away.
She crosses her arms while stepping towards him. ‘I express myself better that way. It’s the only way you’ll take me seriously.’
‘I thought that was the gimmick--me surrendering my better judgement to you?’
She allows herself a smirk. ‘That’s one interpretation as long as you’re not against breaking and entering.’
'Well then, milady, shall we proceed?’ He offers his arm to her, and she links hers through his.
They tread lightly a few feet as she pictures a map of Greendale, pinpointing where that one decent guard lingers around most often. The entrance is too obvious and home to too many alarms (all painted now as dalmatians courtesy of the Dean). The vicinities of the gym and admin buildings sit too close to Parking Lot # 5 where she hears her fellow students engage in all manner of profanities--they did not need to be suspected of procuring or distributing illicit substances or services given their current scheme. The Learning Resource Centre and South Hall, though directly across from the library, offer no reasonable cover should security pass through, meaning they would need to go around, then across the quad to the study room. The cafeteria, by her deduction, therefore presents the sole means of access least likely to lead to their discovery. Troy made a passing comment once about the windows having broken locks (without proffering a reason why he knew about that, though that might’ve been his mouth being full at the time), but she took the tip regardless. One snoop, several thorny bushes, and a few strange looks later, she identified earlier today the exact window she’s leading him to now.
‘I can hear your brain churning,’ he says. ‘What’s the master plan? A mysterious dildo in the study room’s vent?’
‘Thinking about how to avoid security.’ She chews her lip and peers around, tugging on his arm. ‘Come on.’
Her mind hones in on the path they need to take, and her feet follow. He matches her pace at her flank, and she guides him past the building standing tall near the quad, darting behind the tree or other assorted foliage whenever a noise breaks through the night’s air. They encroach onto the quad by following the lines of the shadows the basketball hoops cast, managing to reach the cafeteria’s window without spotting the guard. She fumbles through the bushes and grasps the broken lock, forcing it open with a grunt. Her fingers grab onto the window’s edge, boosting herself up and through, twisting so she finds her footing on the other side. Jeff peeks through after her, landing beside her with a grace she resents, though it vanishes when he offers her a hand up.
She gestures towards the cafeteria’s entrance. ‘Come on. The guard’s due here any minute.’
Jeff offers no protest, only a nod, and they push through the door and break into a sleight-of-foot sprint down the hall to the study room.
She barely makes it to the door first as she puts all her weight into forcing it open. The click of Jeff turning the lock echoes followed by the snap of the blinds behind her. She fights to calm her panting as her hands wring together, peering down over her jacket to her feet, and the sound of his shoes scuffing over the carpets resounds in her ears. The heat of his body against her back signals his closeness, and he chooses then to brush her hair aside and skim his lips over her neck.
‘What now?’ he whispers, and her mind comes up blank. She wets her lips.
‘I want you to strip for me,’ she says, turning in his arms to face him, ‘and make me believe you want this.’
His breathing grows deeper, his hands drifting down to sit at her hips, dangerously close to where her strap-on is concealed. She waits for some quip or even an expletive, but all he does is stare down at her through hooded eyes.
‘Okay,’ he says at last. He steps away from her, his fingertips lingering on the exposed skin of her arm, and proceeds to undo the first button of his shirt.
When he begins unbuttoning the second, she spies a tickle of hair on his chest emerging. He undoes another and another while keeping eye contact, and her gaze darts downward to see his abs, their lines sharpened by the light filtering throughout the room. Her eyes flick back up to his, her mouth half-open as he snickers at her. His fingers make their way down to the last button and liberate it from its confines. He shrugs out of the shirt, his muscles rippling with the movement, before he spins and tosses it into a random corner of the room.
He grips one hand to his hip. ‘Like what you see?’
She awakens from her stupor and gives him a once-over, lingering on the trail of hair disappearing beneath his trousers. The desire to reach out and trace the outline of his pecs strikes her, but she opts instead to cross her arms and tighten her hands into fists.
She nods toward his trousers. ‘Take them off, too.’
The smugness melts off his face, giving way to a look that heightens the thrumming of her heartbeat at her temples. He pauses before reaching down to his zipper, and she breathes through her nose when the sound of his zip reverberates in the quiet of the room. Blood percolates in her ears as he shoves off his trousers to the carpet and steps out of them, clad now solely in his briefs.
The distance between them stretches like a chasm as she watches him observing her. She waits for a pun as she edges toward him, clutching at the spark of courage flitting around in her chest. Her hand reaches over to him and presses against his chest, his brow knitting together. Swallowing, she guides his fingers to her concealed strap-on.
‘Feel it,’ she says.
His mouth parts and his brow relaxes. She imagines the length of her makeshift cock warm and heavy against his palm, revelling in the jolts of sensation that shoot through her pelvis as he begins to stroke. Her folds grow slick at the thought, and her fingertips whisper over her pocket unconsciously. The item nestled inside skims over her hand.
He instead pats down her jacket, breaking her from reverie and building arousal. ‘What’s this?’
Sighing, she removes said item from its hiding spot. ‘What does it look like, Jeff?’
He whistles and plucks it from her grasp. ‘It looks to me like a test run. Have to say, I’ve never had a butt plug corked up there. I might end up feeling like a wine bottle.’
She smacks his hand away, though she struggles to keep her lips from quirking. ‘You’re not doing a great job at selling this.’
‘It’s all part of the foreplay,’ he says, placing the plug back into her palm and closing her fingers over it. He stands there for what seems an eternity before she locks her lips over his.
He leans into her fully, and despite her jacket, she can feel his hardness against the juncture of her thigh. He brings one hand to her cheek, deepening their kiss, and the warmth of the contact makes her forget his stupid sarcasm, his dumb need to take this illusion of control from her. She gathers her resolve and rams him back toward the study table. The back of Jeff’s legs smack into it, jousting his lips from hers, and she takes this chance to settle herself better against him, dizzy at the heat of him radiating across her pelvis. His boxers sit tight at his hips, and she wrenches them off with a huff, ignoring the half-chuckle, half-groan it elicits from him.
Perspiration glistens on his pecs under the dim lights hanging above, and at the sight, an idea pops into her head, and she pauses for only a moment before flicking his left nipple.
He startles off the table, expression caught between shock and pleasure. A swell of pride burrows itself in her chest, prompting her to ring her tongue around the nub again.
A moan tears from his throat, one of his hands tugging at her hair. The tension of it encourages her to continue as she clutches at his thighs. Her gaze travels down over the length of his body to his cock, bobbing in time with Jeff’s shuddering under her. She feels herself grow wet against the harness of her strap-on, and her hips thrust against it instinctively, provoking pulses of sensation through her. Her tongue leaves his nipple, and she remembers the plug in her palm, her thumb running over it as he watches her.
She sets down the plug gingerly on the table and retrieves the lube from her jacket pocket. ‘Are you ready?’
‘Ever ready,’ he says, righting himself onto the table, legs parted.
She squeezes some lube onto the fingertips of one hand, sets the tube down beside him, and begins caressing his perineum with her fingers, trailing kisses down his abdomen all the while. His breathing grows shallower the closer she ventures towards his cock. When she reaches it, her mouth envelops and sucks the head, goading a strangled moan from him, and her lubed digits find their way to his ass, coating the area liberally. Taking a breath, she pushes one finger in.
His sphincter resists at first. She studies Jeff’s face, a thrill rushing through her to see him gritting his teeth, and eases the rest of her finger inside him, happening across a lump three inches in. Her research from earlier guides her to make a come-hither motion over this area, and his reaction is immediate--he inhales sharply, his hips rocking in time with her strokes. Her breath catches, the twitching of his cock, the noises escaping from him, matching every daydream of this moment she’d allowed herself to have. Heart in her ears, she adds another finger and sets a steady rhythm, every thrust she makes loosening him further. The wetness of the sound should mortify her but instead she grows slicker. She gyrates against the harness and flinches at the sensation that cuts through her, interrupting the momentum of her digits inside him. She stills to gather herself and focuses again on Jeff. His gasps heighten in volume when she does so, prompting her to hasten her pace and hone in on his prostate. Her fingers cease their thrusting and begin circling, and a hiss escapes him, escalating to a throaty groan, louder than all the ones before. She persists with the motion while bringing the plug near her thrusting fingers with her other hand.
Jeff looks down at her and raises an eyebrow. ‘Bringing out the handgun,’ he rasps, pointing at the plug, ‘before the AK-47?’
She coughs to hide her laughter. ‘Great metaphor, Jeff, but I don’t hear you complaining about pain. Quite the opposite.’
He smirks at her again as she withdraws her fingers and places the plug against his entrance.
The ring of muscle rebels against the pressure she exerts before the plug slips into him. She surveys his expression then, a pang in her gut rising when his breath comes heavy and his jaw unhinges. Her grip on the plug’s end loosens, and she maneuvers it to rest firmly against that spot within him. He shifts his weight so that the base better sits on the table beneath, and his hips roll, his torso jolting at whatever sensation it inspires.
She stands and finds herself unable to glance away from the sight of him. His cock, red and seeping cum at the head, lies on his abdomen, jostling side to side with each rock of his hips against the plug. Sweat glistens on his forehead under the low light above, and she watches a drop of it trickle down his forehead and between his brows, her mouth dry as the droplet vanishes into the shadow his nose casts over his cheek. Heat tingles between her legs, and unconsciously, her right hand brushes over the harness beneath her skirt. She inhales before she comes back to herself.
Her jacket slips off first. It tumbles to the carpet with thunk, and Jeff’s gaze snaps onto her. She stares back and caresses over her stomach until she reaches the seam of her tank top. Her fingers slip under, pull the tank up and over her head, and drop it somewhere in the vicinity of her jacket. White noise buzzes in her ears as Jeff fixates on her lace bra while bracing himself against the table and raising his head. Her limbs begin tingling under his scrutiny, but she continues to the clasp of her brand and undoes it in one motion. His entire body stiffens when she draws the bra’s straps over her arms, releasing her breasts from their confines, and she becomes self-conscious of how they bounce in her periphery vision. Her attention turns to her skirt and the strap-on beneath, and she slips off her heels. Looking down at her now-bare feet, she steels herself while reaching behind herself to grasp and unzip her skirt. It plummets to the floor, and she kicks it off onto her growing pile of clothing. She peers up to find Jeff beholding her like Christmas has come early, and the thought makes her stand taller and elicits an airy feeling in her chest.
Her feet pull her forward toward him, and every step heightens her awareness of Jeff’s eyes roving over her body, leaving a trail of heat wherever they travelled.
‘You’re so beautiful, Annie,’ he says, his voice a tingle over her spine. ‘I, uh…’
The wistfulness in his tone makes her want to let him envelop her in his arms and make love. Yet unease settles into her bones when he remains quiet, his expression more naked than either of their bodies.
She forces herself to lean into him then, leaving her lips inches away from him and her makeshift cock flush against his. ‘I’m going to fuck you now, Jeff.’
All vulnerability leaves his face, replaced by something darker, more primal. Sensation scorches her skin as her lips take command of his, allowing herself to feel every curve and hard angle of his body. She deepens the kiss, noting the way he groans against her mouth and arches into her. Her tongue slips over his bottom lip, and that is all it takes for him to return the favour with his own while stroking over stomach to cup and knead her shaft. Her mouth breaks away from his to feather light pecks over his neck and cheek, trailing to a patch of sensitive skin behind his ear. She passes her tongue lightly over the area, and his moan almost deafens her. Though the heat of their bodies together attempts to hijack her senses, she persists with her suckling and angles her torso away from his bucking hips. He whines, and she chooses that moment to wrench herself away.
‘Y-you are an absolute minx.’ He points an accusing finger at her, breathless. ‘What happened to “I’m going to fuck you now, Jeff”?’
She keeps her expression blank despite the pang of cold she feels now having stepped away. His chest rises and falls, his lips swollen, and no small amount of pride puffs up within her at the effect of her efforts. This feeling seeps into her legs and feet, propelling her toward him, and her gaze hones in on the plug and catches his eye unblinkingly.
He eyes her with something akin to exasperation. She remains quiet while bending to meet him at eye-level, her hand skimming over the underside of his cock and snaking down over his perineum to grip the plug. He grunts and furrows his brow as she tugs it free, leaving his ass gaping.
‘Move over.’ She motions to the right corner of the table, stands to her full height, and crosses her arms. He has the audacity to pout, likely because her tits are no longer in his line of vision. She bites her tongue to stay her laughter and keeps her expression stern.
He winces while glowering in her direction. ‘Easy for you to say. You didn’t just have a glorified cork up your ass.’
She smacks his arm and clasps his cock, adjusting the tightness of her hold until his groans resound around the room. Her grip stays motionless, not relenting to his frantic efforts to increase the friction against her hand before she chooses to let go.
Jeff topples to his knees, his expression sharp, and she can’t deny to herself the sight pumps adrenaline through her veins.
She clutches a fistful of his hair while he still seems dazed, guiding his mouth to her strap-on.
‘Look at me,’ she whispers.
Confusion sneaks over his face, but he obeys and peers up at her. Sweat prickles on her forehead as her hand exerts pressure on the back of his skull, and his lips part and begins taking in the length of her fake cock.
He sets a safe pace over her shaft, a muffled sound escaping through the seal of his mouth, and shivers rattle through her at the warmth of his breath against her thighs. Her eyelids lower, and her focus draws itself to the gentle rocking of her hips against her harness and the way her strap on hits the back of Jeff’s throat. The thought fuels the pressure building around her clit, quickening the gyrating of her hips and heightening the volume of her breathing in her ears. A moan tears from her, then another--until she rocks her hips and finds his mouth is no longer there.
One foot reaches out to catch her fall. She huffs and spots Jeff sitting on his butt with a grin so wide she wanted to smack it off his face.
She crosses her arms. ‘Bend over the table,’ she says, her tone even, ‘with your back to me.’
All humour drains from his demeanour, and he rises without offering any quips. Her attention snaps to his cock, still red to the tip, begging for her tongue, and she keeps staring even as he sighs and leans against the table, ass poised.
‘Well, Jeff, you’re finally starting to take this--and me--somewhat seriously,’ she says more to herself than to him.
He snorts without swivelling to meet her eye. ‘We both know I get the better end of the deal here.’
His tone sparks something within her, and she steps decisively toward him. Her fingers itch to snatch up the lube sitting adjacent to the delicious sight of him, and seconds later, she does just that, squeezing a generous helping into her palm. She deposits the lube beside them again, then clasps her makeshift cock, applying the lube liberally up and down. She caresses the remainder onto his perineum before venturing to his entrance.
The air leaves her lungs when her fingers enter him again, marvelling at the ease of it now and how silky the lube feels everywhere she caresses inside. His breathing hitches in time with the pace she sets, and it takes only several strokes for his ass to follow the same motion, drawing full-fledged moans from him. Her concentration hones in on maintaining the pressure over that lump inside him, adding another digit to stretch him to the thickness of her cock. He yelps, but a drawn-out groan soon drowns it out.
‘Tell me what you want,’ she murmurs, leaning so her lips brush over his ear. His resulting shiver stabs heat straight to her core, and it is all she can do to keep from thrusting into him.
‘I-I want your cock inside me,’ comes his reply, soft enough that she doubts she heard it at all.
Her hand snakes over his stomach, then between his legs to clasp his shaft, and he keens. ‘ Louder. ’
‘Alright, alright!’ He bats her hand away, frowning at her over his shoulder. ‘I want your fake cock inside me right fucking now before I rip that harness off and fuck you senseless instead.’
Her cheeks begin to hurt from the grin stretching across her face. Her digits slide out, slippery to the touch, before reaching over for the lube and wringing yet more out onto her shaft. Her pulse throbs at her temples as her shaft aligns against his ass, and her stomach threatens to drop all the way to her feet. Seconds pass like nicks on her skin, and Jeff turns his head to consider her.
‘You won’t hurt me.’ His voice rolls over her, tickling every nerve, adding to the mounting heat building between her legs.
She says nothing but meets his gaze, maintaining the eye contact as she presses the head of her shaft into him.
A grimace contorts his features despite her being only a couple of inches in. She stops, breathes in and out, and thrusts in a downward motion, burying the entire length of her strap-on within him. His scowl relaxes then into an expression caught between awe and pain, and her hands hold fast onto his hips, staying his attempts to rock back against her. She counts down to a minute under her breath, hoping it’s enough time for Jeff to adjust to the fullness he must be feeling, but the very thought propels her hips forward of their own accord. He gasps, his knuckles turning white under his tight grip on the table’s edges.
The pace of her thrusts quickens, provoking guttural moans from Jeff despite how clumsy she feels in her movements. Through the harness, she can almost feel what he does as her strap-on drags over his prostate, how every stroke adds to a building pressure behind his own cock. The harness glides over her with every motion, twisting the coil of pleasure within, and somewhere outside her awareness, the rising volume of his groans pierces through. The sight of her cock slipping with ease into him, of this tall, strong, sarcastic man being undone inflames her, and she begins a pounding rhythm.
The noises escaping Jeff heighten to near-screams with every gyration of her hips, accompanied by the squelch of her shaft pumping in and out. His cologne’s cedar wood scent, mingling with perspiration, penetrates her nostrils, and her awareness descends into a deep part of herself, focusing on the building pressure around her clit. Desperation spurs her to take his cock in hand, to spread the pre-cum at the tip before pumping him in time her thrusts. He presses his forehead onto the table, trying to muffle his moaning, but he in no way is fooling her with how he angles his ass higher to meet her.
‘Come for me,’ she says with a particularly rough thrust. ‘You can’t hide.’
He jolts, reaching back to seize her forearm in a vice-like grip. ‘ Jesus, Annie, keep going. Fucking, please, keep going.’
The urgency in his voice paired with the friction of the harness slam into her, and she comes undone.
Tendrils of sensation pulse outward from around her clit, her body trembling under the intensity. She cries out while her hips continue their frantic pumping into him, and his groaning soon matches hers in volume. Her grip on his shaft tautens while her thighs burn under the strain of her thrusting, the pain sharpening her senses and the tremors resounding through her.
‘Fuck, Annie, I love you,’ he says, panting. ‘I’m gonna come. Don’t you dare fucking stop.’
His body shudders in time with hers, his moaning reaching a crescendo as he jerks and comes with a shout, and from somewhere outside herself, her own groaning rips into her consciousness.
She plummets back down to Earth and opens her eyes, uncertain of when she closed them.
The room sharpens into focus again as does Jeff, and her attention snaps to him, a pang in her gut rising to find him gawping at her. Her hand relinquishes his deflating cock, and her fingers rub together, her mouth drying when she feels they are slick to the touch with his come. Under him, it dots the table in filmy splodges, some as far as the most distant corner, and the realisation heats her cheeks.
She suddenly remembers the tissues tucked away in her jacket, spurning her to rush over to where it lay to pinch one, then the whole packet from its pocket. Goosebumps erupt over her skin under the weight of his scrutiny.
‘Hey,’ he says, gently clasping her forearm, ‘you don’t need to say it back.’
She shuffles her feet. ‘You’ve never said it to me before.’
‘Doesn’t make it any less true.’ He sighs but his hold of her remains steadfast. ‘I think you always knew how I felt even when I pretended I didn’t. It’s hard to bullshit you.’
Laughter bursts from her, allowing her to relax into his touch. Once calm, she studies him, and the openness she observes in his body, his face increases her consciousness of her breathing, of the gentleness of his hand on her forearm. Her awareness shifts to her nakedness and how high the strap-on sits on her pelvis, and she suppresses the instinct to cover every inch of it.
Jeff lifts himself off the table, wincing as he does so, and stands, swivelling toward her with a frown. His frame stiffens as he takes a step in her direction.
She knows he reaches her when his feet enter her field of vision and the ghost of his thumb brushes over her cheek. ‘Annie, look at me.’
Despite herself, she glances up. Jeff peers down at her, and her head begins to feel fuzzy like static. ‘You’re safe, and I’m not going anywhere,’ he murmurs. ‘You don’t need to hide any more.’
Her tongue struggles to form a sentence, any sentence. She tucks a trendril of hair behind her ear, breathes deeply in, and clasps Jeff’s hands, rubbing circles over the back of them. The heat radiates from his skin, tingling up her forearm.
‘I know, Jeff,’ she says finally, ‘and that’s why I love you, too.’
The world stills. All she can concentrate on is the shift in Jeff--the gentle curve of his mouth, the crinkles forming around his eyes--and she yanks him down, sealing her lips over his.
The tension of his body registers first in her mind as he returns the kiss and takes a hold of her hips. She allows herself to sink into the contact, skin-to-skin, and the sensation pools into breathlessness in her lungs. The touch of his lips proves less hungry than wistful, and somehow, she intuits a promise he’s giving her, one never hinted at in any of their other encounters, leaving her shutting out anything but the caress of his mouth over hers.
After a few moments, she breaks away. Her forehead leans against his as she sighs. ‘We’ve never kissed like that.’
He smirks. ‘No, we haven’t.’
‘It’s not a bad thing,’ she says, brushing the length of his shoulders. ‘In fact, I’ve never felt so close to you or anyone, really, than right now.’
‘So you trust me?’ His tone reaches inside her, propelling her hand up to cover his cheek.
‘Yes, Jeff.’ She shifts her hips, pressing her shaft against him. ‘As long as you keep letting me use this.’
He quirks an eyebrow. ‘I thought that went without saying.’
‘Better to say it aloud,’ she says, bopping his nose before tilting her head toward the table. ‘We should probably clean that up. That guard should be around soon.’
His laughter penetrates her chest, and her cheeks hurt from the resulting smile. ‘Well, there’s no one else I’d rather be caught in a compromising situation with.’
They part, and with the assistance of Annie’s spare wipes from her other jacket’s pocket, they make short work of scrubbing the table and rushing to don their clothes once more. They spot a flashlight through the blinds seconds after closing them, sharing a conspiratorial chuckle at the close call. Jeff leads Annie out of the study room, through the library, and into the cafeteria, dodging the guard when stumbling out of the window with the broken lock. Her legs spring into a run, Jeff following behind in a race to the parking lot, him easily overtaking her with his goddamn long legs. The instant his Lexus comes into view, relief floods through her, hastening her pace to a sprint. She grasps the car’s handle when it comes into range, throwing open the door, and slamming it closed just as fast, Jeff following suit in time. Pulse thrumming, she permits herself to sink back into the leather seat as Jeff starts the engine, entwining her fingers with his free hand.
Before either of them realises it, Annie has stayed at Jeff’s apartment for two weeks straight. Jeff surprises himself by being the one to acclimatise to this domesticity first, feeling a glow in his chest while Annie prances around cleaning the kitchen with her characteristic singular focus or sneaks her feet underneath his legs as they watch Meerkat Manor. Those three words fall off his tongue more fluidly as time marches on, Annie beaming whenever he says it, whispering the same in the dark of his bedroom or the broad daylight of his balcony. Somehow, some way, he watches as six years of avoidance melts away, replaced by the light of certainty he sees in Annie’s eyes.
Abed, ever observant, notices first. He approaches Annie and Jeff when they arrive at the new Trobed apartment searching for the various momentos she had left behind (or what Troy had chosen to “borrow”). He catches her eye first, expression neutral, before his scrutiny switches to Jeff, lingering on the closeness of his hand to Annie’s, the rigidness of his body language. Abed says nothing, and Jeff supposes this is due to his newfound appreciation for organic development, fiction or otherwise, but gratitude fills Jeff nonetheless. The others prove more oblivious, permitting them both enough peace to explore, solidify whatever is between them--until one accidental text from Annie to Britta describing the upsides of fellatio combusts the ruse.
I knew it! Britta texts back. He’s defiled you. Two yrs ago u didnt even no wat giving head meant!!
An emergency group chat erupts, complete with more exclamation marks and expletives than any other Greendale Seven chats had ever seen. Jeff and Annie peer up at each other from their screens, grimacing, but they let the fuel burn out. Shirley brokers the first ‘That’s nice! :)’ , prompting the others to begin sending similar sentiments, running the gamut from ‘I always knew!’ to ‘Shows character growth’ to ‘If u hurt her, I’ll feed ur intestines to Annie’s boobs!!11!’ Fairly tame compared to previous reactions, they figure, none of which claim to affect their group’s camaraderie the way Jeff and Britt’s entanglement had.
When they enter the cafeteria holding hands later that week, broad daylight streams through the room. Everyone peers up in tandem, and the world seems to zero in on him and Annie, but even under the uncertainty in the gazes of their five friends, he tightens his grip on her hand. He sneaks a glance at Annie to find her already staring back, a soft smile on her lips.
He grins back, and they slide into the booth with everyone, hands still intertwined.