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With a gentle click, the office door closed behind Dennis, closing him in the cosy office for the evening. Professor Robinavitch had a habit of keeping the main light off, working by lamplight when the evening hit, the rest of the school cast in a similar darkness. Truthfully, Dennis didn’t mind at all. He preferred it, even, enjoying the warm glow it casted, soft shadows crawling up the walls. It was a nice office, too; a big wooden desk, a chair placed either side for both Robby and a guest, books upon books and pretty decor that Denis was sure was older than him.
“Good evening,” Robby peered up from behind the rim of his glasses, smiling slightly. He gestured for the young man to come and sit down, as he stood from his own seat.
“Hello,” Dennis smiled back softly, coming at taking a seat. He set down two to-go mugs of steaming liquid - coffee for Robby, tea for himself. His own glasses balanced on the tip of his nose, pushed up as he relaxed.
The small office smelt purely of Robby. His tobacco smoke and whisky aftershave, the scent of cigarettes lingering in the air, the evidence of Robby’s mild addiction laying in a wooden ashtray. When Dennis visited in the morning, there was the added smell of pastries and fresh coffee. “Thanks, kid,” the older man spoke as he came to lean on the desk in front of where Dennis sat, reaching for his paper cup of coffee.
Sipping on his own drink, Dennis hummed gently in response. He tried to keep his eyes from drifting to the older man. From drifting to the crotch of his tweed pants, bulge huge and tempting. It’s hard not to look, really. Sometimes, Dennis is sure it’s looking at him. “What did you need my help with tonight? I’ve already finished most of my marking checks for you,” he spoke quietly, even if they were the only ones in the building at that time.
“Good, thank you.” Robby gazed down at the young man, watching as Dennis peered back at him, hiding behind the safety of his pretty lashes. “You work very hard, Dennis.” he hummed, voice low and soothing.
“Oh…” Dennis swallowed slowly, setting his paper cup back down. “Thank you, Professor Robinavitch,”
“Robby.”
“Sorry, Robby.” He chuckles, cheeks colouring a pretty pink. It’s a bad habit that won’t seem to die, no matter how much the older man insists that it’s okay, Dennis can’t help but feel rude when he uses informal names. He also won’t deny that he finds it oddly, arousing. He won’t deny that the name often tumbles from his lips when he’s in bed. Lonely nights are always warmed and filled with the mental image of his boss and the taste of his name on his tongue.
The older man nodded, cup placed down next to Dennis’s now. He crossed his arms over his chest, eyes still downcast. “It’s alright, Kid.” He reassured, sighing. “You work very hard…you ever make time to relax, hm?”
Dennis laughed softly, shaking his head a little bit at the question. He takes another sip from his tea, letting the hot liquid run down his throat soothingly. It grounds him. Being alone with Robby always had his heart pounding. “I try…but I’m pretty busy, you know?” He shrugged. “It’s okay…one day I’ll have all the time in the world to relax.”
“Don’t get me started,” Robby chuckled, shaking his head a little. “What do you do to relax, Dennis?”
The question has Dennis flushing. “Read…watch movies,” he lies, feeling his cheeks heat. Well, it’s not a total lie, really. He does read books and he does watch movies, but that’s not his favourite way to relax. His favourite way to relax would be with his legs spread, toy fucking in and out of his needy hole until he was coming with a pathetic little moan. Sometimes he’d treat himself to a glass of wine beforehand, too. He couldn’t tell that to his boss, though.
The other man makes a noise, shifting slightly. One hand reaches out, two fingers hooking underneath his chin. “Are you being truthful, Dennis?” He asked, voice twice as…seductive as before. Rich and rumbling. “You are usually very honest with me…I can tell when you’re lying.”
Dennis swallowed thickly, head tilted to force their gaze, Robby’s fingers warm underneath his chin. His mouth fell open, trying desperately to search for words.
“Answer me,” Robby whispered, thumb dragging along the man’s bottom lip.
“N-No, there’s other things I do…” Dennis finally replies, his tongue feeling heavy, cheeks hot. Robby cocks his head in a way that Dennis knows means ‘continue’. “Sometimes I…I’ll have a glass of wine…and…Jesus, Robby…”
The man tuts softly, shaking his head. A wordless command. Continue.
Taking a steadying breath, Dennis continues. “I have a glass of wine…and t-touch myself.” The young man confessed with a soft whine. He isn’t particularly sure where this has come from. This whole time he had been convinced that he was inventing things, convincing himself that Robby wasn’t actually flirting with him. That it was all in his head. That the touches to his back and neck, all the late nights, all the lingering glances meant nothing.
God. Was he a fucking idiot?
Robby’s expression shifts to something pleased and satisfied, his fingers gently pulling Dennis’s mouth open just enough to push his thumb inside. He doesn’t let it touch Dennis’s tongue, tracing his teeth instead. Taking stock. “And when you’re doing that, Mister Whitaker, what is it that you think about?”
Somehow, the office felt smaller all of a sudden. The walls had closed in, and the door felt like it was miles away. Was this even real? Had Dennis fallen asleep and this was all a dream?
Dennis’s eyes shifted from Robby’s face for a moment, briefly tracing his body, getting caught on the sight of Robby’s half-hard bulge. Fuck. It was huge.
Above him, the older man chuckled, eyes creasing in the corners. “I suppose that look answers my question, doesn’t it?” Shyly, Dennis nods. “You’ve been so good for me this year, Whitaker… Why don’t I show you what you’ve been dreaming of, hm? As a reward.”
As pathetic as he feels, Dennis is nodding before the older man has even finished talking, curls bouncing. “Y-Yes, Professor Robby.” He replies before Robby has the chance to change his mind or rescind his offer.
This time, Robby doesn’t correct Dennis for using his formal title, unafraid to admit to himself that he liked the way it sounded on his tongue. With one last touch of Dennis’s bottom lip, Robby pulled his hands back, moving them towards his belt. Deft fingers worked to undo it, pulling at the button and zip on his pants. The pressure that had been building on his cock was lifted almost as soon as his pants were open, a small grunt escaping his lips. Keeping his eyes on his sweet assistant, Robby puled his hard cock free from his underwear.
“Oh…”
Dennis swallowed audibly at the sight before him, mouth hanging open slightly. Robby’s cock bobbed in his face, leaky and red at the tip. It was huge, at least nine inches and most definitely as thick as Dennis’s forearm. At the base was thick pubic hair, and at the tip…almost twinkling under the dim lamp light…was a piercing. Silver. The cherry on top of an already impressive, if not slightly imposing, cock.
“Ever seen one like this before, Kid?” Robby breaks the silence, voice gruff with arousal. His cock twitches, dripping.
“N-No,” Dennis replies quickly, eyes flitting between the man's face and his cock. His mind is racing with about a million indecent thoughts about the man before him. “Can… Can I put it in my mouth?” The question came hesitantly, full of bashful shyness that Robby was constantly enamoured by.
Much to his despair, Robby shook his head. “Not tonight, Dennis.” The man hardly used his first name, it felt like such a treat. So intimate. “Stand up and take your clothes off for me. Fold them, put them on the chair, and then sit on the desk. Ass to the edge.”
The younger man took a few moments to process the instructions before leaping into action. He stood quickly, toeing off his shoes as he undid his own soft slacks, pushing them down with his underwear. He folded both items of clothing, before swiftly moving onto his sweater and shirt, folding both and adding them to the pile. Blushing head to toe, Dennis stood naked before his boss. A man double his age. A man with double his power. A man that could ruin him if he so wished. Though, the power that Dennis had over the man was not lost, either. He panted softly, watching the way Robby’s eyes raked over his body, all the way down to his plush cunt, cock peeking through a mess of curls.
Dennis carefully moved the paper cups out of the way before jumping up to sit on the edge of the desk. He propped his socked feet on the edge, knees falling open to show himself off to the older man, already wet and hard. “Look at you,” Robby stood up properly, moving between Dennis’s legs. “Look at that little cock of yours… Begging to be sucked.” He teased, dropping down to one knee, face pressed right into the hot heat of his assistant's cunt.
Before he could even open his mouth to answer, Roby was wrapping his own lips around Dennis’s clit, sucking firmly. He moaned around the hard, little thing, eyes fluttering shut as he set an even and steady rhythm. His hands came to hold open those milky thighs he had been set on since the term began, tongue dragging from hole to tip in one firm motion. “Ohhhh~ fuck,” Dennis whined sweetly, ead falling back as hs fingers tangled in Robby’s hair. His beard felt fucking amazing against the sensitive skin of Dennis’s inner thighs.
“Not so loud,” Robby grumbled against the boy’s clit, huffing out a small laugh. “Door isn’t locked.”
That should’ve freaked Dennis out, but it didn’t. It only added to the steadily pooling pleasure in his stomach and the fuzziness filling his head. Robby’s warm, sinful mouth returned to his cunt, and Dennis gave into the pleasure. He rocked his hips hungrily, fucking his cock into the man’s mouth, gasping when Robby sucked over it harshly.
It felt so good. So much better than Dennis could’ve ever imagined. “Fuck,” He whined again, toes curling in his white socks, thighs trembling. “Mhn, I-I’ll come if you keep doing…doing that, Robby. Please~”
The older man simply moaned, burying his tongue deeper into Dennis’s slick cunt, before dragging it back to his clit. His tongue was swiftly replaced with two thick fingers, earning a pretty squeak from Dennis. “Go on,” he whispered, pulling his head back to watch the young man for a moment, missing the taste of his cunt almost immediately. “Come for me.”
Robby pumped two fingers in and out of Dennis’s cunt gladly, tongue flicking and dragging over the boy’s throbbing clit. He pressed his nose into the mess of pubic hair, taking a deep and greedy inhale. Better than he ever fucking imagined. He should feel ashamed of himself, but Robby had gotten over the guilt of his attraction pretty quickly. He knew that this would happen, one way or another. Coming to terms with that only made him more excited. He felt Dennis’s hot hole clench and spasm around his thick digits, practically begging for a third. Which he gladly provided.
“Ohholyfuckingshit~” Dennis breathed out with a high pitched noise, toes curling so hard that it hurt. “Ro-Robby…You might~ Ohhhh!” The younger man attempted to babble out a warning, unfortunately cut off by the incoming wave of his orgasm. He quickly clamped a hand over his mouth as he began squirting messily around Robby’s thick and unrelenting fingers, his eyes rolling back into his head when Robby curled said fingers inside him, rubbing at that special spot. The pair moaned in unison, Robby's tongue still moving, enthusiastically drinking the mess that painted his face and dripped down into his beard.
Not wanting to overstimulate the poor thing, yet, Robby slowly pulled his fingers free and got to his feet. His fingers traced the bottom of Dennis’s lips, “Open…That’s it. Taste yourself.” he whispered, looking down his nose as he pushed his fingers into that open, wanting mouth. Dennis closed his lips around them and sucked softly, swirling his tongue around in attempts to get every morsel of himself from Robby’s fingers. They tasted so good together, it made Dennis feel buzzy.
A little whimper slipped from the younger’s lips when his mouth was emptied, the hand tangling in his curls instead. Robby stepped as close as he could get, exposed cock dragging over Dennis’s slick cunt, resting against him. “Oh…Wow,” Dennis whispered as he peered down, swallowing. Robby’s cock was pressed against the plush flesh of his stomach, leaky tip pressed against his bellybutton, piercing demanding all of Dennis’s attention. “What does that…What does it feel like?” he asked curiously, eyes slowly drifting back up to Robby’s dark set.
“This?” Robby asked, rubbing his pierced cockhead over the younger man’s clit as if to make a point. “Feels good…adds extra stimulation for you. For me, it’s a gentle tug with each thrust…makes my cock more sensitive. Same as these,” He takes Dennis’s smaller hand, guiding it to one of his nipples.
“You…” Dennis blinked, thumb brushing over the pierced nipple slowly, cheeks lighting up.
The older man chuckled, endlessly enamoured by the wondrous look on Dennis’s flushed face. He nodded, letting Dennis drop his hand once more, “Did you imagine that when you thought about me in your bed?” he whispered as he dipped his head, kissing along the pale expanse of Dennis’s neck. “About what piercings…tattoos I might have? Making up your own stories for the parts of my body you don’t see?”
Dennis whined softly, tilting his head further in submission, allowing the other man's teeth to drag along his skin. “Robby,” he whispered, back arching slightly as Robby’s hand ghosted his body. “I need you…”
Their lips clashed together once again, and Dennis moaned prettily into his mouth, their glasses clinking together occasionally. Robby continued to tease the other man’s cunt with the tip of his cock, spreading his precome around messily, rubbing their cockheads together. He didn’t want to hurt Dennis, not like this, but he wasn’t particularly sure that he could wait much longer. Self restraint wasn’t exactly something he prided himself on anyway. “If it’s too much, let me know,” he whispered between kisses as he slowly began pushing inside, groaning softly as Dennis’s hole engulfed his cockhead, swallowing him in. “Fuck, kid, tight little cunt you’ve got, huh?”
“Hngh!” Dennis made a wounded noise, hands gripping at the older man’s shoulders almost painfully tight. The feeling was dizzying. He had never had anything quite so big inside him before, and Dennis felt like he was being split in two in the best way possible. It hurt a little, and Dennis was sure that this would be something he would feel for days to come, but that only filled him with more excitement. His eyes rolled back as Robby slowly pushed more and more inside, stopping when he was about four inches deep, both of them panting hotly into one another's mouths. “You’re so…fuck…”
“I know,” Robby cooed gently, large hand coming to cup his assistant's face, tracing his warm cheek. Groaning, he pulled out to the tip and then pushed back inside, fucking the first half of his cock in and out slowly. The gentle tug alongside the wet heat of Dennis’s cunt felt so good, Robby couldn’t help but indulge. He peered down at where they met, watching as the younger man’s cunt began to cream messily, little cock pulsing when Robby pushed in a little deeper. “Need more, sweetheart?”
He nodded, peering at Robby over the rim of his glasses, eyes teary and pupils blown. Dennis moaned lewdly as the older man pushed in deeper, fighting any resistance until he was buried balls deep in the younger man’s cunt, bodies pressed together tightly. It was most definitely a tight squeeze, pain lingering for a moment before it slowly melted into pleasure. Dennis honestly couldn’t believe it. Couldn’t believe that something so big and thick had bullied its way inside of him. His hand shifted to his stomach and…
Oh, God.
“You’re… You’re in my fucking stomach~!” Dennis moaned out, his cunt spasming excitedly. His expression is one that Robby makes an effort to commit to memory, slowly pulling his hips back, watching the bulge in Dennis’s stomach move.
Fuck.
“That’s right,” Robby chuckled softly, fucking back into Dennis’s cunt with an obscene squelching noise. “All the way in your tummy, aren’t I? Does that feel good?” he whispered, his lips once again finding their way to the younger man’s neck, kissing and nipping gently. He was more than happy to take things slowly, to let Dennis adjust to his mildly intimidating size.
The younger man nodded, hiccuping on a moan. “I can’t believe I’m doing this… having sex with my boss… you’re old enough to be my Dad, holy~”
You’re old enough to be my dad.
Those words have Robby inhaling sharply, hands flying to grab at Dennis’s hips. Fuck being slow. With a low grunt, Robby began fucking into Dennis like his life depended on it. His balls smacked softly against the other’s hole, cream gathering and dripping down them messily. The rub and tug of his piercing only added to their joint pleasure, moans and grunts steadily filling the office. Fuck being quiet. Fuck anyone else that heard them. If they got caught, Robby would more than happily quit instantly if it meant he got to keep seeing Dennis and got to keep playing in his hot, filthy cunt.
Robby grunted as he snatched off his own glasses, tossing them onto the table. He tangled one hand in Dennis’s curls, yanking his forward, making him watch as Robby pounded him roughly. “Not stopping you…from fucking me, is it?” he ground out, struggling with the words now that he was entirely drunk on Dennis’s hot cunt. Dennis shook his head, eyes watering. “I’ve always known you were a little pervert, Mister Whitaker. Think I can’t see the way you look at me? In class…around our students. You’re a little slut.” He punctuated his words with an extra firm thrust, moaning loudly by Dennis’s ear.
The younger man whined loudly, little sobs falling from his mouth as Robby fucked him so hard that he was seeing stars. “I-I’m not a slut~” Dennis insisted, shaking his head.
“No?” Robby crooned teasingly, rolling his hips nice and slow, watching as the young man’s eyes rolled right into the back of his head. “You aren’t creaming on your boss's dick? Aren’t fucking someone old enough to be your dad? Where could anyone catch you?” His words are teasing and a little mean, but he can tell that it’s only doing good things for Dennis. He returns back to his punishing pace, thrusting roughly in and out of the boy’s cunt, addicted to watching his tummy bulge with each thrust. He shook his head a little, his own eyes fluttering back into his head a little as his hand moved to the boy’s cunt, rubbing at his clit.
Dennis clenched and whined, toes curling tightly. He felt so good. So, so full. Full to the goddamn brim and overflowing. He could feel Robby carving a place out for himself inside of Dennis, and he knew that no cock would ever compare to the one splitting him open. He had been entirely ruined for anyone else, all thanks to his boss.
“C’mon, let me hear you say it.” Robby whispered, not trusting his voice to go any louder. “Tell me how much of a slut you are…unless you want me to stop?”
Of course it was just a tease. Robby wouldn’t stop even if the Dean walked through his office door then and there. He simply enjoyed watching Dennis squirm and whine, trying desperately to pull coherent words from the mush that was his brain. He’d never had sex that made him feel this way before, like he was in an entirely different headspace all together. Like nothing existed outside of him and Robby. Fuck. The man had asked him something. Swallowing thickly, Dennis finally replied, “N-No, don’t stop! Please, don’t stop…I’m a slut…I’m a slut! I love your cock, please. Please, don’t stop, Pr-Proffessor.” he babbled desperately, trembling hands gripping at the older man’s sweater. Robby was still entirely dressed, cock peeking out. Fuck. Dennis trembled, sweat beading down his forehead.
The older man grinned, rewarding Dennis and his pretty words with a firmer swipe of his thumb. “That’s fuckin’ right.” He nods, rubbing firmly and consistently at Dennis’s throbbing little cock as he pounds him so rough and firm that a book tumbles and crashes onto the floor. “That’s fuckin’ right, Kiddo. G’nna come on Daddy’s cock? G’nna make a mess all over my cock?”
Truly fucked brainless, Dennis could only nod. Yes. Yes, he was going to fucking come all over the older man’s cock. He was going to make a complete mess out of himself and Robby. His mouth fell open as the start of a scream began to pour from his mouth, only to have Robby’s palm clasp firmly over his mouth. Intense shudders rocked through Dennis as Robby continued to fuck him. It was all too much. Too good. One of his feet left the desk, pressing into Robby’s side as he finally tipped over the edge he had been teetering on for minutes. The hand on his face held him firm as gush after gush of arousal began to soak Robby’s dark trousers, wetting both of them wonderfully. Dennis had never squirted so much, the stream seemingly endless, each thrust only triggering another wave of mess. He should be embarrassed and ashamed. It was gross. He was gross. No, nothing that felt this fucking good could ever be gross. His head fell forward, glasses slipping right from his sweaty nose.
Hitting the floor.
Dennis didn’t have it in him to wonder if they had broken or not. He would deal with that later.
“Holy shit,” Robby laughed raggedly, both of his hands now returning back to their rightful place on Dennis’s hips, almost moving the boy up and down on his cock like a fleshlight. The feeling of Dennis clenching and spasming around him would’ve been enough to finish him off happily. But the added sensation of being soaked and the breathtaking view of Dennis falling apart on his cock made the experience almost otherworldly. A small part of him thought to warn Dennis about his own impending mess, but the other, more desperate part of Robby decided against it. He pressed his face into the young man's neck to muffle his own noises, grunting and groaning against sweaty flesh as his balls drew up and his cok throbbed intensely. His teeth sunk into pale skin as his own orgasm washed over him so intensely that he would’ve tumbled forward had the desk not been there to stop him.
It was Dennis’s turn to whisper out a shaky, “Holy shit!” Rope after rope of thick, hot come began to flood his used hole, filling him up so much that Dennis swore his belly bulged even more. The older man pulled out after a moment, much to Dennis’s distress, wrapping a hand around his sticky cock. He stroked himself roughly, panting heavily as he continued to paint the younger man’s pubic hair and plush stomach with his mess. It was fucking endless and pornographic. Actually, it was more pornographic than any online video or DVD Dennis had ever watched. It was almost a minute before Robby stopped, pushing his oversensitive cock back inside.
“Mhm, fuck…” he whispered, pressing their lips back together. His tongue slowly explored the younger man’s mouth, hips rocking slightly to milk them both of anything else they might have left. Dennis brought his hands up to cup Robby’s face finally, one hand tangling in his hair. It was slower, more intimate, but no less desperate. “Did such a good job,” Robby spoke again, pressing kisses to the younger man’s flushed face. “Took my load so well, sweetheart. Such a talented boy.”
The praise went right to the young man’s head, and if he had any energy left, it would’ve gone right to his spent little cock, too. He smiled weakly, making a soft little hum of acknowledgement.
Robby only smiled again, brushing the damp curls from Whitaker’s face. With a small grunt, he wrapped the boy’s legs around his waist and picked him up, only to move and sit in his chair, keeping Dennis on his lap. He ran a hand up and down his back slowly as Dennis returned to himself, reaching for his cup of cool coffee.
The smell of cigarette smoke curled in the air a few minutes later, the hand that was not stroking down Dennis’s back busy holding a cigarette. Robby took a slow drag, angling his head away from the younger man as he blew out the smoke. It was late, and they should both be at their respective homes, but Robby found himself in no rush to get up and leave.
Especially when he heard the soft snores coming from his wonderful little assistant.
–
Come Monday morning, it was time for them to see one another again.
Robby had taken up residency in one of the seats on the front row, smiling slightly to himself as he watched Dennis set up. It was the younger man’s turn to teach the first half of the lesson, something that Dennis was always both eager and nervous about. Especially now, feeling Robby’s eyes on him after everything that had happened a few days before.
Subconsciously, Dennis reached up and rubbed his neck, hand brushing over the ever present hickies on his pale skin.
The older man smiled to himself.
He was going to fuck that boy against the whiteboard after class, ethics and rules be damned.