Mr Brent's longest Day

by DevilBrew69

2 Jul 2019 1708 readers Score 8.4 (23 votes) PDF Mobi ePub Txt


“The outlook for you, Mr. Laurent, is rather bleak. If I may speak frankly, this kind of bullshit might have worked for you in high school, but you’re in university now. In my class, no less.” Darren held up the sophomore’s essay on The Talented Mr. Ripley with a slit-eyed look of condemnation. “If you were foolish enough to base this piece on a movie adaptation, you’d have done much better to use the 1960 French film Plein Soleil.” He sighed as he threw the paper back down on his desk and fell back in his office chair. “I still would’ve have known, however. You can’t fool me, Mr. Laurent.” Darren paused a moment, to give his student an appraising look. “You need to maintain a C average, at least, to remain on the football team... correct?”

“Uh, yes, Professor.” Jack Laurent shifted his weight from foot to foot as he stood meekly before his English Literature professor, head bowed slightly. 

Darren couldn’t hold in the hearty laugh that had started to rise from his throat. He let it out with a twisted satisfaction and regarded his student with a cool, calculating grin. “Mr. Laurent- Jack- with the way you’ve been blowing off my class, I could easily ruin your sports career before it has a chance to really begin.”

Jack threw his head back and stared wide-eyed at the man seated in front of him. “Shit, Professor. Please! I’m just not into books. They’re… boring.”  He came forward and rested his hands on the desktop, leaning in towards the older man. “The team is my life though, I need to play.”

“Hmmm… you really are a bit of a neanderthal, aren’t you?” Darren suppressed a groan. “A bit like that coach of yours.” A thrill went through the professor’s body as he remembered just what had transpired between him and the unrefined, yet personable coach only a couple days before. 

“Well, Jack,” Darren got up from his chair and came around to stand alongside his student, offering a disarming smile. “I believe the two of us could come to an arrangement where everyone has a happy ending.”

Jack straightened up, his body relaxing as he faced his teacher with an air of gratefulness. “Really, Professor Thomas? That’d be so great!”

“Aren’t you a lucky one, Jack.” Darren slipped a hand into his side pocket as he used the other to toy with his tie. “I do happen to offer extra credit.”

“I don’t get it Professor.” The unsuspecting student shrugged his shoulders. “If my grade is that bad, how would extra credit help?”

“Oh my, you are quite simple, aren’t you, boy?” Darren gave the sophomore a careful once-over. “What have you heard about the extra credit work I offer?”

“Well, nothing.”

“Excellent.” Darren let his tie fall from his fingers and gave Jack a pat on the shoulder. “That means other lazy students such as yourself have been keeping their mouths shut, as they agreed to do.”

“Uh… Profes--” Jack looked down at his teacher’s hand, which inexplicably remained on his shoulder. 

“You may feel free to call me Darren… while you are alone here with me.” The educator purred as he dropped his hand down from the younger man’s shoulder and gripped him by the forearm instead. He led his student over to his chair. “You look tense, Jack. Here, have a seat. I insist.”

“Uh…. Darren.” Jack chuckled anxiously. “I’m not…”

“Not into guys?” “As if that matters right now. The team is your life, right,” Darren countered easily. “You need to play. Wouldn’t anything be agreeable, if your life were on the line?”

“I- I just can’t suck another man’s dick.” Jack threw his arms up apologetically. “I’m sorry.”

A deep, throaty laugh rolled off Darren’s tongue as he gently pushed the nervous undergrad back into the office chair and then dropped to his knees. “Who said you’d be doing the sucking?” The cunning literature professor offered up a soft expression and continued in a soothing voice, even as he worked to effortlessly expose the treat he was after. “I assure you, Jack, having another man suck you off doesn’t make you gay… if that’s what you’re worried about.” Darren shifted his gaze down to the lap in front of him and sighed in happy surprise. “My my, aren’t you a naughty boy. Going commando. It’s almost as if you’re expecting a hungry mouth on this…” Darren paused to lick his lips as he admired his view a few moments before raising his eyes to his student’s flushed face. “This beautiful cock of yours.”

Jack looked down at his teacher with a confused mix of shock, embarrassment, and unwanted arousal. “Ummm… if I let you suck me off…”

“You won’t have any problems passing my class and staying on your precious team.” Darren sent up a ravenous smile as he slipped a hand up Jack’s clothed thigh and took a gentle hold of the man’s dick. “Just relax, Mr. Laurent. Let Professor take care of you. You can even close your eyes and imagine I’m one of those ditzy blondes on the cheerleading squad that I’m sure you jocks run trains on after a winning match.” 

“O-ok, Professor.” Giving in to the temptation of unconditional gratification, the lacklustre student closed his eyes and let his body relax down into the soft leather of his professor’s chair. 

“Smart man, Mr. Laurent,” Darren murmured against the flaccid dick in his hand. With not another word or a moment’s hesitation, the older man closed his eyes in anticipation and swallowed his student whole. He held himself still a moment, as he rode out a wave of pleasure. ‘I just love to feel a man growing inside my mouth,’ he thought as he at last began to move, teasing the soft muscle with his tongue and suckling until he had coaxed it into an erect state. 

Darren let go of his treat with an exaggerated ‘pop’ and looked up at the undergrad’s face as he caught his breath. The man’s eyes were lightly shut, his parted lips and relaxed jaw formed a soft oval of surprise and the soft blush on his cheeks served as a testament to the pleasure he felt, thanks to his ethically questionable literature professor. Satisfied, the educator in question came up a little higher on his knees and brought his mouth back down on his student’s wonderfully hard length. He slowly made his way down to the man’s base once more, and held himself still as he ran his tongue up and down the underside of Jack’s shaft for a few passes; making sure to tease the sensitive frenulum with the tip of his tongue.

“Oh fuck. What the fuck, Professor.” Jack groaned and fisted his hair in the older man’s hair. “You shouldn’t be this good. The fuck!” He opened his eyes and stared down at the top of the man’s head, shocked by how good a man could make him feel.

Darren laughed around the hard muscle in his mouth. ‘Of course I’m this good, you idiot,’ he thought as he brought his mouth back up, purposely moaning around Jack as he did so. He brought his hands up from their previous positions on the younger man’s thighs. He cupped Jack’s sac with one hand, while he wrapped the fingers of his other had firmly around the jock’s shaft. He began to bob his head in earnest then, following his mouth with his hand and gently massaging the student’s delicate sac. Darren greedily sucked and licked at the delicacy in his mouth, letting his heady moans escape freely, as he knew perfectly well the sound reverberated around Jack’s dick, acting like a vibrator. He hollowed his cheeks on his way down, and tightened the grip of his hand on Jack’s cock on his way down. It wasn’t long before the man was gripping Darren’s hair almost painfully tight and hissing a steady stream of obscenities.

* * *

Brent strode down the hall, head bobbing in time to the loud rap music playing on his phone. He was looking for his prized player, Jack, in hopes of doing some extra training to get the boy ready for their upcoming match. His younger players weren't exactly known for their brains, so he figured Jack was most likely being held up by one of his teachers. When he’d asked around and discovered that Darren was the one monopolising the boy’s time, a faint chill had ran down Brent’s spine. Truthfully, he’d been avoiding the man ever since their rooftop encounter a couple days prior. Brent had always thought of himself as Mr. Macho; one-hundred percent masculinity and testosterone. Not a single gay bone in his finely chiseled, muscular body. ‘Shit, I’ve got an entire list of one night stands to back that up,’ he reassured himself with a pensive frown.  Darren, however, made him question his self-perception- could he actually be bisexual? He did notice when a player had a pretty, plump ass, but that surely didn't mean anything. ‘I’m straight, not blind!’ Brent scratched his five o’ clock shadow in deep thought. ‘But what straight guy lets another man suck him off?’ He continued on to Darren’s office, relying entirely on muscle memory.

“Knock knock,” he said as he stopped in front of his colleague’s shuttered office and stopped the the playlist on his phone. He opened the door and saw Jack sitting where he’d fully expected Darren to be. Jack’s eyes popped in a clear panic at the sight of his coach, and a strange, strangled grunt burst from his throat. 

Darren had immediately stopped once he heard Brent’s husky voice out in the hall. ‘Shit! I always forget to lock that damn door. I can't let him see me like this!’ His mind exploded in chaos as he desperately tried to think of a way to avoid detection.

“O-oh hey coach! What're you doing here?” Jack forced Darren’s head all the way down on his dick, not knowing what else to do. The last thing he needed was for the opportunistic faculty member to make any suspect noises. 

The suspicious coach arched a brow at his player’s nervous behavior. “ I came to pick you up for practice because I heard that tight ass Darren was holding you up.” Brent scanned the room hopefully as a sick feeling of dread began seeping through his veins. “Where is he anyway?”

‘Oh screw you,’ Darren thought indignantly from his scandalous position under the desk. ‘I'm not not a tight ass. My hole is very well loose. Wait,’ he stopped to reconsider what his unwanted visitor had just said. ‘I don't think that's what he meant.’

Still holding his teacher’s head down out of sight, Jack blurted out the first lie that came to mind. “He said he had a really bad stomach cramp from too much chipotle and Starbucks, so he's gonna be in the bathroom for a while.” 

Brent let out a hearty laugh. “Ha! I swear, all these yuppie white liberals have the same taste in food. That's something he won't teach in his social justice class.” He continued laughing. Jack joined in, the movement of his body forcing his dick even further down Darren’s throat. 

‘What are you baboons laughing at,’ Darren thought even as hot tears streamed down from the corners of his eyes. ‘I have too refined a pallet to be satisfied gorging on Doritos and chugging Mountain Dew everyday.’ Jack’s glans rubbed against Darren’s uvula, making him tear up even more. ‘And if jack doesn't let me go soon, I'll lose my breakfast!’

"Well let's get outta here before that priss shows up,” Brent suggested with a bit more forced than he’d intended. “I need you around for practice."

"Right." Jack finally took his hand off Darren’s head and tried to get out of the seat without exposing himself, but that proved to be a futile endeavour.

‘Fuck, I guess there’s just no acceptable way out of this predicament,’ Darren realized at the same time. ‘Well, Mr. Laurent, it was nice while it lasted.’ He suddenly rounded his mouth and carefully pulled back, letting Jack’s dick slide out. He couldn’t help but smile appreciatively at the way the slick muscle bounced up against the jock’s abdomen. ‘Now then, what shall I do? Is it too naive to think I could just stay under here and avoid detection?’

An odd mix of dread and excitement had the hairs on the nape of Brent’s neck standing to attention. He cocked his head inquisitively and arched his brow yet again. “C’mon, Jack. What’s the hold up?”

“Uh… right. Gimme a second, Coach.” The trapped undergrad tried to offer a reassuring smile, but his lips instead contorted into a painful grimace and he chuckled nervously as he attempted to discreetly do up his jeans.

“Laurent. I know some people would call me a buffoon.” Brent paused to direct a pointed gaze down to the nameplate on the desktop that read ‘Prof. Thomas’. “But I’m not that stupid.” Even though he was filled with the urge to walk right back out the way he’d come and go wash his eyes with holy water, Brent found his feet dragging him forward. “Do I even want to know what you’re doing here?” The anxious football coach stopped just short of the desk, not really wanting to visually confirm his suspicions. “Do I want to know who’s hiding under Professor Priss’ desk?” The question had slipped out past his lips in a deeper, sultrier voice than he’d intended and his eyes widened in surprise at himself. 

Jack gawked up at his coach in utter mortification, finally managing to button up his jeans. He supported himself on the arm of the desk chair as he slowly stood. He wasn’t sure just how much of the weakness in his legs was from panic and how much was from having been so close to orgasm just moments before. “Uh- I was just. I mean.”

Sighing heavily, Darren crawled out from under his desk and stood, straightening out his tie and adjusting his clothes. He leaned forward, placing his hands on the desktop. It may not have been accurate to say it was the last thing he wanted, but he felt it wouldn’t be exactly prudent to stand straight and make his raging erection that much more noticeable. “Mr. Laurent here,” he began airly as he forced himself to meet Brent’s horrified gaze, “is in danger of failing my class and therefore losing his privilege to participate in your sports team.” Darren licked his lips as they began to curl in an unconscious smirk. “I was merely offering him some extra credit work to ensure that doesn’t happen.” Another sigh escaped his mouth as he turned his attention to the hot faced student still standing awkwardly beside his desk. “Mr. Laurent, you need not worry about your grade in my class. Now,” the brazen professor shifted his gaze between his two office guests, “I believe you two have somewhere to be, correct? I myself have a pressing matter that needs attention.” He said with a suggestive chuckle as he stared boldly straight into Brent’s eyes.  

At a complete loss, Brent found himself laughing in disbelief at the absurdity of the situation he’d just walked into. “Dude. Are you deadass right now,” he asked as he raked his fingers through his hair in agitation. “Ok. Right.” He jerked his head to the side, throwing his gaze to his player and inadvertently barking at the hapless undergrad. “Laurent, let’s go.”

Jack gave a sheepish nod and followed his coach out the door. 

Darren waited until both coach and star player had left before he straightened up. He strode over to the door and made sure to lock it. With an irritated huff, he crossed back over to his desk and fell back into his chair. He made quick work of undoing his slacks. Lifting his hips, he pushed both pants and boxers down just far enough to free his trapped erection. He relaxed back into the soft leather of his chair, picking up the bottom hem of his dress shirt and bringing it to his lips. He held the fabric between his teeth and reached down to grab himself roughly. ‘That damn buffoon, interrupting me. He could’ve at least waited until I’d had a good taste of that prized neanderthal of his.’ He closed his eyes as a shudder went through him at the memory of the utterly shocked, definitely disgusted, and slightly aroused look on his colleague's face. ‘Hmmmm, I wouldn’t have minded at all if he’d let me finish with Jack and then taken a turn himself.’ Darren indulged himself in that fantasy as he set himself an easy, languid pace. He had plenty of time before his next class; and he did enjoy a long, slow wank from time to time. Especially when he had such juicy material to jerk off to.     

* * *

Jack dragged himself along the seemingly endless corridor- hands shoved deep in jacket pockets, flushed face tilted downwards, and heart hammering in his chest from the overwhelming embarrassment. Brent walked alongside him, lost in thought. He’d never have pegged Darren as the type to take advantage of his students like that. It just didn’t fit with the Social Justice Warrior image he had built up in his mind. ‘Then again,’ Brent’s mind flashed back to his memory of the other day. He also never would’ve thought Professor Priss could say such lewd things, or be so shameless. Brent snuck a sidelong look down to his favourite player. It most certainly infuriated him to think the kid had been taken advantage of in such a despicable way, but a small part of Brent was even more upset that it hadn’t been him in that office chair instead- and that was terrifying.

“Jack,” Brent began softly, “did you know you were failing his class?”

“Uh… yeah, kinda.” The miserable sophomore turned his face away to the side as his face burned. “His class is boring.”

“Heh,” Brent could only agree. “Yeah, I bet. Why didn’t you tell me, though. You could’ve told me.”

Jack shrugged, feeling that the sentiment was too little, and much too late. 

“Next time, if he gives you any trouble, just come to me.”

“Coach,” Jack finally lifted his head, but still averted his gaze. “Do we really have to train right now? I kinda wanna just go home.”

The two of them came to a stop in front of Brent’s office. “Nah,” the concerned coach opened his door and ushered the boy inside. “We don’t have to. But we need to talk. Come in and have a seat.”

Once they had settled into their respective seats, Brent rested his hands on the desktop and leaned in towards his student, a genuine concern glinting in his eyes. “Jack, I need to know. Did he… force you?”

“No.” Jack timidly brought his face up to finally meet the older man’s gaze. “Not really, Coach. Uh, I thought he was going to make me suck him off, but he didn’t want to.” The boy’s face grew a remarkable shade of crimson. “He laughed at that, actually.”

“And you were…. okay… with letting him suck you?” Brent couldn’t stop from wincing. It pained him to have to ask such a question.

“Well, he told me it was okay because it didn’t make me gay or anything.”

‘He’s a clever fucker, isn’t he,’ Brent thought as he nodded encouragingly. ‘He was feeding you a line to get what he wanted, Laurent.’  

“He even told me to uh-” Jack’s eyes shifted nervously from side to side as he took a small pause. “He said to close my eyes and pretend he was one of the cheer squad bitches and the guys and I were running a train.”

Brent’s whole face lengthened with the rounding of his eyes and the dropping of his jaw. “That Priss… said that?!”

“Y-yes, Coach.”

“The fuck.” Brent cocked his head and blinked rapidly, trying to process what he had just heard. “Deadass?”

“Yessir.” Jack nodded meekly. 

“Now don’t get twisted, Jack. I’m not some perv.” Brent let out a heavy sigh and brought his hands up to massage his temples. He could feel a headache coming on. “I’m asking this because I’m trying to figure out what to do.”

“Y-yes, Coach?”

“D-did you enjoy it?” Brent squeezed his eyes shut and cringed. Jack was his favourite, almost like a son to him. He did not want to have to think of the boy in this context. 

“Ummmm….” Jack rubbed at his cheek anxiously before answering in a small voice. “Yes, Coach. I wish the girls I get with could suck dick like that.”

“So… do you want me to take it to administration, or?”

“No, Coach.” Jack nearly jumped out of his seat. “Please don’t. I’m just really embarrassed. And being caught by you, of all people. I’m just… kind of…”

“I don’t think differently about you, Jack,” Brent said in an even, confident tone. He offered his prazed player a comforting smile. 

Jack didn’t quite believe his ears. “You don’t?” He stood and looked to his coach in grateful shock.

“No,” Brent stood as well and came around his desk. “We’re straight. Everything’s Gucci.”

“For real?”

“Real talk,” Brent agreed as he came up alongside the sophomore and gave him a gentle clap on the shoulder. 

“O-ok.” Jack mirrored his coach’s gesture with a relieved chuckle. “Can we jsut pretend that never happened, then?”

“Of course, Jack.” Brent walked him to the door and held it open for the boy. “Go home. Jack off to some bitches. Forget about today.”

“T-thank you, Coach.” Jack offered up an gratified smile and left with not a single word more, nor a single glance back. 

Brent shut the door carefully, heaved a heavy sigh, and stalked back to his desk. He dropped himself back down into his chair with an irritated groan and stared blankly at the door his pet player had just walked out through. A deafening storm of bewilderment raged in his mind. “What’s with that priss,” he asked himself softly. It never would have occurred to him in all his life that Darren Thomas could say such things, let alone think them. Again, Brent’s mind wandered back to the rooftop. He recalled the bluntness of his colleague’s admission, and the borderline aggression of Darren’s come-on. “And didn’t he say something about glory holes,” the stunned gym teacher thought aloud. 

Then, there was what had just happened, of course. Darren had been so incredibly out of character, it made Brent’s world tilt on its axis. He wondered if maybe Mr. Social Justice had just been putting on a front all this time. “No,” he told himself, “that’s not it. You can’t fake that kind of passion.” Brent spent some time in contemplation before his brain started to form some connections. “No way,” he chuckled to himself as the realization hit-  there must be only one context in which his prissy colleague turned into this strange, unscrupulous beast. 

“What a little cockslut.” Brent said with a devilish grin. He allowed his mind to linger on that possibility a few moments more, until he felt himself beginning to stiffen. “Fuck, what am I thinking,” he growled at himself in confused anger.   


Author Note

This chapter was actually written by a friend of mine I met in an Amino app. I'll leave a link to their archive of our own page for you to see them . I really love their prose and how everything turned out. Darren was kept perfectly I character and is the slutty gentleman I love. If anyone wants to cowrite the next chapter, let me know.

by DevilBrew69

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