How I Learned to Stay Positive in High School

[spermedhole]

Caleb lifted his gaze and looked directly into Mr. Sanchez's eyes. 

"Yes, it is big."

Mr. Sanchez paused as he held Caleb's gaze. "When it gets big like this, Caleb, it hurts. You don't want me in pain, do you?"

Caleb paused and glanced back down again, partly out of nervousness but also out of curiosity. "No, sir."

"Feel how hard it is. Go on."

Caleb extended his hand tentatively, hoping he hadn't misunderstood what his teacher was asking of him.

"Feel how hard it is," Mr. Sanchez repeated.

Caleb let his fingers come into contact with Mr. Sanchez's stiff cock shaft. To Caleb's surprise, Mr. Sanchez's shaft felt even harder than it looked.

"Unless you can help me fix this, Caleb, I'm going to have to let Principal Lenox know about what I saw you doing in the bathroom stall."

Caleb's stomach vaulted into his throat. How he wished he had never installed those damn apps. He had been so excited to download them now that he was finally eighteen. How he had counted the months in anticipation. How could he have forgotten to put his phone on silent before getting to class this morning?

"I'll tell you what. If you help me get rid of this pain you've caused, I'll let you off with a warning. I'd really hate to see you not graduate on time after all the hard work you've done. But you're going to have to work even harder right now to show me you're serious about making up for what you've done."

Leaving his fingers on Mr. Sanchez's engorged member, Caleb looked back up. "I really didn't mean to hurt you, sir."

"Alright, Caleb." With that, Mr. Sanchez wrapped one hand around Caleb's and made Caleb fully grip the teacher's cock firmly. Guiding the teen's hand up and down at the base of his cockhead, Mr. Sanchez focused on how the teen's grip gently tugged and rolled his foreskin over the tip of his large mushroom head.

"So, Caleb, if you're going to help me while we're doing this, I'm going to need you to tell me the truth about a few things." 

"Yes, sir," Caleb replied as he continued stroking Mr. Sanchez.

"What were you doing on that app in the boy's bathroom?"

"Answering messages," Caleb answered without taking his eyes off his teacher's cock.

"Messages from whom?"

"Some guys."

"Oh, some guys, huh? And what were these guys saying to you?" A drop of precum emerged from Mr. Sanchez's cockslit as he continued guiding his student's hand up and down his dick.

"Mostly how they wanted to meet up."

"Meet up for what? To do what? Be specific, Caleb." Mr. Sanchez enclosed his hand more tightly around Caleb's, increasing the pressure from the teen's grip around the teacher's precum-leaking dick.

Caleb paused before replying, "For sex."

Mr. Sanchez confirmed his understanding with an "mhmm." A big drop of precum dripped from the teacher's cock onto Caleb's forearm. "Remind me how old you are, Caleb."

"I just turned eighteen."

"I'm going to need to unlock your phone, Caleb."

"I don't know if that's a good idea, sir."

"Is that so? Well, it's not a request. Would you rather I call the Principal in here so you can show him whatever it is you don't want to show me?" Caleb wondered for a moment how Principal Lenox would react to seeing Mr. Sanchez's hard cock being stroked by a student. 

"No, sir."

"I didn't think so." With his one free hand, Mr. Sanchez reached behind himself, grabbed Caleb's phone from the top of a filing cabinet, and held the screen in front of Caleb's face to unlock it. Caleb's teacher fiddled with the phone for a few minutes while never even so much as slowing the forced handjob. Caleb's heart raced inside his chest.

A much thicker glob of precum leaked from Mr. Sanchez's manhood onto Caleb's forearm as Mr. Sanchez continued scrolling and swiping.

"Keep stroking me," Mr. Sanchez stated without looking up. Caleb felt his teacher's hand release Caleb's as Caleb took over stroking his teacher. Mr. Sanchez began manipulating the phone with both hands. 

After several screenshot sounds and then a bunch of typing, Caleb listened to his teacher sending off several messages, some clearly inside the hookup apps. Others sounded like text messages. Caleb trembled as he wondered what was going on but didn't dare ask. He gripped his teacher's cock with more vigor than before in an effort to appease Mr. Sanchez, or at the very least to distract him.

Another glop of precum escaped Mr. Sanchez's foreskin and oozed onto Caleb's hand. Caleb couldn't help but admire how productive Mr. Sanchez's balls had been during this disciplinary encounter. The smell of his teacher's precum roused Caleb's cock from the grip of nervousness. The teen's dick awakened to the seductive odor of this older man's pre-ejaculate.

Mr. Sanchez returned the phone to its former position atop the filing cabinet. The teacher swatted his student's hand away from its manual seduction and without a word spun Caleb around to face the opposite wall. Caleb felt Mr. Sanchez's hands confidently yank the teen's pants to the floor, exposing his naked lower half.

"Not even underwear, Caleb?", Mr. Sanchez asked without surprise as he swirled one finger in the overflowing precum dripping from his foreskin. "Don't know how I missed that detail in the bathroom." Caleb felt the wetness of his teacher's finger massaging the outside of the teen's warm, tight hole.

"Caleb, I have to say, you're even nastier than I first thought when I saw that party listing of yours before school this morning." 

Caleb stayed quiet while Mr. Sanchez fingered precum into his student's compliant hole. "Bend over and spread your cheeks." Caleb obliged.

"There are some really disgusting men you're talking to on those apps. Do you know that?"

"Disgusting, Mr. Sanchez?" Caleb felt the wet tip of Mr. Sanchez's uncut cock pressing at the entrance to the teen's hole.

"Of course you wouldn't know. How could you when you haven't even asked any of them a single question?" 

"No, sir." Mr. Sanchez slowly pressed the tip of his cock just inside the opening to Caleb's rectum. Caleb winced.

"I see you haven't even bothered to ask even one of them to show you their face, have you?"

Again, Caleb was silent, hoping the question was rhetorical.

Mr. Sanchez spat on his cock and pressed further into his student's velvety insides. Caleb moaned.

"Too bad you put me in this position, Caleb."

"I'm sorry, Mr. Sanchez," Caleb replied as his teacher slowly pressed his engorged cock deeper into his student.

"You're mistaken if you think those men you've been chatting with were going to rubber up, you little slut. Besides, I thought you said you wanted to help me get rid of the pain you caused my dick."

"Yes, sir. Sorry, sir." 

"I'd rather your insides do the apologizing, boy." Caleb felt Mr. Sanchez press his meaty raw cock further into the teen's warm rectum. "In any case, you're going to need lots of help opening this tight hole of yours up if you want to be servicing all these [banned word] you've been talking to online."

Caleb gasped in pain as Mr. Sanchez pressed his raw cock fully into his student.

"If I catch you jacking off in the school bathroom again with those apps popping off like that for everyone to hear, I don't think I'm even going to bother bringing you here into the privacy of my office. You understand me, boy?" Mr. Sanchez began easing his spit-lubed raw dick back and forth inside Caleb.

"Yes, sir." Caleb started imagining what Mr. Sanchez would make him do in the boy's bathroom but his focus was soon stolen by the intense pressure of Mr. Sanchez's surging meat pressing painfully into the walls of his tight hole.

"If you're not careful, Caleb, everyone at St. Denis High is going to end up knowing what a nasty little slut you are. Is that what you want?" Mr. Sanchez continued grinding his meat into his student, picking up pace.

Something in Caleb stirred, and it wasn't just from the raw dick assaulting his insides: it was the thought of everyone knowing what he really desired, his secret lust for every human adult walking around with a cock between their legs. Caleb's teen dick swelled as his teacher started pounding harder.

Just then Caleb heard Mr. Sanchez snapping a pic behind him and then the sound of a message being sent.

"You know, Caleb, many of us here at St. Denis already know what you've been up to online. Mr. Martin for one has been talking about the pictures you've been sending him for weeks."

Mr. Martin, the janitor?, Caleb wondered. There was no way to be sure who all the men he had been messaging were since Caleb didn't ever ask to see their faces.

Mr. Sanchez could feel the orgasm that was swiftly approaching. "You ready to take my load, slut?"

"Yes, sir!" Caleb's hard-on had lent him a new-found enthusiasm as he finally began to appreciate the favor Mr. Sanchez was doing for him. Mr. Sanchez began dick-slamming the teen's hole with such force that surely the sound of the ass pounding could be heard in the hallway outside. 

Just then Caleb felt Mr. Sanchez shudder powerfully as he groaned, releasing the full force of his semen into Caleb's soft insides. Caleb had never felt a raw dick cumming so forcefully before. The pressure of the cum squirting deep into his guts made him yearn for more.

The pounding having stopped but with Mr. Sanchez's softening manhood still lodged inside Caleb, the teacher spoke, "You're keeping my load inside you all day, you understand? At lunch time, I want you back in here in my office. I'm going to check to make sure you've done exactly as you're told. Don't think your punishment is over. You've still got a lot of making up to do."

"Yes, Mr. Sanchez." Mr. Sanchez let his softening dick slowly deflate inside his student.

* * *

[austin_submale]

Nice!  Hope to read more.

[Mysteryman10]

Hot! Caleb is going to get lots of attention-can't wait for the next chapter

[laguyinhou]

Fuck yeah 

[pupslut]

Fucking hot, wish this could have been a school I went too! haha 😈

[PozTalkAuthor]

Longing to read how it goes on! 

[tepegodf]

Very HOT story.  Please continue!

[shinelover]

This is off to a great start! 

[kingbob228]

Very nice man !

[KinkyTallBottom]

Wonderful beginning, I can’t wait to read more about Caleb’s adventures!

[jankoslave]

really hot - can't wait for the next session

[Tractor0773]

Awesome story, can’t wait for the next part! 

[subalex]

Such a hot framework and setup. Well written. Looking forward to how you develop this.

[viking8x6]

Hot writing. Though Mr. Sanchez seems to have no morals whatsoever. Hmmm... that gives me an idea for a story of my own 😈

[spermedhole]

Chapter 2

Who's Who:
- Caleb: main character, 18 y/o senior at St. Denis High School with a strong interest in messaging strangers on sex apps.
- Mr. Sanchez: teacher who caught Caleb jacking off in the school bathroom during class while cruising sex apps; threatened to turn Caleb in to the principal if Caleb didn't satisfy Mr. Sanchez's big dick.

*    *    *

As Mr. Sanchez's office door closed behind him, Caleb's thoughts ricocheted about. He wondered nervously whether he had done enough to keep Mr. Sanchez from making a report to Principal Lenox. With a curious mix of excitement and anxiousness, he wondered what Mr. Sanchez planned to do later at their lunch-time meeting. Moreover, what is it that Mr. Sanchez had been sending and to whom on Caleb's cell?

Snatching his focus from these thoughts, however, was the slickness of the cum lubing Caleb's ass cheeks as he walked down the hallway. Caleb's cock swelled inside his pants as he dwelled on this feeling, which was wholly new and entirely pleasant to him.

Caleb walked himself back to first-period calculus — the same class he had left earlier to go masturbate in the boy's bathroom. Was it still first period, though? Without his phone he couldn't check the time, and for the life of him, he couldn't remember if he had heard the bell or not while Mr. Sanchez had been pounding that big, raw dick into his teen butthole. Whatever the case, Caleb needed to retrieve his backpack.

He swallowed his nerves as he pulled open the door to Mr. Jacobs' room. The familiar eyes of his fellow classmates were on Caleb as he walked into the silent room. It was, indeed, still first period. The books and papers on everyone's desk indicated quiet time for assignment work. In a hushed tone, Mr. Jacobs gently called Caleb over.

"Everything okay, Caleb?"

"Yes, Mr. Jacobs." 

"You were gone for quite a while. I was just about to send someone to check on you."

"I'm fine." Caleb declined to preempt Mr. Jacobs' curiosity as he hurriedly considered the implications of various explanations. By not giving Caleb an excuse note, Mr. Sanchez had put Caleb in an awkward position. How was he to justify the mid-class detour to let Mr. Sanchez please himself inside Caleb's lower intestines?

Brow furrowed, Mr. Jacobs searched Caleb's face for information that words had not furnished. "Is there a reason you were gone for most of class, then?"

"Mr. Sanchez asked me to his office."

"He gave you a pass, yes?"

Caleb fidgeted in the face of Mr. Jacobs' insistence. "No, I think he forgot."

Eyebrow raised, Mr. Jacobs replied, "Mr. Sanchez is not one to forget. If he let you back without a pass, that tends to be for one reason only." Caleb, unaccustomed to having to justify his actions, felt butterflies in his stomach -- a strangely complimentary accompaniment to the soreness in his rear.

Mr. Jacobs opened his desk drawer and pulled out his cell. After a few taps and swipes, he set his cell on the desk, screen down, and looked back up at his nervous student.

"I'm going to need you to stay after class, Caleb. Head back to your seat."

Caleb made his way to the back of the class, moving through the curious glares of his classmates. He surmised their silent efforts to reconcile his behavior that morning with his always-follows-the-rules reputation. 

Mr. Jacobs' statement about the reason for the missing pass bounced around inside Caleb's skull, but he could not bring himself to believe that Mr. Jacobs could possibly know what precisely had transpired in Mr. Sanchez's office. Could such extraordinary events be guessed with so little context? The most forceful doubt that kept the thought turning in Caleb's mind was the fact that Mr. Jacobs had conferred with his cell phone. Why would he want to check his personal device instead of any of the official communication channels internal to their school intranet? 

As Caleb took his seat, the pressure of the chair against his ass made for a fresh reminder of how his hole had been made to satisfy Mr. Sanchez's substantial manhood. Caleb found the feeling both discomforting and satisfying. He wondered how Mr. Sanchez's DNA was fairing inside his freshly fucked rectum. Caleb's hardening cock began to push his pants upward into the underside of his desk.

The rustle of his classmates' belongings signaled the impending bell tone, which followed on cue. The class emptied of all but Caleb and Mr. Jacobs. Unable to hide his erection, Caleb remained at his seat, hoping his post-class conversation with Mr. Jacobs would not force his erection into view.

"Caleb, you can come on up here, please."

Caleb stood up and moved to the front of the room. Mr. Jacobs walked over to the classroom door, and as he was locking it, with his back still to Caleb, said dryly, "Nice erection."

Caleb's eyes widened in embarrassment.

Mr. Jacobs turned to face his silent student. "You know you should be more careful letting a grown man like Mr. Sanchez inseminate you without protection, my dear boy. You're just asking for HIV."

Caleb's stomach flipped. Any doubt that he had about what Mr. Jacobs knew evaporated. The mention of HIV added a more ominous dimension to the trouble that Caleb already knew himself to be in. What else did his math teacher possibly know?

"Take your clothes off, and get up on my desk. Lie on your back and hold your legs all the way back for me. I have to make this quick." 

Caleb's heart felt as though it wanted to leap out of his rib cage. He complied with the old man's instructions, adjusting to the coldness of the desk against his naked back.

"Mr. Sanchez load you up good?"

The crude directness was surprising coming from the mouth of the otherwise straight-laced Mr. Jacobs. Of course, neither would Caleb have imagined presenting his freshly bred hole to a gray-haired, balding, gaunt old man like Mr. Jacobs either. Caleb watched between his lifted legs as his calculus teacher fumbled his thin, long cock out of his unzipped fly.

"You going to answer my question, slut, or are you looking to fail this quiz?"

Without waiting for a response, Mr. Jacobs plunged his index finger deep into Caleb's hole, stirring the fresh cum inside, then pulled it out, and promptly shoved it right into Caleb's mouth.

"Go ahead and suck Mr. Sanchez's baby batter off my finger, slut." Caleb sucked on his calculus teacher's cum-drenched digit eagerly, savoring the unique saltiness of Mr. Sanchez's load. 

Mr. Jacobs withdrew his finger from Caleb's mouth and quickly gripped his surprisingly bright-pink dick, plunging it right into Caleb's cum-lubed hole without warning.

Caleb let out a surprised, "Unh!", as Mr. Jacobs muttered, "Oh fuck!"

Mr. Jacobs' abrupt bottoming out inside the teen's anal cavity left a pained look on Caleb's face.

"Grip my cock as tightly as you can with your ass muscles, Caleb. Mr. Sanchez will absolutely destroy you if you let his load leak out before lunch."

Caleb squeezed his ass muscles tightly around his math teacher's long, bare dick as it continued to press painfully against Caleb's second hole. Mr. Jacobs looked fixated at the place where the base of his cock came into contact with the teen's fuckhole.

"You ever take grandpa cock bare before, Caleb?" Mr. Jacobs slowly started moving his dick back and forth inside Caleb's cum-filled ass.

"No, Mr. Jacobs." Caleb savored the feeling of having a second raw cock forcing its way into his already used fuckchute.

"Well, maybe I should change your homework assignment and have you bring a bottle of dick pills to the assisted living facilities around here to do some community servicing. It would look great on your college applications, for one thing. And I bet you could easily get a dozen loads in your juicy ass before school if you started early enough."

Caleb moaned and then replied, "Yes, Mr. Jacobs." He felt the old man's cockhead poking painfully at his second hole.

"You are every bit the nasty slut Mr. Sanchez said you were." Mr. Jacobs picked up the pace of his fucking. 

"Ow, ow!" Caleb exclaimed softly, trying not to offend Mr. Jacobs but unable to ignore the pain he was feeling.

"You want me to slow down, Caleb?"

Caleb nodded, wincing. Mr. Jacobs looked directly into Caleb's pained eyes and began slamming his cock harder and harder into the boy's hole, pummeling the teen's tightly closed second hole over and over with his snake-like dick.

"Ah, fuck!" Caleb inhaled sharply, still not realizing that his effort to grip Mr. Jacob's cock tightly with his anal opening was also keeping his second hole from relaxing against the assault it was enduring.

"I'm going to make you into my little first period pussyboy, Caleb. Would you like that, slut? You want to be your teacher's little pussyboy?" Mr. Jacobs pounded the teen's fuckchute even faster.

With a pained voice, Caleb managed to say, "Yes,... sir… aah…."

"You come into my classroom smelling freshly fucked and full of cum again, and you can expect exactly the same treatment, you understand, slut?"

"Unh! Yes, sir…." In spite of his efforts, some cum managed to leak from Caleb's hole down his ass crack and pooled on Mr. Jacobs desk.

Mr. Jacobs' thrusts reached their peak as he continued slamming Mr. Sanchez's load deeper into Caleb's guts.

"Here comes my load, pussyboy!" Mr. Jacobs grunted loudly as he began coating the teen's insides with his thick grandpa load, adding to Mr. Sanchez's frothed up cum. Caleb did his best to keep gripping Mr. Jacob's spindly, raw cock as tightly as he could.

"Keep gripping my dick like that, Caleb. I want you to milk every last drop of cum into your pussy."

"Yes, Mr. Jacobs." Caleb watched through his legs as the old man's thrusting slowed and came to a rest. Caleb continued gripping his ass muscles as Mr. Jacobs began his slow, methodical withdraw. 

"Careful not to spill, boy. You gotta keep all that cum in you through lunch, remember."

"Yes, sir," Caleb replied dutifully, the pain in his voice having been replaced by relief.

"Good boy. Now show me your hole." Caleb tilted his pelvis upward and pulled back on his spread legs even more. Mr. Jacobs picked up his cell and snapped some closeups of Caleb's pink, cum-glistening hole. The gray-haired calculus teacher then took a few steps back, pressed something on the screen, and staring into his phone, asked Caleb, "How many loads you got in you, boy?"

"Two, sir."

"Good boy. You going to be my personal pussyboy from now on?"

"Yes, sir."

"Now tell all the horny old men watching this that you love raw senior citizen cock."

Caleb hesitated.

"Say, 'I love raw grandpa cock in my teen pussy.'"

"I love raw grandpa cock in my teen pussy."

"Now get your creamy boypussy to class, slut. You're going to be late." 

*    *    *

Edited August 15, 2023 by spermedhole
Clarity