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How I Learned to Stay Positive in High School


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  • 2 weeks later...
  • 2 months later...

Funny and sexy at the sane time. I hope it continues. I'm eager to see how many loads Caleb can take before school lets out! PE coach? Principal? Fellow students? Those hook-up apps can lead one astray. How many of those loads he's taking are poz? Let's find out!

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  • 3 months later...

Chapter 3

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.

- Mr. Jacobs: the old math teacher who added his raw load to Caleb's hole between classes after finding out from Mr. Sanchez that Caleb is a little fuckslut.

* * *

Fourth period came and went. Caleb was feeling increasingly nervous — and a bit excited — with the swift approach of his lunchtime follow-up with Mr. Sanchez. The student's cum-slick ass crack and the teachers' cum loads sloshing inside his anal cavity had prevented Caleb from focusing during the intervening class periods. What did keep his attention was the effort to remember the feeling of Mr. Sanchez's thick, raw dick pressing into his soft insides that morning. Caleb wished Mr. Sanchez had not confiscated his phone so that Caleb could message one of his hookup contacts the salacious details. Alas, the story would have to wait until Caleb could secure the return of his phone during lunch.

Fifth period biology, his least favorite subject, was next. Caleb made his way into Mr. Park's biology class where his classmates were already offloading the heft of their overstuffed bookbags onto the workbenches. Projected on the screen at the front of the class was the topic and learning objectives for the day, which read:

"Today we will explore the structure and function of DNA. Students will explore DNA's physical characteristics by isolating samples from their own bodies. Students will have the opportunity to understand the role that DNA plays in the human body and to understand DNA's physical characteristics."

"Caleb!," Mr. Park's ever-jubilant voice came from behind. "I hear from Mr. Jacobs that you got a head start on today's lesson!" Mr. Park laughed at his own comment as Caleb's eyes turned to meet his teacher's.

"Mr. Jacobs?," Caleb responded, wondering whether the question was accidentally too apropos.

"Indeed, indeed. He tells me you brought some DNA samples that we might be able to assay today for our lesson." If Mr. Park's eyebrows could have lifted any higher, they would have escaped his face.

Ambiguous though the references were on the surface, Caleb felt a surge of anxiousness. Mr. Park had thrust Caleb into a chess match of innuendo which threatened a verbal checkmate in just a few rather inelegantly direct moves. How was Caleb to respond with so many of his peers around? And furthermore, why was it starting to seem like every last one of his male teachers knew about the raw cocks that had spewn ejaculate into Caleb's rectum that morning?

"Yes, I brought them," Caleb replied, considering each word as it left his lips. He took a brief pause to calculate what followed. "There's a slight issue though. The container has a hole, and I'm worried there's been some leakage." His desire to steer away from the hidden meaning that Mr. Park was so publicly flaunting had only driven Caleb nearer to the precipice of revelation. Mr. Park appeared bemused by Caleb's apparent, if veiled, confession.

"I must say, such sloppiness does not seem characteristic of you, but the good news is there is no hole that Mr. Park can't fill." Caleb wondered whether his biology teacher had lost sight of the infamous sensitivity of high schoolers to sexual double entendre. Sloppiness, indeed. The laughter from around the room made Caleb acutely aware that the conversation with Mr. Park was now a spectacle.

"Class!," Mr. Park needlessly summoned the attention that he already held, "I'm going to have you start working on the reflection prompt on the screen while I step out to help Caleb with something."

Caleb's face felt warm as he followed Mr. Park out of the classroom. They rounded the corner into one of the central campus hallways before Mr. Park spoke again. 

"Mr. Jacobs tells me you are quite the little whore." Mr. Park's sudden directness caught Caleb by surprise. Caleb's cock stirred as he looked around to make sure no one had been in earshot. The biology teacher continued, "I have to applaud you for that oblique reference to your cummy hole that you made just now in front of your classmates."

Mr. Park looked sideways at Caleb and smiled knowingly. "Your slutty profiles on all the hookup apps that you're always logged into have really captured the male faculty's attention, you know." Caleb felt a warm excitement swelling in him.

The biology teacher continued, "Surely a smart student like you understands what an exceptional provocation it is to stay logged into location-based hookup apps during the school day with a profile headline like, 'Pussyboy for use.'"

Breaking for a moment from the rousing implications of Mr. Park's comments, Caleb noticed further down the hallway the towering, broad-shouldered figure of a man leaning in a doorway. It was not an entry to a classroom, but rather one of the many normally closed doors that lead to a windowless room of which the general student populace knew very little. 

Because these various doorways opened into neither classrooms nor study spaces and given that they did not serve one of the several disciplinary or resource-gathering functions typical of an educational institution, most students bore only a passing awareness of them. Had any enterprising student endeavored to inventory all the many closed entries to these rooms of ambiguous function that perforated the St. Denis campus, they may have chanced upon a discovery that would have been at once mundane and extraordinary, for these ill-understood spaces far outnumbered their counterparts of known function. Surely they could not all be supply closets and back entries to faculty offices.

Mr. Park, mistaking Caleb's momentary silence for embarrassment, offered, "There's really no need to feel self-conscious that we've all seen your profiles, you know. You will soon find that an ambitious young slut like you can really make the most out of what St. Denis has to offer. To be totally forthright with you, Caleb, I would be shocked if you didn't get off on the idea of being the campus fleshlight." Caleb's cock swelled against his jeans.

The obscured figure down the hallway was now much closer. As Caleb and Mr. Park approached, Caleb was able to perceive the uniquely defined musculature of the head custodian, Mr. Martin, who was staring Caleb directly in the face. Caleb locked eyes with Mr. Martin, whose gaze was both stern and ravenous. Caleb could never quite tell if the head custodian was angry or just an unaccommodating sort who dispensed with pleasantries and the feigned interest that the rest of the administrative staff had perfected. Only now did Caleb realize that Mr. Martin's thick right arm was plunged deep into his pants where he was fondling himself rather aggressively.

As they came into conversational distance, Mr. Park nodded in acknowledgement at the custodian, stating cordially, "Mr. Martin." The head custodian said nothing in return and instead, looked Caleb up and down. Undeterred by their proximity and Mr. Park's greeting, the muscular hulk of a custodian rubbed his unseen cock under his pants with abandon. At once unsettled and transfixed, Caleb could not take his eyes off Mr. Martin's self-pleasuring in the openness of one of the main campus hallways.

After Mr. Park and his transfixed student had walked past the crotch-fondling head custodian, Mr. Park resumed in a hushed tone, "Between you and me, I wouldn't let Mr. Martin slide up inside you without a pharmacy's supply of antibiotics in the medicine cabinet at home. I would be shocked if that man has ever set foot in a clinic."

Caleb's heartbeat quickened and his throat felt tight. For the first time that day, Caleb felt that he was in over his head. And yet, there was no mistaking that he found the shocking visual of the head custodian fondling himself so openly on school property combined with the details Mr. Park was imparting to be thrilling. Caleb felt like he ought to be repulsed.

The biology teacher came to a stop and turned toward one of the many ill-understood doorways along the hall. After passing a keycard over an access reader, he pulled the door open for Caleb, who entered cautiously, unsure of what precisely he was to do. 

"Head all the way in," Mr. Park offered. Caleb proceeded down the dimly lit passageway before him until he found himself in a room filled with elaborate lighting and camera equipment. Before he could take in the full scene, Caleb felt the warmth of lips kissing his neck from behind. The abruptness of it was startling, but Caleb maintained his composure and acquiesced. The kissing continued up the young man's neck toward his ear, as Caleb felt a hand maneuvering its way past the waist of Caleb's pants and en route to his ass crack. 

There was a tenderness and gentle pacing in the neck kisses that seemed to serve as a cover for the brusqueness of the wandering hand, which had found its way between Caleb's ass cheeks. It was clear that Mr. Park's hand was not waiting for the student's permission to proceed to the cum-soaked hole at the center. Caleb pushed his pelvis back slightly to make access to his cum-fragrant underside easier. A finger pressed firmly against his hole and steadily progressed inside as Caleb whimpered -- as much in ecstasy as surprise.

"You like carrying your teacher's cum around inside you, slut?" Caleb's eyes widened as he realized the man's voice behind him was not that of Mr. Park's. Who was this stranger kissing his neck while sliding a digit inside Caleb's warm, cum-soaked rectum? Where had Mr. Park gone? Caleb tried not to let his shock force his asshole to constrict around the finger working itself deeper into his pre-fucked underside.

"Shhhh…. Keep looking straight ahead. Don't turn around. Do you understand?"

Whose voice was this? Caleb couldn't place it. He felt his heart pounding against his rib cage.

"Yes, sir," Caleb replied softly. A second finger slid confidently into the young student's anal opening. The moistness of the cum inside was more than adequate lubrication for the stranger's fingers. Remembering Mr. Sanchez's demand from earlier, Caleb tried to maintain enough tension in his hole to keep the cum from leaking out. It was a difficult balance to also not fully grip the two fingers that were now fully inside him.

The stranger swirled his fingers in the cum juices inside Caleb's rectum and then pulled them out with a measured slowness. The cum-soaked fingers presented themselves under the student's nose.

"Clean those off, pussyboy." Caleb sucked down the dripping ejaculate. As he swallowed, Caleb cast his eyes downward. A cum-slicked, thick black wedding band glistened. The young man savored the taste and fragrance of the cum as he sucked the strange man's fingers clean. The task complete, the hand withdrew. 

"Drop your pants and spread your ass cheeks for me. If I catch you turning around, I'll have you expelled faster than it takes Mr. Jacobs to cum." Caleb heard a zipper being undone. "Now, show me this cum-filled teen pussy everyone is talking about."

Caleb complied, dropping his pants to his heels and leaning forward slightly. The young man pulled his muscled ass cheeks apart as he wondered if Mr. Park was watching all this transpire in silence.

Caleb had been certain that the footsteps that had followed behind him down the short hallway and into this windowless room had been those of his biology teacher, but the way that the stranger had just appeared behind Caleb in the place where he had assumed Mr. Park to be made the young high school student question his senses. It was as though the strange man had stolen the very sound of the biology teacher's footsteps. To have done so in such a small, noiseless space seemed rehearsed.

All Caleb could hear in that moment were the sounds of fabric moving against fabric. The stranger was summoning his manhood to the surface. Caleb felt the warm soft head of the strange man's cock come into contact with his cum-moistened hole, pressing firmly enough to just part Caleb's cummy ass lips without proceeding further. 

The man's hand grasped Caleb between the shoulder and the neck. "I bet you've never been raw fucked by someone you don't even know." Caleb recalled all the times that he had fantasized about being passed around by a group of masked men with enormous cocks in the woods or an alleyway or behind the supermarket. It was a fantasy that he had had since he had watched his first gay porn. Never, though, did he imagine anything quite like this.

"No," Caleb replied as the stranger's raw cockhead pressed a few centimeters further into the young man's hole, parting his spermy sphincter readily.

"Well, you better get used to it, pretty boy, because it's what your pussy was made for." Reaching around, the stranger brought his other hand up underneath Caleb's chin and, grabbing the young man's lower face, pressed upwards, forcing Caleb to arch his back to protect his neck. 

As the anonymous man did so, he plunged the full length of his raw dick deep into the teen's guts. Caleb gasped in pain as the stranger's cockhead stabbed into his second opening. Caleb felt full and winced at the pain from the unrelenting pressure against his second hole.

The stranger, having forcefully bottomed out inside Caleb, held his raw dick in place, saying to the boy, "A handsome little bubblebutt cumdump like you is going to make Mr. Sanchez a lot of fucking money." 

The strange man kept pushing up on Caleb's chin, his grasp covering the young man's mouth. Caleb, through the pain in his rectum, felt the metal of the man's cum-soaked wedding band pressing into his lower lip. The stranger kept pressing his cock deeply into Caleb, until finally the young man's second hole eased its resistance and opened, defeated and compliant, to the pressure of the massive raw dick.

"Listen to me when I tell you this, nephew," the stranger continued, his grip tightening around Caleb's mouth and chin, "Mr. Sanchez pays me handsomely to make sure little cunts like you don't end up talking to the wrong people about what goes on here at St. Denis. You're his property now, and he expects you to be the cum-filled community fleshlight that he deserves. Do you understand?"

Caleb gulped for air as the pressure against his chin and neck was making breathing more difficult as he replied, "Yes, sir." 

The stranger pulled his cock out suddenly and plunged it immediately back into Caleb's fuckchute with full force. The sound of cum slopping inside the teen's ass accompanied a loud yelp. 

"I'm not your fucking sir. I'm your Uncle Ryan. Mr. Sanchez is your sir now. Tell me you understand, whore."

"Yes, Uncle Ryan. I understand, Uncle Ryan."

"Good, nephew." The stranger began sliding his cum-soaked cock back and forth at the opening to Caleb's second hole, massaging his cockhead deep inside Caleb's warm pussy. "Now I expect you to do everything that Mr. Sanchez tells you. I don't care how you feel about it, the answer is always, 'Yes.' So long as you're on school grounds, you are to be cleaned out and ready."

"Yes, Uncle Ryan." "Uncle Ryan" continued edging his cockhead inside Caleb's second hole.

"You are to take and hold as many loads in your cunt as you can arrange in the morning before school. This morning was the one and only time ever in your life that Mr. Sanchez is going to be loading you first in the day."

Caleb gulped in some air as the pain in his second sphincter began transforming into pleasure that radiated up through his abdomen and into Caleb's nipples. Everything felt more sensitive than it had before. "Yes, Uncle Ryan."

"You are not to let any loads leak out of you. No aborting in the bathroom or in your pants. And no letting another top suck loads out of you. Mr. Sanchez deserves nothing less than a full cum bath for his cock whenever he wants to plow your insides. Do you understand?"

Caleb began relaxing into the intense micro-fucking that his inner sphincter was receiving. "Yes, Uncle Ryan." 

"Hear me when I say that my number one job is keeping Mr. Sanchez happy, and what makes him happy is having a tight, warm community fuckhole available to milk his nut out of him on demand. You are never to say no to any load at any time in any place. I don't care if it's your own father asking to breed you live on the evening news. You open up your pussy before any top even has to ask, and let him blast your insides with his DNA. Have I made myself clear, nephew?" 

The stranger thrust his hips as deep as he could into the young student, driving his dickhead deeper into Caleb's guts. Caleb gasped.

"Yes, Uncle Ryan."

"Good, nephew. Mr. Sanchez put my number in your phone. When he gives you your phone back, I want you to text me a selfie showing your face and cummy hole in the same shot. Now finish milking this nut out of my dick so Mr. Park can get his turn." 

Caleb began sliding his sperm-filled ass up and down Uncle Ryan's large cock, savoring the fullness in his lower abdomen and noticing how the scent of cum had filled the room. The stranger released his hand from around the youth's face and chin and placed his hands around Caleb's waist, pulling the student deeper down onto his dick with each backward thrust.

"God that pussy smells like cum, don't it?"

The voice of Mr. Park emerged for the first time from its diligent silence, "Oh, yes it does!"

"What a sweet piece of AIDS bait this little fuckhole is." 

Caleb's cock leaked a large dollop of cum onto the floor at hearing the stranger call him "AIDS bait."

Caleb kept up the work of massaging the stranger's cock with his cummy boyhole, arching his lower back to demonstrate his compliance and to discourage any of the frothy DNA in his rectum from leaking any more than it may already have been.

Uncle Ryan's words ricocheted around in Caleb's head as the strange man kept drilling his raw cock deeper into the student. The phrases "community fleshlight" and "AIDS bait" held an almost lyrical resonance in Caleb's mind. He felt transfixed. Hypnotized. 

Even more thrilling than a stranger's raw dick sliding in and out of Caleb's used hole was the thought that Mr. Sanchez wanted a dirty little slut boy to be his personal fuckhole and that he wanted Caleb to be that slut. 

As the pounding continued, Caleb wished for nothing more in that moment than for Uncle Ryan to understand that Caleb relished the assignment he had been given, that he could not and would not fail to fulfill all of Mr. Sanchez's most salacious desires, that he would make Uncle Ryan not just satisfied but proud. 

Caleb yearned for the stranger to add his ejaculate to the warm, foamy pool of cummy slosh from Caleb's teachers. Knowing his biology teacher was watching it all transpire from behind was making the young man hungry for more dicking after the stranger was finished. 

Caleb arched his lower back as hard as he could as this so-called "Uncle Ryan" began shuddering. Caleb knew he was taking the stranger's hot load deep in his teen pussy. Caleb held on to the pulsating cockshaft as he imagined ropes of sperm spitting into his soft insides. 

That he didn't even know what Uncle Ryan looked like made the load he just received feel all the more hot. 

Without anyone else knowing it, the teen smiled and bit his lower lip as he let Uncle Ryan finish unloading his balls inside the handsome teen's rectum.

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I wished I were treated like this in school-it was my awakening to male sex & happened once in the toilets with another pupil but a teacher was watching & didn't say anything until we had both finished-all he said was hurry onto class & tidy up lads!!

Keep this going please.....

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Fuck spermed, luv this story!!! It keeps getting hotter and hotter!!! Caleb is such a lucky li'l teen cum dump...now the school's soon to be Poz fuck tramp...a bio-hazard tat is in his near future...and an invitation to the St. Denis Varsity Team...Team Poz!!🧑‍🦰🍊🍆💦☣️☣️🔥😈😛😋

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