Schoolboy Mentoring

mm, oral, spank, nc
Albert Luberschnifter

Ben Tramer attended North Castle High School. The boy was seventeen years of age and already was a high achiever, both academically and physically. He was one of your typical All-American jock boys. A very confident character, he could certainly pick and choose the sexiest of girls at his whim. The boy was a bombshell with a powerfully built physique, blue eyes, blonde hair, and the girls just loved him.


Though it wasn’t the girls who had caught his eyes in recent months, he had now turned to more sinister thoughts of innocent, little boys. He did not know whether he was gay or straight, but that didn’t matter. The mere idea of thrusting his hard cock into the tight ass of a young boy turned him on something awful. He had to make sure he kept his depraved fantasies to himself, though. If one word got out that he was gay, he would surely lose all the credibility he had earned over the years.


He had become disinterested in pussy just recently. Although he had fucked many girls, he had never had the privilege to fuck a boy. Watching a group of thirteen-year-old students run around in their tight gym shorts really got him going with their firm, slender ass cheeks swaying as they ran cross-country. He especially liked it when they were instructed by the coach to do warm-up stretches. Ben would sit on a bench, pretending to do homework. His favorite position was when the boys touched their ankles since this could only be implemented by them bending over. This gave Ben the perfect view of boy ass causing his balls to beg for release. Better still, he wished they were entirely naked so he could watch their small cocks bouncing between their legs.


Being a well-respected senior, Ben was watched continuously by girls and other students alike, so he had to watch himself accordingly and always be on guard. So, going about seducing a boy was going to be a hard task. He was bored of watching internet porn and yearned for the real thing. Recently his grades had been declining in school, often he would doze off in class fantasizing about a young boy wrapping his plump lips around the head of his cock. He was doing it today as he did most days.


“Ben Tramer, are you listening to me, or daydreaming about some fantasy,” said Mr. Smith.


The whole class started laughing. Mr. Smith quickly hushed them up, though, and began teaching boring old religious studies again. Ben was a little embarrassed, though Mr. Smith wasn’t far off. He was fantasizing over a young boy. Rob Philips turned to Ben and began speaking quietly.


“Bet you were thinking about some young slut, Ben. I’m taking a liking to that Cherie Blackstock. You know, the gorgeous little brunette with the big titties and word is she’s some dirty whore.”


“Yeah, she’s okay, but I prefer…” Ben hesitated.


With all the boys he had been fantasizing about recently, he had forgotten all the girls that he used to like. Eventually, he churned out a name, but Rob frowned as he looked into Ben’s eyes. He wasn’t a stupid person. He was just as much of an achiever as Ben was, and he had a knack for finding out people’s secrets.


“Jeez, what were you thinking about? Boys? You like them now, do you?”


The two boys laughed. Ben felt himself blushing to avoid humiliation, and he turned away, resting his head on the desk. He didn’t want Rob Philips to realize he was gay, then the whole school would know.


Ben’s next class was PE. As he was walking down the corridor, he came across two girls who he chatted to briefly. They talked about the usual mundane crap — their hair, makeup, and whom they were fucking, which was all boring talk to Ben. He wanted fresh boy meat to fuck something new in his life.


As he passed through the yard and into the main changing rooms, there was a poster on the wall that caught his attention for recruiting senior counselors to help mentor younger pupils for with either domestic issues or school-related problems. They specifically wanted the help of seniors so that the younger pupils could speak to someone they could relate to. There was to be a meeting held in the study hall at four fifteen. Ben weighed up the situation, and a sudden impulse of energy swept through him. Finally, he was going to get the chance to interact with a younger pupil and on a one to one basis. Better still, they would be young and vulnerable. Perfect for him to seduce. He was getting turned on just thinking about this new opportunity, so he decided to go and knock one out in the toilets, as he didn’t want to turn up at the gym with an erection.


During gym class, the usual banter continued. Guys talking about their cocks. How many girls they’d fucked and so on. Ben kept quiet for a change, though, passing the time with ease, ready for the scheduled meeting. After PE, he said bye to his buddies and proceeded to the study hall. He disclosed this information to his buddies, as he didn’t want his supreme jock status to diminish. The thought of a high school senior tutoring younger kids was a mockery to the cool kids.


He approached the door and knocked. He was becoming very impatient, and all the excitement of the forthcoming events had gotten to him. Looking around the room, the senior girls outnumbered the boys to nearly three to one. They were mainly science or math geeks. Unfortunately, they did not have the looks. Ben was lucky he had both. Around fifteen chairs were situated around the room, creating a semi-circle, and two teachers were stood at the front ready to make a speech. Ben sat down, slouching with his arms behind his head in an arrogant fashion.


“I’m glad that you have all found the time, and most importantly, the heart, to attend this meeting. Obviously, you have read the poster on the bulletin board, and I’m glad to see such an array of new, respectable faces. Now, our school strives for top achievers, and that can only be implemented through students having a good sense of morale. It’s just like in war; soldiers without morale find it much more difficult to survive. Well, it’s the same here at North Castle High.”


Mr. Legioni’s attempt at sarcastic wit failed miserably. He was expecting a little chuckle from the students. No one laughed, though, and he looked somewhat embarrassed, so he carried on.


“Now, each of you will be assigned to one of the younger pupils, each of them around the same age. Although you are mentoring students, I must assure you that any information exchanged between you must be strictly confidential. Some of these students are finding life here at school extremely tough, whether it is due to bullying, domestic issues, or any other aspect of school life. So, please keep that in mind as you were all new students here once. Finally, we would like you to help and reassure the students by being as friendly as possible. Feel free to offer snacks and drinks when mentoring. Remember, help is always at hand at North Castle High.”


‘Yeah, I’ll feel free to offer my wet cock,’ thought Ben.


That would be a nice variation from good old snacks. Ben was eager to find out which student he had been chosen to mentor and decided to ask at the end. Thankfully, Mr. Legioni had finished his daunting speech and asked if anyone had any questions. Ben gleefully raised his hand.


“Ah, yes, Ben Tramer.”


“Oh, yeah, sir, when will we find out which students we will be mentoring, as I am really looking forward to helping the younger kids. My brother has had a lot of problems as well, and he somewhat looks up to me for guidance,” Ben lied, as he hated his brother, and his brother hated him.


“Ah, I am glad to see such enthusiasm, Ben. Well, I’ll read out the names now.”


Mr. Legioni picked up a pad from the desk and began reading out the names. Ben hoped to god that he would get a boy, or all his devious plans will have gone to waste.


“Megan Forstall will be paired with Jennifer Saunders. Anthony Rigbeth will be paired with Timothy Lonsdale.”


Ben crossed his fingers and waited for his name to be called out. Already he had some indication that Mr. Legioni was pairing girls with girls and boys with boys. He was encouraged, and finally, his name was readout.


“Ben Tramer will be paired with Jake Blunsten.”


Yes, thought Ben. Finally, he would be able to shove his monstrous cock into the wet orifice of an innocent boy’s mouth and make him suck his cock as he would a lollipop and then shoot his teenage load down the boy’s throat and over his face. Ben’s thought pattern was rocked by Mr. Legioni’s voice.


“Please be in school tomorrow as meetings have already been arranged. Please report to me in the morning for your meeting place. Thank you.”


‘Please be in school tomorrow. Of course, I’ll fucking be in school. I wouldn’t miss this for the world,’ thought Ben.


Ben rushed out of the classroom, swaggering. He was so happy. The thrill of seeing this boy was beyond belief.


He slept soundly that night, masturbating first, of course. He imagined he was fucking a boy on his back, thrusting his cock in and out of the boy’s anus while he bounced around and screamed. Ben woke up the next day like a five-year-old on Christmas Day. Never had he anticipated a moment quite like this. Not even when meeting a girl who was a virgin.


After his shower, he grabbed a pair of boxers, making sure he picked those that were easily accessible for the naive boy’s mouth. Instead of using a belt, he decided to go all out nigger thug style, trousers barely covering his ass. He arrived at school promptly and reported to Mr. Legioni at once. He was told to meet Jake at three-thirty in the school cafeteria. Then after an introduction, they would be able to go to a private room.


‘Yes,’ thought Ben.


A private room would be perfect for the real initiation proceedings and where they would be secluded and alone.


The school day went fast. The boring lessons were somewhat more stimulating today, and can you think why? One of the other seniors who was mentoring came over to Ben during the day and spoke to him. She was a little older than Ben and was called Francine. She began babbling on to Ben, saying what a nice feeling it was to help these younger students and that it’s a real benefit to yourself. Ben pretty much ignored her banter, and just answered everything she said by either saying yes or really. Ben thought that she probably fancied him, but he did not fancy her one bit as she was utterly repulsive. She was one of those stereotypical science chicks that have no life apart from playing monopoly with her parents on a Saturday night.


Finally, it was three twenty-five; Ben looked at his watch and decided to make his way to the cafeteria. His cock was begging to be sucked, but he prevented himself from having a wank since a little professionalism was in order. Sucky-sucky would come later. The cafeteria was basically empty since school hours were over, and just a few students were chatting together. Jake was sitting in the corner all alone, probably feeling inept and alone. Well, he was not doing counseling for a laugh now, was he?


Ben swaggered over, walking quickly, so he could get a first glimpse of the boy’s face. It wasn’t until he sat down opposite the boy that he realized his dreams had come true. He had been blessed with the cutest, most gorgeous boy possible. He had creamy blonde hair and blue eyes. Each feature on his face was perfectly formed. A small, well-rounded little nose, full but thin ruby red lips, and a pattern of subtle freckles. He looked up at Ben, and they each made eye contact. Ben could see the scared glint in the boy’s eyes. He was noticeably agitated with his eyes staring at the floor, painting a negative picture of himself.


“Hey, I’m Ben. You must be Jake. I’m pleased to meet you.”


Ben raised his arm out, ready to shake the boy’s hand. Jake moved forward as well, and they each connected touching each other's flesh. Ben felt the small, silky hands of the boy, his hands almost engulfing those of Jake’s. Ben immediately knew by this very slight intimacy that the boy had a tight, virgin ass. He raised his hand and brushed Jake’s hair, making sure he got a good feel of him.


“Now, I’m here to help you, Jake, whatever problems you have you can tell me, and in confidence, that means this conversation won’t go any further than you and me. I want to make you feel secure when you’re in my company and rest assured that we can communicate well.”


The boy began to speak softly; he spoke like a little girl. His tender voice had barely broken, beckoning Ben to believe he had just started puberty. He sounded so feeble and defenseless; bullying must be the reason why he is here.


“Can we go and talk somewhere more private? I don’t like it in here with all these people,” he said


There were about ten people in the room. This kid was fucked up and going to get fucked thoroughly, thought Ben.


“Yeah, alright, mate, we’ll go to one of the empty rooms on the third floor, okay?”




As they walked out of the cafeteria, Ben placed a hand on the young boy’s shoulder, firmly, but not painfully, gripping the boy’s shoulder blades. Ben pondered a look at the boy’s ass. It looked, oh, so delectable that getting the chance to see the bare flesh would be even better. They decided to take the elevator up to the third floor since no one else was around, making the journey more accessible. They both stood in silence in the elevator — an eerie silence actually. Jake was too scared to speak.


The room they entered was cold, but empty just as Mr. Legioni had said. The two boys sat down at a desk, Jake pulled up a chair, and they sat directly opposite each other. While Jake was perched upright, Ben slouched a little so he could spread his legs under the table. With one hand, Ben began caressing his growing cock, moving his hand delicately over his cock, but quietly as not to arouse suspicion from Jake. Jake was oblivious, though, and they sat there in silence for a moment until Ben began speaking.


“So what’s troubling you, Jake?”


“Well, I…erm…it’s just everything, really. School mostly, and at home. Some of the bigger kids pick on me. I’m not very big for my age, and they put me down, make me feel stupid. Home isn’t any easier, my Dad is always shouting with my mom, and they take no real interest in me. I have to cook my own dinner and sit in my room alone until the next day.”


Yes, this kid was insecure and seemed very frail. Ben knew he could bribe the boy, make him submit, and the best thing of all was he would keep quiet. The boy looked down at the desk with his eyes lowered and a sad look covering his face. He looked so cute this way. The next best thing would be to see him cry with tears pouring down his adorable, little nose and streaming over his lovely freckles.


“It’s okay, mate. I’ve seen boys like you in this position all the time. Feeling vulnerable like this is part of growing up. You see, the bigger boys are not confident in themselves, so they take their anger out on you. Tell me, Jake, and be honest. I can see something else is worrying you. Remember, we are in total confidence.”


The boy sniffled slightly. Ben could see him getting upset, and his cock lurched even more in his pants. Jake covered his face and slumped over the desk turning his head out of view.


“Hey, it’s alright, look up, Jake. I won’t judge you.”


The boy raised his head, and it was what Ben was anticipating. Tears were descending down his cheeks, and the boy was blubbering softly with a look of fright in his eyes.


“It’s just they make me do things nasty things. At first, they would call me names, like cumdump and cocksucker, but then it got worse. There’s a group of five boys, but it’s only two of them that actually made…made me do it.”


“Made you do what, Jake?”


Ben’s heart stopped for a second. He wasn’t stupid. He knew for sure that this boy had already been used and abused. Though who could blame the boys who did it as Jake was a prime fuck target. He looked so innocent, and a cock in his mouth would feel so good.


‘The time had come,’ Ben thought.


Ben could not take the pain anymore. It was time for fun and games to start. He edged his chair away from the table, screeching the chair legs until he was in full view of the young boy. He stretched his legs far apart so the boy could see his bulging crotch in full view. Jake was puzzled momentarily until he realized what was happening. He looked down at the considerable enticing bulge in Ben’s trousers, and then it dawned on him.


“Made you do what, Jake. Come on. Tell me. You’re a big boy now.”


A devilish grin lit up on Ben’s face. Jake stared back in horror, in terror, in fact. He froze on the chair. The very reason he was here was that he had been subjected to physical, sexual harassment, and here his mentor was rubbing his hard throbbing cock beneath his trousers.


“No, please, no, it’s all happening again. Leave me alone! I thought you were here to help me?”


The boy was shaking as he was mortified beyond belief. He lurched to the door as fast as he could, but the door was locked, preventing him from leaving. He turned round to Ben to see him holding up the key.


“I thought you’d try that one, boy. That’s why I locked the door when we came in. You see, I’m here for one reason, and you too are here for one reason, that is to service me.”


The boy began crying even more, but Ben was not having any of it.


“Stop fucking crying, baby boy, and listen up. There’re two ways we can go about this situation. Did you really think I, a jock boy, was here to help you? I’m a manipulator. Using people to my advantage is a forte of mine. If there’s no prize at the end of the tunnel, then I don’t go there. As soon as I saw you, I knew I was in for a treat. You have just basically told me that other boys have abused you, both mentally and sexually, so you’re in the shit now. As I said, either you can service my needs now, and I’ll keep my mouth shut, or you leave this room, and the whole fucking school finds out about your dirty little secrets.”


Jake clenched his fists like a little school kid, Ben could see the rage mixed with emotions building upon the kid’s face. It was so comic.


“No, I won’t do it. You can’t do this to me. I’ll tell the teachers.”


“Yeah, you can do that. But remember the next day in school you will be the complete laughing stock. Eventually, your parents will find out. How would you like that, boy?”


Jake had second thoughts. It would be embarrassing for the whole school to know. He decided to get this over and done with. If he’d done it before, he could do it again. Little did he know that Ben was going to turn him into nothing more than a cock hungry fuckhole.


“Now, why don’t you come over here and lap up my cock, fag. My cock’s just begging for release.”


By now, Ben had slipped off his trousers and boxers. His eight-inch cock jutted up from his groin, pre-cum oozed from his opening. Jake stared at in terror. He had never seen a cock this big before. Now we know why all the girls loved Ben Tramer. Jake hesitated, his boyish face blushing with humiliation. Thankfully only Ben was in his presence, unlike the previous occasions. He edged closer to the menacing cock and fell to his knees, ready to submit.


“Come on, boy. I want to see some more enthusiasm. Get your cunt lips around my cock and start sucking. Imagine that it’s a hot summer’s day, and you’ve just purchased a Popsicle.”


Ben laughed at his remark, eagerly waiting to plunge his cock into the orifice of the boy’s warm, wet mouth. He had waited for this day for so long, and now it was here. Nothing was going to get in the way.


“Now, grab my legs and force them apart, rest each of your hands on my thighs at either side. Start by licking my balls, and then take them in your mouth and suck, gradually moving up to the base of my cock.”


Jake looked at Ben’s giant-sized nuts, they were at least four times the size of his and covered with an array of hair. A distinct smell emanated from his genitalia, as would be expected from a hormone-raging teenager.


‘Somewhat repulsive smelling,’ Jake thought.


He clasped his mouth around Ben’s balls, taking in the sensitive organs. His mouth was quickly filled, as they were so big. He swirled his tongue around as instructed, making sure he did it delicately but effectively. Ben was in ecstasy. All his wildest fantasies had come true, and he felt his balls pulsate with cum ready to unleash his load down the boy’s throat. He was going to have so much fun with the boy over the next few months since this was just the beginning.


“Hmm, that’s good, bitch. Keep doing that, you’re going to become a professional cocksucker over the next few months.”


The next few months? Jake froze momentarily before carrying on servicing the beast.


‘After today,’ he thought, ‘it would be all over.’


Unfortunately, he was wrong.


The next thing Jake knew, Ben had grabbed his head and pulled him away from his balls. Next, he positioned his head directly over his cock. Without warning, he thrust the boy’s mouth down onto his cock. Jake yelped but was unable to scream, as his mouth was stuffed with an eight-inch cock. Ben harshly grabbed both of the boy’s ears and started to face fuck him brutally, pushing and pulling the boy’s head in a vicious, fast rhythm.


Ben looked into the boy’s eyes. He looked like a fish with his eyes squinting and sunken cheeks. As Jake gagged on the cock, slight, pathetic noises erupted from his mouth. He looked so cute and defenseless in this position. After about three minutes of heaven for Ben, he felt ready to climax.


“Now, listen up, boy, you better take my entire load like a proper little cumdump, do you understand?”


Jake obviously couldn’t speak, but a firm affirmative nod reassured Ben. Within seconds, a thick stream of cum erupted from Ben’s slit, plummeting wads of it down the boy’s throat. Jake swallowed all of the disgusting, sticky, cum as he had done before. After Ben had blown his load, he let his cock subside in the boy’s mouth before pulling it out to flicker a few drips onto the boy’s face.


“Did you enjoy that, boy? My cock tastes good, doesn’t it? I’d advise you to prepare for next time with a bottle or something. My cock is going to bust your tight ass, and then you’re going to lick me clean. I hope you like the taste of shit.”


Ben laughed nastily out loud. He was in complete control, and he just loved it. Jake fell to the floor, sobbing quietly. Fourteen years old, and he was being used as a fuckhole. He felt so degraded. Why did people want to treat him in this way? He had come for help, for a little guidance, and he had come away with a dollop of cum down his throat.


“So, I hope this little session has helped you, Jake. You’ll go to bed feeling much happier with yourself, and wake up tomorrow as right as rain.”


Ben gripped the boy’s neck viciously and pulled him up close. He squeezed the boy’s cheeks, holding tightly to prevent him from looking away. Jake’s tongue hung an inch out of his mouth. They each made eye contact. Leaning over, Ben licked the boy’s face with his wet, sloppy tongue covering the boy’s face in spit. Jake was shit scared now. In a way, this was more perverse than having to suck cock. Ben eventually stopped, though.


“Awww, you look so cute like this, Jake. I wish I had a camera here so we could take a few photos. How’s it feel to be cumdump?


 “Let go of me, man. Get the fuck off me, you fucking freak,” Jake slurred.


Jake could not take it anymore, he lashed out, but his pathetic attempts came to no avail. He tried bitch-slapping Ben, but it was no use. Ben quickly shunted the boy to the floor, kicking him vigorously in the balls.


“Who the fuck do you think you are, you little shit? You’ve just landed yourself in it now, and you’ll pay the price. I was going to bring you down gradually, but now I’ve decided to throw you in at the deep end. Get over to the fucking wall, hands by your side, not moving an inch.”


Ben was fuming. Never had someone undermined him quite like that. Not even people his own age. The little shit was in for a real beating now. Ben quickly unfastened his belt, whipping it away from his trousers, thrashing it through the air it gave that typical whistle noise one gets when wielding a whip. Jake quivered with fear, perspiration covering his body. He knew what was coming from the sounds he heard.


The boy lurched when he felt Ben on his hips. He felt fingers sliding under the waistband of his trousers, and his cold, coarse hands touching his silky, smooth legs. He ripped down the boy’s trousers until they fell down past his knees and down to his ankles. Ben saw Jake’s perfect, plump ass, seconds away from being exposed. He wore cheap, whitey-tighties like small boys wear. Not like Ben’s expensive Armani boxers.


“I’m going to enjoy this boy, really enjoy it!” snapped Ben


He slipped off Jake’s underwear, exposing an insignificant prick and small set of balls and an ass that was so perfect in every respect. Ben swung the belt. He taunted the boy, pretending to whack his ass. After the third time, he began raining down on Jake’s buttocks. Jake screamed as each whack connected with his flesh, Ben was showing no mercy he carried on for twenty-five strokes. Jake’s ass was going a deep shade of red, and most of all, he was humiliated and in extreme pain.


Ben slid his hand underneath the boy’s legs, pushing a finger into the crevice of his ass cheeks. Giving him a feel of what was to come in the future. Finally, he cupped the boy’s small balls, clenching them and digging his nails in. Jake yelped with fear, though he didn’t move. When someone has hold of your balls, the worst thing you can do is move. Ben moved to Jake’s puny cock.


“Your cock must be about two inches, Jake. Wait until mine busts your ass like a bull in heat.”


Jake gulped and froze. He knew what was coming next.