Wilfrid's Boarding School Pt. 01

"Good slut," Simon says staring at him his dark brown eyes showing a sign of joy. He looks to the side and says, "Patrick, he better be as good as you say he is!"

"Oh, he is, he loves it," Tommy hears Patrick say from behind him.

"Get on your knees," Simon orders Tommy.

Feeling the grip release his hair Tommy looks at Simon as he slowly lowers himself to his knees. Face to face with Simon's crotch he turns his head to see Patrick smiling at him.

"Don't look at him focus on me," Simon barks out.

"S-sorry," Tommy says turning his gaze back to Simon's crotch.

Raising his hands Tommy slowly unbuckles Simon's belt and unzips his trousers.

"I knew when I saw you first come here, nearly a year ago, that you were a little cock slut," Simon said with a laugh as Tommy pulls his trousers down.

Looking up Tommy lets out a loud gasp at the sheer size of Simon's cock. It's at least seven inches long and as thick as his forearm. Smooth skin all over with a vein running through it.

The stories are true! Tommy thought to himself.

Pulling his hand up Tommy wraps his fingers around this giant cock. Not being able to get his fingertips to touch Tommy is amazed by the size of this thing.

"Most have this reaction when they first see it," Simon says with a laugh.

Looking up, Simon is giving Tommy a huge grin and tells him, "Well, get sucking. I've heard you're the best on campus."

Licking his lips Tommy takes one more look at this beautiful cock before closing his eyes and leaning forward.

When he feels the heat coming off the cock on his lips, he opens them further and takes him deeper into his mouth. Simon's cock head hits Tommy's tongue and his senses are filled with the taste of his delicious precum.

"Mmmmm," Tommy moans as he wraps his lips around this perfect cock. He's sucked a lot of cocks in the last few months but none have been this big!

"There we go, good boy," Simon moans.

"I told you he was a slut," Patrick laughs from the side.

Tommy doesn't care that he isn't alone his sole focus is on this amazing cock. Rolling his wet tongue around the head of this cock he begins to spread his spit around it as he takes more into his mouth.

Lovingly, Tommy bobs up and down, just taking past the head into his mouth as he runs his tongue all over it. Loving the taste and the texture.

"Does your girlfriend know what a cock whore you are?" Simon asked in a light moan.

"Mhmmm," Tommy moans back to say no.

"Who knows she might be doing the same thing right now," Simon laughed back.

Tommy hasn't seen Leah in so long and not being allowed to have a phone, for all he knows, she is being with other men.

But this didn't bother Tommy right now, right now, he just wanted this cock.

Covering more of his spit over the cock he bobbed faster and faster. Sucking on his lips, to get them tightly around the shaft, Tommy grabs onto Simon's thighs for balance as he pushes his head back and forth.

"Mmmm," He moans over and over around this God like cock.

"Was he able to take you all the way down?" Simon asks to Patrick.

"Oh yeah, with ease," he laughed back.

Tommy then felt Simon's hands gripping his medium to long hair.

"Get ready then cocksucker," he moans.

Relaxing his throat Tommy felt Simon pushing his face down and he felt the cock hitting his throat. His gag reflex was nearly completely gone and he accepted the dick deeper and deeper down. His throat felt like it was being stretched by this giant cock as inch after inch getting going deeper.

"Glllggggg!" Tommy eventually gagged around the biggest cock he has ever sucked.

"Take it you fucking slut!" Simon shouts out, gripping harder onto Tommy's hair, he pushes him deeper down.

Another inch Tommy feels Simon's big smooth balls hitting his chin. Opening his eyes, all he can see is Simon's stomach and he knows he has this entire beast of a cock down his throat.

"GGLLLGGG!" he gags but still manages to flick his tongue along the shaft.

"Fucking hell! What a fucking whore!" Simon moans holding his cock balls deep down Tommy's throat.

With the cock so deep Tommy can't breathe and begins to panic.

"Glllggg!" he groans and slaps Simon's thighs.

Simon releases his hair and Tommy pulls back gasping for air a trail of spit went from Simon's big cock to Tommy's lips.

"Fuck," Tommy gasps as he tries to recover his breath.

Simon's thumb softly presses against Tommy's bottom lips moving around he is spreading the mix of spit and precum around his mouth.

"Do you like my cock?" Simon whispers.

Looking up at him Tommy moans out, "I fucking love it!"

"Good boy, now get back to it," Simon orders.

Not wanting to waste any more time, Tommy wraps his lips back around this huge cock and starts giving his best, sloppiest blowjob. Bobbing up and down forcing himself to gag over and over on this thick piece of meat.

"Oh yeah, the slut loves it!" Simon moaned out.

"Yeah, he looks great," Patrick laughed.

Tommy ignores them talking about him and focuses on savouring the best cock he has ever sucked. His lips loving sucking every inch of the cock as his tongue runs all over it.

Taking the cock from his mouth Tommy holds it up and starts to plant kisses all down the shaft. Pressing his soft, wet, lips against the thick dick lovingly until he makes it to his big balls.

Sticking out his tongue he starts to run his tongue all over the balls. Taking them into his mouth and sucking on them lightly whilst wanking him off.

"Mmmmm!" Tommy moans whilst licking his balls.

"Fucking hell, that's good," Simon moans.

Burying the cock back down his throat, Tommy bobs up and down over and over, wanting to give this amazing man as much pleasure as possible.

"I'm going to cum soon slut! You better swallow it all down!" Simon warns.

"Mmmmmm!" Tommy moaned in agreement desperate to taste his warm cum.

"Fuuuckkk!" Simon shouts out gripping Tommy's hair and Tommy is finally awarded feeling this thick cock firing into his mouth.

The first rope of cum tasted thick and amazing, swallowing it down more and more cum filled his mouth, more than he has ever swallowed before. Like the good cocksucker he is Tommy carried on sucking Simon's cock and milking every last drop of cum from him.

When he pulls out Tommy wipes the spit from his mouth and looks up at Simon.

"That was a good first try bitch," he says.

"Thank you," Tommy said satisfied with the taste of cum in his mouth.

"I heard you don't take it in your arse yet?" Simon asked.

"N-no, I just suck cock," Tommy told him.

"Hmmm, we will see about that," Simon said with a chuckle.

CHAPTER 7

Realisation

What? I.... I sucked dick? How did I forget this? What's happening!

Although Tommy is looking at this blue suit man's green eyes, his head was elsewhere, trying to think about how he managed to forget about sucking Simon's cock, and worse, it was as though it was a regular thing.

Even the feeling of the large dildo fucking his arse was numbing down as he grew accustomed to it.

The blue suit man holds Tommy's hair with his other hand he pries the boy's eyes wide open and a picture appears on the wall in front of him. As though coming through a projector and filling the entire surface.

Looking at it, it took a minute for Tommy to work out what it is, it's an email, which reads:

"Dear Mr and Mrs Lancaster,

Your son, Thomas, is getting on great here at Wilfrid's Boarding School. I believe with a little more effort he could be one of our top students. With this in mind I am requesting that he stays here over the summer holidays for extra credit."

A slight flash and another image appeared on the screen a reply from Tommy's mother.

"Of course, if it's in his best interests then he can definitely stay over the summer holiday."

Reading through Tommy's head was even more of a mess.

"As you can see," the man over the speaker said, "you are here for the foreseeable future."

"Hmmmmmm!" Tommy moaned into the leather strap in his mouth as the blue suit man started to wank his cock fast and furiously.

"Do you want to cum yet?" the speaker asked.

The blue suit man's hand left Tommy's hair and pulled the gag out of his mouth.

"Please!" Tommy shouted, "please let me cum!"

"Are you ready to submit?" the man on the speaker asked.

Tommy's will to fight is gone, knowing he has no way out, he shouts out, "Yes!"

"Good boy," the man on the speaker says out.

Staring at the blue suit man Tommy watches him getting down onto his knees and follows the feeling of a warm mouth around his cock.

"Oooh fuck!" Tommy moans out.

The feeling of the dildo fucking his arse so well, the hours of endless edging, it takes only a few seconds for Tommy to feel his balls tighten up.

"FUUUCKKK!" he moans loudly and his cock erupts into this masked man's mouth.

More cum than he has ever produced fires out of his cock filling this man's mouth who swallows down every drop of cum.

"Fuck, so good," he pants out closing his eyes, as this man continues to bob up and down on his cock, making sure to milk every last drop of cum from him.

Oh, my God, that was fucking amazing! Tommy thought to himself as he kept having constant waves of pleasure throughout his body.

The blue suit man stands up and makes eye contact with Tommy. Without warning he leans in and Tommy feels this man's lips press against his own. Never having kissed a man before, Tommy's initial reaction is disgust, until he forces his tongue into Tommy's mouth.

When Tommy felt this other man's tongue against his and the taste of Tommy's own cum in his mouth, it's as though his senses got raised up to eleven and his cock started to grow again.

"Mmmm," he accidentally moaned not believing how much he is loving the taste of his own cum.

A few seconds later, the man stops making out with Tommy, much to his own disappointment and walks away. He switches off the machine that is fucking Tommy's arse and wheels it out of the room, closing the steel door as he goes.

This is crazy, what's happening to me?!

The steel door creaks open yet again and two men in brown suits, the same as Charlie was wearing, walking into the room, both wearing balaclavas on their faces.

Each one begins to untie Tommy's wrists and ankles and assist him down. Being tied up for so long and going through this ordeal, Tommy is exhausted and has no fight in him.

Not being able to walk the two men assist by carrying Tommy through the steel door and down a dark walkway.

After a few minutes the two men in brown suits take Tommy through another door. Inside is two single beds that are perfectly made with white sheets. They sit Tommy down onto one of them and he instantly feels a little pain from his arsehole.

Looking up the two men in brown suits leave his room and close the door. Closing his eyes, Tommy hears the door re-open.

"Hello?" he hears a man's soft voice speak.

In walks a man who looks the same age as Tommy. He is wearing white trousers and a white shirt his hair is short and brown and his face looked fairly well chiselled.

"You must be new," he says sitting on the other single bed.

Tommy realises that he is still just wearing the jock strap and attempts to cover himself.

"Don't worry about that, we will be seeing plenty of each other," the man tells him.

"What is this place?" Tommy asks.

"That's hard to explain, let's just say, it's a sort of an organisation," he replies which annoys Tommy for not answering fully.

"What are we here for?" Tommy asks.

"Training," he replies.

"Training for what?" Tommy asks.

"I can't say that, it's against the rules, but you will find out," the man replies, "I'm Martin, by the way."

"Tommy," Tommy replies, "so, what do we do now?"

Martin sits back on his bed, closing his eyes, he replies, "Now is the down time. They will be back to continue your training soon. You should get some rest."

"What training?" Tommy asked him still confused.

"You'll find out," he replies.

CHAPTER 8

First Taste

Tommy lays back on his bed getting his usual afternoon blowjob from Charlie that has become a nice routine for him. Feeling his friends mouth wrapped around his cock and bobbing up and down, Tommy is in heaven, closing his eyes and picturing Leah, although as time goes on it's getting harder and harder to picture her.

"Fuuuckk!" Tommy moans as he shoots another load of cum directly into Charlie's mouth who keeps sucking him and swallowing down every last drop.

His friend gets up from his knees, wipes his mouth and gets onto his bed.

"You're getting really good at that," Tommy pants to him.

"Thanks," Charlie says back with a laugh.

"Sorry, I can't sort you out," Tommy says to him feeling bad that he never returns the favour but he just never wants to do that. Getting a blowjob is one thing giving one is a whole other level.

"It's okay, I just like sucking your dick," Charlie says smiling back at his friend.

"Yeah, you do," Tommy laughs.

Lying back Tommy falls into an easy, deep sleep.

"Tommy!" he hears Charlie shouting and feels a harsh nudge on his shoulder.

"What the fuck?" Tommy groans slowly opening his eyes and sees his friend standing over him with panic on his face.

"Your alarm didn't go off! You've nearly missed your entire first class!" Charlie shouts.

"Fuck!" Tommy shouts his reaction forcing him to jump out of bed in panic, "fuck's sake, Professor Jones already hates me!" Tommy shouts grabbing some clothes and quickly putting them on.

"You better hurry," Charlie says sitting back down on his bed. The two don't share the same classes.

Rushing out the door Tommy runs through the dorms and nearly barges into another student.

"Sorry!" he shouts as he carries on running.

Finally getting to his lecture hall Tommy bursts through the door only to see all of the students standing up and packing their bags ready to leave the class.

"Ah, Mr. Lancaster, what a surprise," Professor Jones says in a sarcastic tone.

"I am so sorry, sir. My alarm didn't go off," Tommy panted out at him.

"Sit down I will deal with you when everyone is gone," Professor Jones tells him.

Hanging his head and knowing he is about to get a rollocking, Tommy sits at the corner of the class and watches the rest of the students heading out, all of the guys staring and laughing at him as they leave.

"Mr Lancaster, come up here," Professor Jones shouts from his podium.

Picking himself up from the seat Tommy slowly walks to the front of the lecture hall and stands in front of Professor Jones's podium.

"It seems you have an issue with my class," he says.

"No sir, I'm sorry, I just woke up late," Tommy mumbled looking at the ground.

"I am afraid this was your last chance, I will be informing Head Master Geoff, who will report to your parents that you have failed my class," Professor Jones told him.

Panic overtook Tommy then. "Please sir, I'm sorry! It won't happen again!" Tommy begged.

The last conversation he had with his mother was that if he fails a class then he will be enrolled in the summer school to make up for it and he doesn't want to spend a minute more in this place than he has too.

"I'm afraid there's nothing I can do," Professor Jones told him with a blunt look on his face.

"Please sir, I'll be early for every class for now on!" Tommy begged desperately.

"There is one thing you can do," Professor Jones said staring at Tommy harshly.

"What is it?" Tommy asked.

"I have heard about your outer class activities with your roommate," Professor Jones said instantly Tommy's eyes shot open at the embarrassment that people must know about Charlie sucking his cock.

"So, if you do not want me to kick you out of my class, you are going to perform the same act for me."

"What?" Tommy shouted in utter shock from this, "you want me to suck your dick?"

"As you have gathered there are no women allowed on campus. So, if you want to keep your place in my class, you are going to have to earn it," Professor Jones told him not moving an inch.

"Please, anything else!" Tommy begged.

Although, the last couple of months of Charlie sucking his cock has intrigued Tommy as to what it was like, he wasn't too keen on sucking the cock of an older professor.

"This is the only way," The professor told him.

I've wanted to try it, and if it means I don't have to stay here for summer and get back to Leah, then why not.

Staring at the floor, Tommy whispers, "Okay, I'll do it."

"Good choice Mr. Lancaster, follow me to my office," he says and turns around.

Tommy quickly follows not believing that he is actually about to do this.

Following through the corridors Tommy is grateful that there are no other students around to see him.

He follows Professor Jones into his office, closes the door and turning around he sees the professor staring at him. Dressed in black jeans, a buttoned shirt and tie, he smiles and says, "Well, get on your knees and come here."

Not speaking Tommy lowers himself to the ground and crawls over to his professor. Part of him is in disgust of what he is about to do and the other part is excited.

Face to face with Professor Jones's crotch Tommy raises his hands and slowly undoes his trousers. Pulling them down he gets lost for a moment at staring at his professor's cock.

It's rock hard, smooth all over and nearly as big as Tommy's.

"Staring at it won't keep you in my class," Professor Jones says.

"Yes sir," Tommy whispers.

Pulling his hand up he grips onto the big, hard cock in front of him. The warm feeling sent a wave of pleasure through Tommy's body and his own cock reacted by growing in his pants.

He licks his lips and gives one last look up to his professor who is smiling down at him.

Locking his eyes back onto the cock Tommy leans forward. The first thing he feels is the head of the cock hitting his tongue, the warm, soft texture feeling amazing against him. He instinctively closes his lips and wraps them around this hard cock.

"Mmmmm," Tommy accidentally moans feeling so natural and amazing having this cock in his mouth.

Without thinking, he slowly starts to move his head back and forth, feeling the skin of the cock running against his lips.

Knowing what he likes, Tommy runs his tongue up and down the head of the cock, tasting this older man's precum, which to his surprise tasted delicious.

"There you go, little slut," Professor Jones moans.

Tommy is completely shocked at being called a slut by his own professor and looks up at him.

"Don't stop now, keep sucking my cock," he orders.

Tommy, set on his task, closes his eyes and continues to bob up and down on his professor's cock. Taking more into his mouth until he feels it hitting his throat.

"Fuck!" Tommy pants as he pushes away from the cock, a trail of spit going from his lips to the cock, he sees the professor smiling down at him.

"Good boy, keep going," he says.

Repositioning himself Tommy grabs hold of his professor's cock and leans forward. Once again taking it back into his mouth.

Loving the feeling of this hard cock inside of him Tommy starts to bob up and down with a passion.

"Mmmm," Tommy moans around the cock as more and more precum pours into his mouth.

"Oh yeah, you're going to be doing this a lot for now on," Professor Jones moans and Tommy feels his hands running through his hair.

Not listening, Tommy keeps lovingly bobbing back and forth, flicking his tongue all around the shaft and the head.

He never wants this to end but he hears his professor moans.

"I'm going to cum soon!"

"Mmmm," Tommy moans suddenly desperate to taste this man's cum.