Wilfrid's Boarding School Pt. 01

Everyone in this story is over the age of 18.

This story involves none consent and abusive language. If that is a trigger for you then stop now.

This story will be told from present day and through flashbacks. The flashbacks will not be indicated and you will have to figure them out yourself.

This is a bit of a darker story; I am going for a more story telling prospective with gay sex involved.

CHAPTER 1

The Captive

Urgh, where am I?

Tommy's eyes feel heavy as though he has ten tonne weights holding them down. Moving his arms, they quickly stop. What the hell? he thinks as something is stopping him from moving.

Slowly he builds the strength to raise his head and open her weary eyes. Only for them to shoot open in shock when he sees his wrists have a thick leather strap around them. Following the strap, they go underneath the bed that he has woken up on. In a room he doesn't recognise.

Where am I? he thinks as he looks around. The room is empty except for the white mattress that he lays on and a single camera in the corner aimed directly at him.

Tommy goes to move again but his other arm refuses to move. Looking across he sees that his left wrist is also tied with the same leather strap that disappears under the mattress.

What is going on?

Tommy goes to shout but no sound comes out. His wrists are tied too tightly that he can only just raise them above the mattress. Wriggling his legs, he finds out that his ankles are tied in the same way as his wrists.

His stomach stuck on the mattress; he writhes but it's not use. He can't move more than a few inches. His ankles are not as tight and he can move them more, enough to get onto his knees, except his wrists can only move an inch or so off the mattress.

He tries to think about where he last was but his mind is blank. As though he has forgotten the last few weeks of his life.

Turning his head back, he can see he is in thigh high, black stockings and a white jockstrap. Above that he has on a white t-shirt.

Writhing again in an attempt to break free, shaking his head, Tommy is surprised to see long, brunette hair hitting his face. Surprised because his hair is short not long.

Turning his head back he sees a black door on the grey wall. Then he spots his arse cheek and more shock fills him when he see's a tattoo. It's a black silhouette of a man on his knees with a leash being held by another man who stood over him.

"Finally, you are awake," he hears a voice coming through a speaker although he can't see where the speaker is in the room. All he can see is the bleak, grey walls.

Finally, his voice returns in a croak as he shouts out, "Where am I? Let me go!"

"It seems you have forgotten the agreement that you made," the voice returned over the speaker. It was a man's voice yet it seemed distorted as though to hide their true identity.

"What agreement?" Tommy shouts, "what do you want from me?"

Trying to fight out of the leather straps, but it is useless, he is still just as stuck.

"You belong to us now," the voice said, not in an angered tone, but in a calm one that frightened Tommy more.

Suddenly the door to the room opens. The black door that sounds like thick steel as it moves. Turning his head, he sees a man walking in. Dressed in a blue suit with a white shirt and a navy-blue tie. Except his face is covered with a balaclava.

"Let me out!" he shouts staring at the man.

Tommy is panting for air as this man approaches him holding something that he couldn't quiet see in his hands that are covered in leather gloves.

The man keeps growing closer to him only his footsteps making the sound.

His leathery hand grabs onto his smooth thigh, a thigh that was once hairy, landing just above the stocking and directly onto his skin. He attempts to move away but his grip tightens and holds him still.

"Stop fighting!" the voice over the speaker shouts which causes Tommy to freeze in fear.

"Please, don't," Tommy weakly whispers to the blue suit man whose hand is now pushing further up the back of his thigh.

When it finally lands on his arse cheek his body shivers. Then, his hand grips his right arse cheek firmly, with it's grip it pulls his cheek to the side.

"Stop it," he whispers.

"Do not fight it or you will be punished," the voice of the speaker calls out.

The man in the blue suit pushes his right leg up so it's bent as his left leg remains straight. Giving this unknown man a full view of his open arse cheeks.

Tommy looks back and see's he is holding what looks to be a dildo in his left hand. It's not too big but jet black. He watches as he pours from a tub labelled "lube" over the dildo and spreads it around.

Closing his eyes, not being able to watch, Tommy remains frozen solid as the man's cold, wet hand returns to his arse cheek. His fingertip lands in between Tommy's arse cheeks and he instinctively clenches.

SPANK!

"Ow!" Tommy shouts out in pain.

"I will not tell you again," the voice of the speaker warned again. Tommy knows he is completely at this man's whim stuck with no way out. He closes his eyes and grits his teeth.

Once more this man's fingertips lands between his cheeks and goes directly to his arsehole.

His body shakes when he feels the cold of the lube touching the inside of his thighs. The end of the dildo is being rubbed around his arsehole spreading the lube around.

"Ooohhh!" Tommy calls out when with an easy push the dildo spreads him open and slips inside of him. It surprises Tommy with how easily this dildo went inside of his untouched arsehole.

Feeling the man step away the dildo remains inside and the voice on the speaker calls out again.

"You will remain here until we allow you to move."

A cold hand grips his right ankle and pulls it down harshly and Tommy feels the straps around him tighten. He goes to move but it's too tight now and his legs are forced closed holding the dildo inside of him.

With his eyes still closed, he hears the steel door re-open and then close, assuming the blue suit man has left.

"Ohhhh!" Tommy moaned in shock when the dildo inside of him begins to vibrate. Just a small vibration like that on a phone.

"Whhhhyyyyy?" Tommy moans out as his body reacts to the vibrating inside of him.

"You wanted this. You agreed to everything," the voice on the speaker told him.

Tommy doesn't understand what's happening to him. His body is reacting massively to the dildo and quiet moans keep escaping from his mouth.

"Pleeeassee, stooooppp!" he calls out unable to stop himself from moaning.

"We will return," the voice over the speaker says.

Closing his eyes Tommy tries to focus on anything other than the pleasure she is getting from the dildo. Not believing that he could actually find any joy in this.

What's going on? How did I get here? What do they mean I asked for this?

The vibrating rose harshly.

"Oooh fuck!" Tommy moaned out loudly.

The vibrating was too intense his arsehole is quivering around the small dildo that is stretching him open.

CHAPTER 2

Summertime Blues

"Oooh fuck!" Tommy moans out whilst holding Leah's head in his hands. Her soft, perfect lips bobbing up and down on his five-inch cock. Her hands are rubbing his smooth balls as his orgasm builds higher and higher.

"Fuck, I'm going to cum!" Tommy warns her.

"Mmmmm," Leah moans around his cock as she keeps bobbing up and down.

"Fuuuuckkk!" Tommy moans out filling her mouth with a big load of his cum. Leah keeps bobbing up and down on his cock that is growing soft in her mouth as she swallows down every drop of cum.

"Was that good?" she asked with a smile whilst looking up at him.

"Amazing!" Tommy panted out running his hands through her long, brunette hair.

Sitting back onto his bed Leah joins him and the two hold hands.

"I can't believe you are going to boarding school next week," Leah said in an upset voice.

"I know, neither can I," Tommy replied, "my dickhead stepdad's fault!" Tommy moaned.

"Doesn't your mum want you to stay?" Leah asked.

"She does anything he tells her too, it's no use," Tommy moaned.

Since turning eighteen a few months ago, and just starting to have sex with Leah, Tommy was not ready to go to an all-boys boarding school where Leah isn't allowed to visit.

Lying down on the bed Leah wraps herself around Tommy's muscular body. Tracing her fingertips around his abs and forcing a laugh out of him.

When a knock appears on the door the young couple jump up in a panic. Both were completely naked Leah jumps up and grabs her t-shirt and quickly covers her C cup tits and her beautiful, smooth, tanned skin.

Tommy grabs a pair of jeans and pulls them up just in time for the door to open.

"Tommy?" he hears his step-dad's voice speaking as he enters the room.

His tall, slender body enters and Tommy see's his smug, smooth face. Paul has a chiselled jaw line and short black hair. Although he was a fair bit taller than Tommy, he is quite slender and doesn't look as muscly as Tommy.

"What do you want?" Tommy asked annoyed at the interruption.

"Don't take that tone with me," Paul replied in an annoyed tone his eyes dart around the room and spots Leah who is still flustered.

"You know," Paul said walking closer to Tommy, "maybe when you are done with this boarding school you will have grown up and we won't have these," he nodded towards Leah, "sort of issues."

Looking at Leah Tommy could see the hurt on her face from Paul's disliking of her.

"Just because you convinced Mum to ship me off doesn't mean you control me. I will do what I want, when I want!" Tommy shouted at him.

"We will see about that," Paul whispered back in a defiant manor.

"What do you want anyway?" Tommy asked.

"Your dinner is ready your mum wants you downstairs," Paul told him.

He turned around and headed for the door before leaving he turns his head and has one last look at Leah.

As soon as the door is shut Tommy grunts to himself, "Prick!"

"Why does he hate me so much?" Leah whispers with sadness in her voice.

Looking over to his girlfriend, Tommy rushes over and gives her a hug, whispering in her ear, "He's just a miserable old bastard. Don't worry two years at boarding school and then we are free to do what we want," he says to try and reassure her.

"Two years is a long time," Leah said with a choke in her voice, "am I really not allowed to visit you?" she asks.

"I don't think so," Tommy tells her, "but we can talk on the phone every night and I will be back for holidays."

"Okay," she whispers as Tommy can feel her tears hitting his shoulders.

Leah quickly left their house and Tommy headed into the dining room to see his mum and Paul have already started eating.

"We couldn't wait any longer," Paul says not even looking at Tommy.

Sitting down, Tommy looks at the lasagne on his plate, then back up at his mother who is staring at him.

"Are you looking forward to your new school?" she asks.

"No," he bluntly replies picking up a fork and starting to eat.

"Oh, you will love it," Paul says.

"None of my friends are going to a boarding school I don't get why I have too!" Tommy argues, but before his mum can reply, Paul interrupts, "You are going because you are unruly and need to have some manners put into you."

Spending the rest of the meal in silence Paul grabs the empty plates and takes them into the kitchen and Tommy finds this as a minute to speak to his mum in private.

"Mum, I don't want to go," he tells her.

"Tommy, it'll be good for you," she says, even though she is smiling, her eyes don't look happy.

"Please, Mum, don't make me go," he begs.

"I'm sorry, Tommy. Your dad."

"He's not my dad!" Tommy argues interrupting his mother.

"Tommy! Your dad has been gone for a long time now Paul is as good a dad as you're ever going to have. You can learn a thing or two from him," his mother tells him.

"Like how to be a dickhead," Tommy mutters to himself.

"That's exactly why you need this boarding school," Paul says, entering back into the room and shocking Tommy, "you need to learn some respect."

"You shouldn't be the one to decide on this!" Tommy argues.

"That's enough. My decision is final," Paul says standing over Tommy, "now, go and wash up!" he orders.

Not bringing himself to argue Tommy gives one last look to his mum before standing up and walking into the kitchen to wash up the dishes.

1 Week Later

Sitting in the backseat of his mum's car Tommy sat in silence. Having said goodbye to Leah and packing all of his belongings they are on the way to Wilfrid's Boarding School.

"Not too far off now," his mother says with a happy tone.

Tommy just grunts back in response.

"Oh, come on, you'll have fun.! Maybe make some new friends," his mum says although it doesn't make Tommy feel any better.

As they grow closer and closer the houses in the area look bigger and fancier. Clearly it is an expensive neighbourhood. Tommy dreads to think how much it is costing for him to go here although if it made Paul suffer in anyway then he is happy with that.

They pull up to a large gate that's connected to a thick, light brown brick wall that seems to surround the entire boarding school grounds. A guard walks up to the car and Tommy's mum pulls the window down.

"I am starting my son, Tommy Lancaster," she says to the guard.

Looking at his clip board he raises his head and smiles.

"Carry on through ma'am," and then the gates electronically open.

"Here we are, take a look at your new home," Paul says in a happy yet smug voice.

Looking around the driveway to the main building was huge! Fields upon fields surround it with perfectly cut grass.

As they drive up the road the main building comes more into sight. It's massive looking almost like an old castle. Looking out the window Tommy feels like he is starting at Hogwarts.

After another few minutes' drive, they finally reach the main building. First Paul gets out of the car and is quickly followed by Tommy's mum. Keeping himself firmly in the car Paul taps on the window and whispers, "Hurry up!"

"For fuck's sake," Tommy whispers to himself opening the door and getting out of the car.

He can see a few other guys his age walking around dressed in the school uniform, dark grey trousers and white shirts. The sort of clothing for posh boys that Tommy hates.

"Good afternoon," a man's voice calls out. Tommy turns around and sees a man who must be in his fifties walking towards them. He is in a grey suit similar to the uniform but more impressive. He also is wearing a grey tie. Tommy also notices the small birthmark on his forehead in the shape that Tommy can only describe as a whale.

"You must be the Lancaster's. We are happy to meet you," he says walking to Tommy's mum and to Paul, shaking their hands he says, "I am Head Master Geoff."

"Pleasure to meet you," Paul says shaking his hand back whilst Tommy's mum remains silent.

"You must be Thomas," he says reaching out for Tommy's hand which he ignores.

"It's Tommy," he grunts back.

"Tommy, be polite," his mother whispers to him.

"It's no problem not everyone is excited to first come here. But trust me I'm sure you'll have a wonderful time."

CHAPTER 3

Panic

The vibrating dildo in Tommy's arse has been running for what feels like an eternity. His legs are shaking and his breathing is still heavy.

He doesn't understand what's happening, it's as though the toy is hitting a spot inside of him that's bringing him immense pleasure but not enough to make him cum.

His cock is rock hard, buried between his stomach within the jockstrap and the mattress, and every time that he moves it sends a wave of pleasure through his body.

There's no pain coming from his arsehole that is quivering around the toy. It has fully accepted the intrusion and Tommy hated how much joy it was bringing him.

"FUCK!" Tommy shouts out as the vibration suddenly harshly increases.

"Fuck! Fuck! Fuck!" he keeps panting as his prolonged orgasm builds higher and higher his arse feeling like a pleasure hole for this toy.

Suddenly, the steel door creaks open and Tommy turns his head to see the man in the blue suit entering. Still with the balaclava over his face and the leather gloves on.

He walks over and loosens the straps holding Tommy's legs in place.

"Get onto your knees," the voice over the speaker calls out.

"No!" Tommy shouts back in defiance.

SPANK!

"Ow!" Tommy calls out in pain to the cold leather glove striking his arse.

"Get onto your knees," the voice repeats itself.

"No!" Tommy shouts again determined to not comply.

SPANK! SPANK! SPANK!

"Fuck!" Tommy shouts out in pain as each strike is harder than the last.

"I will not tell you again," the voice on the speaker threatens.

"Okay, okay, please," Tommy whimpers out as his arse cheeks burn.

He slowly pulls himself up to his knees the dildo still remaining fixed inside of him. His wrists are still tight to the bed and when he is in position his face is stuck to the mattress with his hands stretched out and his arse in the air.

"Good boy," the voice on the speaker says.

"Ooohhh," Tommy moans as the dildo is pulled from his arse leaving him feeling empty inside.

Footsteps of the blue suit man sound to be moving away although Tommy's head is too tight to the mattress that he can't move.

"What do you want from me?" Tommy shouts out.

"You are needing training," the voice on the speaker calls out.

"Training for what?" Tommy shouts.

"For total obedience," the speaker says back calmly.

"Obedience to do what?" Tommy shouts, but there's no reply, "Obedience for what?" he shouts again but still has no response.

He hears footsteps re-entering the room followed by what sounds like something on wheels. Although he can hear someone moving behind him, he can't move his head to see what it is.

That is until he suddenly feels something hard and round touching his arsehole yet again. It feel's similar to the last dildo and Tommy assumes it is going back inside of him, except this feels thicker.

He hears a switch being pressed and without warning the head of the dildo begins to slide into his arsehole.

"Oooh fuck!" Tommy moans out as the dildo, that is definitely bigger than the last one, slowly begins to slide into him feeling his hole stretching around it.

It's never ending, Tommy has no idea how much is being pushed into him but the dildo is moving in a smooth and swift fashion. Deeper and deeper, it goes, filling Tommy's insides up.

"Pleeeasseee," he moans out in a mix of pain and pleasure not believing something is so deep inside of him.

Suddenly it stops.

The dildo begins to retract as slowly as it entered him, just when Tommy thought it was about to leave his arsehole, the end stopped and began to push back in.

All the way until his arse felt completely filled again and then it went back out, then back in, then back out.

He was stuck here, on his knees, his arse in the air with this dildo slowly fucking him.

He has no idea where this man was standing the movement of the dildo was too smooth to be a person pushing it in and out of him.

"You currently have a robot arm fucking you in case you were wondering," the voice on the speaker informs him as though reading his mind.

"Oohhhh!" Tommy moans loudly as the fucking from the dildo gets slightly faster.

"Good boy, you won't take too long to break," the speaker said.

"I wooonn'tttt!" Tommy moaned out by accident as his arse was growing to accept the dildo stretching him open and going into his bowels.