Wilfrid's Boarding School Pt. 01

"Don't kid yourself," the voice says, "many have been broken here before you're not the first and you won't be the last."

"You fucking prrriiicck!" Tommy shouted out.

"Hmm, let's see how fast you can take it," the man on the speaker said.

"FUUUCKKK!" Tommy harshly moaned out as the dildo started to rapidly push in and out of his arsehole.

Faster and faster Tommy felt like he was getting fucked by a big a long cock. It was going deeper and deeper the rim of his arsehole pushing in and out as the dildo thrusted in him.

"Ooohh, God!" Tommy moaned not believing how much pleasure this toy is bringing him. He can feel his cock rock hard in the jock strap as his arse took a mighty fucking.

"Seems you are enjoying yourself," the man said over the speaker.

"I'mmmm not!" Tommy tried to argue but he couldn't stop himself from moaning.

With his face pressed against the mattress he closed his eyes and accepted the pleasure from his arse getting wrecked by this dildo. All of his focus was on his arse that was being forced to accept this long toy pushing in and out of him.

"Oh fuck!" Tommy moaned loudly feeling his orgasm on the brink. Then the toy stopped fully inside of him.

"Nooooo," he accidentally moans out before catching himself realising he just moaned for the toy to keep going.

"Oh, so you do like it?" the speaker asked.

"No!" Tommy shouted back not wanting to give in to this hidden man.

"We'll see," he said back and the fucking started again but much slower.

Instead of properly fucking his arse like before it was slowly going deep inside of him and then all the way out. He is helpless to move and is just accepting that his arse is loosening around this toy.

"Next step," the man on the speaker said.

"What next step?" Tommy moaned out with his eyes still closed.

Yet the man didn't reply instead he can hear the footsteps of the man in the room with him. A few fingertips wrap around the front of his jock strap and pull them down so that his five-inch cock was out. Opening his eyes Tommy can see the mass amount of precum that is pouring out of his cock.

Before he knows what's going on, a black, cylindrical object appears in front of his cock.

"What are you..." Tommy was shouting until the leather hand holding the object pushed it forward.

"Oooohhh!" Tommy moaned it felt like the tightest pussy he has ever been in in his life was getting pushed around his cock. He could feel it wrapping tightly around every inch of his cock as it goes deeper and deeper until only his balls are left out.

A tortures pleasure, his arse feeling amazing and this toy around his cock feeling perfect, yet not moving so he can't cum.

"Are you ready to admit you're enjoying yourself?" the speaker man asked.

"Never!" Tommy shouted back although the voice in his head telling him to say anything to cum as it was growing.

CHAPTER 4

Playing with the Boys

"Well, that was a shit party!" Tommy moaned as he walked back into his dorm room.

"It wasn't that bad," Charlie said following behind him and closing the door.

Tommy walked to his single bed and harshly sat down upon in. Although he hates this school at least the beds are comfy.

"Please, there was barely any alcohol and it was boring as everyone just stood around chatting," Tommy moaned whilst sitting back and hitting his head against the wall.

"What do you expect? It's not like we can smuggle many drinks in and if we make too much noise then we will get caught," Charlie said sitting on his single bed opposite Tommy's.

Looking at his roommate Charlie was dressed in expensive trousers, a black shirt and smart black shoes. Not the sort of clothes that he would wear to a party but he is slowly getting used to these posh guys.

"It's been nearly four months since I've even seen a girl, you know," Tommy said closing his eyes and trying to picture what Leah looks like the image of her face slowly fading from his memory.

"You get used to it," Charlie whispered.

"I don't want too," Tommy moaned back, "I don't know how you guys do it."

Then he opened his eyes and saw Charlie looking at the ground.

"You're lucky," Tommy says, "at least you don't know what it's like to be with a woman. I have to live with the knowledge of how good it feels and not getting to experience it."

"I wouldn't class that as lucky," Charlie said with a laugh.

Tommy actually liked Charlie, he is a posh kid, but at least he's a laugh. He is the same age as Tommy but Tommy has taken him under his wing. Since he is a fair bit smaller, some of the other students here used to pick on him, but Tommy soon put an end to that.

"What's it like?" Charlie asked.

"Being with a woman?" Tommy asked back.

"Yeah," He replied.

"Well let me tell you, sex is awesome," then he sits up and looks Charlie dead in the eyes, "but a blowjob is fucking amazing!"

"Really?" Charlie asked as his eyes lit up.

"Mate! I can't even explain it, the feel of a warm, soft mouth wrapped around your cock. Slowly bobbing up and down on you as you feel their tongue running around your dick," Tommy said with a slight moan reminiscing of the last blowjob he got from Leah.

"That does sound nice," Charlie said back staring at Tommy.

"God, what I would do if I could just see Leah. To feel her mouth around my dick and filling it with cum," Tommy said sitting back against the wall and closing his eyes picturing his girlfriend. Before he knew it, he looked down and saw his hard cock poking up in his jeans.

Looking up he sees Charlie staring at his hard cock.

"You alright man?" Tommy asked. It takes Charlie a few seconds to bring his gaze away from Tommy's cock and he finally stutters out.

"Do... Do you want one?"

"What do you mean?" Tommy asks back confused.

"Do you, do you want a blowjob?" Charlie asks diverting his eyes to the ground.

Is he offering to suck my cock? Tommy can't believe what he just heard, His hair is long and blond like a woman, and his facial structure is actually similar to Leah's along with his plump lips.

"Are you serious?" Tommy asked him.

"Y-yeah," Charlie replied.

"Are you gay?" Tommy asked not that he has any problem with gay guys.

"I, I don't think so. I just want to try it," Charlie said quietly.

Taking a minute to think about it Tommy was horny as fuck and he doesn't consider it cheating on Leah as it's with another guy.

"Okay," he said which makes Charlie's eyes almost pop from his head.

"Really?" he said very eagerly.

"Sure," Tommy replied, "but no one finds out!" he said sternly.

"Definitely," Charlie says whilst sliding down onto his knees and getting in front of Tommy.

Spreading his legs Tommy goes to unbuckle his jeans but Charlie's hands beat him to it. Watching his friend pull his trousers down Tommy feels like he is in some strange dream. Lifting his arse up Charlie pulls his trousers down and Tommy's fully hard cock springs free in front of them both.

Oh, God, is this actually happening? Tommy says to himself.

He watches as one of Charlie's small hands lift up and wraps itself around Tommy's cock.

"Oh, God," Tommy moaned out.

"Is this, okay?" Charlie asked looking up at Tommy in panic.

"Yeah, it's fine. I just haven't had anyone other than me touch my cock in so long," Tommy whispered. Having virtually zero alone time whilst at Wilfrid's Boarding school and having to share showers Tommy has very rare opportunities to wank and all of his built-up horniness is pouring out of him.

"Okay," Charlie whispers back and his hand slowly moves up and down Tommy's hard cock.

Feeling another person's skin on his dick feels amazing he sits back and watches his friend slowly wanking him. His own precum starting to appear from the end of his cock.

"Ready?" Charlie asks whilst looking up at Tommy.

Between his legs, he stares at his friend, his long blond hair, his feminine features, there's nothing that could stop Tommy from having this right now.

"Ready," he replies.

Slowly Tommy watches Charlie's plump lips open and move over his cock.

"Oooohhh," Tommy moans closing his eyes.

The familiar feeling of warmth around his cock comes back to him soft lips pressing against his shaft. He opens his eyes and to be fair he could imagine it was a woman between his legs instead of his friend.

Charlie kept his lips fixed just past the head of Tommy's cock. Tommy can feel his wet tongue running along his dick, flicking the head and forcing a twitch out of his leg.

"Mmmm," Charlie moans around Tommy's cock forcing a vibration through him.

"God, I've missed this," Tommy moaned bringing his hand down he rested his fingers into Charlie's soft blonde hair.

In his hands he feels Charlie's head slowly move down and take more of Tommy's cock into his mouth. Like dipping his cock into a warm bath that's met with a tight feeling around his shaft, Charlie's tongue never stopped its assault on the head, he slowly brings his soft lips up and down.

"That's so good," Tommy moans feeling his hands move up and down with Charlie's head.

"Mmmm," Charlie moaned again as he kept bobbing up and down on Tommy's thick cock.

Leaning back Tommy closes his eyes and thinks of Leah. Remembering the time that she woke him up with a blowjob. Just seeing his bed sheets going up and down as he slowly wakes up and the feeling of her mouth around his cock takes over his body.

"Ooooohhh!" Tommy moans loudly as Charlie deep throats him. Looking down he can see his friend's mouth completely taking his entire cock down his throat.

"Fucking hell! Leah could never take it all in!" Tommy panted out, not believing that not only is Charlie holding his cock down his throat, but he can also feel his tongue still massaging his shaft.

"Glllggggg!" Charlie gagged around the thick cock as he brings his mouth back up.

Looking at his friend Tommy can see his cock covered in spit that is going from his dick to Charlie's mouth.

Charlie looks up and smiles at Tommy, "You like?" he asks.

"Hell, yeah!" Tommy replies.

In an instant Charlie wraps his lips around Tommy's cock and effortlessly starts to bob up and down. With ease he is taking Tommy's cock balls deep down his throat at every bob.

"Oh, God, I won't last long," Tommy pants out as a warning not being able to wank in so long is meaning his orgasm is coming fast.

"Mmmm," Charlie moaned around his cock signifying that he is going to swallow.

Tommy rested back and watched Charlie's mouth going up and down his cock his own balls tightening and his cum getting ready to fire out.

"Fuuuuckkk!" Tommy moaned loudly gripping Charlie's hair as his cock erupted down his throat. Shot after shot of cum firing into his friend's mouth who swallowed down every last drop.

With his eyes closed Tommy feels Charlie caring on to bob up and down on his cock and milking out every last drop of cum until his cock becomes too sensitive.

"Woah, woah, woah, stop," Tommy says pulling away.

Charlie wipes his mouth and looks up at Tommy.

"How was it?" Tommy asks his friend.

"Great, what about you?" Charlie asks back remaining on his knees with Tommy's soft cock in front of him.

"I can't believe it, but that's probably the best blowjob I've ever had," Tommy said with a laugh.

Charlie gets to his feet and sits down on his bed. They share an awkward smile before they both get into bed.

Lying down with the lights off Tommy can't help but smile to himself. That arsehole Paul thought he could leave me here to suffer. If only he knew he just sent me somewhere to get sucked off.

CHAPTER 5

Helpless

Tommy woke up not knowing how long he has been asleep for. Last thing he knew he was on his knees with a dildo on a machine slowly sliding in and out of his arse. It went on for so long that eventually his arse felt completely normal being filled and he actually managed to fall asleep.

As his eyes slowly opened, he went to move his head but quickly realised he isn't able to. Feeling something tightly wrapped around his forehead he works out that his head is tied to what feels like a wooden board with a cushion on it.

He's no longer on the mattress, in fact, the mattress doesn't appear to be in the room any longer. He's stood up now well sort of stood up. Being able to move his eyes to the sides and up and down he recognises what he is on. He's seen this before on his extensive porn history that he used to watch.

He was strapped to a St Andrews cross. His ankles tied tightly on the corners, keeping his legs spread and the same with his wrists in the air. Moving his eyes down, he can see that he still has on the jock strap, however the toy that was over it is no longer there.

"Hhhhhhhh!" Tommy goes to shout, only to realise that he has a leathery strap also in his mouth and tied behind his head. Digging his teeth into it, he is helpless to make anything other than muffled moans.

"HHHHH!" He tries to shout and fight the straps but it's no use.

"About time you woke up," the same distorted voice speaks over the speaker.

Staring at the black door Tommy darts his eyes around.

"As you can see, we moved you whilst you were asleep," he said, "now, are you ready to submit?" he asked.

"HHHHHHHH!!" Tommy muffled a moan and tried to shake his head.

"Okay, your choice," the voice said and then the door slowly opens.

In walks the man in the blue suit, his face and hands covered and he is wheeling in a machine. Looking at it, Tommy realises it's the machine that was used to fuck his arse earlier.

He has no idea how long ago that was or how long he was asleep for. An hour? A day? His concept of time is completely gone.

As he wheels the machine in Tommy looks at the dildo that is attached to it. A long, and thick, black dildo covered in what he is guessing is lube.

"Hmmmmm!" Tommy tries to plead with the man but it's no use. He won't even look at Tommy.

The man wheels the machine behind Tommy and out of sight. Then he feels the dildo pressing against his arse. It would seem this St Andrews cross is missing the middle section that covers his arse.

Hearing the flick get switched Tommy bit down onto the leather strap in his mouth and waited for his arse to take another fucking.

"HHhhmmm!" He moaned into the gag as his arsehole begins to stretch around the dildo feeling every inch of its smooth exterior sliding inside him.

The feeling is surreal, as much as he hates it, he loves it at the same time. Feeling his arse opening up for this toy to go deep inside of him. It's a familiar feeling and a brand new one all at once.

Withing a few seconds the toy is now at a steady pace fucking his arsehole. Tommy's cheeks hitting the toy as it moves this is definitely a bigger one than the last.

"Ghhmm, Ggghgg!" Tommy groans into the gag finding some sick pleasure in the toy fucking him.

Looking down Tommy is ashamed to see his own cock rock hard and leaking precum.

The faster and faster this dildo fucks Tommy's helpless body the more his body reacts to it. The more his cock twitches and yearns for pleasure.

Unable to stop himself he is constantly letting out louder and louder moans from the hard fucking in his arsehole.

"Are you still going to say you are not enjoying this?" the voice over the speaker asks.

"Hhhhmmm!" Tommy moans out wanting to be defiant but unable to hide his pleasure.

"Good, send him in," the voice says.

The grey door creaks open once again. The man in the blue suit appears from behind Tommy and stands at the side with his arms crossed. Tommy is trying to look at him but the man won't look back.

When Tommy hears footsteps coming from the doorway his eyes shoot open when he sees Charlie walking through.

"Hhhhmm?" He tries to shout into the gag.

Charlie isn't looking at Tommy more through him as he approaches. Wearing a brown suit, similar to the man in the blue, his long blonde hair swinging through the air as he walks.

Standing just inches away from Tommy Charlie finally looks him in the eyes and smiles.

"Hhhh," Tommy tries to moan into the gag not being able to stop thinking of the big dildo fucking his arse.

"Shhh," Charlie whispers, "it's okay, it's all going to be okay, just enjoy."

Tommy watches as his so-called friend lowers himself to his knees about being able to see the top of his head and the end of his cock.

"MMMMMMM!" Tommy moans out loudly when Charlie's warm mouth wraps around his aching cock.

"Gllg.... gllg...gllg!" Charlie gags onto Tommy's thick cock over and over.

Although he can't see Tommy can feel every movement of Charlie's warm mouth and wet tongue over his cock. He just closes his eyes and forgets about the situation and enjoys the pleasure.

The dildo in his arse, the mouth around his cock, it's all too much, too good!

"MMMM!" Tommy screams into the gag as his cock is on the verge of cumming.

"Stop now!" the man on the speaker shouts.

"HHHHHHH!" Tommy shouts in annoyance as Charlie's mouth releases from his cock just before he was about to cum.

"Do you want to cum?" the voice over the speaker says.

Charlie stands up, slightly unties the gag and pulls it out of Tommy's mouth.

Not able to think of anything else, Tommy shouts out, "Please!"

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

Tommy looks at Charlie in the eyes, his friend smiling at him and he gives him a small nod.

"No!" Tommy shouts back, a tiny part of him still has some fight left, enough to not lose to these bastards!

"Tommy," Charlie goes to speak in a soft tone.

"Silence!" the man on the speaker shouts interrupting Charlie, "put the gag back on."

"Charlie...." Tommy goes to argue but his friend pulls the strap back into his mouth and tightens it.

"Continue," the man on the speaker said.

Charlie's head disappeared, back down to Tommy's cock and his warm lips once again wrapped around his cock.

"Mmmm," Tommy moaned.

It isn't the fast bobbing like before Charlie is lovingly sucking Tommy's cock. Bobbing up and down massaging his shaft with his tongue. Tommy's body was twitching in his restraints and he is letting out louder and louder moans.

Right before he came Charlie's mouth disappeared again.

"Hhhmmm!" Tommy moaned his cock begging him to cum.

After a few seconds Charlie's mouth returns to his cock. Bobbing up and down for only a few seconds until Tommy was about to cum again and then he took it from his mouth.

Over and over Charlie edged Tommy to the point where it feels like a gust of wind can make him cum.

"Enough," the man on the speaker said.

Charlie stands up and gives Tommy another look without saying a word he turns around and walks out of the room with the grey door closing behind him.

"MMMMMMMM!" Tommy moans louder than ever as the dildo starts to fuck his arse faster. Properly fucking him over and over going deep enough for Tommy to feel it in his stomach.

"Mmm!" he moans over and over just not giving him enough pleasure to cum.

The man in the blue suit appears in front of him. He has bright green eyes that show no sign of emotion.

Without warning, his leather covered hands rise up and grip the back on Tommy's long hair and tighten around it, forcing a pain from his head.

CHAPTER 6

King on Campus

"Are you ready you little bitch?" Simon says.

Tommy can feel his harsh grip on the back of his head and the pulling on his hair. It's been months since he was allowed to go off campus and get a hair cut and it's much longer than he was used to.

"Y-yes," Tommy stuttered back.

Staring up at Simon his six-foot four body dwarfing Tommy's. Although Tommy has always been confident with his size and strength, he knows that Simon could easily beat him up.