St. Gilbert's Sports Academy Pt. 07

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St. Gilberts is a scholarship Sports Academy for young men 18-22years from deprived backgrounds around the UK, providing excellence in coaching and tutorship in both Team Sports and Athletics, with the special goal of creating professional Sportsmen of all our graduates.

Each year, a very select quota of highborn young men are also enrolled, to act as School prefects and superintend their classmates.

Established: 1908

Principal: R. Stevens

Part 7: Prefect Bryce Hamilton-Bentley's Letter to his Big Brother Brooks, 19th February 2022

Bro,

The smut in your letters gives me such a jealous boner. Or maybe you give me a broner? lol. Seriously tho, all your boasting about Lucy and Charlotte and Bethany, and how you've been keeping each one busy, pushing your fat dick between their tits and railing them doggy-style without a condom. Fuck, I want to be just like you. It only makes the pussy drought hit harder (and you best believe it's been hard).

Me and my Mates, we're ready to take our place in the World like Real Men. We want to be out there dating gorgeous women and fucking them in our sports cars, like you. But we're confined for the foreseeable, and have to make do with the silly faggots that idolise us. Don't get me wrong, bullying the chavs is all good - especially in a school like St. G's, which honours and respects the good old English class system, and puts privileged wankers like me in charge of the scallies. I got a whole legion of frustrated, sexy oiks under my jurisdiction, and I can demand a blowie anytime I want. #PrefectLife as Conner would say.

Mate, have you seen his TikTok tho? He's going viral, I swear. His stupid skits and pranks are taking off. Everyone loves a school bully, and Conner's the biggest Bellend of them all. His reels are the best wank-bank on the internet, trust. Anytime you want to nut, just scroll his channel - it's one stupid fit chav lad after another, each getting just exactly what he's been asking for and loving it.

He'll never tire of whipping scally ass, but you know, sometimes I want to explore more sensitive passions - the gentle romance a Man reserves for the fairer sex. I was showing-off your letter to Conner and Bradley over a brandy in the Prefects' common room (you gave them both a sly hard-on too), and we agreed it was throbbing shame that we had no sweethearts to chase this Valentine's Day.

We shared a fantasy - That we'd dress up flash, and take our dates to the Michelin Star kitchen in Mable Village. We'd order the best wines on the menu, and gift our girlfriends some expensive piece of jewellery, helping them to get it on. I imagined myself talking about my sporting achievements, and telling her about my grand designs for the future. She'd be gazing at my biceps as they bulged in my shirt sleeves, biting her lip in anticipation of the night to follow. Then we'd have dessert and I'd bring her back to our dorms to fuck her every which way I could think of, doing all the things you wrote me with your classy birds in London.

And that's when the first glimmer of the idea came to me. Every Prefect has his own obedient fag boy to perform any chore we choose. In want of real women, we could drag-up our fags, and make a special night of it.

Conner chattered excitedly, quick to see the potential for humiliation and bullying the scheme afforded, and Bradley smiled silently, clearly picturing just how well his pipsqueak of a fag boy would pass. What started as a raucous joke soon grew in the course of heated discussion into a fully formed plan of action, and I spoke to our Barber about it the very next day.

Gilbert's pays a Barber to visit the school every fortnight. Everyone gets the skin-fade or beard-trim they desire. King Stevens likes to see his troops looking peng. This tattooed hipster Milo brings a team with him from Donning, and they set up in the gents by the atrium. There's hundreds of cuts to be done, it's no small operation, and it takes all day. Some lads line the benches to get their trim, others sit on toilet seats in the cubicles. I asked Milo once if the stink of stale piss bothers him, and he said,

"Are you joking? I fucking love it, Mate! It's the prettiest smell in all the world."

Turns out he requested the urinals as his makeshift shop. Having got the measure of the fellow I pushed the cubicle door shut, and I've been getting a blowjob with my cuts ever since.

"You St. G's lads are so fucking fit!" he whimpers from down between my thighs, looking up at me with watery eyes.

I like to think of my nut as his little gratuity paid for making me look so sexy, and he swallows it like a nice treat too. But last time I didn't nut - I peed. I didn't tell him I was going to do it. I just pointed my pink dick at his open mouth and let out a nice long piss. He was shocked, but got right into it, readjusting his sitting to better guzzle my pee. And he drank most of it, the rest splashing into his beard and soaking his tee.

"Fuck! That was so great," He whined like a bitch, kissing the drips off my tip, "Thank you Bryce, thank you..."

"Shut the fuck up," I told him straight, forcing my semi into his gob so he could finish me off.

How about that one, Bro? Are your classy babes drinking your piss? And thanking you for it after? Didn't think so - one all.

Anyway, I bring it up because he's also a drag artist on the scene in Donning. Every month, Milo dolls himself up and hosts club OMG. Calls himself Ruby Roar - he's a bearded queen, and his chunky tush looks great in a slinky dress. So I DM his Instagram and tell him there's £500 if he'll drag-up our fag boys for Valentine's, and he fucking loves the idea.

Next I call up Raiz, the Restaurant in Mable. Of course they tell me they've been fully booked for months - the night of the 14th being only a week away now. But when I spell out just who they're talking to, suddenly they can make space for an extra table of six. Nice to know we can always rely on the family name to open doors, eh Bro?

One last thing to sort, so me and the squad make a Saturday afternoon stop at the Jewellers in the Village to find our gifts. The old lady in the shop immediately guesses we're making Valentine's purchases,

"Who's the lucky girl?" she asks each of us in turn, as if we didn't all hear her the first time, "I just know you'll win her heart! Oh, such handsome young men, I wish my teenage granddaughters had sweethearts like you!"

Getting overly familiar and rather carried away, she showed us pictures of her girls on her phone - foxy twin redheads, just turned 18, hot AF. I worked my clean-cut charm, and the Granny seemed to forget we were literally just buying presents for other girls. In her rush to play match-maker she even took photos of us and wrote down my number.

Conner did not seem interested at all. Bradley was like,

"One for you, one for me..." but I want to fuck them both. At the same time.

I can just imagine the Twin's embarrassment when their Granny tells them she was taking down numbers for them. But I know when they see my picture they'll secretly hanker. And Bradley's way too complacent to put in the necessary effort to chase this up. So I reckon my chances are pretty good. I'll circle back on this one and let you know how I get on.

Monday night - Valentine's Day - rolls around, and honestly I'm getting butterflies. Kind of nervous about going on a proper date, even if the girl in question isn't a proper girl. I'm swept up in the charade. Milo shows at 6pm, shunting 4 flight-cases up to the Prefect's wing. We set up in my dorm.

We never told our fag boys what we'd been planning, but Valentine's is all about nice surprises! Naturally they're bewildered and abashed, maybe even terrified, but Milo is there to ease them in. As expected, he picks on Bradley's fag Riley first, instantly recognising the weed's awesome potential for passing as a chick,

"You'll be proper cunty, babes," he trills, pulling the boy over to the desk and opening his shadow pallets, "Bryce said we're aiming for 'Footballer's Wives realness', so I'm thinking chavy brows, and plenty of highlighter."

What can I tell you? The Man's an artist, and Riley's mug gets proper beat.

"Get your kit off and we'll sort out your tuck," Milo continues, with a friendly smile.

Poor Riley looks like a rabbit in the headlights. But he does as he's told. Bradley watches his transformation with growing satisfaction, misting himself with cologne and buttoning a slate grey satin shirt. Conner is busy making videos with which to humiliate the boy on his TikTok.

Milo completes his masterpiece with a strawberry-blonde wig of springy curls, and Riley is now a girl. A living, breathing, blushing girl in a silky cocktail dress and heels.

"What, no bust?" Conner blurts, shattering the stupor everyone else has been under.

"Nah, she's too petite," Milo disagrees, defending his decision.

"She looks just right to me," Bradley grins idiotically, another boner making a nuisance of itself in his slim-fit slacks.

"Dinky's getting tits tho, right?" Conner insists.

"I want to call you Natalia," Milo suggests, ignoring Conner and standing back to admire his creation.

The name sticks, and Bradley puts his cringe Valentine's playlist on, leading Natalia into a cheeky slow dance.

Now dinky sits in the chair. He may be short but he's a little bruiser, with a whole lot more bulk than Riley. Even so, Milo works his magic and the bonny boy is made a handsome girl. The aforementioned bust requested is created with a stuffed bra. Then dinky drops his y-fronts to tuck.

"Aw babe! You've got nothing to tuck!" Milo chuckles, "Your peenie is actually too cute! You know I do pubic grooming too? You should come up to Donning and get laser hair removal on this pussy. I'm setting up a new clinic..."

"Oi Dickhead! That's my girlfriend your chatting to!" Conner snaps, interrupting - his voice totally untempered with any good humour.

We're all a bit taken aback by it tbh. Conner really looks like he might lamp the dumb hipster, who makes hurried apologies. I mean, everyone knows dinky has a crush on his fag-Master, but now we're wondering if Conner's fallen in love with his fag boy too? I swear that would be hilarious, we're already razzing him over it.

Dinky slips into a pair of red lace panties without any prep at all. His micropenis doesn't make a dent, and his dress drops down nice and flat. A brunette wig finishes her freckled look, and Milo christens her Hazel. Conner slaps her ass with a tremendous clap as soon as she's on her feet, saying

"They call her Hazel 'cos only hazing gets her wet."

It's legit a hysterical wisecrack, and me and Bradley double over with laughter.

Last (but not least), my own stupid fag boy Daren. Keeping the best for last, Milo reveals that he owns a pair of fucking silicone tits! And he's gonna let my fag boy wear them. When Daren steps out of the chair, tottering in wig and heels, I give the prosthetics a gentle squeeze thru his dress, and the meaty, tensile weight of his breasts gives me an instant erection. Milo calls her Kelsey.

A quick ten minute crash course in walking in heels, and Milo declares the babes ready to slay.

"I'm actually so jealous of you," he pines, "What I wouldn't give to go on a date with a St G's boy..."

Unlucky Milo. Gargling my hot piss is the best you're going to get, mate.

Outside it was snowing. A freak moment of magic in an otherwise grey and unusually warm winter. It gave our Uber ride an otherworldly feel. Arm in arm with our dates, we made the short walk from taxi to restaurant lobby in a swirling drift of pretty snowflakes.

The chav lads had never seen anything like it. I bet the only restaurant they ever set foot in was McDonald's. Fine dining for these plebs was next level. Waiters fussed to take their coats and get us seated. The wonderment in their eyes was great.

"How do you like these fancy places?" I asked Kelsey across our dinner table, and she nodded innocently.

I wish Kelsey and I could have had a more intimate evening. If we'd had a table to ourselves I would have talked more about my achievements and my aspirations, like in my daydream. But Conner kept lowering the tone with dirty bants, and Bradly was easily persuaded to join in.

At least I got to give her that necklace. Of course Conner made crude comments, saying I'd give her a pearl necklace later.

"Me and Hazel are trying for a baby tonight, aren't we Babe?" he smirked, indulging his naughty fantasies without restraint.

But we all saw how dinky stared back at him. This is his choady wet dream come true - the School Bully promising to impregnate him with his mean, filthy seed.

Bradley was equally clueless about how to behave around a woman, having no conversation to offer besides asking his date,

"Do you think I'm sexy?" over and over.

Natalia obliged, seemingly eager to please her Man, but it was tedious, to say the least, for everyone else.

Whatever. We got dessert and took our dates back to our dorms to get slammed. As I laid Kelsey down in my single bed, I could hear Conner guffaw through the wall like a total prick. We were all at it, each slapping his new bird around in his own way - in his own dirty style.

Bradley would be fucking Natalia softly, telling himself he's a real love-maker. Conner would be tormenting Hazel, and she'd be loving every cruel little minute of it. And I was trying to be my Big Brother Brooks, and copy every conquest you boast about in your lurid letters - pushing my stiffy between Kelsey's silicone tits, wanking myself in his rubbery bustcrack.

It's the first time our fag boys woke up in our beds. We usually kick them out as soon as we cum, sending them back to their respective dorms with sore butts and sorry consciences. But just this once we treat them to a little tenderness. A warm, sleepy embrace from the Golden Boys they worship, before all their chores and the inevitable school day begins. They've probably earned a taste of kindness.

Please keep writing, Brooks. I know how much of a busy high-flyer you are, but news of your fat dick's adventures bring so much cheer. I'm gonna be just like you, you'll see. Just as soon as I get out of this place. I'll be pounding so much pussy, you'll have stiff competition Mate.

Peace out Dude x