The Head Girl Club Ch. 01

***A new story and clearly a total fantasy. I hope you like its start.***

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A lot of people boast about having 'the best job in the world' but you know what? They don't know squat. Being headmaster of a small, exclusive girls' boarding school? That's the best job in the world.

Allow me to introduce myself. My name is Will Dowling. I'm 49 years old and blessed with the kind of physique and looks that most men would kill for. I know what you're thinking, but it's not arrogance: it's fact. I still get checked out by women - and men - when I'm out for a drink. I'm 6ft 2in and about 100 kilos, most of which is still powerful muscle. It's easy to work out when you live in a school with its own gym.

At East Bucks we run an exclusive, expensive private school for 300 girls, taking them from 13 all the way up to 18. Each year a healthy percentage of our final year girls head off to Oxbridge's finest colleges. Our head girl always, without fail, goes to the pick of the finest colleges. My role, as head of the school, is to make sure that she leaves having received the finest sexual education any young woman can have: as my personal teen fucktoy.

It's a role I take very seriously. I watch the girls with interest. By the final year I've made my choice. My head girl. Just one, each year, as she turns 18. I'm a sucker for huge tits and big pouty lips, both attributes perfect for fucking.

I'm always amazed how pleased each one is when I tell them I've chosen them. I've come to realise that at some point in their school careers, each and every one of the girls at East Buckland Manor has lain awake at night and thought of me while fingering themselves.

It means that each time I select one they're delighted, if nervous. I don't fuck them straight away of course. Part of the fun is waiting for their 18th birthday (I'm not a monster). Part of the fun of it is in training each girl in turn. The more principled, decent and straight the girl, the greater the thrill as I watch her turn into my own personal cock slave, begging me to fuck her mouth, fuck her arse, put her fuck-collar on, spank her, come on her tits, pull on her leash, come in her mouth, scream her name... you get the picture.

I'm not sentimental though. By the last few weeks of their year with me I've already identified their nubile successor and as I spray my spunk into that year's head girl's mouth for the last time, I'm already mentally imagining her successor's mouth wrapped around my glistening shaft.

That's when I know it's time to take this year's head girl off to the Society for one depraved final evening. But I'm getting ahead of myself. More on all that later.

Each girl is mine to do with as I please. I like to pretend that I make my selection purely on looks, but that wouldn't be completely truthful. Once or twice I've selflessly foregone the most fuckable cleavage in the school and instead opted for a less attractive girl with the most annoying father.

Believe me, there's no satisfaction like ringing up a pompous dullard of a man, just as your 9-inch cock disappears into the soft, warm wet mouth of his 18 year-old daughter.

"Oh Belinda is proving to be every inch the great choice I knew she would be" I say as I grab her hair, her back arching as I slide my sticky thick cock all the way down her throat and she stares up at me adoringly.

"Well you let me know if there's anything we can do our end" he'll say as his daughter runs her tongue slowly up and down my shift. I push it between her tight, plump lips and I begin to slide it into her mouth.

"Funny you should ask..." I'll say, explaining that there's extra coaching for the maths olympiad that weekend for those girls who want to board over the weekend instead of going home (most girls go home each weekend).

Later that day I'll sit approvingly in my quarters as a stocking-clad Belinda crawls to me on her hands and knees, wearing only fishnets, heels and lip gloss, and begins to lube my cock ready for her arse, while I explain to my wife over the phone why I need to stay at the school that weekend.

I started this tradition about 10 years ago, not long after I started. I'd been married nearly 10 years at that point and I was bored, frankly. My wife was, is, gorgeous. And she makes a great home for me and our two teenage children.

But once I'd illicitly fucked my first head girl in a pair of slutty red satin panties that I made her wear under her school skirt, nothing else has ever compared to the rush of watching each and every head girl over the last decade become my own personal slut.

Do I feel bad? Not at all. I wish you could experience for yourself the thrill of the first time you oil and then titfuck a pupil's soft, inviting teenage breasts. Or bend her over your desk and hear her beg for your dick, pulling her panties over her cheeks and pleading for your cock. The first time you fit her with her collar and leash. Her total submission.

The way her tits sway as she crawls towards you on her leash, lips glistening, hunger in her eyes as she stares at your dripping, sticky cock. The first time I yank hard on her leash as I take her from behind. Pulling her head back as my large dick slides in between her pussy's tight velvet lips.

There is something about the wrongness of sliding a ballgag into the mouth of an 18 year-old girl, the total betrayal of trust, that makes me hard just thinking about it.

And the year ahead looks to be my best yet. I swear to you I didn't make her switch schools for the sixth form, but when I found out my best friend's daughter Bianca was applying to join East Bucks, I won't lie, I was hard for hours. And when she started dating my son two months before her final year with us? That was just the icing on the cake.

For the last ten years my head girls have been a very separate part of my life. I'm ready for a change to be honest. Spice things up a bit, you know?

Harry and Jayne Waugh have been part of my life for the last thirty years. Friends from university, Harry has since gone on to make a small fortune from his law firm. The money has definitely changed him too.

He's a man almost as arrogant as me. There is nothing he won't crow about - including his stunning 18 year-old daughter Bianca. To be fair, he's right to show her off. She's drop-dead gorgeous. One of those girls who flusters any man, particularly those over 40 who know they shouldn't be checking her arse out, but can't help it.

She has - I'm guessing her but I'll be able to confirm it soon enough - glorious, heavy, pert 36D tits, long legs for miles and a jutting tight arse. Her dark, glossy hair and bee-stung lips mean that she's already done some modelling work. It was for a local bikini manufacturer and I happen to know Harry was furious with the pics - which were HOT.

Friends since childhood, my son has been punching above his weight every since he started going out with her. But it's time to let a real man take it from here. Bianca has been a role model for our girls since she joined and it's only fair that this teen goddess feels the firm, guiding hands of her head master.

After all, who wouldn't want to fuck their son's girlfriend? Maybe even call the ungrateful little bastard up while you're doing it? Feel her throat fill up with your cock? Listen as she begs you to fuck her arse?

I know, right?

It's going to be a great year. For me, anyway.