I wonder if there are other basically `straight' guys out there who enjoy gay fantasies? Here's one of mine. Feedback welcome...
The boys only grammar school I attended as a boy had a headmaster at the time, who liked giving the cane to naughty boys -- and I mean liked. In fact these thrashings were meted out with honed precision and an unreserved and sadistic relish. I never actually got the cane when I was at school (goody-two-shoes and all that) but was told about it from boys that had. He was good at it -- there was no doubt about it. You didn't go back for more in a hurry, so you were careful not to err again.
Mr Forrest was something of a legend at the school - but for another reason entirely. He was rumoured to be very well-endowed. There was no actual proof of this of course; you didn't have the advantage of pissing alongside any member of staff, let alone the headmaster, so no one had actually seen it.
But we were all fascinated by the stories that were bandied about.
Morning assembly would always provide the best opportunity for a covert glance at his inside trouser leg while he was on stage. Some boys swore they could see the outline of the headmaster's awesome instrument when he was either sitting down, or in the process of getting up to do a reading, saying if you watched very closely you could, on occasions, see a languid swing or movement of something.
I have to confess that from my point of view I was never sure that I could make out a shape that represented a large cock, or any kind of cock for that matter, but I didn't like to stare too long in case he saw me looking. However, the myth persisted.
At this time I would only have been about 12 or 13, but I was becoming more sexually aware, aware of changes to my body -- the arrival of pubic hair, increase in the number of erections, etc. It was about this time I had begun to masturbate regularly (about twice a day) and though I used to think mainly about girls when I was doing it, occasionally I'd find myself thinking about Mr Forrest -- I guess you'd call it 'cock-envy'.
I used to imagine I was he, rubbing until it came, although at that age my own emissions were barely visible We boys used to joke about the headmaster jacking-off' and would speculate on the amount of cum he might produce, how far he could shoot, did he sign his name on the lavatory door - that sort of thing.
Anyway, on with the fantasy...
I am sent to Mr Forrest's office for repeatedly talking in class. He is an overbearing man in the usual attire -- black gown and mortar-board, beneath which he is wearing a grey pin-striped suit. He is tall and slim, about 50 years old, steely-grey hair which is immaculately groomed, deeply-tanned face, but not especially handsome.
I tell him why I've been sent to him (for some infringement of the rules) and he asks me if I know what happens to any person who has that dubious honour. I nod and he pulls up a chair in front of me and sits down. At close range I am able to make out the shape of his beautiful cock resting against his upper thigh. I come over a bit light-headed. So the rumours, it seems, are true. I estimate him to be at least nine inches in repose -- a real milk bottle.
He knows what I'm looking at and asks me to look him in the face. He holds me transfixed with cool blue eyes and I feel myself coming under his spell. I feel strangely compliant and subservient. He asks me what I think should happen to naughty boys like myself and I tell him I've no idea. But for some strange reason my cock starts to twitch.
"You see, Perkins, there are certain boys who I know are not inherently bad and I like to give them the opportunity of redeeming themselves by having them perform some little forfeit -- instead of receiving a sore bottom and then suffering the imposition of not being able to sit down comfortably for at least a week. You don't need me to tell you how some boys can take great sadistic delight in another fellow's suffering and humiliation..."
"Yes sir, they can be cruel sometimes."
"Indeed. But you do not have to give them that opportunity to gloat, Perkins. Some boys deserve a good thrashing. I don't think you're one of them."
"Thank you, sir."
"Therefore, I'd like to offer you the chance of making amends, young man. Come here and kneel down."
I do as he says. My heart beats loudly in my ears.
"What do I have to do, sir?'
"Oh... just some little favour. I just want you to to me a tiny little favour."
"Favour, sir?"
"Yes."
"And what do I have to do, sir -- this favour as you put it?"
"I know how you and other boys are fascinated by a certain part of my anatomy."
"Sir?"
"Oh, don't be so coy, Perkins. You know perfectly well what I am referring to."
"Oh..."
"I'm going to let you have a look at it. But then you've got to suck me off for the privilege."
"Anything's better than a thrashing, isn't it sir?"
The headmaster smiles wryly at my lousy humour. His eyes sparkle and he leans forward and lifts my chin. "That will depend on how good you are, and also whether we can both satisfy each other's curiosity, won't it, Perkins?"
"I suppose so, sir."
Mr Forrest tells me to come closer. Again I feel that strange headiness, accompanied by a growing feeling of willing-subservience.
He smoothes the hair off of my forehead and tells me I'm a very handsome young man. I feel myself blushing. "One might even say pretty...Pretty enough to be a girl, in fact."
"Thank you very much, sir."
"And I'm bound to say, pretty enough to be put in pink panties - perhaps?" Mr Forrest raises his eyebrows. "Hmm?"
"I don't know about that sir"
"Oh well, just an idea. Maybe some other time."
My cock is really hard and uncomfortable now.
He smiles and presses my head into his lap. I can his feel mounting excitement against my flaming cheeks. I turn my head and nuzzle into his crotch, smelling his heat and growing tension inside his pin-striped trousers.
"I know how much you'd like to satisfy your curiosity,," he says, in a quiet but authoritive voice.
"I'd give anything to see your magnificent weapon, sir."
"If I show it to you, and you comply with my request, I will wipe the slate clean. How would that be?"
"Thank you, headmaster. I so much want to please you, but I'm frightened I might not be able to manage it - you being so big?"
"I have every confidence that you will not let me down. Now unbutton me and see for yourself."
I do what he says, my hands shaking uncontrollably, fumbling with his fly buttons, popping them one by one. I thrust my hand in, through the gap in his pants, feeling him. Oh, what such sweet pleasure. My guts just melt. He is enormous and I have trouble freeing him. Finally I manage to pull his monster out and there it is, springing up in front of me, an ivory column of creamy-brown and pink flesh, marbled with engorged blue-veins. My breath catches and, oh my God, I am absolutely awestruck. What a beauty! This was no unfounded rumour. Mr Forrest, Headmaster of St. Peters and superhero to boot!
I lick the purple knob while I look up into his compelling eyes. I taste something slick and sweet. His eyes close slowly and he moans contentedly. I begin sucking in earnest but it makes me gag.
"Careful," he says. "When you get used to it, you can suck me hard and make lots of noise. I like it that way."
"Yes sir!"
"I'm sure you'll be better than the others, so don't worry my boy."
Gradually I get used to taking more of him into my mouth, resisting the urge to gag as his monster cock stretches my cheek and touches the back of my throat. I swirl my tongue around it, the sweetness of the tip giving way to the saltiness of taught foreskin and soon he is moving in sync with me, as if I'm orchestrating his lust. I sense a definite shifting of power. Now it seems as if I am holding the upper hand. What an intoxicating feeling of control!
Soon he is bucking and I feel his shaft pulsing and the cum bubbling up from his balls as he spurts into my mouth. It's a warm, bitter taste, slightly peppery, burning my throat as I swallow every drop of the savoury cream.
He says I'm the best boy he's ever had and asks whether I'd like him to do it to me? I'm so worked up and excited that I can hardly get the words out quick enough to agree. He tells me to stand in front of him with my hands on my head. He gets my cock out, feels me up a bit, takes me in his mouth and proceeds to suck me to a fantastic climax inside 30 seconds.
But he doesn't stop there. He sucks me until I come twice more (all the time meanwhile, I have to keep my hands on my head. For some reason this turns him on) before he finally lets me rest.
Then suddenly he resumes his officious manner and tells me to get up and tidy my clothing. He offers me a clean hankie to wipe myself before dismissing me as if nothing has happened.
I always feel a bit guilty after making myself cum to this fantasy, but the guilt soon passes. It's still one of my favourites. I sometimes wonder about the headmaster, where he is now, what happened to him. He'd be very old now of course -- if he's still around that is.
END