You should go to the Housemaster's room tonight.
It's all but expect from you, with both the man himself and even the Headmaster making it very clear that such a thing is expected of you, for one reason or another.
Then why do you instead find yourself heading to the Headmaster instead?
This is a dreadful mistake. You feel it in every step you take. If you're caught by Housemaster Michaelis, you're dead, or as good as. If he were to discover you making your way into another man's private chambers…
The Headmaster is the one to blame. You would have been more than satisfied with spending the night with the man so carefully instructing you in the ways of sex, had it not been for his stunt in the corridor earlier. Any lingering sensation of the Housemaster's hands on you had been replaced in an instant, these less familiar hands the only ones plaguing your mind. Oh how you long for those clever fingers to touch you again, with ever-growing intimacy and familiarity.
He'll send you away. You're almost certain of it. In his mind, you're an informant first and foremost, despite the lack of information you've actually given him thus far. He's probably only interested in you sexually as a way of getting one over on the Housemaster. In fact, given his earlier comments, you're almost certain that's the only reason he's interested in his 'Alumna'. Why then are you willing to risk so much just to see him?
You wish you knew; your body seems to be the one in control tonight.
So it is with great anxiety that you find yourself facing the door to the Headmaster's office. You're beginning to feel rather foolish now that you're here. Why would he still be in his office at this late hour? Surely his private rooms are located elsewhere. Just because Housemaster Michaelis has his private chambers located in the same area as his office, that doesn't mean it rings true for all the other faculty members. Maybe you should go the Housemaster after all, let him pick up where he left off…
A soft voice catches your attention from behind the door. 'I didn't expect you to come to my door tonight. It's unlocked, if you wish to speak with me privately, Alumna.' Of course he knows you're here. Why wouldn't he? The man is as omnipotent as he is mysterious, in your eyes at least.
Still, it would be rude to reject such an open invitation; you quietly let yourself in, holding your breath until the door clicks shut behind you.
You'd expect to find the Headmaster dressed in his normal garb, head hidden in paperwork as he tirelessly inspects the school's progress and issues. What you don't expect is to find him sat in his dressing gown, sipping tea and reading a paper at his desk. It's the kind of sight you'd expect to see first thing, not at the end of the day! Is he always like this in private?
Your gawking must have been noticed, because the Headmaster sweeps his hair away so he can show you a raised brow. 'Does this disturb you in some way? I'm merely catching up on the day's events in the comfort of my own office. As busy as I am, I seldom get the chance to do so first thing as most do. Or do you dislike the idea that something other than yourself has my full attention?' You'd almost be put off by the pseudo-smug grin on his lips if his whole face wasn't so… distracting. For the sake of women everywhere (and men, come to think of it) you're glad he hides it beneath his hair as it does. It's probably just as much for his own benefit as much as theirs; it must be tiring having people throwing themselves at you every time you look their way. While you've seen him like this before, you can't say it doesn't still do things to you. You can only imagine what it feels like waking up next to him...
You take a deep breath, trying to ignore the hyperactivity in your chest. 'It's just unexpected. As you're still in your office, I was expecting you to be dressed and acting accordingly.' Does that make sense? Are you still forming sentences correctly? You're finding it hard to focus on anything that isn't the man in front of you.
The Headmaster grins. 'Not half as unexpected as a woman coming to visit me in the dead of night. Got lost on your way to Michaelis, did you? Or have you come here to tell me that you refuse to act as my little mole?' Placing his paper and teacup on his desk, the Headmaster leans forward. 'Dare I hope that I'm mistaken? Have you in fact come to me because it feels wrong to enter the bed of another man when I'm playing so heavily on your mind?' You want to tell him that he isn't mistaken, that you're here to fall on your sword and leave the school. The words refuse to leave your mouth; you just can't bring yourself to vocalise such a blatant lie.
When you choke on your answer, the Headmaster approaches you, his movements deliberately slow. It's almost as if he's a fox, closing in on a rabbit. You're not so timid as that; you know that this conversation will only go one of two ways.
Finally reaching you, the Headmaster's hands grasp your hips firmly, bringing your body in close so he can purr his words in your ear. 'I should be furious with you. I gave you strict instructions to visit me tomorrow morning. Have you had collected information from Michaelis already, perhaps? Am I jumping to yet more false conclusions?' Why can't you just speak to him? He's reasonable, or seems it at least. If you could yet tell him that you're here because you'd much rather warm his bed tonight…
Finally, words escape your mouth. 'I couldn't bring myself to go to him tonight. Not after what you did to me.' Just the memory of his fingers touch you in the most sinful way you can fathom has you blushing, and he's certain to notice as much.
The Headmaster chuckles without humour. 'You rather enjoyed that, didn't you? Maybe I should have you bend over the desk so that I can give you the real thing? I can guarantee that you'll prefer it.' His words shouldn't arouse you like they do, but you can't help yourself at this point; he certainly knows how to push your buttons.
Relieved that he seems to have overlooked your disobedience for now, you nod firmly. 'I'd really like that, sir.' Just the thought of doing something like that on his desk is enough that you want to beg him for it, but you doubt you'll need to.
To your great disappointment, the Headmaster sighs. 'I was hoping you'd see that as more of a punishment than a reward. Looks like I shall be having company in my bed tonight. As much as I'd love to uncover all of Michaelis' secrets, he can go back to hell right now. He's been a thorn in my side for longer than I care to mention, so just this once I think I'll take my petty revenge. After all, he's been cultivating you so beautifully, but it would be a shame to see such effort wasted on him. As selfless a man he is, I'm sure he wouldn't mind if I was to see the fruits of his effort for myself.' The sarcasm and sin drips effortlessly from his lips, and you take a deep breath, unknowing of his next move. At least with Michaelis, his intentions are always clear. You have no idea what the Headmaster is thinking; the man is wildly unpredictable. Perhaps that's what makes him so appealing…
Without another word, the Headmaster brings his lips to your neck, coaxing your head to one side to gain better access.
For a man that seems to be out for petty revenge, the Headmaster is surprisingly gentle, his lips a little more than a ghost on your flesh. It contrasts greatly with the way both him and the Housemaster have treated you in the past; the sensation causes shivers down your spine.
Moving his lips back to the shell of your ear, the Headmaster whispers again. 'Follow me, Alumna. It's time you felt the touch of a man that knows what he's doing.' You blush at that, the promise in his voice clear. How many others have given into him? How many virgins has he guided into womanhood? While you're sure Michaelis is experienced, you've never taken a moment to consider that he's been with an unspecified number of other women. Now you're starting to feel insecure, uncertain if you'll match up to the Headmasters' previous lovers…
As the Headmaster pulls away, he grabs both your hands, leading you towards a door you've never noticed before; undoubtedly, the way to his private chambers.
By the time you make it to the door, uncertainty has taken control of your thoughts, your eyes unable to meet the eyes of your soon-to-be lover. Why is it only now that you feel so hesitant? You didn't hesitate earlier when he had his fingers inside your-
The Headmaster places a hand beneath your chin, forcing you to look at him while keeping his other hand in your own. 'Your blush is quite adorable, but your shyness is concerning. Are you having second thoughts?' You're not sure. Should you back out? Tell him this was a dreadful mistake after all? Would he accept that? Would he let you leave?
As you try to piece together your thoughts, you feel a gentle pressure against your lips; the Headmaster kissed you!
The contact is brief, but it's devastating; what were you worried about again?
As you stare at him wide-eyed, the Headmaster sighs. 'Such sweet lips, I just couldn't resist any longer. May I taste them again?' Since when was a kiss as seductive as this? The few times the Housemaster has kissed you were more like encouragements or rewards. Not like this. This almost feels… intimate.
Your eyes have grown heavy with desire, so you close them, your lips parting slightly with a smile. 'Please do.' It barely takes a second to feel his lips on yours again, only this time they stay longer, and the pressure builds from barely a touch to a passionate kiss, his tongue leaving his mouth to push against your lips. Uncertain of what to do, you try to keep your mouth closed, but he's not having it; realising his hold on your hand, he roughly squeezes your ass, making you gasp. He slides his tongue in whilst you're distracted, before coaxing yours into his mouth.
When he finally pulls away for air, the Headmaster is grinning wildly. 'You have such a wonderful mouth. A little persuasion, and it's so willing and lenient. I might like to kiss you more, but I feel you'll be more comfortable on my bed. Shall we?' He's asking you the question, but with his hand is still attached to your ass, all but dragging you along as he lets go of your face to open the door.
It's just as well his kiss eased a lot of your hesitation; it would be a shame to back out now, given how determined you'd been on arrival.
When you're finally in his room, the Headmaster shuts and locks it behind you both, before delicately encouraging you to settle on the bed. You sit there expectantly, looking up at him with curiosity. What now? What does he plan to do with you next? Now that he has you where he wants you, will he just tear your clothes off and take what he wants?
As if reading your unspoken question, the Headmaster begins to lazily undo the buttons on your blazer, before pushing it past your shoulders. He gives your shirt and tie the same careful treatment, leaving your top half covered in nothing but bandages.
The Headmaster frowns. 'I hate these things. It isn't healthy to hide your breasts like this, especially breasts as full as yours. I think I should apologise to them personally, don't you?' Understanding his hidden order, you unwrap the bandages, revealing your breasts to him.
Instantly, the Headmaster pushes his face into them, forcing your back against the bed. He alternates between biting and sucking as his mouth eagerly explores them, carefully avoiding your nipples.
You gasp suddenly, the Headmaster's hand forcefully grabbing your hips as his mouth leaves your body to talk. 'I've missed these so much. Never have I found a pair that match their magnificence. I could spend all day suckling on them like a voracious babe, but I fear then I'd miss out on the reason I'm here. So for now, I want you on your hands and knees so I'm not distracted.' He doesn't give you the chance to position yourself, forcefully grabbing your hips and making your body turn for him. You scramble onto your knees, keenly aware that there's very little separating him from his target.
It becomes even less when he forces your trousers and underwear down together, exposing you to him.
The Headmaster brings his hand down hard on one of your cheeks, and you gasp; you hadn't expected that!
Before you can protest the slap, The Headmaster slips his hands between your legs, testing for wetness. 'Hmmm… not half as wet as I was hoping for. I was half-hoping you'd be so eager for me, I could just slam myself in without a fuss. Maybe I should stick something in your ass? You went wild for that earlier, you filthy girl. Maybe I'll take both tonight, make sure you're beyond ruined for the Housemaster? Would you like me to ruin you? To fuck you in every way I can think of?' What happened to the almost gentlemanly Headmaster from the corridor? He seems so much cruder now…
… You feel a lot wetter now.
The Headmaster seems to notice that, lazily stroking your folds. 'You're a slut for filthy words, are you? Well then, let's see what I can do.
'Why don't I tell you about my darkest fantasy? I think you'll like it. It does involve you, after all.
'I imagine what it would be like, having you as my secretary. I'd make you dress in the shortest cut dress you can imagine, the fabric stopping an inch from your slit. I wouldn't permit you to wear underwear; it would just get in the way. I'd want instant access on a whim, because my job can be oh-so boring, but you are oh-so exciting. Your breasts would be on display too, of course; it's unfair to keep them all hidden away to yourself.' So lost in his words, you barely register that he's got two fingers in you, carefully sliding them in and out of you.
'Oh, the things I'd do to you. Having you constantly available to be is a luxury I'd abuse. I'd make sure you're always wet, always ready for me to fuck you. We could do it all over the school. In the library, the chapel… we could even do it in front of Michaelis. Imagine that. Imagine the look on his face as I fuck you over and over again, filling you with load after load until it starts leaking out with every relentless thrusts, lubricating me so I go deeper and deeper, bring me flush against your cervix as I just keep going and going and going…' You scream at the top of your lungs, an orgasm you weren't even aware of hitting you brutally hard. Your mind begins to alternate between the Headmaster's fantasy and reality, to the point where you're not sure what's happening anymore. Your breathing becomes heavy, mind desperately trying to clear itself.
Before you get a chance, you're vaguely aware of your legs being forced down, so the last of your clothing can be yanked off properly. When it's gone, you instinctively move back into position, spreading your legs a little wider now that you're not restricted. You know what comes next, even in your dazed mind; he'll lubricate you good, then he'll slide himself in. You can hardly wait; if his fingers can break your mind, imagine how incredible the rest of him feels.
You hear the Headmaster's dressing gown fall with a dull thud, before you feel something hard rub between your legs, firm hands gripping your hips.
As his tip presses inside you slightly, the Headmaster whispers to you. 'I knew it. Virgin or no, you're the dirtiest bitch I've ever had my hands on. You're so wet down there, I think you're ready for me. This'll probably sting a bit, but give it time, and you'll love it. If it does get too sore, or if it's too much, I can always switch to plan a; then we can try again later.' One of his fingertips presses lightly into your second opening, a hint at what plan a is. You're so distracted that you don't notice he's pushing forward until he shoves himself inside of you completely, stretching you around him.
You cry out again, but from pleasure or pain you're not sure; you've never felt anything quite like this before.
The Headmaster groans, digging his nails in. 'Shit, you're incredible. I knew you'd feel perfect. Tell me when you're ready for me pound you into the bed; though if I'm honest, I don't think this first round will last long.' Is that… a good thing? You're not sure, and right now, you don't care; you don't care about anything other than the feelings between your legs.
After a few moments, you take a deep breath. 'I think I'm ready for you to move now.' Ready, and if you're honest, craving something beyond the stillness.
The Headmaster doesn't need to be told twice; he doesn't hesitate to pull out and slam back in, with enough force to shake the bed.
His pace is unyielding and harsh, but that only spurs you on; as rough as he is, you can't get enough of him. You only get wetter as his pace continues, one hand leaving your hip to play with the breasts he likes so much.
Biting down hard on your shoulder blade, The Headmaster begins panting out words. 'Incredible. I'm so glad… I'm not sending you off to the Housemaster again. I've changed my mind. I want you here with me. You're mine now, understand? Mine, mine, mine…' His thrusts are becoming uneven, and you realise he must be close to orgasm.
You decide to help him out, doing your best to squeeze yourself around him. 'Yes, sir. All yours.' That's all it takes; he grabs your hips firmly as he thrusts a finally few times, spilling himself inside you.
Somehow keeping himself upright despite his orgasm, the Headmaster strokes your back lazily, your breasts forgotten again. 'So, how was that for a first time? Do you feel more a woman now? Sorry if I got a little carried away… you're just too much for a man to resist.' Does it actually count as over if he doesn't pull out? Because you can still feel him inside of you…
You ask him as much, and the Headmaster just chuckles. 'Oh, but that's right. I'm not finished with you yet. I'll just have to ask you in the morning when I'm finished with you; I hope you don't mind, but you're not leaving here until I'm satisfied I've ruined you for any other man, the Housemaster included. I meant what I said about keeping you; you're too delightful to let go of now that I have you.' He places a gentle kiss onto your spine, and your body shivers.
It's going to be a very long night.