The evening of your next trip to the Housemaster's office comes around with alarming swiftness, made worse by his seeming omnipresence the week leading up to said visit.
For an entire week, it seemed as if Housemaster Michaelis was following you, showing up at the most unexpected of times to check up on you (and your fellow students, though you suspect he didn't pay them half as much mind as he did you). He'd made a habit of pulling you to one side at least three times a day, questioning you on your 'homework', and teasing you with all the thing he apparently has planned for tonight.
'It must be hard, having to abstain from touching yourself.' He'd said two days ago, his voice dropping with sin. 'I bet the slightest touch could have you calling out my name. Perhaps I should drag you into the nearest alcove and play with you a while. Doesn't that sound like fun?' You'd rejected the offer immediately, knowing it to be a test.
Instead of being rewarded for your patience, you'd received a few strokes of the cane, the strikes not as intense as before due to your clothing. If only he'd yanked your trousers down beforehand, you could have had some real fun…
Anyway, that was then, and this is now. Right now, you're outside Housemaster Michaelis' office door, your fist a second away from making contact with the wood. What does he have in store for you tonight? After last time, you're inclined to believe that he's going to deflower you tonight. After all, why else does he want you in his private quarters? It must be a special occasion, and you can't think of anything more special than having a man take you for the first time…
The door opens before you get the chance to knock, your hand freezing in midair in shock.
In the door's place is your Housemaster, his face the very picture of sin. His mouth twists into a licentious smile as his weed roam over your body, clearly assessing you for some reason. 'Perfect. Exactly on time. Oh, but you do look appetising tonight. My room is this way. If you would follow me…' he stands aside, gesturing you into the room. Your legs move of their own free will, body already anticipating Housemaster Michaelis' next move.
His next move turns out to be locking the door, before walking over to a near identical door located the other side of his office. You follow him as instructed, up a flight of stairs and into his private room.
There's a second door on this floor, one that separates it from the stairs. He locks that one too, ensuring your total privacy for the evening.
With your privacy sorted, the Housemaster approaches you again, before uttering a single command.
'Strip.'
It takes a few seconds for his words to register. No one has seen you naked since your nanny bathed you as a child! Yet here you are, being asked to strip by a man who's blackmailing you into doing so. For the sake of your honour and decency, you should leave this place.
Honour and decency make no move to stop your arms as they begins removing your uniform.
Blackmail or not, there's something about Housemaster Michaelis that you find utterly hypnotic. Your body doesn't feel like your own when he's around; it answers to his commands in a way that it's never once answered to yours. After all, if it had listened to you, you'd have probably left by now.
You start with your top half, pushing your blazer away without a second thought. Then comes your shirt and tie, once again easily disposed of. The only difficult thing to remove is your binding, something which Housemaster Michaelis is now glaring at.
He shakes his head at you. 'This in and of itself should be a punishable offence. You dare to hide your breasts from the world? From me? Oh, but I am going to punish for it anyhow. After all, this is my room; I am the one in control. Now, I want these bindings gone by the time I've fetched the instrument of my punishment. If they're not, you'll earn an additional punishment. Understood?' You nod furiously, trying to remove them in record time. Knowing your luck, a second punishment will mean orgasm denial, and there's no way you could cope with that. Housemaster Michaelis has opened a need within you; if he doesn't fulfil it, you don't know what you'll do.
Thankfully, these last few years have made you a master of binding application and removal, meaning that you manage to finish your task first.
When he notices this, the Housemaster pouts. 'Pity. I was looking forward to caning you again. Never mind…' he shows you the object he plans to punish you with; they look like thumbscrews with a small chain on the end.
The Housemaster smirks at your evident confusion. 'They're for your nipples, in case you were wondering. One on each, to be tightened and loosen as I so will it. I also have a set where the two claps are connected, but these will do for now. Now, if you'd kindly sit on the bed, we can begin.' That may sound like a request, but you're certain he means it as a command; fail to do what he says, and he'll make you do it, then punish you for disobedience.
Dutifully, you sit on the Housemaster's bed. The bed itself is a four poster, the wood covered in ornate carving that may be as old as the school itself. You'd love to flop down onto it and sink into the mattress, but you're certain that would earn you a caning, so you resist the urge. Instead, you've sat yourself right on the edge, and put your arms behind your back, puffing your chest out in Housemaster Michaelis' direction.
The Housemaster smiles. 'Oh my, but aren't you being good this evening. I think you're expecting an extra special reward tonight. Tell me, have you touched yourself at all since our last meeting?' You shake your head, too excited to form words. You just know you'll be getting a special treat tonight…
To your shock, the Housemaster frowns at you. 'Oh dear. You've just ruined your streak. You see, when I ask you a question, I expect an answer. Nodding at me like an imbecile is not an answer. I'm now beginning to rethink giving you that reward I thought you wanted so desperately. Such a pity. I was going to have you screaming my name and everything. Perhaps it would be best if you left now.' What? He's kicking you out? Just because you didn't answer his question verbally? What does that mean did your situation? Is he going to tell the Headmaster?!
Terrified he'll do just that, you decide to plead with him. 'I'm so sorry, Sir. I should have given you a proper answer. Please don't kick me out. I'll make it up to you.' His eyes gleam menacingly, and you realise you've just fallen into a trap…
Keeping his gaze firmly set on you, the Housemaster gives his orders. 'I have the perfect apology in mind for such an indiscretion as it happens, one I know you'll be happy to dish out. But first, I think it's time I showed you how these go on.' He holds up the clamps in his hand, tangling then in your direction. Anticipation shoots through you; you only hope they aren't as painful as they sound.
Before you have time to ask that very thing, Housemaster Michaelis launches himself at you, his mouth covering your nipple completely before he starts teasing it with his teeth.
You squirm helplessly on the bed, trying to create friction between your legs. The feeling of have your nipple teased and nipped is foreign yet wonderful, and the lust that flows through is intense. You're about to consider rubbing your crotch against the Housemaster's body when he pulls away, once again dangling one of the clams in front of you.
Headmaster Michaelis admires his handiwork before smirking at you. 'Perfection. I need your nipples hard, or else getting these clams on will be next to impossible.
'Now then, I'm going to place the first one on now. I shan't make it too tight, but should you misbehave, do not think for a moment I won't tighten it. Understand?' You should probably give him a verbal answer this time, given how poorly he took your nodding a moment ago…
Your voice doesn't sound as confident as you'd like it to when you answer. 'I understand, Sir. I promise I'll be good now. I'm still hoping I can earn a reward, after all.' You're about to flutter your eyelashes, but you think better of it, knowing that such a thing would probably irritate the Housemaster.
Your response earns you a smirk. 'We shall see. Now then, this may pinch a bit. Feel free to tell me if it hurts; I shan't stop, but I am curious as to how well you can take certain things.' With that, he brings one of the clamps to your nipple, places the sensitive flesh between the two clamp heads, and begins to trap your nipple inside.
It pinches, that much become obvious immediately. You're half concerned it'll cut off the circulation, but you trust that your Housemaster will be watching for signs of such a thing.
Trust? More like hope…
As you get used to the foreign object around your nipple, your Housemaster assaults its twin, though this time he decides to slip a hand between your legs, teasing you through the fabric of your trousers. This man will surely be the death of you tonight…
When your other nipple is ready, Housemaster Michaelis clamps it too, just as firmly as he did the first. It feels just as unusual too; these are not something you could ever see yourself fully comfortable wearing.
With both clamps in place, Housemaster Michaelis stands before you, his eyes hungrily devouring your body. 'Delicious. I could stare at you all day. If the other males in this school got so much as a glimpse of you now, you'd spend the rest of your academic life in the centre of a never-ending orgy. Oh, but I suppose you don't know what that is, do you? Perhaps I'll explain later.' Given the context, you're willing to bet it involves halving people look at you while they pleasure themselves or something. Unless it's more involved…
No, it couldn't be! How are you supposed to have sex with more than one person at a time? It just doesn't make sense.
Apparently tired of merely looking, Housemaster Michaelis places a hand under your chin, and uses it to make sure you maintain eye contact as he speaks. 'Now that you're new toys are in place, you can finish undressing. Then, I want you on your hands and knees, legs parted enough to show me your vaginal opening. I plan to reunite you with some friends of yours tonight; they've missed you.' Friends? What friends? You have no friends, not that he could have with him right now!
That's not what concerns you right now though; you're more concerned about what Housemaster Michaelis didn't say.
As you stand and remove the remainder of your clothing (nipples aching every time you bend over), you ask a question. 'Am I to get down on all fours on the floor or on the bed, Sir?' You're aware he's yet to punish your for your lack of words; perhaps having you on all fours on the floor is that punishment.
Your concerned your question will earn you a slap or something; all it earns is a slight smile and an answer. 'As much as I'd love to see you crawling on the ground like a common whore, I fear it would be detrimental to my plans. You are therefore permitted to return to the bed. Oh, and make sure that you are facing me, rather than the headboard.' He doesn't ask for confirmation that you understand him, which is a relief; you're not sure if your voice even works after that he just said. Is it wrong that hearing such words from your Housemaster's mouth is a tremendous turn on?
When you're finally naked, you get into position, watching your Housemaster as he retrieves something from across the room. Your heart stops as you realise what he meant by 'friends of yours'…
… it's the wooden poles from your last visit.
You count them quickly; it looks like he still has all five. Does that means he's going to see how many you can fit? Or will he pushing you by putting them all inside? You're beginning to panic now…
Said panic must be evident, as your Housemaster immediately reassures you. 'Recognise these, I see. Well, fear not. You've already proven yourself capable of three, so tonight, I intend to stick four things inside you. If you can take that, I'll give you that reward you're so desperate for. If not, then prepare to be disappointed.' This isn't fair! You had trouble doing three not so long ago, now you have to take four?! This punishment isn't fair! Then again, neither is blackmailing someone, but that didn't stop him from doing just that the moment you were formally introduced. You're going to be so sore in the morning…
Without another word, your Housemaster walks behind you, and runs a finger over you opening. 'You're not nearly as wet as I'd though you'd be. Are you truly that nervous? Or have I yet to do anything to excite you sufficiently?' You can't see his face, but you can picture the pout he's almost certainly doing. You could destroy his ego right now, if you had a mind to.
Regrettably, you lack your Housemaster's sadistic streak, so you answer truthfully. 'It's nerves, Sir. I'm still so new to all of this.' You're mostly just relieved that nobody else knows about these 'meetings'. If your father knew what you'd been up to, he'd disown you, family business be damned!
The room is filled with silence for a moment. Then, without warning, Housemaster Michaelis begins teasing your opening with his fingers, before leaning his head in closer to yours.
His voice resonates with sin. 'You'd do well not to remind me of your inexperience. Oh, but how I crave taking it from you. My mind is constantly consumed by thoughts of you, and how I'm going to ruin you completely. I've considered deflowering you on my desk, in the library, in my bed… I've even considered sneaking into the Headmaster's office with you, just to add danger to the situation. There is one thought that I enjoy the most though. Shall I tell you what that is?' It takes everything you have to choke out the word 'please', which is mercifully enough to keep the Housemaster talking. 'Alright then. The fantasy that consumes me the most is one in which I sneak into your dorm at night, crawl into your bed, wake you with a few harsh nips to your neck, and steal your innocence like a thief in the night, right underneath the noses of everyone in your dorm. It would surely make for delightful viewing, watching you stifle your moans for fear of waking them. I'd still try to tease them from you, but you wouldn't give in, would you? You'd keep your pretty little mouth closed, for fear of everyone finding out the truth. That is your greatest weakness, after all. Well, that and some basic stimulation, it would seem; you're positively dripping now.' He slips a finger inside to illustrate his point, and your whole face reddens at the obscene noise that follows.
Housemaster Michaelis removes his finger just as quickly as it put it in, before placing the digit in front of your face. 'Suck.' You can't do it. He can't honestly expect you to taste yourself, can he? That's obscene!
When you make no move to obey, Housemaster Michaelis moves his hands down to your breasts, tightening both clamps. You wince, unprepared for such a sensation. As sore as it's made your nipples, you can't deny that the sensation is fast becoming quite enjoyable…
Unable to contain yourself, you let out a moan, something which seems to anger your Housemaster. 'The point of a punishment is that you're supposed to hate it. I fear I've underestimated just how much of a whore you are. Now, you can either taste yourself, or I can tighten those clamps until it's cuts off your circulation. I doubt you'll be moaning when you have to see the nurse tomorrow, now will you? So, I'll tell you one more time; suck.' He places his finger barely an inch from your lips, and this time you comply, closing your eyes in embarrassment.
To your great surprise, it's not as unbearable as you'd thought. It's not the most pleasant taste, but it's tolerable. If you had to do it again, you would.
Satisfied, Housemaster Michaelis withdraws his finger, wiping it off on your bottom lip. He doesn't say another word, but you can hear the sound of wood hitting wood behind you; he must be preparing those 'toys' of his.
Sure enough, within seconds he has one of them buried within you, it's tip nudging the entrance to your womb again.
It feels much the same as it did last time, a great surprise given the lack of external lubrication; you really must be 'dripping', in that case.
Apparently feeling sadistic tonight, Housemaster Michaelis twists the object inside you, a low chuckle escaping his throat as you cry out at the sensation. You can't decide if it feels right or wrong, but one thing is certain; it feels so good.
Satisfied that you're handling it well, Housemaster Michaelis inserts another one, once again pushing it fully inside. The stretch aches a little this time, but it's not quite as hideous as it was last time. Maybe you'll be able to take three, after all…
As soon as the third one slips inside, you know such an assumption was a mistake.
It still aches just as much as it did the other day. The stretch is too much. How are you supposed to take four of them? It's still too much too quick. You just can't do it!
To your great relief, Housemaster Michaelis stands, leaving the two spare poles on the bed. He stalks around the bed slowly, taking in your current state. You can see a bulge forming at the front of his trousers, a clear sign that he very much likes what he sees.
When his viewing is complete, Housemaster Michaelis stands before you, his trademark smirk in place on his lips. 'Days like this, I really wish I had one of those newfangled camera machines. Oh, but how I'd love to commemorate this occasion with a photograph. It's just as well I have a perfect memory, really.
'Well, now that I have you ready, I think it's time I gave you that punishment.' His unzips his trousers and pulls his underwear down enough to reveal his erection, the very tip of it leaking in anticipation. 'I believe I told you I'd be placing four things inside you. In case your current state has destroyed any cognitive functionality, this is number four. I think this is a fitting punishment for you; you refused to use your mouth to answer me, so now, I'm going to use your mouth. So, be a good girl, and open wide. Oh, and I still expect you to swallow down every last drop of my release. As much as I'd love to see you covered in my release, that's a sight for another day.' He walks closer to you, and you open your mouth as requested. You wonder if it'll be the same as it was last time. Does he expect you to tease him with your tongue? Should you position it as such? Maybe you should as-
Before you get the chance to even consider asking, Housemaster Michaelis unceremoniously shoves himself inside your open mouth, causing you to gag. He gives you a few seconds to get over it before slipping out and ramming himself back in, his hand grabbing a handful of your hair to keep your head in position.
From there on out, his pace is brutal, Housemaster Michaelis forgoing you comfort in favour of pleasuring himself with your mouth. The force of his movement makes your whole body shake, bringing your attention to your nipples; they feel amazing. It's like someone is underneath your body, teasing and tugging them constantly. It's sending a mass of heat straight to your groin, something that's somehow made even better by the wooden things inside you. If this is what sex feels like, you're tired of being a virgin. You crave having Housemaster Michaelis inside of you, any aching or pain be damned. If only you had something stimulating that little bundle of nerves above your opening. Just a few brushes of something against that, and you'd fall apart in seconds.
Housemaster Michaelis seems to realise this, as his voice sounds out above you, his tone remarkably calm and collected given where his erection is. 'I imagine you're desperate for release right now, aren't you? I bet you'd do anything I wanted in exchange for something to rub your clitoris against. Well, as your behaviour has been… acceptable, I think you've earned a reward. However, I'm not going to give it to you. You have until I fill your mouth with my essence to push yourself over the edge. Fail to do so, and I'll spend the rest of the night denying you release until you beg for me to fill you up properly. Your time starts now. Best of luck.' Bastard! That's a cruel task, evil almost. What if the pressure is too much? What if you can't finish? You're going to have to think fast…
Oh. Your hand! If you're careful, you can balance yourself on one hand, while pleasuring yourself with the other! It's going to be a challenge, but you have to try, before your Housemaster drives you insane with his torturous plan.
Cautiously, you place your weight on one hand before taking the other away, directing it at your clitoris. Your body sways around worryingly, and for a moment you're convinced you're going to collapse. That is, until Housemaster Michaelis intervenes, using the hand not already threaded in your hair to keep you upright.
His small act of mercy ends up being your saving grace; no longer concerned about falling over, you begin pleasuring yourself in earnest.
It takes less than a minute for you to fall apart.
It's just as well you were so swift; your Housemaster finishes seconds after, filling your mouth with his release.
Satisfied and exhausted, it takes all of your strength to stop yourself collapsing into a heap on the bed. The same can't be said of Housemaster Michaelis, who tucks himself back in without so much as a tired sigh, before walking down your body to remove the objects still nestled inside you.
When they're all removed, he helps you to lie on your back, getting you comfortable before removing the clamps. They tingle like mad as the blood starts rushing back into them properly, something that seems to spike your arousal again. Not that you intend to act on it; right now, you're struggling to do anything more taxing than lying down.
With everything removed, Housemaster Michaelis manages to get you under the covers, a fond smile on his face. His voice seems softer now; whether it actually is, or if it's just that your body is so tired you can't ear properly, you can't say.
You definitely hear his word though. 'Rest now. You were extraordinary tonight. I have a few papers to review, so I'll be sitting just over there.' He gestured to a desk you hadn't noticed before. Why does he have a desk in here if his office is literally a small flight of stairs away? 'Should you wake to find yourself in need of a glass of water or the like, you have but to ask. You indulged me wonderfully tonight; if I can indulge you at all, just say the word.' Is that so? Normally, you'd be too afraid to ask for anything. However, given that your mind isn't all there still, you decide to push your luck.
You give your Housemaster a sleepy smile. 'Does that mean you'll wake me with a cup of tea?' You doubt it. He's just using you, after all; if he really cared, he wouldn't be blackmailing you.
Still, your request earns you a smile. 'A cup of tea for the lady it is. In fact, as you've been so good to me, I may even bring you breakfast in bed. However, that is tomorrow, and this is now. Right now, the only thing you should concern yourself with is sleep. I hope you find my bed to your liking. If not, then that's unfortunate, as you'll be seeing rather a lot of it in the coming months.' He leans down, and does something you'd never expected; he kisses you once on the lips. It lasts for barely a moment, but you can feel your lips tingling long after the fact. Is this becoming more than blackmail?
You have no time to think on it further, as you soon find yourself drifting off into a deep sleep.