It's six by the time you finally return to the Housemaster's door.
After taking the shower you'd been all but ordered to have, you'd managed to catch the tail end of the cricket practice.
As suspected, your house was quite abysmal once again.
Still, it wasn't a total waste of an hour or so; The Housemaster's eyes never seemed to leave your body for long. It makes you almost certain that you're still on for tonight…
You knock confidently on the door, knowing that no one will be around to hear you. Even if they were, it's hardly suspicious; you'll just tell them he's forcing you to do paperwork again.
The door opens only a moment after your hand leaves it, revealing The Housemaster, a salacious smile on his face. 'Come in.' His voice is impossibly low and dangerous, sending shivers of pleasure racing down your spine. So, he still wants you then…
The moment you enter the room, you're forced against the door, the Housemaster locking it practiced ease as he brings his mouth to your ear. 'You've showered since I last saw you. Trying to wash away the sin, were you? A pity that no amount of water shall ever truly cleanse you now. Unless you intend to bathe in holy water, but by the time we are done here tonight, I fear that it would burn your skin.' You shiver with delight, knees almost giving in. He still very much wants you, that much is obvious now…
Feeling bold, you begin to tease the buttons of the Housemaster's shirt open. 'If I wanted to clear myself of sin, I wouldn't have returned to you tonight, Sebastian.' While it's only the second time, you've ever spoken his name, it feels almost familiar on your tongue, like a promise between lovers.
Your Housemaster, Sebastian, groans. 'I must say, I'm delighted with this monster of mine. When first we met, you'd never so much as touched yourself. Now you're here, all but begging me to rob you of your inexperience. Ah, but I suppose I do have a right to claim it. I've spent so much time cultivating you, teasing you out of your shell…' One of his hands slides into your underwear, and he gives you a few teasing strokes before sliding a finger into you. 'I was half-expecting to find you dry and unyielding. A lot of women find it difficult to become aroused under such a situation. It's common to be nervous about feeling a man inside of you for the first time. Not you though. You know that I won't do anything to hurt you. All of this training hasn't been for nothing. I want to make this painless for you if I can. After all, you've been such a good little whore, it really is the least I can do…' His thumb begins to stroke your clit as he slowly moves his finger in and out, his movements even and precise.
You cry out in pleasure, only to find a hand pushed against your mouth. 'Be quiet for me, now. I don't want any interruptions. I am going to take what is mine this time, and nothing will stop me. You came here tonight knowing full well what I had planned, and that is a good enough reason for me to believe that you want this. You lost your chance to back out the moment you knocked on my door. You're mine, now; do you understand?' He twists his finger, and you moan into his hand. How does he expect you to me quiet?!
In answer to his question, you nod your head, and he rewards you with a second finger. You manage to stifle yourself this time, which seems to spur him on, his fingers moving faster.
As your legs begin to twitch and writhe at the feeling of an oncoming orgasm, you expect Housemaster Michaelis to stop, to leave you hanging as he had earlier.
Instead, he whispers to you again. 'Oh, but I am torn. Do I deny you this pleasure, so that the feeling of your virginal muscles contracting in ecstasy is enjoyed by this desperate erection of mine?' He rubs his crotch against your leg, letting you feel just how much he wants you. 'Or shall I allow you to reach an end, so that I may take my pleasure later with no regard for yours? What a terrible choice I must make. Tell me, when was your last orgasm?' He takes his hand away, clearly expecting an answer.
What do you tell him?!
With his fingers thrusting in and out, and his thumb's merciless teasing of your clit, lying is surely impossible. Yet telling him the truth…
In a breathy whisper, you create a merger of the two. 'After I left here. I… I touched myself in the shower.' Fuck, you hope he believes you…
Housemaster Michaelis groans, his hand moving faster. 'Oh, did you now? Did you finger yourself like this? Did you imagine me inside of you? Details, now.' He slides in a third finger, and you realise you've backed yourself into a corner.
So, you tell him another half-truth. 'I… I fingered… not my…' it would be easier to admit if you weren't on the verge of an orgasm…
Without warning, The Housemaster tears your uniform apart with his spare hand, the buttons of your shirt spilling onto the floor. Your bindings are yanked off forcefully, his mouth claiming a breast the second it appears. You have to stop yourself screaming as your climax hits without warning, your hips thrusting into His hand erratically.
The moment he's sure your done, Housemaster Michaelis picks you up, unceremoniously throwing you over his shoulder as he all but sprints up to his room.
You find yourself thrown onto your back in the centre of the bed without care, as strong hands make remarkably quick work of the remainder of your clothing.
Once your clothes are disposed of, you're flipped over, your legs are dragged off of the bed, and a sharp smack is delivered to one cheek.
You stifle the sound, only to have your hair pulled roughly. 'We're in my domain now; no one can hear you scream except me, and I want to hear it all.' Your head falls down with a sudden thump as he lets go, only to hit your ass again.
This time, you cry out properly.
A dark chuckle sounds behind you, as both the Housemaster's hands grab your hips. 'Yes, perfect. I bet he doesn't make you scream like this, does he? The Headmaster doesn't make you moan like can.' All the blood drains away from your face; he knows?!
Oh fuck!
Sebastian's nails dig into your skin painfully, hard enough to draw blood in some places. 'Did you honestly think I wouldn't find out? That I wouldn't be able to smell his filth all over you? Or hear the lies on your tongue? You give me far too little credit, my sweet little whore.' You're sure he's leaving bruises along side the nail marks now. There's no escaping his grasp. If he holds you any tighter, he'll break your hips.
Terrified, you begin to sob. 'He-he's blackmailing me. Said if I don't do as he asks he-'
Sebastian's grip on you softens, and a hand moves to stroke your hair, stopping you mid-sentence. 'Shush now, it's alright. I'm disappointed that you lied to me, but I understand. I suppose he asked you to spy on me, did he? He suspects I'm here under false pretences?' You nod into the bed. 'I see. I suspected as much. The young master isn't going to be pleased…' Even through your tears, you understand that his sentence is off.
Trying to find clarity, you choke out more words. 'Wh-aht youn-g master?' One of the other boys? That would explain why the Headmaster has started his search at the ground level so to speak…
Sebastian tuts. 'That's unimportant to you. For now, I need details. This is twice now that dreadful man has managed to ruin my plans for you; I need to know the exact nature of your agreement with him. I want full disclosure. This is your one chance at forgiveness from me. Keep anything from me now, and I'll use you as my personal sex toy for a solid week before I feed you to the lions. Believe me when I say, you'll do better remaining as my whore.' You're curious as to what the difference is, but you get the feeling you won't like the answer.
So indeed, you come clean. 'He wants me to spy on you. To give him information. He wants to know why you're here, who you're with… and what we do together. He also expect me to… he wants me to be his whore too.' While he might not have specified that, his intentions seem clear enough; he's just as interested in your body as the man standing behind you.
You swear you can hear a vein burst in Sebastian's face. 'Where has he touched you? What has he done to you?!' You can feel the rage coming off of his body, and you thank everyone you can think of that the Headmaster hasn't beaten him to your virginity.
Taking a deep breath, you try to hide your embarrassment long enough to confess properly. 'He's touched my breasts, rubbed himself against my… against my vulva, and stuck fingers in the place I said I had earlier. I'm so sorry for lying to you, but he told me that if you found out, I'd be expelled, so I had no choice. Please, have mercy on me.' His idea of mercy is probably an average man's idea of punishment, but you'll take it over what he could do to you…
The air is tense and silent for a moment, before you finally hear a sigh of relief. 'For a moment there, I worried I had been robbed of my prize. I would have taken no responsibility for my actions had that happened. I would have broken both of you for such a thing. As it is…
'He's what you're going to do for me. I'm going to tell you what to report. You'll feed the Headmaster information, on the condition that he never touches what's mine again. If he rejects that, or threatens you with expulsion, I want you to call his bluff, and threaten to tell me everything. If that still isn't enough to discourage him, then I'll take matters into my own hands, but I'd like to avoid that if I can. Are we clear on this?' It's really that easy? He's not going to hurt you? Not going to blow your cover completely?
While your sobs may have subsided, fresh tears spill down your cheeks. 'Thank you, sir. Thank you. I was so scared of what you'd do to me. I swear, he'll never touch me again.' It might be tough, but you'll follow your orders, and hope that the Headmaster isn't as good at sniffing out a liar as the Housemaster is.
Sebastian's hands both settle on your ass, giving both cheeks a fire squeeze. 'If you'd like to thank me properly, you know what you can do.' Under his slender fingers, you can feel your dying arousal bring itself back to life.
Still, best to clarify that he still wants what you think he does. 'Tell me how to please you, sir. I'll do anything to make this right. Do you want my mouth? My breasts? Or do you plan to take me… in the more conventional way?' One day, you'll get over your inability to name your own genitalia, but for now…
Sebastian hums. 'You know, I'm not certain. It feels… wrong, claiming my prize while you have tears in your eyes. Then again, I have never been one to care for right and wrong, and you do smell so irresistible…' He slides a hand between your legs again, pleased that you're still wet. 'I have no intention of wasting my chance, or else I may yet lose you to that thing parading as Headmaster.' He grabs your thighs then, spreading them as wide as he can before pining them on the bed. You've never felt quite so exposed as this; you'd be lying if you said you didn't like it.
His voice is dangerously low now. 'Eyes forward, legs wide. I've told you this before, and I'll tell you again; move, and there will be consequences.' You don't doubt that there would be serious consequences, if the mood took him. You'd be wise to obey him on this; you've already pushed your luck with him way past it's normal capacity. Anyone else would certainly not be shown this level of mercy…
Content that you'll do as he instructed, Sebastian strokes your opening a few times, before sliding two of his fingers inside of you again. They move with purpose, determined to stretch you in preparation for a much bigger intrusion. You let out a wanton moan as the thought crosses your mind; he won't be kept from his prize tonight. In a matter of moments, he'll be inside of you, filling you right to the brim with his almost fearsome erection. Will it hurt? Will he take the time to be gentle? Or will he simply take from you what he wants without care, use your body as little more than a glorified sleeve for his cock?
You think you finally understand the difference between being his toy and being his whore.
As if to drive the point home, Sebastian pulls out briefly, walking across the room just out of view before dangling a familiar bottle in front of your eyes; the lubricant.
When you gasp in surprise, he chuckles. 'I'm uncertain where this shock of yours comes from. Did I not tell you of my intentions the last time I had you in this position? While I may have acted with haste earlier, tonight I act only with purpose. I will allow you to remain pure no longer. I shall make sure you're suitably lubricated, then I shall end my self-inflicted torment.
'I should have had you on my desk the moment I reddened this beautiful backside with my cane. This game of ours has been fun, but the ache in my groin, and the desire to rectify my mistake every time you come into view has been agony for me. At least now I shan't have to control myself for long. A few gentle sessions at first, but then I shall hold none of my passion back. You shall always be sated and sore, yet somehow desperate for more. You'll crave me in time. There shall be no other who's touch will ever compete. Only I can ever truly satisfy you; I guarantee that.' As if to make a point of it, Sebastian keeps his hands in front of you as he coats his fingers in lube, even going so far as to make a scissoring motion with them. You cry out in surprise as he thrusts them inside of you, moving with such speed you didn't even register them leaving your field of view.
With his fingers working you for the last time, the Housemaster's other hand also disappears from view, it's departure followed by the sound of trousers being unfastened; he will have his prize tonight, and nothing will stop him.
After what feels like hours of gentle torment, the fingers are slowly withdrawn, and you hear the lubricant being opened and applied again; when his fingers don't return, you assume it's his erection that has been covered in it this time.
Just as you're about to ask, you feel Sebastian position himself at your entrance; this is really it. One last push, and…
Sebastian lowers his mouth to your ear, still primed at your opening. 'This might sting a little at first, but you'll get used to it. Are you ready?' He's… why ask? He's already made it clear that he is going to be inside of you tonight…
You nod, but that isn't enough; Sebastian grabs your hair, forcing your head up a little. 'That is not an answer, and you know it. How do you expect me to take pleasure in this if I don't know it's wanted? Either tell me you want this, or leave. I've no use for a whore who won't speak her mind.' He drops your hair, and you take a moment to regain your position; he did tell you not to move, after all.
Taking a few steadying breaths, you consider your options. While it would almost certainly be within your family's best interest to have a daughter who's still pure, your burning desire for the man behind you, and the hormones raging in your body, you really only have one choice.
So you speak, with what you hope is confidence. 'I'm ready for you. But… please be gentle.' You're hoping that's enough for him; you're not sure there's anything you can say.
To your relief, you hear a faint chuckle. 'But of course. Anything for you.' With those final words, Sebastian's hands grip your already-bruised hips, and you feel him slowly slide inside of you.
As you try to relax your muscles, you close your eyes, focusing on the sensation. It stings, he wasn't lying about that, but it's the most delightful ache you've ever felt. It's too much, you're not sure you can take him, but at the same time, you want nothing more. As he pushes more and more of himself inside of you, the full feeling he gives you is unlike anything else. You're glad he took the time to prepare your body for this moment, because you can only imagine how much more painful it would be otherwise.
When he's finally fully inside of you, Sebastian grunts, and you feel the fabric of his remaining clothes press against your skin as he leans flush against you.
His voice has a foreign softness to it. 'A perfect fit, if I ever found one. Proof that you are indeed the perfect whore for me. I shall give you a moment to adjust, and to stop myself spilling inside of you right here and now.' Is he truly that affected? He must think you feel wonderful…
When the 'moment' ends, Sebastian slowly withdraws himself, before thrusting back in firmly. While you still feel the ache, it begins to become less and less pressing as Sebastian continues his movements. Your legs begin to ache with the strain of being stretched so far, but you ignore it, ignore anything that isn't the man currently claiming you for the first time.
Sebastian's nails dig in again, but this time it's because his thrusts are becoming faster and more forceful. Your mouth hangs open, a stream of moans and screams falling out unbidden, punctuated with the occasional cry of the Housemaster's name. Those are the cries that spur him on the most, that accompany his most forceful thrust.
Almost too soon, you find your body grasping at him frantically, desperate to finish. If only you had a little more stimulation on your clit…
As if reading your mind, Sebastian calls out to you, his voice lower than ever before. 'I can feel you quivering. You seek release, I presume? Then I shall give it to you, but only because I fear I shan't last much longer myself. That, and you've been such a wonderful student, you deserve a treat.' Without another word, one of his hands slips forward to massage your clit, and that's all you need to fall apart, a final exhausted cry of your name forced from your mouth.
Content that you're satisfied, Sebastian finds his own end, thrusting in as deep as he can before allowing himself to release inside of you.
For a few moments, neither of you move, your joint breaths the only sound in the room. Then, with little warning, the Housemaster slides out of you, a trickle of fluids flowing down your thigh. He takes you carefully into his arms, before he settles you into his bed, kissing the top of your head tenderly.
Then, he does something that surprises you; he redresses, finding his discarded lower half and reapplying them quickly. You're confused; you'd always though part of being with someone like this meant sleeping in each other's arms. Does he not want that? Is that too intimate for a whore?
You've answered your own question; he owes you no intimacy. You should just be grateful he's not forcing you back to your dorm like this…
As if reading your mind yet again, Sebastian walks over, smiles softly, and places a finger under your chin, coaxing your chin up so you can look at him. 'Duty calls, I'm afraid. Besides, as I destroyed your uniform, I think it best that I be the one to seek a replacement. I shall return when I'm able, but for now, sleep. If I find you still awake when I return, there's no telling what I might do, and I think your body has had enough of me for one night.' He leans forward, and manages to stop your heart for a second by placing a single kiss on your lips.
Then he's gone, a shadow in the darkness.
As you settle down in the Housemaster's bed, you can help but wish you'd requested a washcloth or something; his sheets are soon going to be completely soiled by your combined fluids. Does he expect you to change the bed for him? Or is he planning to punish you for this?
Either way, you're too tired to care; sleep takes you the moment your eyes close.