You wait about five minutes before crawling out from under Housemaster Michaelis' bed.
You think it's been that long, anyhow, but you're uncertain. Time always seems to pass in a haze after you let that man touch you. It's almost intoxicating the way he makes you feel, and you can't help but crave him more and move every time you see him.
Dressing as quickly as you can with your body still weak with arousal, you manage to make it to the main office without falling down the stairs. A quick peak through his slightly-open door shows that no one has migrated into the common area since you entered the office; except the messenger who stole away your fun, of course. Little git, ruining the moment like that. You were so close to a brand new world of pleasure…
With the coast clear, you leave the office, and begin to contemplate what to do now. You could return to your studies, but you're certain it would be fruitless; you're far too distracted right now. You'd consider showering, but you've no idea how long everyone else will be on the cricket field; the last thing you want is a group of sweaty yet energised men finding a naked woman in their shower room. The thought makes you shudder, but after your fantasy involving the two men already in sexual pursuit of you, you're not sure if it's born of disgust or arousal. Perhaps once you graduate, you'll find a way to explore that side of your sexuality, but for now, you should try to focus on pleasing the two men separately.
Well, as you have nothing else to do with your afternoon, perhaps watching the cricket isn't the worst thing you could do. If nothing else, it'll give you the chance to tease your Housemaster even further. After all, if he claims to have smelt your arousal from his office while you were the other side of a closed door, he should be able to smell you mere meters away in the fresh air. With your body still very much begging for his touch, the smell is bound to be almost unbearable. While it may gain you punishment, it should also guarantee that he'll have you tonight no matter what. The next student to get in his way will surely meet a most unfortunate end; you wouldn't put it past a man willing to so shamelessly abuse his position to net himself a 'whore' to commit a murder.
Now that you know how you'll be spending your day, all that's left is to walk outside.
While you could quite easily take the exit nearest you and walk along the playing fields to the green, you decide to walk down a few more corridors first. The heat rarely agrees with you, and you'd hate the smell of your arousal to be tainted by the stench of sweat. Unless Housemaster Michaelis has some bizarre predilection you're as yet unaware of, you're quite certain it would be quite the turn off.
The corridor in which you find yourself now is eerily silent, given that you know most of these rooms have students in them. Your footsteps, and the faint sound of quill on parchment is all you can here. You're half-expecting a teacher to appear from one of the room and lecture you for being so loud, so you brace yourself for the sound of a door opening.
What you're not bracing for is for a pair of arms to wrap themselves around you, one around your waist and another covering your mouth.
As you try your best to cry out, you're dragged into a nearby alcove, a dark space known to be a favoured spot of students wanting to play truant. From the corridor, you have to squint to see into the darkness, which delights those wishing to hide; but right now, it terrifies you to the core.
That is, until your capture finally whispers to you. 'Stop struggling, alumna. Or would you like us to be discovered?' You immediately stop trying to escape; there's only one person who calls you 'alumna', and he's not likely to hurt you.
Once you're both right at the back of the alcove, the hands settle on your hips, and you can finally speak. 'I though you were helping with cricket practice, sir?' He must have been, surely. How else would he know your Housemaster was missing?
The Headmaster chuckles in your ear. 'I snuck away. I find cricket to be such a dull affair. I'd much rather spend my time listening to you, hearing that you've done as I've asked… you have done as I asked, yes?' With him in such close proximity, and your hormones already going wild, you find it hard to recall exactly what he asked of you.
Somehow, you manage to remember. 'Yes and no, sir. While I've spent time with the man, there is little to report. We were interrupted by that boy you sent moments before we were able to… um…' why can't you say it? You were begging for it a moment ago…
Still, your message seemed to be received loud and clear; the Headmaster slides a hand into your underwear, groaning when he realises the mess you've made of yourself (or rather, the mess the Housemaster has made of you).
Stroking your soaked flesh firmly, the Headmasters voice takes on a firm edge. 'He was almost there, wasn't he? You're all slick, but it's not just your own nectar I'm feeling. He's gotten you all stretched out and lubricated, ready for a man to slide into you and take the final mark of innocence from you. Such thoughtful preparation of you, wasted. I bet he's aching for you, lamenting every wasted second he spends teaching posh brats how to hold a bat properly. What a shame it is, having to leave such a paradise unclaimed. Wouldn't it be a shame to waste such an effort? After all, I have no such obligations anymore. I can see to it that you're filled up nicely. I bet you'd feel amazing, wrapped around my erection. Not to mention how good it would feel, getting to spill myself in you. As wet as you are, I bet it would all come pouring out of you. I'd make you lick up every drop of me you spill. You'd thank me too, wouldn't you? Wouldn't you, alumna?' He moves his fingers to caress your clit, and you're certain that he means every word of what he just said.
Fighting the urge to cry out, you nod your head and close your eyes tightly. 'Y-yes, sir.' If he keeps teasing you like this, you're going to fall apart under his touch…
In response, the Headmaster's free hand tugs at your binding forcefully, one of your breasts coming free. He grabs it tightly, before pulling you against him, making your rub against his erection as you did the last time you saw him.
His voice is hot and heavy, his fading self-control evident in every word that passes through his lips. 'I would do it, you know. I'd gladly send you off to Housemaster Michaelis full of my release. What would he do, do you think? Would he still fuck you, or would he kill me first? Make me pay for spoiling his fun? Maybe I should have my fill of you first. After all, he'd up to no good; maybe this would force his hand.
'However, I happen to like the game we're playing now. Even if it is brand new, I'd hate to spoil it so soon. I like the thought of you coming to me after he's had your fill of you, and letting me drink my fill too, defiling you so fully that all of his work is in vein. Imagine how you'll feel when I fill you up straight after him. Do you think you can take it from two men so soon after each other? I'd make it immediate if I could, but he won't share his toy with me. I think that's so unfair. I'd share you…
'Oh, it's so hard for me to decide what to do! What do you think, alumna? What should I do to you, here in our secret place? Choose carefully mind, because who knows if one of the boys in these rooms will leave to use the bathroom. Whatever you choose, there will be no going back. If we gain an audience, I'll only get faster and more possessive of you. I won't stop for anything, once I have you where I want you. Beg me for something, and I'll make sure you're left satisfied.' How are you supposed to say anything more? You're so hot, so ready, so willing to do anything just to feel release, that you can't even think about forming words right now!
When you stay silent a little too long, the hands on your body move away, and the Headmaster tuts disapprovingly. 'I can't even make my star pupil beg for me. I've lost my touch. I don't think I deserve to sample your sweet, sweet heaven right now. I suppose it'll have to be my second choice, then.' At that moment, you feel fabric move across you mouth before being tied behind your head; he's gagged you.
Unceremoniously, the Headmaster forces you against the wall, keeping your head in place with one hand as he pulls at your hips. Knowing his intentions, you put your arms against the wall and bend at the waist, spreading your legs slightly as a way of presenting yourself.
Satisfied, the Headmaster yanks your trousers and underwear down to your knees, giving your ass a hard slap. 'You're delightful. Inexperience can often get in the way of fun, but you're so eager… But I can't take you like I want. I have to be patient. I still need to know why Housemaster Michaelis is here. I still need you to spy on him. I can't risk my involvement being discovered so soon. But, that doesn't mean I can't teach you a thing or two in the meantime. Tell me, alumna…' the way he says that word sends shivers down your spine this time. '… Do you know what sodomy is?' You moan so loudly against the gag you're scared someone will come to investigate; you know exactly what that means.
You hear a chuckle from behind you. 'I'll take that as a yes. Have you ever tried it?' You shake your head. 'And yet you moan like you're desperate for it. I think you're keen to try it. You're curious, at least. Do you want to try it?' Honestly? You're not sure. You've been told so many times by Housemaster Michaelis to give it no mind until after you've been deflowered that you've put it from your mind.
Yet leaning here, so perfectly on display, in such a perfect position to submit to the every whim of the Headmaster… you'd let him take you in every way he can think of.
Face flushed from your lewd thoughts, you nod. 'I knew it. It's the taboo, isn't it? Allowing the man who holds your future in his hands to finger you is one thing, but to have him sodomise you is the ultimate act of debauchery, isn't it? In truth, I don't think you need a man inside of you to corrupt you; I think your innocence is already long gone now. It was gone the moment you discovered just how wonderful sex can be, no matter what gets stuck where. Tell me I'm wrong.' You can't, and not just because he's gagged you. If he had put you into this position a few weeks ago, you'd have protested. Now all you want is for him to shut up and make good on his words!
Challenging him, you move a hand down to your ass, spreading a cheek to one side to give him a clear view of his target.
The Headmaster grins. 'Perfection.' With that, he slips a hand into his jacket, producing a bottle remarkably similar to the one you've noticed Housemaster Michaelis use. Your suspicion is confirmed when he applies a generous amount to your often-ignored entrance, before he coats a finger with it.
Tentatively, he begins to slide his finger inside of you, and you cry out, the sensation strange yet pleasurable. Your mind is screaming at you, telling you that this is wrong, a sin, and for once you'll agree; only sin could feel this good.
As he begins to work his finger in and out of you slowly, your mind begins racing. The fantasy you had earlier begins to change, as you image Housemaster Michaelis -Sebastian, as he'd make you scream- in front of you, biting into your neck as he relentlessly thrusts into your freshly-deflowered opening. Meanwhile, the Headmaster is behind you, his hands obsessing over the breasts he paid such careful attention to last time as he fills your other hole. The two men are almost brutal with you, desperately competing with each other, each trying to make you scream louder than the other.
Meanwhile, you're busy moaning both names one after the other, so caught up in your own bliss that you don't know who's doing what anymore. All you know is that between them, both men have your body weak and needy, crying out for more, and more, and more…
You barely register the fact that the real Headmaster, the one who has managed to slip a second finger inside of you while you were lost in fantasy, has started to stroke at your clit. It's only when you're whole body convulses violently enough to force tears of pure ecstasy from your eyes that you realise he's teased you to your peak, and you have to fight hard to remain upright as he continues with his relentless assault on your senses.
Then, just as last time, he stops the moment you're done, withdrawing his hands with the most obscenely satisfying noises you've ever heard in your life. He removes the gag from your mouth, and leans in to whisper to you. 'This is twice now that I have allowed myself to remain unsatisfied. I have no doubt that Michaelis intends to pick up tonight where you left off earlier. Am I correct?' You can only nod, too dazed to speak. 'Good. My office, first thing. No detours. No matter what transpires tonight, I shall have my pleasure tomorrow, in whatever form it may come.
'Now, get dressed, and clean yourself up. The boys will be on the green for a good hour yet; you have time. Don't forget why I'm letting you stay here; I need more from you than knowledge of Michaelis' sexual preferences. Bring me something, anything, that will give me a line of inquiry, and you can't even begin to imagine the rewards I'll lavish upon you. Until tomorrow, alumna.' He walks away without another word, leaving you to dress yourself.
No sooner have you corrected your binding, the school bell chimes, indicating the end of class. Is that why the Headmaster left in such a hurry? He didn't want to risk discovery? It makes perfect sense, but then, why start something he couldn't possibly finish?
Well, at least he finished you; you'll take that.
With his last request now more a prerequisite (you need to remove the evidence of him tampering with your body), you make a beeline to the showers, hoping they are as vacant as the Headmaster had indicated.
As the fog of sex slowly clears from your mind, it occurs to you that sometime within the next twenty four hours, one of these men will almost certainly cross that final barrier, and you will cease to be a virgin anymore (though in all honest, after what they've done, you don't feel like much of one anyhow). Who will t be that crosses the line? Michaelis seems the obvious choice, as he is the one you'll be seeing first, but there's no guarantee. He might have changed his mind, might be determined to tease you further.
Then what of the Headmaster? He's made it clear that he doesn't want to make the first move, yet how long will that conviction hold? After all, the man who seemed content to torment your body had almost lost his way just a short while ago; can the Headmaster control his own desires for long?
As you wash away the evidence of your multiple sins, one thing becomes abundantly clear;
This whole situation no longer feels as difficult as used to.