A.N. Hello all! Before we begin, just a quick shout out to my friend LonelyStargazer. She has a Sebastian x OC story called Wicked Game, which has just reached its sixteenth chapter! So, if you want a fantastic Sebastian story with a lot of content, please check it out ^.^
Now, on with the story :)
It's now been a full week since your visit to your housemaster's office. One week of pining, sexual longing, and subtle experimentation late at night in your dorm. You've been set some very interesting homework, and you'd hate your housemaster to think you're not a dedicated study.
However, you've found yourself facing quite the problem; try as you might, you just can't reach climax as instructed.
As soon as you'd left Michaelis' office last week, you'd gone to the showers, hoping to find release there. Yet try as you might, you just couldn't bring yourself to ecstasy as he had the first time you visited his office! Your own hands felt no where near as sensual as his, which had caused you a great deal of frustration. In the end, you were so fixated on your own shortcomings that all of your arousal had dried up, and you found that any friction on your genitals caused you to feel sore, rather than aroused.
After that failure, you've tried every night to bring yourself to climax, but with almost identical results; you get yourself wet, you realise you can't pleasure yourself as well as your housemaster, you lose your arousal. It's beginning to drive you mad, your body so desperate for release. You'd give anything to be able to get yourself off, but you just can't manage it!
That's why, with a great sense of fear and reluctance, you find yourself stood outside his office door yet again, trying to find the courage to tell him you've failed, and to beg him not to reveal your secret as punishment.
You've been outside said office for a good ten minutes now, your hands shaking. You're glad your fellow students are all busy doing things elsewhere, otherwise you'd look very strange indeed. You're not even certain your housemaster is in his office. He could be with the headmaster for all you know, telling him your secret…
No. He wouldn't do that. Not yet, at least…
You take in a deep breath, trying to steel your resolve. Maybe he'll show you mercy if you do what you did last time? Fellatio, was it? Maybe if you offer him that, he'll go easy on you?
Curling your shaking hand into a fist, you raise it aloft, and direct it towards the door.
Before your hand has the chance to touch the wood, you hear a voice from behind it. 'Enter.' You recoil in shock; has he known about your presence all this time?!
After trying to physically shake off your nerves, you do as instructed, entering his office before closing the door behind you.
Contrary to the way he looked last time you visited him, Housemaster Michaelis looks flawlessly tidy. His bow tie is properly affixed to his fully-buttoned shirt, and his spectacles are right back against his face, as opposed to perched on the end of his nose. He looks the very model of propriety; that makes what you've come to talk to him about seem even more depraved.
Housemaster Michaelis smirks at you as always, a familiar twinkle in his eyes. 'Well, well. It seems my favourite pupil has come to pay me a visit. Tell me, did you complete your homework as instructed? You seemed so throughly aroused the last time I saw you, so I doubt you had any issues.' Shit, you really are in for it, aren't you? All these years of education ruined because you couldn't make yourself climax…
Fate is a bitch.
Swallowing reflexively, you hesitate a moment before answering, your voice little more that a whisper. 'Actually, Sir, I- I couldn't do it. I tried so hard, really I did! Every day I tried to make myself reach orgasm, but I just couldn't do it! I- I tried touching myself all over, I tried thinking about you… yet every time without fail I found myself craving your experienced touch, rather than my inexperience one. The frustration always makes me lose any arousal I've built up. I am so, so sorry. I'll do anything to make up for it.' You hang your head in shame. You hope that Housemaster Michaelis knows just how sincere you are, and that you really are willing to do anything to make things right.
Housemaster Michaelis stands, his height greatly intimidating. He walks around his desk, stands in front of you, and uses a single finger to force your eyes up to meet his own.
His voice is as silky smooth as always. 'Dear Girl, it's alright. I have no doubt you tried your very best. Failure is as much a part of learning as success, so you shouldn't feel ashamed. If anything, the thought of you having to come to me in order to find release is quite delightful.' He plants a chaste kiss on your lips, and you feel your heart skip a beat. You're really not in trouble? Thank goodness!
Your housemaster's smirk grows wider. 'Speaking of which, I bet you're desperate for release, aren't you? Well, thankfully I could use a distraction; paperwork is so very tedious. I'll put my papers to one side so you can sit that perfect behind of yours on my desk. It's time for your next lesson. I think you'll enjoy this one.' With that, he removes his finger from beneath your chin, walks back over to his desk, puts his papers to one side as stated, and sits back down, before crooking his finger indicatively. Taking the hint, you walk over to him, and sit on his desk.
Almost immediately, Housemaster Michaelis' hands grab your thighs. 'Now then, lesson three is a practical anatomy lesson, followed by cunnilingus. Do you know what that means?' You've never heard the term before, but you think you can guess.
Trying not to sound as apprehensive as you actually are, you give him your answer. 'Is it a bit like what we did last time, but reversed? So your mouth and my… my… downstairs?' Well, so much for trying to sound confident. You can already feel your face beginning to heat up, and you've not even started your 'lesson'.
Your response earns your thighs a squeeze. 'You are quite correct, girl. However, I would not have but it quite like that. I would have said that cunnilingus is the act of someone placing their head betwixt a woman's thighs and tasting her quim until she begs for mercy. Points for trying, though.
'Now, how about we take off these trousers of yours, hm? I think it's time we commenced this lesson properly.' Without waiting for a response, Housemaster Michaelis moves strait to the fastenings of your trousers.
You can't help but feel a little giddy. Finally, you get the chance for release! You need it so badly it hurts! Even if the man about to pleasure you is technically blackmailing you…
All thought temporarily ceases when you feel the cold air of the room against you now-exposed opening.
You gasp as you feel Housemaster Michaelis run a finger along your slit. 'Still so sensitive. I bet all of your failed attempts at masturbation have you on edge. Now, I'm going to fetch a mirror from my drawer. I'm then going to aim it between these sweet thighs of yours, and teach you all about the female anatomy. Pay close attention, as I'll be testing you the next time I see you. Now then, spread yourself as wide as you can, and put your feet on the desk.' You're glad that he had the foresight to remove your socks and shoes when he took your trousers and underthings, or this would be terribly uncomfortable and slippery. As it is, your bare feet hold firm on the table, as you position yourself as instructed on the desk.
Housemaster Michaelis produces a mirror as stated, and positions it just in front of your opening. You blush as you catch sight of yourself down there for the first time in your life; is that really what your opening looks like?!
A laugh brings you out of your temporary fixation with the image in the mirror. 'Dear me, have you never seen yourself like this before? Such a pity. A quim as beautiful as yours shouldn't be hidden away. It's almost enough to make me tell the headmaster the truth, if only so he'll get the chance to behold it.' You begin to panic at his words, until he continues. 'Alas, I do not share my prey. I am the only one that gets to touch you, just as I shall be the one to take your innocence.' As if to illustrate his point, he pushes his finger inside you, causing you to hiss at the slight ache.
Your reaction earns you a soft kiss on your knee. 'Relax, girl. Your purity shan't be tainted by me today. As tempting as that may be…' You watch in the mirror as he pulls his finger out of you, the obscene act making you even more desperate for release. All you want now is to get this first part over and done with, so that you can learn if your Housemaster is as talented with his tongue as he is his fingers…
Housemaster Michaelis begins by bringing his finger to a small nub a few inches above your opening. 'Now, this delightful little thing is called the clitoris. It's home to over 8000 nerve endings, and is comprised of the clitoral hood and the clitoral glands. Now, what do you feel when I stroke it?' He strokes his finger across it, and you can't help but cry out in pleasure. 'Pleasurable, isn't it? Stimulation of the clitoris is vital during coitus. However, overstimulation is to be avoided at all costs. If you are too rough with it, or toy with it for too long without applying proper lubrication, it becomes sore, and thus causes discomfort that can ruin any kind of sexual enjoyment. I imagine this is one of the problems you've been having.' He strokes it again, and your legs twitch. You hope he knows how much is too much…
Your housemaster's finger moves down slightly. 'These two flaps of skin are your labia minora. They cover and protect your clitoris when you're not aroused, and shift to expose it when you are. You also have their counterpart, the labia majora, which are these thicker ridges here. They serve a similar purpose.' He trails his finger straight past your opening, and onto the piece of skin just below it.
Housemaster Michaelis smiles to himself. 'This is the perineum. It separates your vagina from this hole down here.' His traces his finger around your anus, and you gasp.
His smile transforms into a smirk. 'I'm sure you don't need me to explain what an anus is. However, I will tell you that the anus can be utilised during intercourse, both as a tool to create arousal, and as a point of entry. However, a virgin like you should not be sullied like that. No, I must wait until I have made you a woman before I do that to you.' He brings his finger back up to your opening, ceasing movement just below it.
You feel your body tremble as you watch him circling your opening in the mirror, fascinated by the reflection before you. You've always assumed that your genitals must look horrible, judging by the church's insistence that you must keep them hidden at all times. Yet seeing them like this, being caressed by another… they look quite delightful.
You're quickly snapped out of your thoughts when you feel his finger push inside you once again. 'This is the vaginal opening. This is where the act of sex itself takes place. It was specifically designed to take a man, and take a man you shall. For now though, I think my finger shall suffice.
'So, did you enjoy your guided tour? I hope you were paying attention, as it is your homework for the week to memorise the names of each part. I shall be testing you, of course. Should you succeed, I shall give you a reward. Fail, and I shall have to punish you again. Understood, girl?'
You nod your head in response. That does not go down well.
With a heavy sigh, Housemaster Michaelis forces two more fingers inside you, causing you to cry out in pain; it aches so much!
He begins tutting. 'When I ask you a question, girl, I expect an answer. Now, do you understand?' He twists his fingers, and this time when you cry out it isn't entirely from pain.
You give him the response you assume he's after. 'Yes, Sir. Sorry, Sir. I swear not to do it again, Sir.'
Housemaster Michaelis' smirk returns, and he removes two of his fingers. 'See how easy things are when you behave? I'm beginning to think you need more discipline, rather than a reward. Still, I did promise to demonstrate cunnilingus for you. Now, put your back flat against the desk and close your eyes. You are not to open them until you rach climax. If you do so beforehand, I will drag you off this table and force you to perform fellatio again. Is that understood?'
Not wanting to risk angering him again, you answer verbally. 'Yes, Sir.' You say, a little breathless, before getting into position as instructed. He hasn't told you to move your legs, so you keep them as they are, spread open for him.
As you close your eyes, anticipation washes over you. Will it really feel nice? Will you taste alright? Will he even let you finish as promised?
Suddenly, you feel something wet against your clit, and you begin to lose all semblance of thought.
Housemaster Michaelis swirls his tongue around your clitoris, teasing it with what seems to be practiced grace. Your whole body seems to be heating up in response, and you're certain your arousal must be drenching his finger, as he gently begins moving it in and out of you.
His tongue begins to explore the rest of the area between your legs, flitting to one place before returning to your clit. You can already feel yourself working up towards orgasm, the frustration of failing to climax so many times on your own all seeking to culminate in one final explosion of pleasure. You prey that your orgasm really does come soon; you're not sure how many more failed orgasms you can take.
You feel a vibration against your clit, and realise that your housemaster has started talking. 'That's it, good girl. I don't think it'll be long now. You really shouldn't have waited a whole week to come and see me. Had I known what difficulties you were suffering, I could have helped you sooner. Then again, I suppose the fear of disappointing me kept you away. Probably just as well, really. Had I thought you had not been putting in the right amount of effort, I would have given you another caning.'
Just the thought of him doing that to you again is enough to trigger your release, as you cry out into his office, really hoping that no one is outside. You really must find a more secluded venue to approach him in…
As the pleasure washes through your body, you feel your housemaster sneak in another finger. To your surprise, it doesn't sting like it did a moment ago…
When you finally come down, you hear a soft chuckle. 'Well done, girl. That concludes our lesson for the day. Now, if you'd kindly redress, I do believe I have paperwork to finish. I shall see you again in a week to test your anatomical knowledge. Dismissed.'
You sit up on the desk, open your eyes, and let yourself off of the table and onto your trembling legs. They feel like jelly as you silently redress yourself, your housemaster watching your every move. You happen to notice there's a sizeable bulge in his trousers now, but you don't mention it. After all, he has it work to do, and so do you.
Once you're all put together again, you leave the office without looking back, and head straight towards the library.
After all, you can't really be expected to remember anything he told you; right now, you're amazed you even remember your name.
You just hope nobody in the library notices your trembling.