by J Phillips
A tiny moan vibrated against the head of my cock. Whether it was with fear of what was to come, or with pleasure from the knowledge that your punishment was not yet complete, I can only guess, but either way it didn’t matter to me in the slightest. I withdrew my erection, watching as a silky thread of your saliva slipped from its tip to fall across your chin.
Leaving your mouth was one of the hardest things I have ever had to do, but it was quite necessary so that we might move on to the next stage of your ordeal.
Quickly straightening my clothing once more, fastening my trousers only loosely around my swollen penis as I hadn’t quite finished using it on you just yet, I held out my hands. You reached up and allowed me to carefully guide you to your feet. Glassy eyes stared up at me, and I in turn, smiled kindly back at you.
‘You’re accepting your punishment admirably so far,’ I praised you, ‘but it is not over quite yet. You still need to accept what a naughty girl you are. I know that disciplining you in this manner might seem a little... how shall I put it... unorthodox, to you, but it will prove extremely effective, believe me. Now, place your hands on the desk like this...’
I positioned your palms a little more than shoulder width apart on my oak desktop. My hands pressed against the soft flesh of your inner thighs as I guided your legs wide apart, and a little way back so that you were forced to bend forward and to support your weight on arms. I couldn’t stop myself from sliding my fingertips up and stroking the tip of a thumb across the succulent flesh of your waxed-smooth pussy, as I stepped away and you gasped and tightened your buttocks in response.
And there you stood, angled over the front of my desk, your shapely legs parted wide, toned muscles straining, and your naked bottom barely concealed beneath that tiny gymslip. You looked as pretty as a peach, but I needed to see more so I reached forward to lift your skirt, leaving it bunched loosely around your waist.
I listened to you release a series of soft, anxious moans, which I assume was a result of the new level of exposure I had subjected you to. I suppose that by now you must have accepted what a tough headmaster I could be, and really, who could blame you for feeling a little nervous?
I stood back, stroking the contour of my frustrated hard-on through my trousers as I contemplated your stunning, youthful body. You were an undiluted vision of sexy loveliness with your juicy pussy, soft and pouting between those smooth thighs and ass cheeks.
And it was at precisely that moment that I finally knew I was going to fuck you, not just dream about it, as I had done for quite some time. Gazing at you bending forward like that I had no real choice in the matter; but still the time was not quite right. You really did need punishing and I was strong-willed enough of a man to set aside my own pleasure so that I might teach you the lesson you clearly needed to learn.
‘This may sting a little, my dear,’ I announced, ‘but it will perhaps make you think twice about playing with yourself during school hours.’ And with my last word I brought a palm swinging down against your right buttock. You yelped loudly with the shock of the first contact and I couldn’t help but smile as I watched your skin flush a deep, angry crimson.
Again I spanked you, the left buttock this time, and once more you reflexively tightened your muscles and gasped with shock and distress. One cheek after the other, I rained down spank after spank, watching how the blood would surge to the surface and no doubt irritate with a burning intensity.
My God you looked good, tensing and releasing your backside with every stinging smack of my palm. In time I began to temper the cruelness of my spanks with vigorous rubs of my fingertips where my hand had just fallen. It was certainly my intention to soothe you, but I was also well aware that I would be increasing your sense of frustration in another, perhaps more dangerous way.
I really don’t recall placing it there, but I soon realised that my free hand was pressing lightly against the silky-smooth flesh of your inner thigh. Slowly I began to draw it higher, brushing the pads of my fingertips in rising circles until, inevitably, they found the soft swell of your wet cunt. With a single finger I began to caress back and forth against your pouting sex lips.
In just the same way that I was offering you the outrageous contrast of biting slaps and gentle caresses, I began to use my words against you similarly, telling you one moment that you were doing well, and that it would all be over soon, before reminding you of what a wanton trollop you were the next.
A second finger joined the first against your pussy, and applying just a touch more pressure it was not long before they were smeared sticky with your cream. I suppose I had known it all along anyway, but your body offered you no way to deny your true desires, and I’m afraid this only encouraged me to spank you all the harder while my fingers pushed their way between your lips and proceeded to lightly fuck your entrance back and forth. You continued to cry out with every searing smack of my palm, yet there was something needful, almost desperate, about your sobs now. I couldn’t help but notice how low you were leaning over the desk, and how you were allowing your hips to writhe back and forth quite outrageously.
Finally I stepped away, breathing hard and congratulating myself on the blotchy marks I’d painted on your poor bottom. My fingers glistened with your juices, and I was just about to lewdly suck them clean when a far better idea came to mind.
‘You really are too much, girl,’ I berated. ‘Here I am, trying to teach you a lesson, trying to show you the error of your ways, and I find that even now you are still preoccupied with your own selfish gratification. You are actually enjoying your punishment, look!’
I brought my fingers round to your lips and smeared them against you, coating you in your own fragrant juices. I don’t know how I had expected you to respond, but it was certainly not in the way that you did, as quickly you sank your lips around my fingers, sucking them avidly before licking them clean. You were amazing; a sexy girl who was clearly incapable of understanding the difference between right and wrong, and I could see there was really only one way left for me to teach you the consequences of your ways.
‘I’m afraid you leave me no other option but to fuck you now,’ I announced, and my cock jerked reflexively to the sound of the husky sob you gasped in response. ‘If you’re going to behave like a little slut – playing with your pussy in public places, and clearly enjoying have your bottom spanked, for example – then it is my duty, as your headmaster, to show you exactly what you’ll be letting yourself in for should you decide not to mend your ways.’
Again I drank in the vision of your semi-naked form bent prone across my desk and, my goodness, you looked good enough to eat. No longer willing or able to wait, I quickly unfastened my trousers again and dropped them and my underwear to the floor. Positioning myself right behind you, my legs planted between yours, I cupped each of your ripe, blotchy-red buttocks in my hands and eased them apart.
‘Now,’ I said in your ear, ‘try to relax a little...’
My cock stood just about as hard and as proud as ever it has, a tangible salute to your ability to turn me on. I released one succulent buttock, gripped my eager erection in my fist, and aimed it towards your luscious entrance. Pressing the swollen, scarlet head against the softest folds imaginable, I drew slowly up and down, coating it in your wonderful juices and lubricating myself nicely, before pushing forward from my hips just a little. Your arousal was such that your body accepted me eagerly at first, the heat of your wetness permeating the head of my prick. Soon enough, however, I felt the resistance of your tight channel, yet I pressed on. It was my duty to do so, clearly.
Moving my hands back to the lower curves of your buttocks I once more spread them wide, and the sight of my aching cock finally sinking into your cunt was just about the most incredible thing I have ever seen. For a fleeting moment I wondered if it was not too late to stop, to send you on your way with a final scolding and to pretend that this whole outrageous incident had
never occurred. But then, how could I? Not only would I be neglecting my responsibilities as the head of the school, but also, I would be failing to take advantage of your beautiful body and tight, wet cunt.
With a last swallow I thrust my hips forward, stretching your pussy and plunging my engorged shaft deep within. I threw back my head and released a hiss of pure rapture as I felt your body grip me with a searing heat, but any sounds I expelled were matched by the whimpers and sobs you uttered in response to being penetrated so completely.
I held myself utterly still, offering you a moment to compose yourself and for me to luxuriate in the sensations of your throbbing pussy sucking so sweetly against me. But then, slowly, I pulled back, and just as the ridge of my swollen head began to pull at your entrance, just as I was about to leave you, I shunted forward again. I built my rhythm, my cock sliding in and out, harder, deeper and quicker with every stroke. I stared down at the wonderful view before me; the entire length of my cock shining and glossy with your cream, and then a little higher, at that other tiny aperture of yours, and for an instant I wondered if there might be another lesson still to be taught, but no, that would have been a step too far.
I noticed how you were standing on tiptoe now, how you angled your hips to feel me just the way you wanted to, as deep inside you as possible, and it was plain to see that you were not suffering at all through the ordeal of your punishment.
Finally, increasing my pace still further, I released my grip on your behind and moved my hands up around your waist to pull you back against me with every forward thrust of my groin. Your whimpers and moans increased, and you were biting a knuckle, your brow furrowed and your nostrils flaring as I fucked you hard from behind. It was clear you were only moments away from your orgasm. I was close too, as electric shocks of pleasure fired from the base of my spine to the tip of my cock with an intensity that caused me to grit my teeth and release guttural groans from the back of my throat.
It was time for me to bring your lesson to a close and to find selfish release within your wonderful body. Harder and faster I thrust, slamming my hips forward so that my abdomen slapped noisily against your tight little ass. But then you sobbed with dismay as at the very last moment, just as I stood on the very precipice, I withdrew completely, lifted your exhausted body from my trusty old desk, spun you round to face me and pressed your spanked bottom back against it. With one hand I hastily lifted your skirt and nudged your feet apart with a toe of my shoe, pumping my cock in my free fist as I did so. I wanted to see your face, and I wanted you to see mine, and I can still remember the look on yours as you gazed dreamily back at me, your eyes wide and your cheeks flushed as finally I gave in.
‘Jesus!’ I hissed, as jet after hot, sticky jet of cum erupted and splattered across your thighs, more arcing into the air and coating your naked pussy. I gasped and I moaned, my orgasm refusing to abate, as I continued to milk every last drop from my tender cock.
Eventually I felt my body begin to slow, and with a deep, shuddering sigh, I relaxed completely, my spent penis starting to wilt in my sticky hand.
Utterly drained I collapsed back into the armchair behind me, where the seduction process had all begun. I closed my eyes and the gravity of what I had just allowed to occur came crashing down around me. All too late I wondered exactly how much trouble I had let myself in for. Could I deny it, suggest it was little more than the product of a mischievous young woman’s imagination? No, of course I couldn’t; that would have been immoral.
It was in that exact same moment, when I had accepted the seriousness and possible ramifications of my actions, that a soft sound once more alerted me to your presence. Tiny sobs and gasps were followed by a few whispered expletives that a good girl really ought not to know. But you weren’t a good girl, were you? You were a wonderfully naughty girl, and I looked up to see you still leaning back against my desk, eyes tightly shut, head lolling back and your lips parted as you blatantly and unashamedly teased your delicious pussy right before me.
I watched in wonder as you rubbed your cum-spattered clit with a desperate, yearning need. It truly was a joyous sight to observe, and I actually felt rather proud of you as your fingers worked rapidly up and down. I could tell by your expression, hear by your moans, that you were so close to your own release, and it was nothing less than a sheer delight, even an honour, to sit back and watch you bring yourself off right in front of my eyes.
Suddenly you fell silent, holding yourself utterly rigid for just an instant before, with an anguished cry, your climax exploded within you. You panted, you squealed and you moaned, two fingers held in a ‘V’ stretching the tender flesh of your pussy one moment, and then rubbing your clit the next.
Inevitably, and somewhat sadly, your orgasm began to subside. I was speechless. You had shamelessly brought yourself off in front of your headmaster, in his study, against his desk, apparently with no regard for what I might think of you.
And I thought you were wonderful.
As you finally relaxed completely I stood up, pulling up my trousers and settling back down again behind my desk, once more returning to the role of head of the school.
‘Well, young lady, I hope you’ve learnt a valuable lesson here today,’ I said, in a firm and collected tone that surprised even me. ‘Now tidy yourself up and we’ll say no more about the matter, understand?’
Nodding shyly you went on unsteady legs through to my small adjoining washroom. When you were freshened up and your clothes straightened and looking decent again you returned to my office, in front of my desk, staring down at the floor in just the same way as when you had first entered.
‘You accepted your punishment well and I can tell that you’re a good girl deep down,’ I said kindly. ‘Now, run along back to class and I don’t expect to see you in my office for quite some time to come. Is that understood?’
You muttered some kind of inaudible affirmation before, turning on your heels, you left me to contemplate the inevitable downfall of my career.
Five days later and the school board still hadn’t called to demand my resignation, nor had the authorities arrived to question my abuse of power. In fact, up until that moment when my secretary, Jane, buzzed through on the intercom, I’d heard absolutely nothing further from or about you whatsoever.
But my pulse certainly quickened and a sickening feeling of dread gripped my insides when Jane said your name.
‘What... what does she want?’ I asked anxiously.
‘Well that’s the strange thing, headmaster,’ Jane said. ‘She says she’s been naughty again and needs to report herself to you.’
‘Ah, w-well, um,’ I stammered, trying to gather my thoughts and my composure at this unexpected but not unwelcome development.
‘Um, give me five minutes to finish what I’m doing, Jane, and then send her through. Oh, and Jane... you may as well go home early this afternoon; I might be quite some time with the young lady, as I suspect she’s been a very naughty girl indeed.’
My Sweet Degradation
The story I’m about to share begins one sunny afternoon in late July when me and my brother were back home from university. Josh had recently graduated and was looking for a fulltime job, whereas I was simply kicking back and sponging off my folks for the summer holidays. On this particular day mum and dad had been invited out to their friends’ for dinner, and as it was quite a drive away they’d decided to stay overnight.
Now, despite the fact that I was a twenty-year-old back then and Josh was twenty-two, we had been given strict instructions to behave ourselves and were permitted no more than one friend each to stay. I promptly invited Julie – an old girlfriend from schooldays – and Josh, two of his mates from university. I was mildly peeved that big brother had broken the rules without warning me in advance, especially as mum and dad still saw him as being the ‘sensible’ one, but when his friends arrived somewhere around three o’clock that Saturda
y afternoon I must confess, I was rather pleased that he had cheated.
Josh’s pals turned out to be extremely handsome young men. They all knew each other from the university rowing club, and both boys had bodies to make a good girl blush.
First off I was introduced to Christian, who was tall, blond and had what American’s would call a ‘preppy’ look about him. It was clear to see that he loved himself a little too much, but as he really was pretty damned gorgeous I was prepared to forgive him his cockiness. Next came Ben with his square-jawed good looks, piercing blue eyes and dark hair, clipper-cut short to the scalp. Ben’s greatest weapon was a boyish smile that could be used to devastating effect whenever he chose to use it.
By the way I was dressed you wouldn’t have thought I’d made any special effort in honour of our guests, as I was wearing little more than a short denim skirt and a tight, black, sleeveless tee. That said, I do like to make an impression and I’d made sure that I looked pretty damn hot – if I do say so myself – but in a subtle kind of a way.
While waiting for Julie to arrive we all got to know each other a little better over a couple of beers in the garden. As the drinks flowed and inhibitions fell away it was clear to see that I was having some kind of an effect on Josh’s friends. Christian was confirming my initial suspicions by proving to be more than a little up himself, what with him being far too happy to regale me with his superior athletic and academic achievements, while making no effort to disguise the fact that his eyes would linger on the naked flesh at the top of my thighs or on the swell of my tits. If I’m honest, I was starting to think Christian was a bit of a dick, but all the same, I couldn’t stop myself from enjoying his attentions.
Ben joined in the conversation whenever he could, and he too undressed me with his gaze, but perhaps a little less blatantly than his friend.