Debbie’s Always In Trouble
6 hours ago
The little minx waited about a week before she again tried her little ruse. She quite deceived me, for her conduct during the next several days at our lessons was exemplary. She seemed to flush whenever our eyes met, and her voice was soft and meek, even when she was explaining or reciting the lesson, which she usually did prior to that with a cool confidence.
About a week after I had introduced Miss Eileen's spacious pink and white bottom to the sole, I announced a written test which would cover all the ground we had covered since our first lesson together. She had had two days' warning, and had assured me just the day before, when I asked her, that she was quite ready.
"I'm sure you know that you have failed this examination, Eileen. I ask myself why, with your good scholarship, you find it necessary to go out of your way to irritate me. Or perhaps you think that having once punished you rather seriously, I am not capable of doing so again. Is that it?"
She rolled her eyes and didn't speak, but once again I saw that giveaway twitching of her lips which meant that she was trying to hide a smile. That was just too much. Abruptly I got up, went to the door and locked it. The leather sole was still in the drawer of my desk, and I meant to use it this time till she really cried for mercy. However, this time I intended to impose upon her a posture less embarrassing to both of us.
"I take your silence as an answer in the affirmative," I told her. "You will go over to that chesterfield, kneel on it facing the back, lift your skirt and slip well above your waist, and let down your panties. When you are ready, I will attend to you."
She drew a deep breath and rose, without a word, and walked over to the chesterfield. She quickly lifted her outer garments, hurriedly lowered her panties to just above her knees, and knelt down as I had bidden, bowing her head and shoulders over the back. I took out the leather sole, walked over to her, and maneuvered her wrists together then clamped my hand firmly over them.
I applied a stinging crack of the leather sole over the plump summit of her right buttock, and then almost instantaneously, one on the other globe. She caught her breath, wriggled a little, glancing back at me with widened eyes, but otherwise made no sound. This obstinacy galled me.
I laid on the sole rather smartly, using the method of first the one cheek and then the other till I had reached the base of her now slightly squirming and reddened behind. She raised her head several times, but did not turn her face to me after the first two spanks. Her breathing was quickened and audible.
I paused a moment to readjust my grip on the sole, and then I began to apply the spanks in a vertical manner, again alternating on her fleshy buttocks. This almost at once had some more satisfactory effect, because now she began to gasp and to call out with little tremulous cries, "Ouch, oh!" And "Ooooh, dear!" while her hips lunged and jerked, drawing away from the chastising weapon only to proffer themselves again at the very next instant.
I did not pause until I had given her about thirty spanks. I waited then, watching her twist and squirm her fiery hips about, and saw how uncomfortably she was shifting her knees back and forth to find a more secure position on the chesterfield. I said, "I haven't finished with you yet, my girl," and then I applied two or three good solid horizontally applied smacks with the sole over the lower part of her bottom. She at once burst into tears, and I felt her wrists jerk against my grip, but I settled myself and gave her three or four more in the same place. Then she broke down and sobbed, "Aaaahh, oh, lord, oh, it does hurt so! I'm so sorry, I really mean it this time, please not to hard any more, Mr. W!"
"I wonder if these are crocodile tears yet, Eileen," I commented drily as I tapped the sole lightly over one of her flaming buttocks. Then she looked back at me, tears running down her face, and she stammered, "Oh, sir, if you are going to go on and smack me, won't you please let me go over your lap? I'm afraid I shall be a big baby, because it's awfully uncomfortable kneeling like this. My legs are getting awfully weak, please, sir."
At this last stroke which had bitten home against the base of her left buttock, I kept the sole resting on her twitching skin and paused. Then I asked her calmly, "Are you beginning to feel sorry for your cheekiness, Eileen?" This time she didn't look up, but in a voice that was quivering and somewhat higher in pitch than her usual tone, answered, "Ah-oh, why-yes, Mr. W. I am sorry for what I've done, really!"
I was quite inexperienced when it came to chastisement, but still I told myself that if only fourteen spanks had so improved Eileen's disposition to be meek and deferential, a few more might not go amiss. So, after another moment or two, I took firmer hold of the taped heel of my spanking aid and lifted it up. Eileen recognized this as a signal that I was going to resume, and I heard her give a little sigh of "Oh my!" while at the same time she pushed herself a little closer to me, tightening all her muscles in readiness.
I hesitated a moment, then applied the resuming strokes across both of her bottomcheeks at the very base. I have since found that this is one of the most sensitive of all areas of the female posterior in spanking, and Eileen's reaction demonstrated the general rule: her hips seemed to wrench from side to side, then to arch up spectacularly, and for the first time she turned back her face to me to emit a shrill little "Ooch, oh, I did feel that one, sir!"
"I am relieved to hear you say that, Eileen. I had thought that perhaps you were such a grown up young lady that a childish bottomsmacking like this made no impression on you whatsoever. Now if you are ready again, I shall continue with the rest of your correction."
She uttered a long, tremulous sigh, and turned her face back and bowed her head again, stiffening her entire body once more.
I then began to smack her upturned seat with slightly quicker spanks of the leather sole, but this time I saw to it that each stroke attacked both cheeks of her behind rather than a single one as had been done during the first portion of her allotment. It took me seven or eight more spanks to reach the tops of her ample hips, and each of these crisply-intoned applications of the leather drew little squeaks from her, and an occasional convulsive tip-back of one foot or the other, and a continuous restless kind of squirming over my lap.
I perceived that the colour I had so liberally bestowed over those satiny hemispheres was now a furious bright red, so I considered that she had had a sufficient penalty this time. Lifting up the sole again, I asked, "If I let you go back to your place, Eileen, do you think you can spend the rest of the afternoon in concentrated study without any more of your impertinence?" And before she could answer, I delivered the final spank, straight across both globes at their ripest curve.
Her bottom jerked to the left, then to the right, then arched up, then flattened itself, as with a sobbing "Oh, ouch, ouch, oh yes, Mr. W, I'm sure I can, oh please!"
I don't know what possessed me at that moment, but seeing that her panties had, during the frequent twistings of her legs and kicking of her feet, become tangled about her ankles. I leaned down and drew them off and placed them on the edge of my desk, saying, "Very well, then, Eileen, you may go back to your seat. But just to make sure that you don't forget this smacking for the rest of the afternoon, you will leave off your panties. Now you may get up."
With this, as she slowly tried to raise herself from over my lap, I hastily pulled down her skirt and slip, took hold of her elbows and stood her on her feet. Her face was quite flushed, and her eyes were red, filled with tears. Her lips were trembling, and she was breathing rather quickly. Nonetheless, when she finally looked at me, the ghost of a smile made itself manifest on her full, soft mouth as she whispered, "I did deserve that, I know. And I'll try to do better, truly I will."
For the rest of the study period she was as meek and quiet as an angel. I then assigned her another composition, and made no further mention of the smacking. I walked away from the desk and saw, out of the corner of my eye, that she very swiftly and stealthily retrieved her panties and hid them between her books as she left the room.
But this was not to be the final chastisement she was to receive from me.
In spite of my being a mature male, I was still quite naïve about the behaviour of the opposite sex. But I was to discover my error and also learn something about Eileen exactly two days after that punitive session.
At last I thought of a suitable correctional aid, and went up to my room. I had an old pair of bedroom slippers with leather soles which I had brought along when I moved my belongings to my new situation, and I thought that there I might find an ideal instrument. It was certain to smack noisily, and the humiliation of that sound would be a chastening element in the proposed rehabilitation of my young friend. It was also certain to sting very nicely, and I did not think that she would be quite so impervious as she had been on the other occasion lying across my lap while I stung my hand on her ample, resilient buttocks.
After examining the slippers, I selected one of them and took my penknife and cut away the leather sole itself. To make a kind of solid grip, I next put adhesive tape around the end of the heel. When I had finished, I brandished it in the air a few times experimentally, and the balance felt quite satisfactory.
"I guess I'm due for it again, aren't I? I know I've been asking for a walloping."
"Yes, you certainly have, Eileen, and this time I shall do my best to see that you get it, and a proper one."
Once again I pushed back my chair from the desk and I sternly ordered, "Now then, Eileen, you have earned yourself a bare-bottom smacking. Take down your panties, lift your skirt and slip over your waist and place yourself across my lap." She promptly rose from her chair, but a slow blush began to spread over her cheeks. Ah, I thought to myself, 'that won't be the only place where she blushes!
She half turned away from me, tucked up her skirt and petticoat, tucked them under her arms, then hastily grasped the waistband of her pink silk panties and lowered them to her lower thighs. She went across my lap very quickly as if to say she was in a hurry to get it over with.
She was wearing a garter belt which held up brown silk stockings, and now I had occasion to observe what fair soft skin she had, and also what an ample area for chastisement. As she lay docilely across my lap, head down and once again her palms positioning herself, I put my left palm on her rolled-up skirt and slip, then reached for the leather sole, laid it across her pink and white buttocks and remarked, "I am going to smack your impertinent bottom till I think you are sufficiently punished. Are you ready?"
She answered in a low, quiet voice, "Yes sir, I am. I know I shouldn't have tried your patience so. I'm sorry, sir." Well, this engaging and voluntary remark just when she was ready to receive her first bare bottom smacking somewhat took me aback. I felt that I ought to modify my planned sentence, which was to smack that plump backside of hers until she was really in tears and distress. But if I let her off too easily, she might consider me soft-hearted, and once again ply her little pranks.
I laid the leather sole directly over the plumpest part of both buttocks, and was rewarded by Eileen's stifled little "Ohhh!" and a tightening of all her muscles. Keeping my left palm pressed firmly on her upper back, I lifted the sole and brought it down sharply over the outer edge of the top of her right buttock. I must say that both of us were startled by the loud explosive noise. Eileen turned her face back and up to regard me with a grudgingly respectful glance, and at the same time her body jerked convulsively over my lap, one pretty foot involuntarily lifting from the floor, then resuming its place. The mark the sole had left on her finely grained carnation skin was quite bright, and registered faithfully the outline of the entire sole
I waited a few seconds, then dealt her an equally loud smack over the corresponding area of the other bottomcheek. Once again she let out a startled "Ohh!" and this time she crossed both ankles, bearing down for support with the toe of just one shoe. As the sole met bare skin, there was a corresponding spasmodic flexion of the muscles of her bottom and upper thighs. This time the mark was slightly brighter than its twin.
I proceeded to apply the sole with methodical regularity on first one buttock and then the other, traveling downwards from the two top marks towards the base of her amply rounded bottomcheeks, and allowing a sufficient pause between spanks so that the stinging could permeate not only the flesh but her highly-spirited mind to let her observe that I would no longer be fair play to her little tricks.
It took about fourteen spanks to reach the lower portion of her fleshy but very firm and satiny behind. After the first few tiny gasps of surprised annoyance to find how loud and smarting the strokes of a leather sole were as against the feel of my palm that other time, Eileen managed to take this first portion of her dosage without an outcry.