Dean of Discipline: More Tales of Old-School Punishment

by Allen Bare

  I looked down at her plump, rose-striped buttocks, awaiting humbly the final ministration of the cane. What a woman! Carefully I took aim at the remaining open space, which was wide enough thanks to my previous error. I tried to make it light, without holding back enough to take all the sting out of it. Of course, with the condition Connie's backside was in at this point, there was little chance of that. The cane bit in, and Connie bellowed again, and wriggled and squirmed. I thought I heard a tiny note of relief amid the agony. Her shoulders relaxed, and she lay there sobbing, but remembering not to rise without permission. I patted her shoulder lovingly and told her she could get up now.

  Connie stood up, pulled a handkerchief from her sleeve, and blew her nose. Replacing the handkerchief, she turned briefly away from us to pull up her panties, turned back, put both hands to the seat of her skirt and pressed hard. "Ouch," she said softly and emphatically. "I think I'd like permission to leave the room for a minute." I had made Kate the same concession, so of course I agreed.

  While we listened to Connie pacing in the corridor, I turned to Kate for the first time since Connie's caning had begun. I saw her hand move quickly away from her lap. She had been sitting on the sofa, or something like sitting, for I saw that she was tilted well over on her beam-end, wanting to put as little weight as possible on her sore bottom, even though the sofa was well upholstered. She looked at me wordlessly, face flushed and dark eyes wide. "Still hurts?" I asked gently.

  The dark head nodded slowly. "Hurts hardly does it justice," she said quietly. "I may never be able to sit again."

  "Poor darling," I said, careful not to let my tone suggest mockery. "It's all over now. Want a hug?"

  Kate nodded and got eagerly to her feet. I took her in and squeezed sympathetically, noticing how warm and moist she was in my arms.

  "Hey, me too," said Connie, opening the door. Letting Kate go, I hugged her warmly, feeling even more warmth and moisture, though in a considerably smaller package. She leaned her cheek on my chest, trembling.

  "Well," I said a moment later, "All paid up. You both took your punishment like"

  "Like men?" smiled Connie.

  "Hardly. Like good, brave women. Good, brave, naughty women," I amended quickly, lest there be any doubt that I still thought the punishment had been deserved. "But it's all over now, and the books are clear."

  "Thank God," sniffed Kate, who had teared up a little when I hugged her.

  "I suppose the books are clear," muttered Connie, still in my arms, "but I think you took more out of us than we did out of you."

  "All the better for deterrence," I told her. "I trust you won't be tempted to vandalize my humble abode again for a while, at least." I slipped my hand down and gave her haunch a tender pat, which, light as it was, made her wince.

  "No, sir!" Kate nodded her agreement.

  "Since you've done so much damage to our backsides," said Connie, "I think you ought to do something to make up for it."

  "I was about to offer you both a drink."

  "That's a good start, but I was thinking of something else."

  "And what might that be?"

  "There's a bottle of aloe vera lotion in the bedroom"

  Startled, I looked from her to Kate and back again. My mouth formed a silent question: "Both of you?"

  "You walloped both of us; you ought to be willing to help both of us deal with the aftereffects," Connie answered coolly.

  I looked at Kate again. She nodded.

  "Get the lotion, sugar. I'll make us mint juleps. And, Kate honey, you put another log on that fire."

  So it came about that, a short time later, I lay on the floor in front of the fireplace, which was now the only source of light in the room. On either side of me, gazing dreamily into the flames, reclined a lovely woman, her bottom elevated by a sofa cushion. We sipped our drinks for a while, then I turned over and sat up. "Ready, ladies?"

  "Mmmmm," said a voice from each side. I moved a little to put both bottoms within easy reach. "All right," I said. "Uncover." Without the slightest complaint or hesitation, each of my two naughty sweethearts raised her skirt and skinned down her panties. The firelight showed two well-reddened bare bottoms, clearly striped by the cane. I poured out a dollop of lotion and spread it on both hands. Gently I placed the left on a buttock that bore six stripes and the right on a buttock that bore twelve. Carefully I began a very light rubbing. Connie sighed, and so did Kate. I rubbed the lotion gently all over the reddened area, my hands sliding over the round globes of each bottom. It was a wild sensation, touching both of them at once like that.

  The lotion on my hand didn't go far, so I took the bottle and poured a dab on the nearest buttock of each bottom. Before it could run, I covered it and rubbed again, spreading the lotion. Experimentally, I increased the pressure a little, using my fingers to squeeze and ripple the flesh, not pressing too hard. "Ooooh," said Connie.

  "Does that hurt?" I asked hastily, stopping my motions.

  "Silly man! It hurts good!" she replied.

  "Real good," Kate added from her side. "Don't stop now."

  So I went on stroking and squeezing and kneading, my hands very conscious of the smooth skin and rounded shapes they were feeling. I had never had two lovely female bottoms under my hands at one time, and I was powerfully aroused. I had, of course, been aroused by the canings, but had been so involved in the job that I almost hadn't noticed.

  The sighs had continued, and I even heard a moan or two, so I figured I wasn't the only occupant of the room in this state. I had no idea, however, what direction the evening was going to take. I had never been a sexual extremist, and one woman at a time had always satisfied my lusts and, if truth be told, my fantasies. Now, however, I had a different soft, slippery, squirming, bare bottom under each of my hands, and I began to be aware of new possibilities.

  The squirming had grown more vigorous on either hand, and so had the sighing and moaning. I had recourse once more to the lotion bottle, and rubbed it on harder, rubbing quickly until it was as warm as the flesh beneath my fingers. On both sides, I extended the range of my rubbing and kneading somewhat, covering the bottom of each buttock, the fold, and the upper thighs. Immediately, as if communicating by telepathy, each woman moved her legs apart. I accepted this clear invitation, and my questing fingers were soon deep inside each of them, seeking and finding the hidden pleasure place. A moment later, yowling like cats in heat, both women came simultaneously and lay shuddering. I sat there, able to think of nothing, waiting for the erection of my life to subside.

  After a few moments, Connie said, "Do you know what you're going to do now?" I didn't, so I waited to hear. "You spanked our bottoms, and then you gave us our supper, and then you spanked our bottoms again, and then you gave us a very special but slightly messy treat, and now it's very late."

  "Uh-huh."

  "So now," said my darling, "you're going to give us our bath and put us to bed."

  I woke alone in my bed, sunlight streaming through the window. My mind was full of the most incredible images: two beautiful bodies, one tall and one short, carefully fitted into my large, old-fashioned tub, naked shoulders, breasts, bellies and flanks shining with warm water and suds. I longed to join them, but the tub wasn't that large. I knelt outside and lathered and stroked away, my hands going everywhere, eagerly guided. Later, toweling two glowing bodies, dropping one of my sweatshirts over each head, leading two clean, warm, sweatshirt-clad women to my bed, which was the only one big enough for the two of them. I tucked them both in, kissed them goodnight and turned to head for the guest room. "Stop right there," commanded Connie. "Where do you think you're going?"

  "You said you wanted to be put to bed, not taken."

  "Isn't he cute?" she said to Kate. "Listen, you lummox, you knew what I meant, or at least you should have. Now get those clothes off and get in here." I stared uncertainly at her and at Kate, not quite ready to move. Two sweatshirts came flying at me, one covering my face. I brushed it off, undress
ed quickly and dove in. It was a long, long night, and my phallic phenomenon, which quickly came back to life, was not allowed to go to waste.

  Now I put on a robe and headed for the kitchen, smelling coffee and bacon as I came down the stairs. Connie was alone at the stove. "Is Kate in the bathroom?" I guessed.

  "No, she went home before it got light. Said it wouldn't do for the neighbors to wake up and find both of our cars outside."

  "I honestly don't think they'd notice."

  "No, neither do I, but I think Kate was starting to feel a little awkward about what happened."

  "Mmmm." I wasn't surprised. "How about you?"

  "Well, it went a lot farther than I expected when I cooked the whole thing up, but when push came to shove"-she stopped to grin at me lewdly-"well, I guess it just seemed like a good idea at the time. Of course, I don't think I'd want it to become a habit."

  Thinking it over, I agreed that this was not an activity we could add to our regular schedules if we wanted to keep our heads, hearts, and relationships straight. All the same, I had to admit to myself that I wouldn't mind if it just happened to happen again. But I was smart enough to understand that I couldn't initiate it, and, in fact, the less I said on the subject, the better. I told Connie she was right, and let it go at that.

  A little before six on Tuesday, when Mrs. McCutcheon had gone home, there was a knock at my office door, and Kate poked her head in. I wasn't too surprised to see her. "Hi," she said. "I saw your car outside. Is this an OK time to talk?"

  "None better," I said. "I'm through for the day. Come in and sit down, why don't you?"

  "Er, about the other night" she said, after sitting down, fiddling with her handbag, and blushing a bit. She didn't seem quite sure what to say after that.

  "It was special," I said, "not as in 'Isn't that special,' but as in 'unusual, unanticipated, outside the sphere of the ordinary.' Or at least that's how it seems to me. You too?"

  She nodded. "But I don't want you and Connie to think"

  "We don't," I assured her. "What happened-well, none of us was expecting it, but when the time came, we all wanted it to happen, no one of us more or less than another. We didn't plan it, and I don't think it was anything that could be planned. It could only just happen, and it did." She nodded. "Nothing the other night changed the way I feel about Connie, or the way she feels about me," I added, "or for that matter the way either of us feels about you. Of course, if we tried to make something like this less spontaneous in the future-I mean if we tried to plan what we can't and shouldn't plan, I think we might begin to have problems keeping our feelings sorted out. That's why I think we should all regard the other night as a unique and probably unrepeatable event."

  "Probably?"

  "Well, you can't predict what's by definition unpredictable. I'm not pretending to be wiser than the universe."

  Kate scowled down at the desktop, thinking it over. She was twisting a strand of hair, as on her first visit to this office. Finally, she relaxed and looked up. "I guess there's no harm done, then."

  "Oh, far from it." I grinned. "It did me a world of good. Hope it did you."

  She laughed and blushed at the same time. "I'm getting out of here,' was all she said.

  I had spanked only two girls that morning, and on Thursday there was only one, the unreformable Virginia Saltonstall. I should perhaps withdraw that adjective, because this was only the second paddling of the semester for the tall, thin sophomore. It had been four weeks since the first, so perhaps my effort to make the previous occasion a rousing one had borne some fruit. I endeavored to make today's paddling equally effective, if possible, and sent Virginia away with plenty to think about-and she wouldn't be able to avoid thinking about it every time she sat down, for a few days at least.

  Friday night, however, the unnatural spell of good behavior on the campus came to a end, and I received a call from campus security reporting the suppression of an alfresco wine-tasting in the woods behind Auchincloss Hall. Seven young women had been apprehended, and a special disciplinary tribunal would have to be held on Saturday morning. I phoned all the members of the board except Connie, whom I didn't have to phone because she was in bed beside me. My last call was to Jo Ruggles. I told her to come to my office at 9:30 the following morning if she was still interested in observing the ways of Emberley discipline. She said she'd be there.

  Jo hasn't lost interest, I see," Connie said when I put down the phone.

  "Far from it. I got the impression she'd been counting the hours."

  "Pretty eager, wouldn't you say, for someone whose only interest in this business is moral?"

  I laughed. "I conceded that point to you long ago. I haven't a doubt that Jo, way deep down, is one of us. She's still having a lot of trouble with the idea, though."

  "I wonder what tomorrow will do for her."

  "Get her juices flowing lavishly, I hope."

  "Why, you old lecher!" Connie took a swipe at me with the pillow, ineffectively, because she was still lying down.

  "Madam, I protest my innocence!" I put my hand over my heart and rolled my eyes skyward, like a calendar saint. "If anyone benefits from Jo's getting randy, I trust it will be her loving husband, Ed. I'm simply hoping that she'll resolve her conflict and become a happy a happy um, whatever we are."

  Connie smiled, but she said, "Don't be surprised if she recoils, at least at first. I don't expect her to pop out of the closet and ask where to sign up."

  "You think she'll be turned off instead of on, when she sees an actual paddling in all its gory details?"

  "Oh, no, not at all. I expect she'll be turned on, strongly. But I wouldn't be surprised if she's frightened by that. It may take her quite a while to come around, and even when she does she may never let you or me know it."

  "I hope she'll let Ed know it, at least."

  "Mmm. I'm getting cold. Get back down here and warm me up."

  Saturday dawned damp and autumnal, with a light rain falling and smell of fallen leaves. Connie and I drove to the campus together in my car, and found Jo Ruggles waiting for us in the parking lot. She was wearing a waterproof windbreaker over a dark blue sweater, and her snugly fitting jeans reminded me what a nice figure she had. Jo looked a little tense, and we didn't say much more than hello as we went up the steps and entered the administration building.

  I had given Connie the key to the infamous closet, and told Jo that she would show her where to go. I added "It will be a while before anything happens-anything in my office, that is. I'm sorry you'll have to spend that time waiting in the dark, but I wouldn't want any light to show where you are."

  "Okay," said Jo, nodding. She was pale, and looked as nervous as if her own bottom was due for a paddling. I couldn't help imagining briefly what a fine sight that would be. She and Connie disappeared up the stairs, and Connie soon reappeared. There were still at least ten minutes before any of the Disciplinary Board would show up.

  Our solemn tribunal, when it finally convened, did its business with almost the usual dispatch, though we were delayed slightly by the unexpectedly vigorous defense put up by a junior named Paige Williams. She claimed to have been cutting through the grove on the way back to her dorm from the library, and said she had been included in the general roundup through an unfortunate mistake. Looks of disgust passed among some of the other culprits when they heard this, and I almost thought that if we had needed a prosecuting attorney we might have found several volunteers among their ranks. Patiently, old Professor Windermere of the psychology department questioned her and the arresting campus policeman, in due course establishing that, first, the grove in question was not located between the library and Paige's dormitory, but required a detour of almost half a mile, and that, second, Paige had had no books in her possession when apprehended. She had, however, had a plastic cup half full of Chardonnay, which she had tried furtively but unsuccessfully to toss into the bushes before it was seen. The committee, after due deliberation, asked me, as Dean of Students
, to be mindful, when administering punishment, of the blatant untruthfulness of the defense. Paige, a pretty, long-haired blonde of 22, grimaced miserably when she heard this, knowing she was in for a worse paddling than her sisters in crime-some of whom might have looked triumphant, had they not been too concerned with the anticipatory tingling in their own hindquarters.

  The process hadn't taken very long, but I reckoned that, before I got back to my office, took out the paddle, and called the first culprit, Jo had been sitting in the dark little room above for the better part of an hour. I hoped she had been able to bear the waiting as comfortably as possible in her agitated state.

  At the moment, however, I had little time to think about Jo; there were seven guilty bottoms waiting to be spanked. The first to be called in was a slim, sandy-haired girl doomed to that position by lack of seniority-she was a freshman-and by the alphabet, for her name was Annie Budd. In my usual calm tones, I reminded her of the serious offense by which she had gotten herself into this fix and bade her come forward and pay the expected penalty. Annie was not a stranger to the ritual, having been punished once before (for boisterousness after midnight, I seemed to recall), and, though she bit her lip grimly, she lowered her underpants and bent gingerly forward over my lap without requiring detailed instructions. I raised her gray flannel skirt to reveal a smooth, fresh little bottom of a lovely peach color. A pair of plain white nylon panties was scrunched into a narrow band around her smooth, slender thighs.

  Hope you're ready for this, Jo, I thought. Justice delayed is justice denied. I raised the paddle and brought it down with a hard snap across the two pale mounds before me. Annie twitched and gasped while I paddled briskly away, raising the maximum heat in that cute little derriere, which wriggled and squirmed as it reddened under the paddle. Annie never cried out loud, but tears were running down both cheeks when I finally let her up, and she sniffled loudly as she resumed her panties and smoothed down her skirt (carefully-and with who knows how great an effort-keeping her hands away from her seat). Mastering herself with a final sniff, Annie squared her shoulders and departed, both her walk and her upper lip as stiff as circumstances would permit. It was a brave performance, especially for a freshman, and I hoped Jo had appreciated it.