Kaylee's Keeper

by Maren Smith

  And he answered. “Certainly, ladies. Stand.”

  Three rows of schoolgirl marionettes stood up at their desks, startling Kaylee all over again. Her bottom tingled intensely as she followed suit, her sweaty fingertips dancing and tapping nervously at her open schoolbook and along the sides of her narrow desk top.

  That slender switch no longer tucked behind him, Mr. Emerson took up his position to the right of the first girl in the front right row. “Bend,” he said, and like one, every girl put herself flat over her desk.

  Kaylee belatedly followed their lead—hands grasping onto the far side of her desk, her bottom rounding prominently. Most of those around her held themselves straight and properly still. Some, like Selena, wiggled in nervous excitement. Some were quivering, like the girl directly in front of her. Kaylee had a really good view of her and the peekaboo of black thong panties under the pleated folds of her schoolgirl skirt. She tried not to look.

  “Skirts up,” Mr. Emerson ordered, and eleven good little marionettes hiked their skirts all the way up to their waists, each baring her own bottom for castigation.

  Kaylee tried not to, but she couldn’t stop herself. She stared at the round curves of the bottom directly ahead of her—trim, plump, a cute butt, really, and already bisected by four hot and evenly spaced welts.

  She could do this. For crying out loud, she’d come all this way just so she could do this! So what if it felt a little…contrived and…ridiculous. This was a fantasy. Role-playing make-believe, something she had personally done a thousand times in her own head while tucked into bed, one hand squeezing at her breast and the other busily working between her thighs. Maybe everyone felt like this the first time. Maybe there was a learning curve to roleplaying. Maybe, once she’d taken a few licks, she’d be able to relax a little and then she’d sink right into the proper headspace and have a wonderful time.

  Maybe.

  Trembling just a bit, marionette number eleven, she held on tightly to her desk and was silently grateful that no one was sitting behind her. She tried to relax, but she just could not make her bottom stop clenching.

  “I believe this is our third round of discipline, isn’t it?” Mr. Emerson asked, and nodded when he was met with a sing-song chorus of agreement. “The count, then, is trois.”

  “Trois,” said the girl in the first row when he tapped the switch full across her plump buttocks.

  Being the proud owner of a veritable library of erotica books on the subject, Kaylee thought she knew what would happen next. According to all those well-thumbed pages, this was where Mr. Emerson was supposed to swish the switch once or twice through the air, test its flexibility and/or durability, then measure for precision against his victim’s quivering backside and strike. She lay tense on top of her desk, mentally ticking down through that list of actions, secure in the knowledge that at least she knew how it was going to happen and so she could brace herself accordingly.

  Apparently, Mr. Emerson did not read the same books Kaylee did. He did none of those things. He simple raised the switch and the only swish Kaylee heard was the one that preceded the snick of impact.

  The girl caught her breath; Kaylee came completely up off her desk, her eyes huge as she stared over the backs of everyone in between her and that first desk one row over. The girl wiggled, shimmying her hips ever so slightly, and as Kaylee watched in startled fascination, a neat red line began to flush and swell, spreading out on both sides beyond the white elastic of her panties, adding another rung to the ladder already in evidence.

  Maybe he saw the flash of her movement, or maybe Kaylee made a sound. Either way, Mr. Emerson turned and looked at her. He pointed at her with his switch, and then he pointed at her desk. Kaylee dropped her chest to the smooth wood and quickly grabbed back onto edge. She swallowed hard, determined not to let go again.

  “You do not want me to have to tell you again,” he warned and stepped down the row to the next "student" in line.

  “Trois,” she said, with only the slightest quiver in her voice.

  “I see you took advantage of first break to change into regulation underwear.”

  “Yes, sir.”

  “Good girl. Trois it is.” Snick! “You may also go up to the blackboard and erase the check behind your name.”

  “Mm!” Her shimmy was slightly more squirmy than her predecessor. “Th-thank you, sir.”

  “Not at all.”

  Another few steps, another bottom bent, round and waiting for his attention.

  “Hello, Margaret,” he said, his voice somehow authoritative, sympathetic, sternly paternal and friendly all at the same time. Kaylee didn’t know how, but that tone was doing things to her, melting her, weakening her knees and amplifying the tingle that had suffused her from behind. It must have been doing something to the young woman bending before him too, because she was already squirming and he hadn’t even raised the switch yet.

  “Hello, sir.”

  “Unlike Amanda, I see you decided not to change your panties.”

  Kaylee tried to lie still, but she couldn’t help it. Tentatively, she raised her head high enough to steal a quick peek. The panties in question were straight lace, sheer in back but at least covered her fully, unlike the thong-wearer directly ahead of Kaylee.

  “Are you enjoying your switching?”

  “No, sir.”

  “Oh, but I think you must be. Otherwise you’d be wearing regulation underpants instead of being told now to take them entirely off. I mean that. Stand up. All the way off and hand them to me.”

  Mr. Emerson waited, tsking while she straightened back off her desk. If she wasn’t truly reluctant about removing her panties in front of everyone, then she playacted it extremely well. When she bent back into position, he pulled a pair of safety pins from his pocket and, folding the excess of her skirt into neat thirds, pinned the fabric to the back of her shirt.

  “Count,” he said. “And keep your hands on your desk.”

  Her bottom tensed, clenching slightly as she recited, “Trois.”

  Three times in rapid succession, the switch sliced the air. He gave her no pause in between, simply snick-snick-snick, laying three new lines and extending the ladder of weals across the pale swells of her defenseless bottom. The girl sucked a breath, her bottom tucking on the first stroke, then bucking outward into the next two. Her back arched, her hips rolled, and she accidentally hit her chair when her feet kicked up off the floor.

  “Feet,” Mr. Emerson reminded.

  “I’m sorry, sir!” she gasped, her hands clenching and re-clenching along the edge of her desk.

  He tsked again, and then—snick!—the switch snapped off her dancing bottom and he was done. “Stand up.”

  Her hips ground against the edge of her desk, a lewd humping motion that accompanied the rise and flush of that newest line which had fallen across a previous one. She didn’t let go with her hands, though, and that was the telling thing. Kaylee didn’t think she could have kept herself from grabbing, squeezing and rubbing to scrub out the hurt.

  Hands on the wall. Shivers rippled her as Master Marshall’s command echoed in her mind. You will not cum before I say.

  Mr. Emerson said no such thing to the girl in his charge. “I see little point in continuing your discipline when you so obviously enjoy it.” He gave her shoulder a nudge. “Join Kristi at the blackboard. Panties in the wastebasket, hands on your head, no talking. You’re to hold that position until the next break, and then, my girl, we are going to see if you and your cohort in crime enjoy the paddle as much you seem to like the switch.”

  Unable to stop herself, Kaylee rose higher enough to watch Margaret accepted her underwear back from Mr. Emerson and headed up to the front of the room to join the dunce in the corner.

  “Sarah…Sarah!”

  Kaylee startled, suddenly remembering that was supposed to be her new identity. Mr. Emerson pointed his switch at her, the Look he was giving her infinitely more serious than it had been before. “I
am going to be with you in just a moment. How bad do you want it to be?”

  The whippy tip of that switch gestured to the desk and Kaylee dropped to lie on it.

  “Plus one for needing to be told twice. If I have to warn you again, it’ll be a baker’s dozen, underpants down, followed by your nose on that blackboard and my undivided attention come the next break. Now, who’s next? Laura.”

  And just like that, he moved on. The bad-girl streak broken, he administered one sharp slice of the switch upon receiving her soft-spoken Trois and while she breathed and squirmed her way through the symphony of sting he’d orchestrated, Mr. Emerson shifted his attention to the middle row.

  He started at the front, gradually working his way one snap of that switch at a time until he reached Selena. The middle row was the ‘good girl’ row. Three of the four girls received single strokes over the crisp white surface of their white cotton panties. It was no surprise to Kaylee that Selena was that row’s only odd-man-out. Apparently, it was no surprise to Mr. Emerson either. He was only halfway down the aisle when, unable to contain her bouncy self any longer, Selena whispered to Kaylee, “Isn’t the waiting just awful?”

  With a snap of his switch, Mr. Emerson finished with his current pupil and then walked up to the head of the room where, without a word, he added the names Sarah and Amy to the list already taking up the blackboard. Behind Selena’s alias, he chalked two checks; Kaylee received one. Still without a word, he returned to the middle row and continued where he’d left off. Desk number three. “Hello, Rebecca.”

  And on it continued, while Kaylee stared at her name on the board and wondered what that check was going to mean.

  Oops, sorry, Selena mouthed when their eyes met again. But she was fighting back giggles as she did it, and it was all Kaylee could do not to jump half out of her skin when she heard the snap of the switch. The girl directly in front of Selena arched up onto her tiptoes. She gasped, her hands coming up off her desk. She wavered, but obviously thought better about grabbing her bottom. She caught the desk again instead.

  “Very good,” Mr. Emerson congratulated, and then he was standing at Selena’s side. “Amy, young lady, what am I going to do with you?”

  It was the king of all rhetorical questions, and Selena giggled as she answered, “I don’t know, sir.”

  “You were in my class last year, weren’t you?”

  Selena shifted slightly, her grip on the edge of her desk tightening. “Yes, sir.”

  “I thought so. I’ve had literally hundreds of students between then and now, but I find it damn near impossible to forget the only woman who consistently baited me to increase the count number no matter how many I gave her and who had the absolute gall to orgasm right in the middle of her detention spanking.” Mr. Emerson caught the back of Selena’s underwear, his fingers and thumb hooking the elastic on both sides and pulling her panties right up into the crack of her ass. White cotton stretched, cutting into the most liberal wedgie that Kaylee had ever personally witnessed and it brought Selena dancing up onto her toes in an effort to alleviate the pressure.

  “Oh,” she breathed, obviously more turned on than she was dismayed.

  “What do you think?” Mr. Emerson asked, enjoying the view. “You’ve earned two checks on the blackboard already. Something tells me you don’t intend to be a model pupil for me this year, either.”

  For the first time since they’d met, Selena lost her smile. Her eyes had turned smoky, though, and a pretty blush had stolen up over her cheeks. “No, sir.”

  That made it official. Kaylee stared at Selena; the girl had to be insane.

  “Ah, the refreshing taste of honesty.” Smiling fondly down at her, Mr. Emerson shook his head once. He also lay the switch across her bottom, tapping lightly twice as he measured. “Relax your bottom.”

  Selena shivered, trying to comply.

  “Good girl. What’s the count?”

  Swallowing hard, Selena licked her lips. “Trois, sir.”

  Like most of the girls in that row, he gave her one sizzling strike of that switch, no softer and no harder than anyone else. Selena caught her breath and closed her eyes. Her bottom cheeks jammed together, as if trying to hold onto the sting. Other than that, she did not squirm around.

  Releasing her underwear but leaving it wedged, Mr. Emerson bent over her. “How long are you here for?”

  It was whispered so softly, had Kaylee not been sitting right there, she never would have heard what he’d asked.

  “Just the weekend,” Selena whispered back.

  “Every one of your nights is going to be spent in detention,” he replied. “You may take it in the actual Detention Hall with the others, or privately after school with me. Think about it.”

  “You,” she whispered without hesitation.

  Kaylee saw him smile, briefly close his eyes, shake his head. “Think about it,” he murmured, for her ears alone. “The orgasms will not be one way this year. The things I plan to do to you would justifiably land a real teacher on the national sex offender registry for the rest of their lives.”

  “You.” For the first time, she squirmed, a muted undulation of her hips that had absolutely nothing to do with the pink line swelling behind her. “I want you, sir.”

  Mr. Emerson stroked her hair once and in that instance, Kaylee suddenly realized what was missing from this scenario. More than costumes and play misbehavior for the sake of experiencing the fleeting snap and sting of having her bottom spanked, she wanted that—that familiarity, that soft smile and the caress of a comforting hand combing through her hair.

  On the heels of that realization came another: she wasn’t going to find any of that dressed up like a schoolgirl and taking her licks in a let’s-pretend classroom.

  Suddenly noticing Kaylee watching them, the softness vanished from Mr. Emerson’s face. He straightened, becoming properly teacher-like and perhaps even a little irate. Half a step, that’s all it took for him to switch sides from Selena to Kaylee.

  “I warned you,” was all he said as he caught the back of her underwear.

  Kaylee yelped, arching up onto tiptoes when he yanked the white cotton of her panties right into the crack of her ass now as well. It did not feel anywhere near as magical as it had looked when he’d done this to Selena. His face had been soft then; his manner, teasing. Now, all Kaylee felt was…well, cut in half, clearly, but also ridiculous. She was twenty-six years old, a costumed Catholic schoolgirl being given a royal wedgie by a man who, she was beginning to suspect, didn’t even have a real teaching degree.

  Gone were those fragile erotic threads that had tugged at her while she’d been watching him tend to the others. She tried for deep breaths. She tried to get back into character, to squash down the rapid-rising urge to simply get up and walk out. It all just felt so…false.

  The first snick of his switch caught her completely by surprise in two distinct ways: first, the initial impact wasn’t half as bad as she’d thought it would be; and second, she very quickly learned that it wasn’t the initial impact she was supposed to fear. It was the stinging swarm of sensation that waited two or three seconds before crawling across her bottom, growing in volume and intensity, that caught her completely by surprise.

  Her hands spasmed on the edge of her desk, wanting so desperately to grab hold of her bottom instead. Were she not already caught in Mr. Emerson’s wedgie grip, she’d have come dancing right up onto her tiptoes all over again.

  “Oh wow,” she gasped, completely amazed by the sensation and helpless to stop her hips from writhing and squirming along with the forming welt.

  Soft as a kiss, the switch branded her bottom with line after line of absolute smart. It stung. It chewed. And half a second later, when the switch bounced back off her for the last and final time, those first lines caught on throbbing fire.

  Suddenly, Kaylee understood why Margaret had kicked her chair; she kicked hers as well, her legs taking on a writhing life all their own. She tried to keep her f
eet on the floor, but there simply was no holding still. There was no keeping her hands on her desk, either. The instant sting turned to fire and she reached back, grabbing her buttocks with both hands, squeezing in gasping disbelief. She could feel the welts forming between her fingers. She tried to rub them out, but her touch only served to enflame the heat that much hotter and it did not escape Mr. Emerson’s frowning notice.

  He tapped the switch against the backs of her wrists and Kaylee listened. Abandoning her bottom, she grabbed onto the desk again. “I’m sorry.”

  “You’re new,” he intoned dryly. “I’m going to let that slide, but only this one time. Are we clear?”

  “Yes, sir.”

  There was no relief quite as powerful as the one that shivered her when Mr. Emerson walked away. He only went as far as the girl directly in front of her, but that switch was now someone else’s immediate concern and Kaylee was more than happy to see it go.

  Except that…no, that wasn’t quite true.

  With every passing second, the fire was changing. It was sinking deeper into her. It was spreading, that once dreadful but now magical throbbing no longer centered within that ladder of welts, but deeper inside her. Her panties were still wedged, and now she was throbbing there too, the pulsing sensation so amplified that her whole body felt rocked by it, overwhelmed by it, thoroughly and completely consumed by it.

  The girl without panties received four sharp snicks and a one-way trip to the blackboard. The girl ahead of her, received only one and as he walked away from her, Mr. Emerson ruffled her hair in what could have been interpreted as a gesture of sheer fondness if only Kaylee didn’t notice that his gaze wandered unerringly back to Selena. He looked at her only a few short seconds, but it was a look reserved for lovers. It held secrets; it held dark promises of sensual ordeals to come, but for Selena and Selena alone. Kaylee was nothing more than a voyeur at the window, looking wistfully in at something she wasn’t meant to see and wouldn’t be able to participate in.