There are many things I love about Fall-but one thing in particular is the return of blue jeans after a summer of khaki shorts. Very few sounds more rewarding than swats over tight jeans.
The plan made perfect sense as Alex explained it. Just because Colleen had never taken a caning doesn’t mean she couldn’t dish one out. It was a fine line, her secretary administering punishments to students but under her supervision. She was sure that it wouldn’t be a problem. Besides, this was a lesson the young woman would have to learn eventually anyway if she was going to move up the administrative ladder at the Academy so why not now? Colleen saw the sense in it but she hesitated. This was a part of campus life, of life-life, that she had avoided.
“What if I, I don’t know…freeze up? Hit too hard….I don’t know.”
Alex was only half listening as her secretary flustered through her concerns. Instead, she was allowing butterflies to awaken and flitter around in her chest as an idea took shape. Since her damn elbow problem she had been denied the kind of physical release-the endorphin rush-that came from running around the tennis courts. Brisk walks weren’t cutting it.
Staring out the window she had remembered the tremendous feeling of release that she had gotten from the cane years before. Schoolwork, tennis, all the self-imposed pressure that she had carried with her seemed to lift as her skirt did. Her coach at the time, dear Mrs. Welting, had caught on and always found a reason to deliver a few well-placed strokes right across the center of her bottom (so that nothing might show when she bent low to return a volley) before big matches to help her focus.
Now she might have another outlet. Having made her decision, Alex fairly popped out of her chair cutting off Colleen’s incessant nervous nattering. “Nothing to it”, Alex clipped. “We’ll get you up to speed.”
She went to the umbrella stand beside the credenza and withdrew a cane. It was a solid but whippy bamboo, not some dowel rod bought at the hardware store. “Shut the door”, Alex told her. By the time Colleen had done that and turned back into the room Alex had slipped off her sling and was standing at her desk weighing the cane in her weakened right hand.
“Alex…?” Colleen froze.
“Would you get over here, please”, Alex asked sternly, rolling her eyes.
The girl flushed and came forward slowly on unsteady legs. This was going to happen, she thought biting her lip to keep it from quivering. Colleen respected Alex as a boss and liked her as a person-they were friends. Even more, the woman had been mentor to her throughout her time at Mt. Ashby and would continue to be, she was sure. So she wasn’t about to question what she was doing. She didn’t like it-hoped she wouldn’t cry through it-but wouldn’t question it. Swallowing air in small, quick gasps Colleen focused her eyes on the edge of the desk where she would be placing her hands.
She stopped when Alex reached out to hand her the cane. She took it slowly, hesitantly. Alex turned her back to her and, gingerly straightening her bad elbow, bent over her desk. “Lift my skirt.” The younger woman didn’t move. “Jesus, Colleen-I can’t reach back there easily…”
Colleen snapped to, a complete jumble of relief tinged with worried anticipation. “Sorry, sorry…” She had seen canings in this office-knew the routine- Alex just wanted her to get comfortable in this position. That had to be it. Setting the cane on the desk top she bent down and took the hem of her boss’ snug blue pinstriped skirt and lifted it up her legs over her back, revealing a pair of stylishly cut mosaic patterned blue and green panties.
“Those are cute…” commented Colleen nervously at a loss for something to say.
“I really didn’t expect anyone to see them today.”
Colleen’s focus moved from the panties to the bottom itself and Alex felt the scrutiny back there. This was the center of Alex’s unending battle with that extra ten pounds-this was where it always wanted to take up residence. She knew her thighs had thickened a bit and her bottom was…ample without being large. The last time she had been in this position her backside had been as tight and smooth as a dolphin’s back. Now there was no fighting the few cellulite puckers that Alex knew would be peeking out below her panties, but what could she do?
“Well”, said Alex looking straight ahead out the window and planting her feet. “Let’s see what you got.”
Still hesitant, Colleen asked if she was sure this is what she wanted.
“Get on with it”, Alex commanded.
Colleen stood behind her and off to her left. She measured with the cane and flicked it over the tightly stretched panties. Looking back over her shoulder, Alex said, “You have GOT to be kidding me…”
“Sorry”, her secretary stammered, “ That wasn’t much. Here I’ll try again.” She flicked the cane over the panties again in the same spot.
“Come on Colleen…”
“Sorry, sorry…” the younger woman stammered. She stroked again, lower this time, across the full width of Alex’s backside. She thought this stroke was better.
Alex didn’t even bother to look back-instead speaking sternly to the campus beyond the window. “Did I misjudge you, Colleen? Are you not up to this?”
“If you can’t do any better than that we might have to trade places so I can spend the afternoon working on my left handed stroke.”
“No, Alex…please”, she fairly sputtered. “They would probably hurt more if they were on the bare…” She caught herself.
“Cute. Nice try”, Alex said having had no intention of baring her bottom to her secretary.
“Really” the girl said nervously, stepping from foot to foot. “You would feel it more, right? That’s why you always cane on the bare. Right?”
The girl had a point, Alex thought. How many kids had begged her to let them keep their panties on for a caning. She could have, she guessed. It just wasn’t the process-it wasn’t the way things were done here. And what was the difference really? She was already bent over her desk showing her panties anyway. What was one thin sheen of silk between friends?
She looked back and made eye contact with Colleen who stopped fidgeting about. She nodded and turned her attention back out the window. “Go ahead then…” she said.
“Take them down.”
“Dammit Colleen! If I have to switch places with you, I promise you will not enjoy it.”
Without any further hesitation, Colleen put the cane on the floor and slipped her thumbs under the waist band of her boss’ panties. With a deep breath she rolled them down the creamy globes of the older woman’s bottom letting them catch half way down the thighs. Alex unexpectedly, almost trembled as she felt the air caress her nakedness.
Colleen thought she might be embarrassed with the thought of caning a naked bottom. She had been a college athlete and had spent enough time in locker rooms to have seen plenty of naked bottoms. They didn’t do anything for her as they passed into and out of her gaze. But here-looking at Alex like this-she fairly couldn’t take her eyes off the backside before her. No doubt this was part of Alex’s plan-to get her used to what could be a very awkward situation.
“You see anything back there?”
“Any marks-you gave be three strokes didn’t you?”
The bum appeared as unmarked as a snowbank, but Colleen leaned closer. “I think I see a line…”
“A line?” Alex scoffed.
“Right here” said Colleen brazenly tracing a finger gently across the middle of her bottom. “I think this was the third stroke.” Alex didn’t show that her secretary’s touch had registered like a shock of static electricity through her body.
“Well, get on with it then. You don’t have many strokes left to impress me.”
Leaving nothing to chance, Colleen patted the cane to the center of the right cheek to set the target then pulled back-using her arm and shoulder this time. The bamboo bit into the soft flesh and Alex jumped a little.
“OK?” asked Colleen watching a tiny pink strawberry bloom where the bamboo had kissed.
“Better. Try again.”
Another stroke like the last. “Better?”
“Yes, better…keep going…”
A few more strokes landed, each one slightly stronger than the last. Alex shuffled her feet slightly-enough to cause the panties to flutter to the floor-but otherwise didn’t outwardly react to the blows. Colleen had stopped asking how she was doing. How either of them was doing for that matter. The globes of Alex’s backside were crisscrossed with a few welts in varying shades of pink.
“Try lower…down here”. Alex reached back and rubbed the spot where the bottom meets the top of the thigh. “Right there.”
Colleen took careful aim and stroked the spot hard. Alex twitched hard and let out a soft moan-the first sound that she’d made that wasn’t an order or a direction.
“Wait”, she said breathlessly and Colleen thought that last stroke had ended the lesson. Instead Alex lowered herself onto the desk and let her arms stretch out in front of her. Her bottom caught the desk edge and bloomed outward in a most revealing way as she lay her head on the cool mahogany surface. While Alex was getting settled, Colleen had unbuttoned her right sleeve and rolled up the cuff.
“OK”, she said softly with her eyes closed. “Continue.”
Her secretary patted Alex’s rump gently high on the hip. Then she leaned back and let fly.
Every searing cut of the cane produced a wave of warmth that rolled from Alex’s tortured bottom through her loins and belly finally settling into and enwrapping her very being. She let her mouth fall open a bit and let that warmth wash everything away.
As she strode briskly across campus, Alex Tao was frustrated that the pressures of the morning did not slide off of her as easily as she would have liked. Even in the tennis shoes she had changed into, she really wasn’t getting a workout-which is what she really needed to clear her head.
Plus, a walk like this wasn’t meant to be a single-minded workout; it was a mixer of sorts. She did not shy from greeting students crossing her path which slowed her down on the one hand but helped to tighten the bonds she felt with the campus community. She sometimes imagined herself as the Dragon Lady in this small upstate institution. When she sat at her desk in the third floor office suite literally overseeing the school she had been a part of for twenty years, she felt that she was holding it all together by force of will. She was responsible for setting academic standards, setting admission guidelines, making tenure decisions, approving curricula, all issues of testing, ensuring that the professors all had what they needed, setting and enforcing the standards of student behavior, fighting off the incursions of The Chancellor…on and on.
Until recently, the stress of her day had been released by an almost daily regimen of tennis on the courts out back or on the varsity courts up campus. Until recently, that is. Too much tennis wore on aging tendons. Now she was relegated to brisk walks across campus to try to blow off steam. She still carried a version of the discipline and self-control that she exhibited behind her desk when she walked the quad but she was much looser-able to relax and let her personality shine through; get a feel for the campus-overhear what the students might be saying.
“Good morning Ms. Tao”, a fresh faced little blonde called out as she hurried through a cross path.
“Hi Cindy!” Ms. Tao called back with a smile.
“Hope you’re feeling better, Ms. Tao”, said a young boy passing her on the way to Chemistry lab.
“Getting there”, she smiled, sort of shrugging with her right arm immobilized in a sling.
“Looking forward to seeing you back on the courts!”
The kids loved to watch her play tennis. She wasn’t much good anymore-at least by her own strict standards-but she didn’t mind having the reputation as an athlete gone slightly to seed; as long as “athlete” was in the thought. Alex Tao had been a competitive player when she was a student at Mt. Ashby-once winning a conference title and always placing in tournaments with her counter-punching heady style of play. Opponents who didn’t know her mistook the sweet, smiling little girl across the net for a defensive player, happy to absorb attacks at the net and volley, until she spotted the tiniest opening and BAM! It was her style that made her an excellent coach for a few years after graduation.
Now she was a hacker who used the court to blow off steam and fend off the extra fifteen pounds that comes with sitting behind a desk or in meetings most of the day. Some evenings she would play practice matches with the current team or beat, or lose to, any ex-high school hot shot who came to campus and wanted to take on this woman that could have been their mother. Well, mathematically just barely, but to the kids, everyone who wasn’t in class was their parent’s age.
“Hey, Ms. T!”
She slowed her pace to greet Bobby Black. “Hello, young Robert-you’re off to…..Antebellum America, right?” He smiled in the affirmative a little flattered that she knew his schedule that well. “Work is going well?”
“Yes, very well-I’m in for a B at this point.”
“Great!” she enthused. “Professor Baxter is tough-but smart. Knows his stuff.”
“What’s with the…” he nodded toward her sling.
“Tendinitis. The elbow…Have to immobilize it for a couple of weeks.”
He cocked his head to one side so that she could almost see the twinkle in his eye behind the Ray Bans. “Would’ve been nice a couple of months ago.”
She laughed and turned away, continuing her walk. “Get to class, Robert. And keep the work up!”
These kind of exchanges were why she walked the campus. Two months before Bobby Black was in her office having been busted for under-age drinking. The rules were clearly defined and enforced by her. Lose a letter grade, which could mean a failure of a term, a range of academic strictures…or a caning. Robert Black wasn’t the first freshman, nor would he be the last, to hear these rules, sign off on them, then forget them until being called on the carpet.
Bobby had blushed fiercely when it became clear that the only way to rescue his term after only a month on campus was to accept a caning from the Dean of Studies, a woman no less, but it was worse when she had told him it would have to be on the bare. He had asked for an exception of course-didn’t beg, didn’t want to appear weak-that it had been his first offence. He’d never been caned before…could he please keep his underwear on…all the usual.
Alex’s heart went out to him-it really did. She had been in his spot years before and remembered the fear, the embarrassment the….trapped feeling. But she also remembered the feeling of closure-the relief she felt-after being rightly punished for something she had done. The code of Alex Tao was to stay with a system that worked. This had worked for her and for the students of Mt. Ashby for years and she just couldn’t see changing it on her watch.
She offered him a chance to call a friend-a witness. Some kids liked to have somebody with them. Girls brought roommates or sorority sisters, some came alone but asked for Colleen, her secretary, to sit in…boys were always solo. As it was with Bobby.
His eyes had filled with tears and she looked away as he fumbled clumsily with the button of his khakis. She stood behind him and coached soothingly-just push your pants down, now your underwear, don’t step out of them-that’s OK…He had stood there facing her desk with his clothes in a puddle at his feet. “Just bend over”, she said gently. “Put your hands on the desk and we’ll get this over with.”
His soft white bottom was boyishly slender and tensed when Alex tapped it with the cane. She took the disciplinary responsibility seriously and wanted to do it right-but within guidelines. “Don’t tense,” she said. “Just relax. I’ll do the work”.
His cheeks softened and she stroked him hard across the center of his butt. He gasped loudly. She knew the pain would have been a surprise, a deep burn searing through the skin. The second stroke fell expertly below the first, eliciting a grunt then a moan when the third dug into the soft flesh at the bottom of his right cheek. She stepped back as he rose on his toes and pushed back trying to dissipate the pain. By the end she had given him eight strokes-four less than the usual and two more than the minimum.
Finishing up she knew that he would be careful about wearing a towel in the showers for a few days because the purple welts that she left him with would-like autumn leave-change hues but colorfully stain his bottom for a week. While he had unashamedly stood and rubbed his burning butt Alex had reached over his shoulder with a wad of tissue knowing that he would rather take another caning than let her see him cry.
After he pulled up his pants she had him sit down-albeit gingerly-on the couch while she sat in the chair opposite to give him a few moments to calm down and let the flush leave his cheeks. He ended up staying almost an hour-It had been an informal chat-really how formal could it have been? Walls usually come down when pants do. He talked about himself, what he was hoping to get out of school, his overall plans…by the time she got up, effectively ending their conversation, she knew as much about Bobby Black as she knew about anyone on campus. He had even given her a quick surprising hug as he left.
Admittedly, this kind of open sharing was rare but Alex was convinced that the cane, a superb corrective and deterrent, could, when applied correctly, open avenues of intimate conversation and interaction like nothing else. She had seen it happen over and over and was why she was so committed to what she saw as the Mt. Ashby way.
On the other hand, Mr. Wallace Foster, the Chancellor and her only superior at Mt. Ashby was a bit of a martinet. Before he came to campus five years before all discipline unquestionably fell to the Dean of Studies. The Chancellor, handling the money side of Mr. Ashby from the top floor of the Administration Center across campus stayed out of it. Lately though, over the last few months, he had wanted to spread his wings a bit and had called some students to his office over paperwork issues-incomplete financial forms, things like that. Technically he was in his right to mete out whatever discipline he felt fit to but Alex thought it was a little much to flip up a freshman’s skirt and stroke her across the panties for a paperwork error. Seemed to her a bit capricious and…recreational on his part. Definitely not the Mt. Ashby way.
Which is why this tendinitis had come at such and inopportune time. She knew that Mr. Wallace would happily take on more of the disciplinary responsibilities from a Dean of Studies who could not swing a cane. Her left arm was embarrassingly useless-she might be able to work on it, but doubted it. Damn! She was back at her building already. She took the steps two at a time trying to pump her heart rate for than even her brisk walking pace did. This was the kind of thing that she needed the tennis court for; to blow out the cobwebs and clear her mind.
She moved quickly through the open door of her outer office. “Hi Alex”, Colleen, her secretary, a willowy, ruddy blonde, greeted her. She had hired Colleen a year before knowing that she wanted to be on a career path similar to her own. An ex-tennis player (who consistently beat Alex on the strength of her stride alone) she was taking classes at night to fill out her Master’s and saw herself-in her dreams- as a Mt. Ashby lifer.
“Any calls, disasters or catastrophes happen when I was out?” She lingered at the desk.
“All quiet…You do remember your four o’clock with Professor Barren, right?”
“Yes, yes”, then seeing another chance to move, “….Call her will you? Tell her I’ll come over to her office instead of her hauling herself up here.”
“And make me a cup of tea would you? Green, decaf”.
When Colleen came in with the tea-finished off with a squeeze of lemon-she found her boss swiveled round in her chair looking out over the campus or more precisely, the trees on the quad. She set the cup and saucer on the corner of her desk and stood by a moment. Alex was lost in her thoughts rubbing the thumb of her left hand along her jawline. “Anything else?” she asked.
“You’ve never been caned, have you?” asked Alex without looking away from the window.
“Ah-no. No, never.” Her voice got a high breathless sound to it. “Why? Have I done something?…I…I”
“Relax”, Alex reassured her turning back to the room. “Nothing like that…”
“Jesus! Don’t scare me like that-I feel like I have to pee now.”
“You’re such a baby-I was just curious. I mean you’ve heard enough punishments through the door…came in and witnessed a few; but never had one yourself.” With a smile, “Are you really that good?”
“I’m really that petrified!”
“I was paddled once. In seventh grade by my gym teacher: Mrs. Silvers. She caught me handing a note to my boyfriend out the window when he was at recess. That was a big no-no back then. As soon as I saw her see me, my knees almost buckled. I had to go to her office behind the gym after school. I had to wait all day! In and out of the bathroom all afternoon. I almost had a heart attack.”
“What was it like finally?”
“Horrible. Because it was her, really. We all had the idea-we all knew-that she liked doing it. I was bent over, hands on my knees, straight legs…the worst was hearing her shuffling around behind me-picking up the paddle, stepping from one side to the other, staring at my backside, measuring me-all that.”
“Nope-silent. Four swats-one right after the other. Bam-bam-bam-bam! Hurt like hell!”
“Did you cry?”
“Wouldn’t give her the satisfaction. Later though, yeah. And my butt was still red when I got home. And bruised the next day.”
“I can’t believe you never told me about this.”
“I didn’t want to talk about it…From that day on I did everything I could to avoid the paddle or the cane here. Some kids at school they take a caning as ‘the cost of doing business’-if they get caught, they’ll take it. Not me. I became Miss Color Inside the Lines, Goody-Two Shoes.”
“And she liked doing it-this gym teacher.”
“Oh yeah…She’d try to catch people at something so she could bend them over”.
“Not like we do here.”
“Night and day. You care about us…about the students, I mean. This is a safe place, even for those being punished.”
Alex smiled and nodded slightly. “That’s good to hear. Thank you.”
“It’s the truth.”
“You know what Chancellor Foster has been doing in admin, right?”
“Yes, I’ve heard. Reminds me of Mrs. Silvers.”
“I believe that it’s important for me to control the discipline and punishments at Mt. Ashley here. Out of this office. Do you agree?”
A thick silence fell over the room and the tableau remained. Colleen followed Alex’s gaze back to the trees outside where it remained entwined with the branches as her boss formulated a plan. Actually, as she formulated a couple of plans. After a few moments, Alex told the tree, “You’ll have to become my good right arm.”
“How?” Colleen asked.
To Be Continued
“As long as there’s such a thing as time, everybody’s damaged in the end, changed into something else. It always happens sooner or later…But if it happens, you’ve got to have a place you can retrace your steps to…”
Haruki Murakami – “Kafka On The Shore”
Ellison eyed him from behind the wide varnished desk. This would be the time to invite him to have a seat if she was of a mind. She wasn’t. He was in his mid-twenties, a good decade younger than she, but still built like the athlete he must have been in college. Even six feet-maybe six one-no more than 200 pounds. Solidly muscled across the arms and shoulders with what looked like tight abs and strong legs. His hair was unfashionably long but clean and he had a tan and a smile that she was sure could and had melted coeds at Bryson. The khaki Dockers, moccasins, and light blue crew neck completed the picture.
He met her gaze when he came into the office but was now distracted. Ellison had left a riding crop on the corner of her desk-so far away from her that she couldn’t reach it easily without getting up but directly in his line of vision when he approached her. The crop was tightly wound and supple-with a small leather loop on the business end. The handle was wrapped leather with a wrist strap so that she wouldn’t lose it in action. This is where his attention was focused.
This is the time of the office visit where it becomes crystal clear to the visitor what he is doing there and the small flutter that he felt in his chest coming across the threshold increases to a gentle pounding.
“Take your pants off.”
“Take them down?” he asked hopefully.
“No, off”, she answered. “Course you’ll have to take your shoes off-do what you want with the socks, on or off, I don’t care. And underwear off. Naked from the waist down. Put everything on that chair over there.” Ellison gestured at a wooden chair beside her desk.
His hands wanted to shake a little as he worked at the laces on his shoes, but he kept them in check. Off went the shoes and he took off his socks and slipped them into the shoes. As he unbuckled his belt and unsnapped his trousers he watched Ellison out of the corner of his eye as she arranged the chair in front of her desk.
Ellison busied herself with the chair so she wouldn’t watch him undressing although she wanted to. It was a large overstuffed chair with big rolled arms. She slipped the ottoman from the front of the chair to the side-next to one of the arms. Even now, with his pants around his ankles and his thumbs in the waistband of his boxers he couldn’t stop himself from eyeing Ellison’s slender ass encased in her tight black jeans as she pushed and pulled at the furniture. Even in his current predicament, the sight of her bending over in front of him-it had to be on purpose-brought his cock to semi-erect life. Hopefully she wouldn’t see it. He folded his pants and placed them on the chair with the underwear on top. When he turned back to the chair, Ellison had placed a throw pillow on the seat.
She stood casually next to him-as if they were on a street corner waiting for a bus.
“This is a new set-up for me. You’re the first to try it.”
“Am I honored?”
“Thought it might be better than the old bend over the desk, deal. Especially for this one-since you’ll be getting a pretty strong punishment.”
“Really? Isn’t this my first offense?”
She was standing right next to him. If she moved her hand six inches to the right she would have been able to cup his ass-maybe rub and kneed it just enough to see if his cock would enliven a little more than she’d already noticed. And then what if it did? She felt a little rustle in her own chest as she stole a glance toward the floor to see if he was stiffening. She felt that if he was, she was in danger of putting herself into a serious misconduct situation.
They were all adults here; there was nothing preventing them from doing whatever they wanted off-campus or out of the office. But this situation-where she was required to wield the stick-such as it was-the lines were pretty strongly drawn. Only once or twice in the times she was in this position had Ellison veered into the forbidden zone. And she had regretted it both times. But this guy was tempting to her in a way that he didn’t know and she couldn’t understand. She calmed her voice to ensure there was no quiver when she spoke.
“Your first provable offense. The first you admitted to. I never questioned you about the other three that we discussed. I know you would not lie to me if I asked you, so I haven’t. Do you want me to ask you about those three other nights?”
Even with his eyes down, she could see his face flush crimson. This guy was something special-he was standing next to her smelling of shampoo and expensive aftershave, bare-ass in preparation to get his bottom whipped and he blushed at the thought of telling a lie.
“You don’t have to ask”, he said quietly. “It was me.”
He followed her directions and knelt on the ottoman-laying across the padded chair arm. The cushion on the seat supported his middle but the chair arm was the highest part of the assemblage and thrust his hips and bottom up and out. She watched from behind as he fidgeted to place his manhood, which had shrunken, into a comfortable position. This would be a better position for a woman-who didn’t need to deal finding a spot for the snake to lay. He used his hand to position it up along his belly and Ellison let him settle in actually feeling a little guilty about watching his tight bottom cheeks tense then relax as he slid his knees about shoulder width apart and exposing everything that he had to her.
That’s the way it generally was with men-at least with her. Women would bend over and hold their cheeks so tightly that you couldn’t slip a dime between them. At least in the beginning-until the paddle, or cane or strap or crop made writhing unavoidable-then they would show all in vain attempts to avoid the swats. Guys though-she was treated to the strong backside, the tight hamstrings and the balls hanging free between the legs.
“Simple rules, now that you’re situated. I will whip you until I’m done. You will take what I dish out. No reaching back, no covering, no getting up when you are in position-which you now are. You understand?”
“Yes”, he said, muffled, talking into the pillow.
Time to get started. She touched his right cheek with the leather tipped end of the crop and watched him jump a bit. It was just a twitch, but she smiled. It was always the way. With a quick draw and a snapping forehand she brought the crop down on the exact spot she had just touched; just above center on the right cheek. He gasped and dug into the arm of the chair. The second stroke was a little stronger, hitting the same cheek-about an inch lower. He didn’t jump but Ellison saw his back tensing as he tried to redirect the pain into his shoulders and back. She swung the third stroke short to catch the left-nearest cheek-dead center. He grunted loudly and spread his legs a little wider so he could push off his knees to further dissipate the pain.
That movement proved to be his undoing as he moved after Ellison had already begun her next stroke. She swung full strength meaning to strike hard in the crease of the left cheek-where the leg met the bottom-hoping to raise the first welt of the session. His slight movement opened his legs a little wider and the crop’s leather tip bit hard into the soft puckered skin of his backward peeking scrotum.
The pain registered like nothing had to this point-like nothing ever would. He thought sure that she had poked him with a cattle prod-or dropped a hot coal back there. He bucked backward off the chair and a gasp escaped his clenched teeth. Tears welled in his eyes as he slammed his legs shut kicking his feet from the knees. “Jesus!” he hissed.
She stepped back startled. It had happened so quickly that as she saw the crop dig deeply into his most sensitive skin she felt powerless to stop it. His buttocks were clenched tightly and his legs seemed carved out of stone. His back raised and lowered as he recovered normal breathing. Ellison put the crop in her off hand and patted his bottom-one cheek then the other.
“I’m sorry”, she said gently. “That’s why I need you to stay still, understand?” He nodded quickly as she moved slowly from patting to rubbing. There was one mark on his butt so far-not much to show-but she had to relax him before she could get back to it. “Don’t tense now-loosen up a little. It will be worse if you keep your bottom hard”. She stroked until his cheeks softened and his breath settled. Then she did something she had never done before. “Here-open up“ she fairly whispered as she put her hand between his legs. He slid his knees apart a little and, when she patted the inside of his thigh, a little more. Gently-almost clinically-she reached between and took his scrotum in her hand. He lifted a little to give himself a little freedom. She rubbed the small purple bruise with her thumb feeling the rustle in her chest increase to a roar. She always enjoyed the feeling of power being in this position gave her but this was something more.
She controlled her hand and her voice as she released him. “You’re OK. A little bruised-but fine. I’m going to give you another dozen or so then we’ll see where we are. They’ll be pretty hard, but can’t imagine they’ll hurt you worse than the last one. You OK with that?” She waited for it…”Yes M’am”, he said quietly as she smiled.
She took aim at the lower right cheek and let fly into the soft skin at the top of the thigh. He jumped. Then another in the same spot followed by a loud yelp. Three more whipping strokes dug deeply as he lost all inhibition about crying out. Each “thwack!” was followed by an “OWW!” or “Ouch!” each louder than the previous. When he first laid across this chair arm he was determined to suffer his punishment in silence. He especially didn’t want the girl in the outer office-to know what was happening in here. Of course she knew-but he imagined himself the strong silent type.
Ellison moved up the bum to the top-landing four hard strokes-“OW!” “WHIP!-AHHH!” across the top of both cheeks. The two on the right raised welts immediately-one hot pink and another tomato-red. She had the power to bring out deep purple weals-she had drawn blood in her day-but was doing enough for now. The next stroke bit deeply into the middle of his right cheek. “OWWWW!” he cried out and straightened his legs-thrusting his butt firmly into the air. Ellison obliged what looked like an invitation and stroked hard into the left moon. His cry was more of a grunt as he gritted his teeth and further tensed his body so that nothing was touching the chair but his chest and elbows.
She would normally pause here to let the subject relax and reset himself but that just dragged it out. She wanted to be as merciful as she could and at this point and she figured the easiest way to do that was to get it over with. She reached high and stroked hard into the center of his board-hard butt. He wailed like a bee-stung child and collapsed back on the chair arm and twisted. She hoped he wouldn’t cry-not so much for her but for him.
“One more”, Ellison said softly as he flattened back into place. “OK”, he breathed. His butt was criss-crossed with stripes and a few small red blisters where the end had bit deeply. Those coupled with the unplanned shot to his balls had made for a more unpleasant day for him than she had planned. She pulled back and stroked into the nearest cheek, if not gently, certainly not as hard as the others. He didn’t even jump-just relaxed and exhaled quickly. “Thank you”, he coughed, realizing that she had eased up on him. “It’s OK”, she said placing the crop on the desk, “you did well. Now stay put.”
He relaxed a bit and lifted his hips to reposition his cock which had begun to thicken as he struggled against the leather of the chair arm. Funny how fifteen minutes ago he was mortified at the thought of this woman maybe seeing his bare ass but now he could feel her eyes on him as she moved behind the desk and she was seeing more of him than anyone ever had.
He heard a drawer open and she walked back to stand to his left. He looked back over his shoulder to see what she was doing. “Worried?” she asked with a smile in her voice. “Curious”, he answered. She held up a small plastic bottle. “Aloe and vitamin E mostly”, she said as she squeezed a dollop into her right hand. “Relax now.” He put his head back down on the pillow as her fingers with the cooling gel touched his hot, tight skin. “ahhh…” he sighed. She applied the lotion liberally to all of the welts and bruises then generally rubbed it over his whole backside. “Better?” “Oh, God yes!” he answered. “Almost makes it worth it, huh?” she joked. “I wouldn’t go that far”, he said smiling into the pillow.
He felt her hand part his legs and he pushed backward to give her access but also to relieve the pressure of his growing erection which was pushing against the chair arm. Ellison’s fingers found his bruised scrotum and rubbed the cooling lotion onto what was becoming a very taut little bag indeed. When he moaned this time, it was less about the pain and more about the stimulation she was providing.
“Get up”, she said with a gentle pat on the rump. He pushed back to his knees revealing everything as he stood straddling the ottoman.