The Mentor

A fictional tale based on a real-life event

By Kenny Walters

“You can get changed in here. When you’re ready, come out into the hallway and stand here, facing the wall. You have ten minutes.”

Karen Chatway smiled her thanks and entered the room. The door closed behind her as she looked around. It was a bedroom, a nice clean bedroom with pale blue walls and a white ceiling. She went over to the window and looked out onto a tidy garden surrounded by high hedges that meant no one could look in unless they were actually in the garden.

She put her bag on the bed and slid open the zip. A glance towards the closed door showed there was no lock or bolt that she could fasten, but she didn’t mind. She trusted Mr Whittaker, even though she had met him for the first time just twenty minutes ago. She stripped off her blue jeans and white woollen top, kicked off her tan coloured comfortable shoes and sat on the edge of the bed in just her black lacy French knickers and bra.

Karen had arrived promptly at eleven o’clock. She’d arrived at the address twenty-five minutes early and then sat in the car until one minute to eleven. Then she’d grabbed her bag, swiftly walked up the short path and pressed the doorbell.

Mr Whittaker seemed more friendly than she’d imagined after speaking to him on the telephone. He welcomed her into his house and into the small lounge, prepared coffee for them both and sat with her while they exchanged pleasantries. Declining the offer of a second cup, Karen had then asked what the order of proceedings would be.

Getting changed was first on the agenda. Now alone in the bedroom, and remembering she had just ten minutes to get ready, Karen stood up and quickly stripped off her bra and knickers. Delving into her bag, she extracted fairly brief bottle green panties and a white bra. With these on, she looked in her bag again and pulled out a white cotton blouse. A full length mirror adorned one door of a line of built-in wardrobes and she looked at herself as she buttoned up the blouse. The top button was tight, almost uncomfortably tight, so she left it unfastened. Another sortie into her bag brought forth a pleated dark green skirt which she stepped into and fastened the side button and zip. She pulled the hem of her blouse down, outside her skirt.

Smoothing down the skirt and blouse, looking at herself in the mirror, Karen thought she looked the perfect schoolgirl, albeit a forty-three year old schoolgirl. It just needed the final touches. Karen hadn’t worn a tie since her own genuine school days, and she struggled to fasten the green and yellow tie she’d bought in town a few days ago. Despite her best efforts, the knot looked untidily insecure. She pulled the knot tighter, but that didn’t seem to really improve things.

‘It will have to do,’ she thought.

Back to her bag, and Karen pulled out the green blazer she’d bought from a second hand charity shop and put it on. A few tugs and a little smoothing down, and it looked quite smart. Lastly, new flat black shoes completed her ensemble.

After looking at herself in the mirror and checking her appearance was as good as she could reasonably make it, she sat down again on the edge of the bed. It had taken a great deal of effort to reach this point. Emails had been exchanged, Karen’s requirements carefully explored and then, just days ago, the phone call to confirm everything was ready for her. Suddenly, she thought about the time. She got up, checked herself again with a quick swirl in the mirror and went back out to the hallway.

Karen soon found the spot she was told to occupy and turned to face the wall. Her heart was starting to race, her mind began to panic. Was she supposed to place her hands on her head? No, he hadn’t mentioned that, had he? She squared her shoulders and stretched her arms down by her sides. Then, just to make sure, she pulled her blazer hem down all around, and replaced her arms by her side. She hadn’t combed her hair! She ran her fingers through her blond shoulder length hair until it felt at least smooth, and considered and then rejected the thought of going back into the bedroom to comb her hair properly. ‘Too late!’ she thought.

After several more minutes, which Karen spent facing the wall but with continuous fidgeting as she checked and rechecked various aspects of her attire, the door to the front room opened and Mr Whittaker came out into the hallway.

“Karen, I’ve been watching you in the small security camera mounted close to the ceiling up there.”

He pointed and Karen looked up at the ceiling over the front door where indeed there was mounted a small and unobtrusive camera. Karen bit her lip, wondering whether she’d done anything wrong while she waited. She couldn’t think of anything.

“Firstly, Karen, you spent twelve minutes getting changed before you came out into this hallway. I gave you just ten minutes. Correct?”

“Yes, sir.” He hadn’t asked her to call him ‘sir’; it just seemed appropriate, and he didn’t tell her otherwise.

“In my book, ten minutes means ten minutes, not twelve.” Mr Whittaker reinforced his statement by giving Karen’s bottom two hard smacks that fell across the lower back of her blazer. “Understood?”

“Yes, sir.” Karen said, wincing at the two smacks that now made her bottom tingle. “Sorry, sir.”

“You’ve then stood here for six minutes doing little else other than fidget about. I told you to stand facing the wall, nothing else. Correct?” This time, the message was reinforced with four sharp smacks to Karen’s bottom.

“Yes, sir. Sorry, sir.” Karen was expecting the smacks this time and tried to stand robustly against them as she was slapped.

“You will learn to do as you are told, nothing more, nothing less.”

“Yes, sir.”

“Now, go into the study and stand in front of the desk.”

Karen didn’t reply; she promptly and steadily entered the front room, saw a desk with a large armed swivel chair behind it, and went to stand in front of it. Mr Whittaker followed her in and sat down behind the desk. He looked her up and down.

“So, Karen, you’re here to experience the cane for the first time. As we discussed on the telephone, I think six strokes will be sufficient for your first time here. As we also discussed, they will be administered across your bottom over your underwear. Understood?”

“Yes, sir.”

During their earlier exchanges of emails, Karen had volunteered to take twelve strokes but Mr Whittaker had advised against it. “Take six, and if you feel you want more then we can think again,” he’d told her. “In any event, I shall be monitoring your behaviour and if necessary I shall impose further punishments during your time here.” Karen, her bottom still smarting from the smacks in the hallway, now had some idea of what he meant!

“Before we go on to your caning, though, I think a uniform inspection might be in order, don’t you?”

“Yes, sir.”

Mr Whittaker had suggested this to Karen, and she had readily agreed. The choice of a green uniform was Karen’s idea; it was similar to the uniform she’d worn as a schoolgirl.

“Very well.” Mr Whittaker stood up and went to the centre of the room. “Come over here, please.”

Karen followed and stood facing her mentor.

“Turn round.”

Karen made a 180 degree turn. She felt Mr Whittaker’s eyes looking down the back of her blazer, then felt his fingers looking under her collar.

“One moment.” Mr Whittaker went over to a chest of drawers, found a plain wooden backed clothes brush, and returned. Soon, Karen felt her blazer being roughly brushed across the shoulders, down the back even to her bottom, then he came round and brushed the front. A certain amount of dust seemed to float through the air.

“Did you brush this blazer before coming here? Did you take it to the dry cleaners or even press it yourself?”

“No, sir.”

“No, you clearly didn’t.” With the clothes brush held in his left hand, Mr Whittaker gave Karen another four hard smacks to her bottom. “Either take it to the dry cleaners, or at least give it a good brushing and press it yourself. Understand?” Another two smacks stung Karen’s bottom.

“Yes, sir.” She replied sharply as her bottom smarted from the blows.

“Very well, remove your blazer and hand it on the hook on the door.”

Karen looked round, saw the hook and began taking off her blazer. While she went over to the door, Mr Whittaker returned the clothes brush to the chest of drawers. They met back at the centre of the room.

“That tie is the most untidy example I have ever seen.”

“Yes, I’m sorry, sir. It’s just that I haven’t had to knot a tie for years.”

“Then let me show you.” The mentor stood in front of Karen and took hold of her green and yellow tie, pulling the knot apart. “Why isn’t your top shirt button fastened, girl?”

“It felt a little tight, sir.”

“Let’s see.” Mr Whittaker left the two ends of the tie dangling down Karen’s chest and turned his attention to the white blouse. He soon had the collar fastened. “Not too tight at all,” he commented as he checked by inserting two fingers into the collar.

“Perhaps it’s because I don’t usually wear tight collars, sir.”

“Possibly. Now, to fasten your tie you hold this end like this, bring the other end across and under, then across like this, through here and down through there.” The mentor soon had the tie neatly secured under Karen’s chin. “Have you got that?”

“I think so, sir.”

“Good. Now, let’s look at your blouse. Yes, clean and ironed. Well done, Karen. But why is it not tucked into the waistband of your skirt?”

“I thought it looked nicer that way, sir.”

Mr Whittaker walked round behind Karen. “Well, it doesn’t. Blouses should always be tucked into the waistband of skirts and trousers. Understand?” He smacked Karen’s bottom twice.

“Y-yes sir.” Karen winced at the smarting whacks to the seat of her skirt.

“Now, your skirt. Good colour, good pleats. And clean. Well done, Karen.”

“Thank you, sir.”

“Shoes. They look new, Karen.”

“They are, sir.”

“Make sure you keep them well polished.”

“Yes, sir.”

“But, no socks?”

“Oh, I forgot, sir. They’re in my bag. Shall I go and put them on?”

“In a moment, Karen. Before that, underwear. White bra, green pants?”

“Yes, sir.”

“I hope so, Karen. If not, there will be additional punishment. Understood?”

“Yes, sir.”

“Stand up straight, girl. Don’t slouch.”

“Yes, sir.” Karen straightened up and stood to attention.

“Better. Now, go and put your socks on and report back here. Quick as you can.”

“Yes, sir.”

Karen left the room and went back to the bedroom. She searched through her bag but couldn’t find the white knee length socks she’d bought specially. Then she remembered. She’d left them on the kitchen table in her own house, thinking it would help her remember to take them. With a sigh, Karen knew the only thing she could do is return to face her mentor without them, and take any penalty that might be, probably would be, awarded.

“I’m sorry, sir,” Karen blurted out as she entered the front room, “But I’ve left the socks at home. I’ll bring them next time for sure.”

“Do you not knock before entering my study, girl?” Mr Whittaker was now seated at his desk.

“Oh, yes, um, sorry, sir.”

“So, bad memory and bad manners?”

“Er, well, yes, I suppose so, sir.” Karen stood in front of the desk looking guiltily down at the hard wooden floor. “Sorry, sir.”

“That seems to be a favourite saying of yours, Karen. ‘Sorry, sir’.”

“Yes, I’m afraid it seems that way, sir. I’ll try much harder next time, sir.” Karen replied hopefully.

“I hope so, girl. In the meantime, I think a good spanking is in order, don’t you?”

Karen’s heart missed a beat. She tried hard not to smile, and nearly succeeded. “Yes, sir,” she whispered.

Mr Whittaker stood up and came out from behind his desk. He went to one side of the room, collected a small upright chair from its place against the far wall and brought it out into the centre of the room. He sat down.

“Right, Karen, come and stand to my right.”

The slim blond woman had been watching every move. She turned and took the four steps over to where her mentor now sat. She looked down at the grey trousered legs that awaited her.

“Bend over. Come across my lap, girl.”

“Yes, sir.” Her voice faltered.

It was awkward getting down across her mentor’s lap, and Karen had at one point to place her hand on Mr Whittaker’s thigh, but eventually she managed to position herself face down and ready to be spanked. She felt herself being gripped by her hips and moved forward slightly, then her right arm was folded behind her back and held there.

“As we discussed earlier, Karen, later you are going to be caned across the seat of your knickers. I see no reason why this spanking should not be conducted in the same fashion, do you?”

“Um, no, sir.” Karen answered, not sure whether she should reach back with her one free hand and pull her own skirt up.

A tickling sensation at the back of her thighs followed by a slight coolness signified that her mentor had the matter in hand. Karen felt her green pleated skirt being carefully folded well up her back.

“Indeed you are wearing the required dark green knickers, Karen.” Mr Whittaker observed.

“Yes, sir.” Karen smiled, pleased by the apparent approval. That smile soon left her face when the first smack landed on the very centre of her knickers. “Ow!”

Mr Whittaker spanked her sharply and often, spreading the smacks across both buttocks and up and down, all over Karen’s bottom. The spanks continued to rain down and firstly stung and smarted, and then imparted a sore feeling right across the woman’s bottom.

“That certainly hurts!” Karen gushed breathlessly.

“It’s supposed to. It’s a punishment!”

“Yes, sir. It’s working!”

Karen tried to struggle as she lay across Mr Whittaker’s lap but found his grip on her arm reduced her to simply wriggling as the spanks continued to render her bottom ever more hot and sore.

“This spanking will continue until you learn to hold still and take your punishment, girl!”

With tears now rolling down her face, Karen tried to do as she was told. The sharpness of the spanks seemed to reduce slightly, and then they stopped.

“Okay, Karen, that will do for now. Go and stand facing that wall. Hold your skirt above your waist.”

Karen struggled to her feet, having again to lean on her mentor’s thighs to help herself up. She quickly pushed her skirt back down and then tenderly massaged her sore bottom over the seat of her skirt.

“Turn round!”

Karen turned so her back was towards Mr Whittaker. She felt confused by the new instruction. Six hard smacks to her bottom were accompanied by the words: “Did I give you permission to let your skirt down? Did I say you could provide any comfort to your bottom?”

“No, sir.” Karen replied quickly, hoping to avoid any more smacks across her aching backside.

“Right, now lift your skirt up at the back and go and stand facing that wall!” He indicated the wall opposite.

“May I wipe the tears away first, sir?” Karen sniffled.

Mr Whittaker responded by opening a drawer in his desk and pulling half a dozen tissues from a box. He handed the tissues to Karen and she wiped her face several times before throwing the now wet tissues into a wastepaper basket held up by her mentor.

“Thank you, sir,” Karen whispered before she reached down and lifted up her skirt. Then she turned and walked awkwardly across to the far wall.

“You will remain like that for fifteen minutes, girl! I will be back shortly.” The mentor then left the room.

Karen desperately wanted to soothe her sore bottom, but was reluctant to do so after being caught out previously when she was out in the hallway. She tried moving her head slightly to one side and then the other in an effort to see whether another camera was positioned so her actions could be observed. She couldn’t see one, but that didn’t mean it wasn’t there, somewhere. Karen decided strict compliance to her mentor’s instructions was the best policy. She stood starchly upright, both hands gripping her skirt and holding it above her waist. It wasn’t long before Mr Whittaker returned.

“Glad to see you’ve at last learned to behave and do as you are told, Karen.”

“Yes, sir.” Karen could hear faint scratching, as though her mentor was writing, but she didn’t dare turn around and look.

Her bottom still throbbing, Karen felt she’d been standing there for longer than fifteen minutes. She sighed, more bored by the monotony rather than feeling any foolishness at the position she was in.

“Petulance is not a good emotion, Karen.”

“No, sir.” She really wasn’t used to this minute examination of her every move.

“Right, Karen, you may come over and sit on this chair.”

Karen turned and saw the small chair Mr Whittaker had sat on to spank her was now positioned by the side of his desk. She let her skirt drop into place and smoothed it down.

“Thank you, sir,” she answered as she sat on the thin padding of the chair seat.

“I set high standards and you will soon learn to comply, Karen.”

“Yes, sir.”

“So now we come to the main reason for you being here today. You told me you wanted to experience being caned. Is that correct?”

“Yes, sir.”

“Presumably, then, it’s not something you’ve experienced before?”

“No, sir.”

“Were you punished as a child?”

“No, sir, except maybe not being taken out for a treat or something. I got two detentions at school, but that’s about it.”

Mr Whittaker looked Karen directly in the eye, and she quite liked that, finding something warm and secure in his bright blue eyes.

“The cane hurts, Karen. I’ll be administering six strokes to your bottom, and each one will be a quick and very sharp shock when it hits you. That’s the whole purpose. Six short, sharp shocks to teach you a lesson. Understand?”

“Yes, sir.” Karen sounded doubtful.

“You have a question, Karen?”

“Yes, sir.” She answered, pleasantly surprised he was sufficiently sensitive to spot that. “You said earlier that you were going to cane me across my knickers. I was half expecting to get it across my bare bottom. And six doesn’t sound very many strokes, sir.”

“This is our first session together, Karen. You will find six strokes pretty painful, I can assure you. As for caning you across your knickers, well, we are still relative strangers and I’m sure you will find your underwear doesn’t offer much protection. We may at some stage in the future remove your knickers to provide extra embarrassment and humiliation, but that’s for another time.”

Karen nodded. “I see. Yes, that sounds quite sensible, if a grown woman presenting herself for punishment sounds at all sensible.” She grinned.

“There are many like you, Karen. I find myself quite busy.”

Karen smiled again, but didn’t answer.

“So, time for your punishment, I think, Karen.”

“Yes, sir.” She replied with some enthusiasm. This was, after all, what she had come here for.

“Please go back to the wall and stand facing it while I get everything ready. This time, I want you to place your hands on your head.”

Karen did as she was told, feeling very schoolgirl-like as she clasped her hands together on top of her head. Although pangs of fear and trepidation flittered through her mind, she was looking forward to what was coming next. She could hear Mr Whittaker moving about. At one stage, he went to a small cupboard and opened the door. Soon after the cupboard door closed again, Karen heard the unmistakeable sound of something being swished through the air, and she knew that had to be the cane with which she was to be chastised.

Moments later, Karen received the command she was waiting for.

“Right, young lady, you may put your hands down and come over to my desk.”

Letting her hands drop to her sides, Karen turned and found the desk now devoid of everything except a crook handled cane and a small exercise book. Mr Whittaker was standing to one side of the desk.

“Stand close to the desk, please.”

Karen did as she was told, her eyes focused on the slender cane.

“Is that what you were expecting, Karen?” Mr Whittaker responded to her interest in the cane.

“It’s shorter and thinner,” she answered.

“They can be longer and thicker, that’s true, but this is what many head teachers used to use. It’s similar to the ones I used when I was teaching. It will do the job, I assure you.”

“Yes, sir.” Karen sounded a little doubtful, not because she questioned her mentor’s words but because she was beginning to have qualms about letting herself be whipped with this small cane. “This is going to hurt, isn’t it?” she added without really thinking.

“Yes, Karen. That is why we are here. Now, please bend over across the desk.”

Karen hesitated for several moments before taking a deep breath and leaning forward.

“Get right down onto the desk,” Mr Whittaker encouraged. “Wrap your fingers over the further edge.”

Karen laid herself across the desk, reached out and gripped the further edge. With just minor fidgeting she found a position that was half comfortable, even though the desk pressed into the tops of her thighs. She thought about pulling her skirt up to reveal her knickers, but previous experience had already shown that it was better to do just as Mr Whittaker told her, nothing less, nothing more.

After some seconds, Karen felt the hem of her skirt being taken hold of and then lifted up until it was folded across her back. The air felt cool against the backs of her now naked thighs. Then Mr Whittaker picked up the cane from beside her. Karen shivered. This was it; the moment she’d both been looking forward to, and the moment she now feared and dreaded. Her breathing became shallow as she tensed.

“Yeeow!” The cane whipped across her bottom and created instantly a feeling like she’d been shot across both buttocks. “My god, that hurt!”

Mr Whittaker ignored her. He was already lining up the second stroke, but waiting until he felt Karen had endured fully the effects of the first. After about twenty seconds, he slammed the cane across her bottom, slightly higher.

Karen wasn’t ready for it. She was still trying to cope with the burning, stinging pain that still hadn’t noticeably subsided.

“Uh-huh!” She gasped, as a fresh bout of burning agony shot across both buttocks. For a few moments, she began to doubt her ability to cope with the level of pain inflicted by what seemed such and innocuously small cane. Then, comparing the two strokes, she felt the second no worse than the first, and then knew she could and would endure.

On an impulse, Mr Whittaker swiftly administered another stroke even higher than the two previous ones.

“Uh!” Karen grunted. She wasn’t caught out by the sudden burst of pain this time, now she was beginning to understand the way the caning was being carried out. The pain was just as incredible, but her inner strength was now kicking in and allowing her to cope.

She waited. And waited some more.

“Hah!” Finally, the fourth stroke lashed her bottom, much lower down than she’d expected. The force pushed her up and over the desk even more, until she settled back. The pain was incredible, and yet something inside her head also found it almost therapeutic, a release from the tensions and stresses of her everyday life.

“Okay!” Mr Whittaker seemed concerned.

“Yes,” Karen whispered, sounding breathless.

Her mentor paused. He knew he was going to apply both the remaining strokes to the centre of the panty clad target, but should he continue with the previous gaps between strokes, or should he whip the final two down quickly so the poor woman could get her punishment over and done with?

“Aaah!” A single stroke cracked across Karen’s bottom. It hurt just like all the others, and she had to repulse her natural instinct to leap up and soothe her poor sore bottom. Her mind was in some turmoil, a whole mixture of emotions, even disappointment the next would be the last of the six strokes she’d been offered.

“Yeessh!!” That final stroke seemed harder, heavier, whippier. “My god, that stung!” She uttered without thinking.

“That completes your punishment, Karen. You may get up when you’re ready.”

Karen inhaled and exhaled three times; long deep breaths that expanded her chest and somehow made the pain across her bottom that bit easier to tolerate. She reached back with her left hand and touched the seat of her green knickers, exploring gently for signs of damage to her soft buttocks underneath. She could feel ridges, sore angry ridges that smarted as she touched them. Finally she eased herself up from the desk.

“It hurts, doesn’t it?” Mr Whittaker said softly.

“Mmm, yes.” Karen answered, feeling uncomfortably sore, yet somehow satisfied.

Mr Whittaker placed the cane down along one edge of his desk and stood close to Karen. She moved towards him until she pressed her body against his. He put both arms around her, drawing her in. They embraced for over two minutes, neither speaking.

It was Karen that broke away first. “Is that it for today?”

Her mentor thought for a few moments before answering. “Yes, that’s it for today. How did you find it?”

“Good. Yes, good.” She nodded, still feeling the ridges across her bottom through the pleated skirt that had now fallen back into place.

“What you wanted? What you expected?”

“Yes, I think so. I mean, the pain from the caning was something I couldn’t really anticipate. I can certainly see why it was such an effective deterrent when it was used in schools.”

“Yes, many of us have rued the day it was removed.”

Karen smiled ruefully. “So, can we do this again? Maybe in a couple of weeks?”

“I’ll check.” Mr Whittaker sat down behind his desk and pulled a diary from one of the drawers. “Let’s see. Yes, two weeks from today? Same time?”

“Yes, I get the same day off every week. What will we do next time?”

“Perhaps we might introduce you to the slipper. Plus anything you feel you’d like to do.”

“I’d like to be caned again.” Karen said thoughtfully. “Perhaps just six again?”

“We can certainly do that.”

Having completed their goodbyes, Mr Whittaker showed Karen to the front door. She reached up and kissed him on the cheek, then turned and left. She turned left at the gate and walked along the pavement for over a hundred yards until she reached the car she’d arrived in. She got into the front passenger seat, wincing as her bottom pressed into the upholstery.

“He hasn’t murdered you then?” The dark haired woman in the driver’s seat observed.

“No, thank you Susan. I’m still alive and not been abducted and sold to some desert harem.”

“You wish!”

Karen blushed. “No, actually Susan, it was very good. He created the perfect atmosphere. He was in charge and I had to do as I was told. It was actually very relaxing in a strange kind of way.”

“Relaxing? Really? I thought the idea was to give you a good hiding.”

“It was, and he did. I got a spanking and then six strokes of the cane.”

“That doesn’t sound a lot. Bare bottom?”

“No, we’d agreed beforehand I’d be caned across my panties. He’s quite ‘old school’ so didn’t try to take any liberties.” Karen replied. “It was a pretty sound spanking, though, and the cane really stung. That was surprising as it looked quite small and harmless, but it really whipped into my bum and smarted like crazy.”

“Are you going again?”

“Yes, in two weeks’ time.”

“Do you want me to drive you here again?”

“Up to you. I’m sure Mr Whittaker is completely trustworthy though, now I’ve actually met him.”

“It’s okay, I’ll drive you.”

“You’re sounding very keen. Want to come in with me?” Karen looked at her friend. “I’m sure it could be arranged quite easily.”

Susan blushed.

The End

© Kenny Walters 2018

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