Headmaster Smyth in Winter

"My God! Where did you learn to do that?" he hissed.

"From the books. Remember?" she said. She felt her confidence returning and she smiled at him.

Without further prompting she turned and stepped to his desk, bent at the waist, and placed her forearms and hands on the blotter. She looked back at him over her left shoulder.

"Like this?" she asked.

He knew her last question was a direct quote from the same book, and asking that question confirmed their continuing collaboration. Her acquiescence gave him assurance to continue and even deviate from the script. She would have her taste of the cane but not a full dozen strokes. No, he knew from those same books another way to carry out her sentence.

Smyth approached her and pressed his left hand on the small of her back, pressing her breasts into the cool desktop. "Keep your back flat and your legs straight. If you rise up, that stroke won't count. Look straight ahead."

She peered into the dimness behind his desk and focused on a the spine of a book. It was really going to happen. She was about to get the dreaded cane!

The first stroke caught her unawares. Before she felt anything she heard a short swish! followed by a loud swack! A fraction of a second later she felt an intense burning pain across her bottom that stopped her breath. She kept still as the pain built and crescendoed at an almost unbearable peak, then began to slowly fade.

She was letting out her breath when the second stroke fell.

Swish, swack! Not fair! Not so soon! The new pain built on the first, rising to a peak a little closer to unbearable. She began loudly panting.

Swish, swack! Oh, no! The urge to stand and rub her bottom was nearly overpowering! The burning pain piggybacked on the previous two strokes to push her to her limit. She arched her back but kept her arms on the desk. This was too, too much!

Swish, swack! "Aieeeee!" she shrilled, her eyes brimming with tears and her nose suddenly running. She beat her hands against the desk top and stamped her feet as another line of fire seared across her bottom.

She was sobbing when Smyth calmly leaned over to brush her wild hair back behind her ears.

"There, there, Miss Bradford. Perhaps we should take a break while you compose yourself, now that you've experienced the deterrent power of the cane."

Without waiting for an answer, he began rubbing her bottom with his right hand, his left hand lying on her back, both hands gently rubbing. He picked up a bottle of lotion from his desk, poured a copious amount on his hands, and began rubbing her burning skin with the cool emollient. He felt the tension in her back release and her sobbing quiet. He added more lotion and slowly rubbed her bottom with gentle squeezing and kneading. Her sobbing gradually transitioned to contented sighs and she relaxed onto the desktop, her arms cradling her head.

"I must confess, Miss Bradshaw, I was very much taken aback by your elegant disrobing. And may I compliment you on your beauty? You are a vision of loveliness. I'm so glad you and I have read the same books, and I'm so glad to have personally attended to your discipline, rather than delegate it to Miss Nash."

Trudy had sufficiently composed herself to reply, albeit breathless and exhausted from her ordeal.

"Headmaster, I'm sorry. I...I'm not always in charge of myself...I'm...impulsive and rash and heedless of consequences. Like just now when I...took off my clothes. I know I shouldn't have, and I know you shouldn't have asked me to, either.

"But I wanted to. I dreaded the cane but knew I deserved it, just like Fiona and Sonya. I was curious about it. And...well...because of the books. I couldn't believe that a woman could want the cane. The humiliation, the pain...which is just dreadful...and the excitement...I...uh...ahhhh..."

Here she trailed off and appeared to fall into a transitory state between sleep and awake. Smyth applied more lotion to her thighs and calves, running his lotioned hands up and down her legs. He began paying particular attention to the inside surfaces of her thighs, allowing his hands to reach higher and higher without quite reaching her apex.

She adjusted her position to allow his hand fuller access, spreading her feet and adjusting the curve of her low back. On his next upward stroke his finger tips lightly brushed her sex and she stiffened. His fingers traveled fore and aft, delicately spreading her labia and smearing her slick fluids along her cleft.

"Uhh...Oh! Ohhh!" she moaned, pushing her pelvis back against his fingers.

"Does that feel nice, Miss Bradshaw? Would you like me to continue?"

"Ohhh, yes, please, Headmaster. That feels sooo very nice..." she breathed, arching her back and jutting her bottom upward in an obscene display.

Now he concentrated his efforts exclusively on her vulva, exploring and caressing, adjusting his manipulations in response to her movements and moans. They soon fell into a rhythm and worked together. He gradually increased the speed and firmness to match her crescendo of cries and whimpers. When he judged the time right he placed his thumb against the tight star of her anus and pushed while continuing to stroke with his fingers. With his other hand he grasped a handful of hair and pulled her head back. The result was instantaneous and spectacular.

"Oh! Ohh! OHHH! OH MY GAWDDD! UNNGGHH!" she cried, spasming and convulsing under his stroking fingers. Her legs snapped tightly shut around his right hand, trapping it against her now very sensitive folds.

"Oh! Oh, please, it's too much, please, please!" she cried when his trapped fingers continued to lightly tease and play.

A minute of episodic jerks and tremors followed, then she suddenly released a soft sigh and relaxed onto the desk. Smyth assisted her to her feet and led her to the couch and helped her lay down. For a moment he admired her naked form, then he tucked the blanket around her. He added more coal to the fire, added the kettle, and made himself another cup of tea. He settled into a chair to watch her sleep.

*****

"Miss Bradshaw. Trudy. Wake up. It's time to get dressed to catch your train," he said, gently shaking her awake. "We have less than an hour."

"Huh? What? Oh. OH!" she said, suddenly awake and aware of her nakedness under the blanket. She clutched the blanket to her chest and blinked rapidly.

"Here. I've placed your clothes on this chair. I'll step out while you dress."

*****

The snow had stopped and the air felt frigid as they walked to the train station. Overhead, the clouds had cleared and the stars shown brightly but the mood was reserved.

"Miss Brown will meet you at the station. It's the second stop, Hamilton Crossing, only a short ride," he said.

"Thank-you, Headmaster. For your kindness, and for pointing out and correcting my failings. I want you to know I bear you no ill, none at all. I hope I can be a valuable employee. I'm quite looking forward to working for you and Miss Nash. And thank-you...for that other thing you did."

She looked up at him and blushed a bright crimson under the lights of the station. They stopped on the platform. There were only a few other passengers waiting, none nearby.

"Right. Well, perhaps I was too zealous in my duties."

"No, Headmaster, I don't think so. It wasn't altogether unpleasant, you know." She suppressed a giggle and continued. "I learnt a valuable lesson...or two. Thank-you for being my teacher."

The train arrived and he helped her board, passing her suitcase up when she turned around at the top of the stairs. She looked right and left, and seeing no one watching, blew him a kiss.

*****

Monday morning was bright and the weather much colder. As was his custom, Headmaster Smyth arrived before Miss Nash and watched for her approach through his office window. He prepared her tea when he saw her enter the building.

"Good morning, Headmaster," she said, hanging up her coat. He handed her a cup of tea and for a moment they stood together looking at each other, a funny smile on her face. She turned and walked back to her office.

Headmaster Smyth knew the teasing game she was playing. At mid-morning tea he finally started the conversation he was eager to have.

"How are you and Miss Bradshaw getting on? Has she been a good houseguest?" he asked between sips of tea and bites of biscuit.

"Very well indeed, Headmaster. You seem to have made a new friend, a rather surprising development considering you gave her the cane. Four strokes, she said."

"I took pity on her. Christmas and all, I suppose. Four seemed enough. Perhaps four would have been enough for Fiona and Sonya, too," he replied.

"Hmmm..." she answered, drinking her tea.

Headmaster Smyth did not further reply. He could play cat and mouse, too.

*****

The next morning at her flat, Evelyn Nash was discussing with Trudy Bradshaw the coming day's events.

"It's completely up to you, Trudy. Come in with me today and I'll get you started learning the office routine. But if you're still too sore I'll understand. How is your poor bottom today? I see you sitting rather gingerly," said Evelyn as she ate her breakfast porridge.

"I'd like to come in today, if I may. I want Headmaster to see I'm made of stern stuff. I don't intend to show him weakness. How long do these cane marks last?"

"Mine lasted a week, maybe ten days before they were all gone. The cane leaves a lasting impression."

"You've been caned?" Trudy said with surprise. She could hardly imagine that prim and proper Miss Nash had ever done anything to warrant the cane.

"Oh, yes, and more than once," she replied. "I'm not always a good girl, Trudy."

"I find that hard to believe. You? The cane is no joke. I'm glad he stopped at four; I doubt I could have survived a dozen," Trudy said.

"Why did he stop at four? Did he say?" Evelyn innocently asked. "Your punishment was twelve strokes which seems to me excessive, but still. He let you off with only four?"

"I thought twelve was a lot, too. I begged him and really put up a fuss. But he made me agree to twelve. That's twice what Fiona and Sonya got. I had no idea how awful it would be."

"Yes. Well, now you know. But why twelve and not six?" Evelyn asked, looking sincere.

Trudy felt a blush starting in her cheeks and turned away. Evelyn pressed on.

"Did it have something to do with some books found in your quarters? Some naughty books, perhaps?"

"You know?"

"Yes, I do. Both Headmaster and I have looked at them. Quite unusual interests for a young woman. Well, your interest in sex is understandable, but the spankings? The ropes? The coercion? That seems rather outre for a woman so young as you. Those interests don't usually arise until one is older and with more experience. And you say you have no experience?"

"No, Ma'am. Well, other than that brief grope in the alley that got me into so much trouble."

"The policeman said you were stroking his cock," added Evelyn.

"Yes, I... I touched his penis," said Trudy.

"It's a cock, Trudy. When you have a man's penis in your hand and you're stroking it, it's more properly called a cock. And you were right to stroke it; I'm sure it pleased your young man."

"I...uh...he's not my young man; I don't have one. I had just met him in the alley and I'm not even sure of his name."

"Really? My, but you are a bold one. I shall have to keep my eye on you, dear," she said, laughing. "Let's get ready or we shall miss our train."

*****

Trudy Bradshaw's first day on the job started with tea and conversation. It was a genteel sort of workplace and while formalities were observed, she noticed mutual respect and admiration between Headmaster and Miss Nash. Headmaster often deferred to Miss Nash's judgment regarding day to day matters, while reserving to himself decisions of a more strategic nature.

As the days passed Trudy notice something else, too. Miss Nash -- first names weren't used at work--was expert at manipulating Headmaster with a sly look and a half-smile, almost as if something was going on between them. But try as she might, she could not discern anything more. Was it just her imagination?

For her part, Miss Nash watched Headmaster's and Miss Bradshaw's interactions with amusement. Trudy's unabashed hero worship of Headmaster was obvious. Her desire to please both Headmaster and herself made Miss Bradshaw a conscientious employee, but Miss Nash's curiosity was piqued. What, exactly, had transpired between Headmaster and young Miss Bradshaw to cause such feelings in her? One might expect a caning to engender resentment and hostility, but exactly the opposite seemed to be the case.

*****

Christmas passed, the students returned, and Trudy Bradshaw found herself something of a celebrity among her former fellow students. They were surprised to learn she was no longer a student but a school employee working directly for the headmaster. She was often seen in the hallways delivering mail and in the school library with a stack of books, reading and taking notes for Headmaster. She no longer dressed in a school uniform but wore long woolen skirts and flats. Some days she wore her hair up, but other days she wore it down, her auburn cresses brushing her shoulders.

She found her salary adequate to live and share expenses with Miss Nash, and she had established a regular schedule to pay back her school debts.

Much to Trudy's relief, the mystery of the third student remained a mystery and was soon forgotten. Trudy's caning by the headmaster also remained hidden from the students, and most certainly the other salacious details of that night were kept a deep secret from everyone.

Evelyn Nash knew of Trudy's caning, of course, but Smyth had told her nothing of Trudy's complete disrobing for him nor his fingering her to an orgasm.

One afternoon in his office the subject was Lord Byron's lyric poetry, which Trudy had been reading. They were discussing the sexuality of Byron's poetic imagery when Trudy leaned across his desk and whispered to Smyth that his fingering had caused her first orgasm by a man. Smyth had to fight his erection for the remainder of the afternoon. He was glad of Miss Nash's presence in the outer office to temper further discussion and to prevent any overt action on his part.

It was evident to Smyth and others that Miss Bradshaw displayed newfound maturity. Her new job and her daily association with Miss Nash had given her confidence and poise.

If Smyth had known what his secretary already knew about the night he caned Miss Bradshaw, events might have played out differently. Instead, the truth came out by somewhat different means.

*****

It began on a Friday morning in late January when Miss Bradford had a particularly bad episode of menstrual cramping. Without consulting Headmaster, Miss Nash sent her home on the noon train with a box of salicylate powders and directions to rest in bed and drink a glass of water mixed with a packet of powder.

Headmaster returned in the afternoon, inquired after Miss Bradford, and was told the particulars by Miss Nash.

"But something else, Headmaster. I was looking in your cabinet for the powders and I found these in the drawer with the canes," she said, holding up a pair of woman's regulation underpants. It was evident they had been worn, and Miss Nash wore a concerned look on her face.

Headmaster regarded the proffered panties with alarm but kept his composure. He went to her outer office, checked the hallway, and pulled the door closed.

"I suspect those are Miss Bradford's but I can't be sure," he said. "I didn't see them when I put away the cane, but it's possible she left them there for me to find."

"How could you not see that?" she asked, incredulous.

Headmaster hesitated a moment before answering, a hesitation duly noted by Miss Nash.

"I...ah...had left the room momentarily...in order that Miss Bradford might compose herself after taking the cane. She took it very well, I must say. Brave girl," he added.

"Headmaster, I must know. Did you cane her on the bare?"

Headmaster Smyth looked into the unsmiling face of his secretary and saw steel resolve. Then he saw the tiniest hint of smile forming in one corner of her mouth and knew the game was afoot.

"Of course," he replied.

"Isn't that unusual, Headmaster? Caning a young woman on the bare without a chaperone?" she challenged.

"Yes, it's unusual but not prohibited, Miss Nash. Miss Bradshaw is an unusual young woman, you may have noticed. She has certain...proclivities, certain inclinations. The books? One in particular, I think? I believe the books are still in your office. You must have read them all by now. 'My Year in Captivity'? Miss Bradshaw told me it was her favorite."

At this accusation Miss Nash herself hesitated but pressed on. It was time to tip her hand, to lay out her cards.

"Actually, I have read them, Headmaster, all of them. In fact, Trudy and I have talked at length about them. I warned her about acting out these types of fantasies. Not all men are as trustworthy as you."

"As me?" he asked. How much did she know?

"I told her the world is full of men who would take advantage of her naivety. She needs experience and tempering before indulging in these more...sophisticated pleasures."

At this, Miss Nash took a step closer to Smyth and lightly placed her hand on his arm.

"In another two hours the sun goes down, Headmaster, and then I want you to tell me what you did to Miss Bradshaw. Everything."

*****

Time dragged for Smyth. What should he tell Miss Nash? She busied herself in her outer office and acted her usual, efficient self. Only once did she look in on him, her face pleasant and unconcerned.

He could deny everything, he thought, but he dismissed that option. Living together in Miss Nash's flat, those two women must have talked by now. Miss Nash's persistent and expert questioning had surely drawn the truth from Miss Bradshaw, trickle by drop. Miss Nash must already know the truth and yet she persisted in acting this out. To what end, he thought?

A late afternoon visit closed out his regular day. An alumnus, newly married into wealth and title, had unexpectedly dropped by to chat, and not incidentally leave a sizable donation. Headmaster allowed her all the time she wanted, even serving her a dram of his diminishing reserve of scotch whisky, a courtesy she very much appreciated.

"And you are as yet unmarried, Headmaster? How can that be?" she said, smiling and gesturing toward his closed office door and Miss Nash. "You are doubtless a busy man, but do take time along the way to smell the roses. In a few months it will be spring again and flowers will be blooming all over campus. I'll stop by to see the cherry blossoms and gauge your progress. Next time you're in London, do come by for lunch."

"I will, Lady Lancaster. Perhaps I will have some good news for you, one never knows."

She kissed him on the cheek as she left, saying softly, "Gather ye rosebuds while ye may, Headmaster. Old time is still a-flying; and this same flower that smiles today, tomorrow will be dying."

Headmaster Smyth sat at his desk in the gathering twilight, deep in thought. The future was uncertain, the war a big unknown, and outside the sun was going down. He thought of the second stanza:

'The glorious lamp of heaven, the sun,

The higher he's a-getting,

The sooner will his race be run,

And nearer he's to setting.'

It was time to make up his mind.

His contemplations were in interrupted by Miss Nash entering his office.

"I've closed up the building and turned out the lights, Headmaster. Everyone has gone home. Except us, of course."