Jozwill's First Time

by jozwill < >

For three weeks during July Terrence Baldwin, a newly appointed junior housemaster at St Anselm's College, Monks Risborough, Buckinghamshire, was the sole member of staff in residence. Only five boarders were being accommodated at St Anselm's during the long vacation, and it had been decided that a junior housemaster could reasonably be left in sole charge for some of that period. A woman from the village looked in daily to cook and twice weekly undertook general cleaning duties as well.

Yet the junior master was troubled. Whilst the five boarders who had not been able to join their families for the vacation were all senior students and were permitted considerable freedom, some constraints necessarily obtained. Howard Morrison, a member of the Upper Sixth and a probationary prefect, had defied the most important of these constraints, having absented himself from the college precincts for an entire night. The four remaining students had, when questioned by a panic-stricken Terrance Baldwin at approximately 11.00 p.m., claimed ignorance of his whereabouts. A telephone call to the local police station at 6.30 the next morning had merely resulted in the anxious junior master being informed by a very sleepy and somewhat disgruntled police sergeant that "a seventeen-year old lad from St A's can look after himself", that "boys will be boys", and that if Howard had not returned by midday the troubled master should "ring again and inquiries will be initiated". 'He'll be back soon after 9.00., sir, very sorry and full of excuses, you'll see!" the sergeant had dourly observed before terminating the conversation.

Howard had, as the sergeant had predicted, returned at approximately 9.30 to the college, none the worse for wear. Informed by his fellow students that his absence had been noted, he had obligingly presented himself to Terrance Baldwin, who had just completed a letter of resignation addressed to the Principal and signed 'Terrance Baldwin M.A. (Oxon)'. (The recently acquired degree was still a source of pride, and the penning of 'M.A. (Oxon)' somehow compensated for the humiliation of tendering a resignation after less than a month's employment.)

The exchange between the relieved but infuriated junior master and the errant senior student had been strained. Whilst freely confessing to his absence, the boy had stubbornly refused to indicate where he had spent the night. After reminding -- quite unnecessarily -- the student that his absence overnight constituted a very serious breach of one of the few rules governing the behaviour of 'in residence' senior students ("I know that, sir") , Terrence had thrust his signed resignation under the boy's nose. "Look at what you have forced me to do! Resign! I and I alone am 'in loco parentis'! You are my responsibility! I will be blamed! Dr Hughes will be furious, and rightly so! I only hope that, when acquainted with your behaviour, you too depart from St Anselm's, but in your case not voluntarily!"

The boy had looked startled. "But sir, there's no need for Dr Hughes to be involved. I knew what I was doing. I hoped that I wouldn't be caught, but I was caught. You're in charge and, as you said, sir, you're 'in loco parentis'. You have full punishment privileges. You know where Dr Hughes keeps his cane -- and if you don't, I do. I don't see the problem, sir. Dawson last year did what I did, and earned himself a thrashed bottom! That's all that has to be done, sir! That's what Dr Hughes would expect!"

"I want to think about it!" the junior master had replied. "Go to your dormitory and report back here to my study at -- um -- midday. But before you do, bring me Dr Hughes' cane."

The sixth former had left, but returned some four or five minutes later bearing what students had, within Terrance's hearing, referred to as the 'rump ripper': a forty inch long, half an inch in diameter, rattan cane. "It's been over a year since I last felt this" the student had commented when he handed over the cane to the junior master. As he had seen himself out of the study, he had turned and given Terrance a half smile.

It was nearly midday. Terrence had experimented with the cane, the first cane he had ever seen let alone handled. He had swished it through the air and twice brought it savagely down across a cushion on his sofa. As he had done so, he could not but visualise the well-built sixth-former, soon to make an appearance. Captain of St Anselm's cricket team, his white cricket trousers had, at least for Terrence, drawn attention to the firm contours of his buttocks. In imagination Terrence saw the cane cutting not into an inert cushion, but into a quivering pair of conveniently positioned buttocks. "If only Howard was wearing his cricketing whites!" Terrance had mused.

A knock at the door. Astonishingly, Terrance experienced a moment of virtual panic. "One moment!" he heard himself say. He laid the rattan cane on his desk and seated himself behind it, acutely aware of what he feared might be an all too apparent erection. If only he had thought to have procured and donned his academic gown!

"Come in!"

Howard entered, softly closed the door behind him, and moved to the desk. He was wearing his full school uniform. He looked at the rattan cane for a moment, then raised his eyes to meet those of Terrance. "I'm ready sir" he quietly said.

Somewhat breathlessly, the junior master spoke. "On this occasion," he heard himself saying, "I have decided to deal with matters myself. I shall say nothing to Dr Hughes, whom I believe may well have expelled you for the way you flauted one of the few rules specified for students availing themselves of the College's generosity in making accommodation available during the long vac. I intend to -- er -- cane you. Severely. Have you anything to say?"

"No sir!" the boy replied, the strange smile returning to his face. "I guess I asked for it. You win some; you lose some!".

"Well, you know the routine. Get ready!"

The boy looked at the junior master. Again the half=smile. "Yes sir, I know the routine. Very well. But do you, sir?"

Terrence was speechless. But Howard continued, his voice soft. "I'm your first, aren't I sir?"

"Not 'aren't I' -- 'am I not' is the correct construction" Terrence found himself retorting.

Again the boy quietly smiled. The smile, strangely, was more shy than impertinent. "I'm the first guy you've caned, am I not, sir?" Howard repeated. "It's quite simple, sir, although you do all the work! I just stay put and take it. I'll bend over that chair -- we'll move it slightly forward so you have room -- and I'll position my bottom so you can do it properly. You just take aim and then give me a good cut across the middle of my bottom. You then continue, alternating above and below that cut until my whole rump is covered. You'll decide how many, though nine is usual for very serious offences."

Astonished, Terrence watched as the boy turned and made his way to an armchair. He moved it forwards, then bent himself across the back of it, gripping the arms. He looked over his shoulder. "That gives you ample room, sir. Or do you want me to move it further?"

"That's -- that's fine. Er -- how many did you say, um ...."

"I would imagine Dr Hughes would give me nine, sir. One in the middle. Then four above and four below, the lowest right in my bum crease. But you're in charge, sir! As you said, 'in loco parentis'."

"I know that. Well -- er -- get ready."

Again that quiet smile. Almost leisurely, Howard removed his jacket, neatly folding it and placing it on the floor. He then crouched down and untied then removed his shoes, placing them neatly beside his folded jacket. He then stood, unbuckled his belt, undid several buttons and a zip fastener, and removed his trousers. These he also folded and carefully laid on top of his jacket. He then glanced over his shoulder at the stunned junior master, sighed, thrust down. kicked aside, and then retrieved his underpants. He folded them and placed them on the growing pile of shed garments. He then made his way to the chair, rolled up his shirt until it almost reached shoulder level, and positioned himself over the chair. "Is that satisfactory, sir?" he asked. "I think that my bottom is correctly positioned."

"Quite. Quite. Um -- ".

"For God's sake do it, sir! And do it properly, sir! I'm not a junior who has earned himself a couple of stingers with a toy cane! I can take the rump ripper and take it full force. But please get it over and done with sir! If you wouldn't mind, sir!"

Almost in a trance, the junior master picked up the cane and made his way towards the chair. His eyes drank in the firm and muscular body. The legs and back were tanned, but the rounded buttocks were white. The boy had so bent over that those buttocks were still 'fleshy', not so tightly presented that they possessed no 'bounce'. Clearly Howard had spent many hours in the outdoor swimming pool or had elsewhere sunned himself only wearing a brief pair of trunks. The conveniently positioned buttocks were quivering slightly, possibly, thought Terence, from fear, although the boy's words had been anything but fearful. Nervously, Terence laid the cane across the waiting rump. It quivered more noticably, but then grew still. Terrence slightly raised the cane, then gently laid it again across its intended target.

"Just do it, sir! Hard! I'll keep position!"

And do it Terrence did. He raised the rattan cane until it was behind him, paused, then brought it down with as much strength as he could muster across the vulnerable buttocks. For a split second there was no reaction. Then suddenly the boy stiffened. "Christ!' he gasped, but manfully held his position. Terrance watched, fascinated, as the buttocks jerked in a paroxysm of pain. Slowly, a savage red weal, outlined in a darker almost purplish red, formed right across the quivering rump. In a strained voice Howard spoke. "That's one. sir. Thank you sir."

Terrence paused. After a moment, Howard again spoke, his voice calmer. "Please get on with it, sir. Don't draw it out, sir -- at least not too long."

With slow deliberation the junior master did as the miscreant -- for so he reminded himself Howard was -- had instructed. A biting stroke above the first weal. Again the momentary pause, the spasm-like response of the buttocks, and the strained "That's two, sir. Thank you sir." Then again, this time under the initial weal. And so it continued, until the strained voice at last managed to say, "That's nine, sir. Thank you sir. Sir -- may I now stand, sir?"

"Stand!" Howard heard himself say.

Gingerly, the boy straightened himself. Tentatively at first, the boy touched, then carefully clasped, his raw and ravaged buttocks. He slowly arched himself, his hands cupping his buttocks as he thrust his pelvis fowards. "Oh sir! Oh sir! Oh my arse, my arse! Oh sir!"

The hands that initially had cupped the buttocks began kneading them, as though the pain could be somehow squeezed out. "You did good, sir, real good. Oh sir!"

"Did well" Terrence automatically responded.

"Did well, sir, you did real well. Oh my bum; it's really throbbing, sir!"

Terrence was tempted to correct the 'real' to 'really' but said nothing, watching the muscular body writhing and the hands continuing to knead an all too obviously throbbing rump. Then the boy slowly turned and faced his tormenter. Incredibly, the boy was half smiling, although his eyes were glistening. Awkwardly, he thrust out his hand. "No hard feelings, sir?"

The junior master took the outstreched hand. "No, no hard feelings." He was aware of his own erection, but even more aware the the boy's quite spectacular erection.

There was an awkward silence.

"Do you want to -- examine my bum and assess the caning?" Howard asked, his voice again controlled and low. "Or is there something else you want to do? Like Dr Hughes sometimes does?"

"No" the junior master almost whispered. "No. That's it. It's over. You can get dressed and go. When you've composed yourself"

Howard looked deeply into the eyes of the junior master. "You done real good, sir!" he said. Gently he laid his hand on the right hand of the junior master. "Or should I say, 'You did really well, sir!' Keep the cane here, sir, I suggest. You cane well, sir, very well. There's another week to go. I think -- just think -- there might be a next time!"