Chapter 19: An Anal Introduction

The tension surrounding Gail Ashby's thunderous arrival and triumphal departure had evaporated, not like steam or morning mist, but like the sparks and glitters from a firework fired high in the night sky. Into this vacuum rushed kind of temporary insanity. As in the aftermath of a disaster, the sense of relief was almost palpable and the normal rules and courtesies seemed to be suspended.

In the continuing fine weather, dress code was relaxed to the point of non-existence. Girls went bra-less and stocking-less, shirts were carelessly left undone, skirts became shorts - of the sort that justified the name; tight garments in lycra or stretchy cotton. In one of his more sober moments, Adam reflected that it was this very thing that had caused him so much mental and emotional agony not so long ago. Now he was revelling in it, lapping up the visions of teenage loveliness that daily paraded before his eyes.

And the relaxation was not only in dress. In class the girls sprawled at their desks, giving him views of firm thighs, lacy panties and swelling breasts. They began to answer him back, seeming to delight in double-edged banter. He knew he should call them to task; get a grip, but he was infected with the same madness as they.

Outwith the classroom, girls kissed and cuddled openly in the corridors and common rooms. Conversation in the staff room was brisk and brittle and the smiles bright. Even Helen seemed to unwind a little and actually smiled from time to time.

On his way to his room on day he happened to pass Jacqueline's closed door. From behind it he could her the familiar sounds of leather on flesh. Intrigued, he stopped to listen. Other than the sounds of spanking and Jacqueline's indistinct voice, he could hear nothing else. Unable to resist the temptation, he carefully turned the handle and opened the door a crack, grateful that the old doors had been properly maintained. He applied his eye to the crack. Five 3rd years were bent over the front row of desks in a line, their skirts hoisted up over their waists. Jacqueline was walking up and down the line applying a tawse, seemingly at random, to the exposed bottoms. The recipients all had red marks across their exposed skin and were twisting and twitching as the heavy leather strap did its work. They were all sobbing quietly.

"I'm not interested in excuses," she was saying. "I will not tolerate such behaviour in my classroom."

He discreetly withdrew, closing the door carefully behind him, even more intrigued as to what sort of mischief the girls had been up to to warrant a mass punishment.

Later that day he had occasion to visit the storeroom to collect some equipment for the physics lab. Being an old building, there was often a number of ways of getting from one point to another and, this time, his way took him down a little-used corridor. He turned a corner and stopped dead in his tracks. Ahead of him were two girls locked in a passionate embrace. The taller of the two was Miranda, known as 'Randy' for obvious reasons, she had a smaller girl pinned against the wall and was kissing her hard. The smaller girl, whom he reckoned was Lola, had her arms wrapped around her partner's neck and was giving as good as she got. Both girls had their blouses undone and their skirts pulled up over their waists and were grinding their mounds together, Lola standing on tiptoes to bring her level with the older girl. He stood and watched this erotic vision for several minutes, intrigued by the contrast between Miranda's mane of chestnut hair and Lola's blonde locks.

Holly had been restless all lesson; unable to sit still, wriggling about in her seat as if she had ants in her pants.

"You're looking a bit flushed, Holly. Is something the matter?" he asked eventually.

"No, no, sir. It's nothing." The girl flushed and tried to sit upright.

"You've been restless all lesson. Are you, perhaps, a trifle sore? A sore bottom, perhaps?"

Holly flushed even more deeply and said quickly, "Oh, no, sir. Nothing like that."

"OK. Then try to sit quietly, please."

Holly bent over her books again but, before long, she was twisting and turning again. He had to speak to her twice more during the lesson. Finally the bell rang. Holly was first on her feet, seeming almost desperate to get out of the classroom.

"Holly," he called. "Please remain behind."

Reluctantly, the young girl stopped and came towards his desk with lowered head.

"Now, Holly, what's the problem?"

"Nothing, sir. There's no problem," she mumbled, gazing fixedly at her feet.

"Come on, Holly. You're normally very good in class but, today, you haven't sat still for more than five minutes. Have you been naughty and had a spanking."

"I haven't had a spanking, sir. There's nothing wrong, honestly."

"I don't believe you, Holly. Perhaps I'd better take a look. Turn round and raise your skirt."

The girl looked at him wildly. "Oh, no, sir. Please. Do I have to?"

"I think so, Holly," he said gently but firmly. "Now lift your skirt like a good girl."

With trembling fingers, Holly turned her back to him, took the hem of her skirt and slowly raised it up above her waist. She was wearing a pair of demure white satin panties. There were no marks on her bottom and no immediate evidence of a spanking. He noticed, however, that there appeared a strange bulge inside the panties.

"Hmmm," he said thoughtfully. "Turn around and show me the front, please."

Even more reluctantly the girl turned and lifted the front of her skirt. The bulge was even more pronounced at the front. He took a step towards her and put his hand on her panties. Beneath his hand he felt the soft silkiness of her panties and, inside, something tubular and flexible.

"Well, well, Holly. What have we here? Open you legs, please."

He squeezed to object and felt it give like stiff jelly. He traced its outline and felt it's contours curve from her vagina to her anus. He started to move it about and heard the girl's hiss of indrawn breath.

"I see," he said smiling. "It's no wonder you had trouble sitting still, young lady."

"Ohhh, sir. Don't, please," gasped Holly but she parted her knees wider. He manoeuvred the bendy dildo in and out of her cunt and arse.

"You really are a very naughty girl, Holly," he said. "A toy like this is very distracting. Why did you do it?"

"It was a dare, sir."

"A dare?"

"Yes, sir. One of the others dared me to do it."

All the time he was speaking, he continued to manipulate the toy. "Indeed. And who was that?"

She looked at the floor. "I couldn't say, sir."

"You were very disruptive. I think you need a good spanking, don't you?"

She was panting and moaning softly as he worked the dildo more forcefully. "Oh, please, sir. Please don't make me say."

Her eyes were closed and she had slumped slightly, allowing him freer access and moving her hips almost involuntarily in response to the soft, slick plastic sliding in and out of her cunt and ass. She was trembling all over and covered in a slight sheen of sweat. She was really wet down below, too, and her juices were running down the dildo and soaking her panties.

"Yes," he said, withdrawing his hand. "A rather severe spanking."

"Ohhhh," groaned the girl with a mixture of frustration and fear. "If I tell you will you not spank me?"

He appeared to consider. "I don't think I can do that. But if you don't tell me it will be very much worse. He placed the flat of his hand on her panties and pushed upwards. The slick plastic was forced painfully into both her holes. She gasped and her eyes flew open.

"Oh, sir. That hurts."

He pushed harder, forcing her on tiptoes and wiggled the plastic back and forth. He finger tried to prise him away.

"It was Carol and Vanessa, sir," she cried. "They did it."

He let her go. "Carol and Vanessa, eh? Thank you Holly."

She stood slumped, defeated. It was only a schoolgirl prank and now it had gone horribly wrong. She was aware of his hands at her skirt.

"Wha... What are you doing?"

Neatly, almost fussily, he rolled the skirt up and tucked the hem securely into the waistband.

"I told you. I'm going to spank you."

"But I told you who dared me." She was close to tears.

"I know, but you still disrupted my class. Now come over here. And don't touch yourself."

He made her stand about 2 feet away from his desk and lean against the edge with her feet spread wide. She made an erotic picture with her long legs and pert bottom tensed, her white satin panties so damp they were almost transparent and the outline of the pink dildo was clearly visible He took a wooden paddle from his drawer and stepped behind her.

"Take off your panties."

"Oh, sir."

"Quickly now."

The girl straightened and began to wriggle the soaking panties down over her hips, being careful not to disturb the pink intruder. He knelt and pulled them down her legs, allowing her to step out of them without raising her knees.

"Now, Holly, you will play with yourself as I spank you. You do not need to count as I shall continue until you cum. Is that understood?"

"Yes, Mr Hazel," she said subdued.

"You may start."

She lifted one hand from the desk and, supporting her weight with the other, brought it down between her legs to grip the dildo. Very tentatively, she began to move it back and forward.

"If you move at that speed we shall be here all day," he said, bringing the paddle smartly down on one out-thrust buttock.

"Aaiiieee," the girl squealed as the pain seared across her bottom. She tried to jerk forward but the dildo in her arse only caused her to grip it tightly. He smacked her other cheek.

"Come on, girl," he commanded.

She gripped the dildo more firmly and began to work it in and out of her openings her more determinedly. He revelled in the obscene sight of the slick pink dildo curling round, sliding in and out of her arse hole and vagina. With mounting excitement, he applied the paddle to her cheeks.

Holly cried out as the blows rained down until the tears were streaming down her cheeks - but she never stopped driving the curving pink dildo back and forth, pushing it deep into her arse one way and deep into her cunt the other. The intense mixture of pain and pleasure were confusing her senses and driving her wild. She knew, though, that he meant what he said and would continue to inflict pain on her bottom until she came. She was so close, yet, somehow, the stinging in her bottom prevented her from reaching that critical point. Desperately, she tried to shut out the pain and concentrate on the pleasure generated by the dildo.

Then, all of a sudden, she was there. She arched her back and tried to stuff the dildo into both holes at once as her body twitched and jerked with the most intense orgasm she had ever had. It seemed to last for ever, blotting out even the fact that the blows on her bottom had stopped. Spent, she pulled out the dido and let it drop as she slumped forwards over the desk, shaking and sobbing.

Adam's cock was a hard and painful lump in his trousers. He desperately wanted to take it out and ram it into the teenager's arsehole so wantonly exposed and open where she lay across his desk. But he knew he should not. It would be better to wait - to let her absorb this experience. Then, when she had fully realised the ecstasy induced by mixing pleasure and pain - then she would be ripe!

He controlled his impulses and helped the sobbing girl to stand. He took her in his arms and smoothed her hair tenderly, making small comforting noises as she slowly recovered her senses. When, at last, she was reduced to irregular sniffles, he produced some paper handkerchiefs and wiped away her tears.

"There now," he said gently. "It's over."

"Oh, Mr Hazel," she wailed. "I'm sorry... I don't..."

"Never mind. Tell me, did you enjoy having that thing in your bottom?"

She nodded sheepishly. "It was... very strange."

"But you liked it?"

"Yes. It gave me funny feelings inside."

"Good. You'd better go now."

He handed her her panties and, in a fit of girlish modesty, she turned her back as she pulled them on, wincing as the elastic pressed against her tender behind. She rolled down her skirt, demurely trying to smooth out the creases, and prepared to go.

"Don't forget this," he said, handing her the sticky dildo.

She flushed deeply as she took it. "I won't ever use it again," she stated.

"Oh, no," he said in a fit of madness. "You must. You must use it - and often. It will help to relax your bottom and make it easier for me to enter it."

She looked aghast. "You don't mean... ?"

"I do indeed. Someday soon I'm going to fuck your bottom. Not today, but soon."

Her expression was one of apprehension and uncertainty but the stiff nipples visible under her shirt showed that her body had already made up its mind.

The image of the pink dildo in Holly's rear stayed with him and seemed to ignite a spark. He had considered it before in passing, and mostly in relation to Felicia whose bottom he practically worshipped, but he became fixated with anal sex. He found himself eyeing the girls' bottoms and picturing his cock buried deep inside them. A wicked plan formed in his mind.

"Anne," he said casually one evening, "I've been thinking and it occurs to me that there's one area of the girls' education we've forgotten."

"I always get worried when you start thinking," said Anne fondly. "But tell me the worst, anyway."

She was basking in the glow of a particularly satisfying session with him and Felicia and the younger girl had fallen asleep, exhausted after being suspended upside down and made to bring each of them to a climax orally while being soundly whipped by the other.

"It occurred to me that we haven't had the girls experience anal sex yet. And I think that's a gap in their education."

"Anal sex? What's brought this on?"

He described the scene with Holly, keeping it deliberately casual and low key. "It was only afterwards that it came to me that she had liked having the dildo in her bottom. And that made me think that, perhaps, we'd overlooked that aspect of sex."

He took a sip of his drink, apparently relaxed but excited inside. Anne took the bait.

"Yes," she said thoughtfully. "I confess I've enjoyed it in the past. Perhaps you have a point. Let me think about it."

"Okay. It was just a thought."

Anne, of course, was unable to resist. She took her vocation as an educator seriously and the idea that she might not be giving her girls the best she could bothered her. Adam contained his impatience as best he could. Finally, she agreed and informed him that they would start introducing the girls to anal sex, starting with the 3rd year later that day. Adam was thrilled, especially as it was the 3rd year for he found them all particularly attractive.

He entered the training room to find three girls, all dressed in their customary training outfits; white stockings, suspenders and high-heeled shoes. He had once asked Anne why she insisted the girls dress like this. She had replied that men found stockings and high heels sexy and she wanted the girls to associate sexy activity with sexy clothing - a reason he couldn't fault.

"Today we're going to explore the delights of anal sex," announced Anne when they had all assembled.

"Anal sex?" said Susan.

"Bum fucking," said Paula, scornfully. "Don't you know anything?"

"That will be enough, Paula," said Anne sharply. "Somewhere along the line, you will be required to have anal sex. Many men are fascinated, not to say obsessed with it. Some girls enjoy it, others do not. Often it depends on how your partner behaves. The anus is very sensitive, the entrance is very tight and the rectum is not a natural place in which to have a large, stiff object. Preparation is everything. Cleanliness is essential."

She handed out large syringes with instructions on how to use them. She went with them to the bathroom to supervise.

She made them all strip while she filled the syringes with soapy water. Each, in turn was made to bend over while she injected the water into their rear passages. They were told to hold their sphincters tight for several minutes before releasing the water.

"Eeugh, this is gross," said Susan.

"Oh, I rather like it," said Cat. "It feels all warm and wet."

"I'm not sure I'm looking forward to having Mr Hazel put his thing up my bum," said Susan.

"It's not a 'thing'," said Paula. "It's a cock."

"Whatever. It seems dirty to me."

"I know, but it's nice" said Cat.

"Have you done it than?"

"Not quite. But I've had a finger up there."

"What's it like?"

"It is not easy to describe. A bit strange at first, but nice once you get used to it."

"Isn't it sore?"

"A bit at first..."

"Come along girls," interrupted Anne. "Get a move on."

The procedure was repeated with clean water and Anne pronounced herself satisfied.

Back in the training room the girls were made to stand with their toes tucked under a low bench then bend over and grip the seat. To do this they had to bend their knees and stick out their bottoms. Anne and Adam passed down the row plying the tense, outthrust bottoms with a fly-whisk whip - not an implement to cause any major pain but enough to burn a stimulating tingle. By end of it, the girls were fidgety, clenching their cheeks in a vain attempt to reduce the stinging.

"I do love the sight of twitching bottoms," he murmured to Anne.

"It is rather attractive," she said, then leered at him. "The more so when you know you're soon going to screw them." He had the grace to blush. "Now I think we need to apply some lubrication."

She knelt down behind Susan and held the young girl's thighs. "Be still now, Susan," she commanded and applied her tongue to the teenager's exposed crack.

"Oh. Ah. What... ," the surprised girl cried as she felt Anne's tongue trace a route up down the slit of her pussy and between her ass cheeks. The tongue found her anal opening and she jumped in surprise. Anne held her firmly and began to circle the pinky-brown opening. Prising the girl's buttocks apart she stiffened her tongue and began to probe at the puckered hole.

"Oooh, Ahhh." Small cries and moans emerged form Susan at this unexpected but not unpleasant assault. Her classmates, still bent double, craned their necks to try and see what was happening.

Adam had been watching, enthralled, as the beautiful blonde woman pressed her face between the young girl's buttocks. Shaking himself from his reverie he decided he had better play his part.

Selecting Paula, whose high, tight bottom concealed an enticingly dark hole, he copied the actions of his Headmistress.

The girl's reaction was as gratifying as her classmate's. She gave a little cry of surprise when she first felt his tongue probe between her labial lips then pushed back, trying to open herself to him further as he worked his tongue up and down her slit. When he was satisfied she was receptive, he turned his attentions to her ass crack, licking up and around her crinkled nether passage.

She stiffened slightly, being unused to such attention being paid to her rear hole. He circled the edge, swirling his tongue round and round and flicking it over the entrance itself. AS she got used to the feeling, she began to respond with little murmurs of pleasure and a slight wriggle of her bottom.

He grasped her buttocks, delighting in their muscular elasticity, and pulled them apart with his thumbs. Stiffening his tongue, he poked it into her sphincter.

"Oh, God," she cried. "That feels so... Ohhh."

He worked away, licking around and over her rear hole and all the time probing and prodding at the entrance. Paula began to respond, pushing herself back as if to impale herself on his tongue. The push did it, her nether hole opened slightly and the tip of his tongue slipped inside. Paula squealed and clamped her sphincter shut, squeezing his tongue painfully. 'She'll be a really tight fuck, ' he though excitedly as he hastily withdrew his tongue.