Taken by Miss Strokewell

'No, Headmistress.'

'So let's dry them a little bit.' Miss Strokewell dropped the knickers neatly over Henry's head with the wet patch against his face and rubbed it against his face and hair. Through the leg holes, Henry caught glimpses of Gretna with her hand to her mouth and her eyes full of shocked delight.

When Miss Strokewell had removed the panties (revealing Henry's hair in a state of spiky disarray) and popped them into one of the large pockets on the front of Gretna's dress, she said to Gretna, 'So you see, my assistant, we have a pupil here we can use any way we like. So how shall we use him?'

'Oh, Mrs Headmistress. I do not know.'

'Hmm. Well, I've an idea. Henry, lower your head.' Henry knelt forward, but Miss Strokewell crooked the cane under his chin and said, 'Don't face the floor, boy.' Henry looked straight forward and found himself staring at Gretna's crotch. 'Now, Assistant Gretna, move forward.' Gretna took a step. 'Closer than that, pet. Let me help you.' And she tapped Gretna smartly on the rump. Gretna gave a yelp of surprise and jumped so that her blue cotton dress brushed Henry's nose.

'Now, Assistant Gretna, what you have here is your very own living sex toy.'

Gretna was puzzled. 'What can you mean, Headmistress?'

'You'll soon find out if you just lift up the front of your dress, pet.'

'Oh. Oh! I understand. But oh, but Mrs Elizabeth, I have much hair down there. I am not presentable to company.'

'Don't you worry about that, pet. These older gentleman grew up with bushy ladies.'

'Mrs Headmistress, I am wet like a floor-mop there. He will be unable to enjoy.'

'He's not meant to enjoy. He's been a bad pupil. Just pop the front of your dress over him, hold his head and make him do what you want.' Behind Miss Strokewell's archly persuasive tone was a hint of exasperation. 'Go on, obey the Headmistress.'

'Headmistress, I will try it, but I will compromise.' Gretna took Henry's head rather tentatively between both hands, and moved her hips forward so that his face pressed against the soft cotton.

Henry was desperate with frustration. As he inhaled the rich aroma of her vagina and felt the spring of pubic hair under the fabric, he wished that the flimsy barrier was out of the way. He pressed his face to where he guessed her crack to be, rubbed his mouth against her, and was rewarded with a long 'ohh...' from Gretna. Suddenly she was gripping him more tightly and squirming her crotch against him.

'That's better,' said Miss Strokewell approvingly. But after a minute or two Henry felt her grip his hair and found his head pulled away from Gretna's crotch. 'Are you enjoying this, you revolting groin-grinder?'

'Why yes, Headmistress.'

'Then stop at once. Assistant, step back. Pupil, stand up.' Henry felt himself pulled upright by his hair. 'Look what you've done. Is there no end to your muckiness? You've made a wet patch on her dress!'

'But Headmistress, that's her own pussy-juice.'

'How dare you argue with me! Assistant Gretna, we must punish him some more.'

Gretna was red in the face and breathing heavily, so perhaps Henry should not have been surprised when she jumped forward, embraced him ardently and thrust her tongue between his lips. For a moment Miss Strokewell could not speak for laughing.

'Stop that at once, Assistant Gretna! Disgraceful behaviour!' But Gretna did not stop. 'Very well, I shall be forced to -' There came a sharp slap from the direction of Gretna's rear end. Miss Strokewell had used her cane.

Gretna said 'ow' and stepped back at once. 'I am so sorry, Mrs Headmistress.'

Henry guessed that Miss Strokewell had been aiming to work Gretna up to such a pitch that she would join fully in their game. She had plainly succeeded.

'Help me with his punishment, Gretna, and I may let you use him while it's going on. The first thing is to be sure he'll keep still. Heap all the pillows in the middle of the bed.' While Gretna did this Miss Strokewell amused herself by rhythmically tugging on the chain until Henry was breathing hard and his eyes were half-closed in pleasure.

'Now, assistant Gretna, there are two leather cuffs on the middle shelf in there,' Miss Strokewell pointed with the cane to one of the built-in wardrobes near the door, 'so fetch them, please.'

Gretna did as she was told. Her voice took on a hollow, woody tone as she spoke into the wardrobe from beyond its open door: 'Oh, Mrs Headmistress, there are many unusual items in here.'

'You'll shortly be seeing what one or two of them are for, Assistant Gretna, but first come here with the cuffs. And Henry, you will be a good puppy-pupil and follow where I lead you.' Pulling him by the chain, Miss Strokewell led Henry to the foot of the bed. 'Now, my wicked pupil, you're to lie over that heap of pillows with your bottom in the air.'

'Yes, Headmistress,' said Henry, scrambling awkwardly into place with his hands still cuffed behind his back.

'I think I can let go of the chain now,' said Miss Strokewell, 'but you will obey, boy, or I may forget that caning is banned.' These words caused an unexpected tingling in Henry's buttocks, but at the same time he was not sure he was ready for the reality of a caning.

Gretna asked eagerly, 'Oh, Mrs Headmistress, will this pupil get beaten on his posterior?'

'Sorry to disappoint you, pet. Caning is a little bit run-of-the-mill for this headmistress. Now, cuff both of his ankles, and chain the cuffs to the legs of the bed.'

Henry heard a clink. Evidently the ankle-cuffs had chains attached. Moments later first his right, then his left ankle was cuffed. Then they were drawn apart as the chains were fixed to the legs of the bed. He heard some whispered conversation, until Gretna burst out delightedly: 'Oh Mrs Headmistress, that is so rude!'

Next Gretna climbed onto the bed and straddled his back. He felt a sopping bush of hair as she rested her weight on him.

Miss Strokewell said, 'Hold this, Assistant Gretna.' Henry could not guess what 'this' was. 'Now, Gretna, help me give our bad Henry some serious Sydney discipline. Henry, I'm going to ask you some questions, and if you give me any disobedient, dirty, or just plain sinful answers, my worthy assistant here will deliver some punishment. Gretna, I know all your cleaning must have given you good strong hand-muscles.'

Gretna's answer was a giggle of anticipation.

'Now, you mucky, jumped-up, worthless willy-wanger, can you guess what I have in my hands?'

'No, Headmistress.'

'Well now. It's smooth, and purple, and inflatable. Does that tell you anything?' The mattress dipped near Henry's feet. Miss Strokewell was kneeling on it.

'I - can't imagine, Headmistress.'

'I'm coating it with lubricant now, and I have a lovely view of where I can put it. What do you say to that, boy?'

'Oh, Miss Strokewell, please, no!'

'Wrong answer, boy! You will be taught to be grateful for your lessons. As you've guessed, I have in my hand an inflatable dildo, and Gretna is holding the bulb that inflates it. Because you gave a wrong answer, this dildo is going in your arse. If you give more wrong answers, I will order Gretna to inflate it. One squeeze of the bulb for each wrong answer.'

Henry felt something firm and slippery, about as big as two fingers, in the crack between his buttocks. For a few seconds Miss Strokewell rubbed the tight sphincter with it. Henry was now so submissive that he had no will to resist, but as it made its entry his anus tightened on it. Then Miss Strokewell gently slid it further in, and his body began to accept the invasion.

'Now: what was the right answer, disgusting boy?'

'Please, Headmistress, please discipline me.'

'That's better, boy. And since you beg so nicely, you shall have what you ask for. Gretna, start stretching him!'

There was a short hiss of air, and Henry felt the dildo expand. The sensation was distinctly erotic.

'I believe you have sinful thoughts, boy. Would you like to kiss your headmistress on her lips?'

'I want that very much, Headmistress.'

'How dare you! Presumptuous boy! Gretna!'

The dildo expanded again. Gretna was clearly aroused by her role: she was working her pudenda with small rocking movements against Henry's back.

'And I know you'd like to kiss my breasts too, filthy pup. Am I right?'

'I do want that, Headmistress. So much.'

This time Gretna was too impatient to wait for the command, and Henry's anus was stretched to the point where he felt a dull ache that brought a thrill of submission with it.

'Now, now, assistant Gretna,' said Miss Strokewell severely. 'Wait for my command. Lets try that again, shall we? Now, Gretna.' And Henry received another enlargement. He felt a movement in the dildo: Miss Strokewell must have taken hold of it, and a moment later, with a soft buzzing sound, it began to vibrate. The vibration spread a glow of pleasure that relaxed his anus and made it eager for more.

'Supposing I made you lick out my pussy, boy? Are you so degraded you'd do that?'

Henry groaned. 'I want that desperately, Headmistress.'

'Another sinful answer. Gretna!'

The dildo was becoming quite stout.

'Boy, I hardly dare ask this. I know you're a disgusting, filthy, depraved young whelp, but I hope - I sincerely hope - that even you don't dare wish to - to - not to put too fine a point on it, to fuck your Headmistress?'

'Oh yes, Headmistress, I want to fuck you again and again.'

Gretna's response to this was a fit of giggling that almost seemed to choke her. Miss Strokewell moved the dildo slightly, said, 'Hmm, could be tighter,' to herself, and then gave the order, 'Gretna, do it four times!'

The dildo enlarged once, twice, and three times, increasing Henry's pleasurable suffering greatly; then Gretna said, 'Mrs Headmistress, it is getting hard to do.'

'Use both hands, pet, and don't be cautious. I know all about this sort of punishment.'

Gretna responded with vigour: the girth of the dildo increased so much that Henry felt he was filled to the maximum. He breathed out a long, ecstatic groan.

'By the sound of it we have taught the revolting boy his lesson. Do you have anything to say, boy?'

'Thank you so much for my punishment, Headmistress. I - I...'

'Yes?'

'I really liked it, Headmistress.'

This drew more joyful laughter from Gretna, who was still busy spreading a large patch of wetness on Henry's back, but Miss Strokewell seemed to be shocked. 'Well, my revolting pupil, if you've enjoyed it, you clearly haven't been punished hard enough. You admit you want to fuck me. The punishment is going to fit the crime and no mistake.'

Henry felt the dildo being withdrawn.

'Now you are going to be obedient and submit to your Headmistress any way she likes. Aren't you?'

'Yes, Headmistress. Please use me however you like.'

'Mm, excellent.' A silky hunger was in her voice. 'Assistant Gretna, these two wrist cuffs can be disconnected from each other, and I'll get extra chains from the wardrobe. Get him on his back with his bum right on the foot of the bed, and fix the wrist-chains so he's spread out flat. And put two pillows under his head so he's not staring at the ceiling. Let's see... the other pillows - and we'd better have the cushions off the armchairs - put them on the floor at the foot of the bed.'

A few minutes later Henry was spread-eagled on the bed. Miss Strokewell, meanwhile, was hidden by the open door of the cupboard. Gretna kept the chain connected to Henry's genitals taut while she ogled his penis, which jutted so stiffly that it seemed to be immune to gravity. She breathed, 'He has a French loaf.' This exaggeration drew a stifled laugh from Miss Strokewell.

After a minute or so Miss Strokewell said, 'Assistant Gretna, please come here.' Gretna joined Miss Strokewell behind the door, where they whispered together. Then Miss Strokewell came back into view and stood at the end of the bed. 'So, boy Henry, you want to lose your virginity by having sex with your headmistress. Well, you're going to - but not quite the way you've been hoping. Gretna, show him.'

Gretna stepped behind Miss Strokewell and slipped the grey academic gown down off her shoulders. It fell to the floor, revealing something she was wearing, something that matched her stockings and suspenders...

She wore a purple strap-on dildo. A smooth silicone strap-on dildo a good eight inches long, the head gleaming with lubricant, the harness revealing a few teasing locks of precisely-trimmed pubic hair at its edges.

Miss Strokewell's tongue played across her lips. 'Gretna pet, do what I told you.'

'Yes, Mrs Headmistress.' Gretna climbed up onto the bed and then, kneeling, passed one leg over Henry's body to straddle him again, so that he was looking at her back and broad, plump bottom under the navy cotton dress.

'Henry, lift your legs up. Right up, so Assistant Gretna can reach them.' Henry did as he was ordered. The cuffs and chains were still attached. 'Gretna, hold the chains.' Gretna leaned forward and he felt his legs drawn firmly towards her.

Now Gretna was shuffling back on her knees. As she passed over his face, Henry saw under her dress and glimpsed a tangle of black, curly hair. Then she was kneeling behind his head.

'Assistant Gretna, open his legs.'

Gretna spread her arms and the chains drew Henry's legs apart. He saw Miss Strokewell framed between them, grasping the strap-on near the base, her lips pursed severely. His anus felt very defenceless against her. She leaned forward and looked haughtily into his face. 'Now, my pupil, you are going to be my boy-slut. Ask to be used.'

'Please, Headmistress, use me.'

'Beg harder, slut-boy.'

'Please, please Headmistress Strokewell, please use me any way you like. Please teach me how to be your fuck-toy. Your used pupil. Your slutty learner-whore. I'm pleading for it, Headmistress. Use me any way you like, Headmistress.'

'That's better. Can you guess what I'm going to do to you, boy-bitch?'

'No, Headmistress.'

'Well, my boy, you have a virgin arsehole. You wished to lose your virginity to your respected headmistress, so your respected headmistress is going to make your wish come true. Now do you understand?'

'Oh, Headmistress,' Henry breathed. 'Please - please be gentle. I'm just a boy. So... inexperienced.'

'Slut,' she replied contemptuously, 'you asked to be used any way I like. Understand?'

'But - Headmistress - please, I've never been fucked -'

'Silence, my whore, or I will make Gretna shut your mouth with her wet hairy cunt, and you won't be able to see your Headmistress as she takes your anal virginity. Is that what you want?'

'No, Headmistress.'

'Now, ask nicely, and remember to thank me afterwards.'

'Please, Headmistress, fuck my virgin fuck-hole. Fill it, please. Stretch it. It needs stretching. Please.'

'You are going to get what you ask for, slutty, subby boy.' Miss Strokewell dropped to her knees onto the cushions, so that the dildo was level with Henry's anus - which was now yearning to be taken. As far as he could tell, the dildo was thicker than the inflatable one at its biggest.

Now she was rubbing the head of the dildo against his hole, the cool slipperiness of the lubricant stimulating it to relax further. Next, the round, blunt tip was beginning to enter, moving in and out with small, firm thrusts, spreading the muscle. Then a hard, steady thrust. As the dildo began to slide fully in he felt himself opened, then impaled, until all his defences were vanquished and he could only surrender and feel wholly taken by the gorgeous woman using him.

Miss Strokewell's body was against his legs, the full length of the dildo buried in him. She held each ankle and pulled his legs further apart, then began to fuck Henry with a luxurious slowness, her big breasts bobbing gently in time with the movement of her hips.

Gretna said, 'Oh Mrs Elizabeth, I want to get naked too please.'

'Go ahead, pet. Get right into the swing of things.'

Henry's eyes were fixed on Miss Strokewell's body until he caught a glimpse of movement above him and looked up to see Gretna, her dress having vanished, fondling her own nipples while she continued to stare at his cock.

'Gretna pet,' Miss Strokewell gasped as she thrust, 'let go of the chains and take the clamps off him.'

'Yes, Headmistress,' said Gretna. 'Mrs Headmistress, which are the clamps?'

'On his nipples, pet.'

'Yes, Headmistress.' Gretna moved forward so that Henry's head was between her naked thighs. When the clamps were removed she said, 'These nipples are squeezed flat sideways, Headmistress.'

'Yes pet, and they're incredibly sensitive now,' Miss Strokewell panted out. 'Suck them back into shape.'

Gretna bent over Henry, the cross pendant resting on his throat and her breasts one on either side of his face. Then she sucked his left nipple, and the pain that filled it was erotic ecstasy. Now she was sucking his right nipple. He turned his head, and saw one of Gretna's own dark, thick nipples near his mouth - he was able to nuzzle against it, then draw it into his mouth with his lips. He sucked it hard and rubbed it with his tongue.

Gretna began to moan softly, until she gasped out, 'Mrs Headmistress, my pussy is too hot now.'

Miss Strokewell laughed. 'I'll let you put it on my obedient slut's face.'

Gretna almost leapt forward, to put her weight on her arms and bring her bushy triangle to Henry's mouth. She was pressing her sopping wet crack against it and her crisp black hair was rubbing his chin and cheeks. With his tongue he gathered up a lavish quantity of juice from the opening of her cunt, and greedily swallowed it. Then the questing tip of his tongue explored between her inner lips, found the firm smoothness of her clitoris, and rubbed it.

Meanwhile, Miss Strokewell's fucking was making his cock jerk with her thrusts. He could feel a cool puddle of preseminal fluid near his navel. Something hard rubbed in the puddle - Miss Strokewell must have been able to reach the cane and pick it up without breaking her rhythm. A moment later the cane was hooked round his penis and was smearing the fluid on it. Then she said in a firm tone, 'Teaching Assistant Gretna, lick off that cock-juice.'

Panting with arousal, Gretna gasped out, 'Oh - oh, but Mrs Elizabeth, I have never - never done such a rude thing.'

'High time you tried it, then.'

In the midst of his bliss, Henry felt Gretna lower her upper body. The cross teased the skin of his stomach. He felt her breath on his throbbing hardness. Then the cane pressed his cock to one side and he felt the softness of Gretna's cheek against it. The cane moved his cock, rubbing it against the side of Gretna's face.

'Oh Mrs Headmistress - you are a good teacher - I trust you - I will do it.' Gretna's hand gripped the base of his cock, and next moment she was licking the precum from the shaft, then the head - and then the head was in her mouth, being sucked at first cautiously, then with mounting enthusiasm.

'Give it a bit of attention with your tongue, pet, but don't try to take it deep this time,' Miss Strokewell advised.

Henry felt himself being carried rapidly towards a climax until suddenly Miss Strokewell commanded, 'That's enough, Gretna! Let the slutty boy see his Headmistress humiliating him.' With a sigh, Gretna knelt up and lifted her vagina away from Henry's face. 'Well done, pet,' said Miss Strokewell. 'I like an obedient assistant.'

Henry could see his divine Headmistress again, a little pink-cheeked with her exertions. She increased the speed and force of her fucking, and soon her breasts were bouncing vigorously, a sight which made Henry desperate to cum. Seeing the cane in her hand added spice to his pleasure. Then she reached out with the hooked end and gently rubbed the most sensitive part of the head of his cock with it.