Further Into the Background

From Blushes 19, continuing the adventures of Gilbert from In the Background

It occurred to Gilbert Hoskins — after the most extraordinary and exciting events at Milward’s school — that Hilda Conway, the headmistress, was not exactly the highly principled woman he had always assumed.

The visit to the sixth form gym class… the punishment of Amanda over the horse subsequently… had these not, quite possibly been contrived for his benefit? She knew he was wealthy and generous; was she not inducing him to be even more generous towards the school? Not to mention herself? That business about a sick mother. Was it true? He had no way of telling, without getting over-exposed. The funny thing was, he had intended to give her some sort of financial reward for what she had arranged. Doing it very discreetly. Yet, as it turned out, it was she who had set the ball rolling.

Did it matter?

Perhaps it was better this way. She had divined that he was an addict for girls in the gymnasium. Not to mention being a spanking enthusiast. So, if he wanted this very special kind of fun, he was going to have to pay for it. Miss Conway, without saying a thing, had set the pattern. He would visit more regularly and see the sort of thing he wanted. And pay up. Gilbert didn’t mind about the money. He had more than he needed. In fact, it somehow regularised the situation to be paying. He wouldn’t have to do any more hinting and hoping; nor be dependent on her whims. Without a word being spoken, everything was understood between them.

How deliciously conspiratorial, thought Gilbert. It appealed to his basic character. A wish to arrange things deviously rather than openly. The constant desire to be at the scene of events, yet remain in the background. That Miss Conway was astute as well as academic had been confirmed. She wanted money and was using her position to acquire it. Nothing too wrong in that. People had been doing it since time immemorial. As far as Gilbert was concerned, this woman was giving him opportunities for pleasurable indulgence which he had never believed would ever come his way.

He must keep close to her. Play along with her. Yet never should he let on that he knew he was paying for ‘services rendered’.

‘Mr Hoskins… you haven’t paid us a visit lately.’

‘I’ve been rather busy, Miss Conway,’ Gilbert lied. He was so glad the woman had telephoned. Several times he had been on the point of contacting her, but it was far preferable that she phoned him in the first instance. Stupid to appear over-eager. ‘Was there something?’

‘I thought you might like to see how good a start has been made on the swimming pool which you are so generously giving us.’

‘Ah yes… well… maybe…’

‘And look around the school generally, of course. Since you are one of its greatest benefactors.’ There was a long pause. ‘Then, there’s always the gym sessions.’ Was there not a definite hint of suggestiveness in that voice?

‘Ah yes… the gym.’ Gilbert took up the challenge. ‘Has anyone else been… er… slacking lately?’

‘Funny you should ask that, Mr Hoskins. As a matter of fact, yes.’ Gilbert experienced a positive shiver of pleasure, deep inside. There was no doubt that he and Miss Conway understood each other perfectly. ‘There’s a girl in the Fifth. Only 16. Really undisciplined about her exercises.’

‘Ahhh… I’m sorry to hear that. Still, you’ll know how to deal with it.’

‘Of course, Mr Hoskins. So I can expect you on Thursday afternoon then?’

It was being laid on; for his benefit. All he had to do was pay. ‘Very well then, Miss Conway. Three o’clock?’

‘That will be just right…’

‘How is your mother?’

‘Oh… my mother’s much better. Now that she’s in that home, I mean.’

‘I’m very glad to hear it,’ said Gilbert. Then put down the receiver. There was no doubt he would shortly be writing another cheque to help Miss Conway’s poor old mother!

----//----

It was a delight for Gilbert to be back in the gymnasium. As before, he and Miss Conway took a discreet seat in a kind of minstrels’ gallery at one end. From there one could look down on the rows of leotard-clad figures without being conspicuous. Indeed, probably not seen at all. That also suited Gilbert’s temperament.

The first thing he noticed was that, quite naturally, the girls of the Fifth were slightly younger than those in the Sixth. Most of them just 16, he would have said; possibly a few 17-year-olds. It was so difficult to tell, for girls developed so young these days it seemed. Though some of them were on the skinny side, most of them had burgeoning figures… swelling breasts and buttocks. Swelling but firm. And the flesh (so much of it exposed on account of the brief leotards worn) was of the softest, smoothest kind. Seen only on young, teenage girls.

Gilbert was both fascinated and excited as he watched the fifteen or so youngsters exercising. He had to admit, he liked it best of all when they were repeatedly bending over and touching their toes, tautening the skin of those beautifully rounded bottoms. He began to wonder which girl was for ‘the high jump’ that afternoon. He didn’t like to ask Miss Conway directly, so looked around for someone not working too enthusiastically. He finally decided that a blonde girl in the front row was not giving of her best. Sometimes she didn’t even get right down to touch her toes.

His suspicions were confirmed when the girls began to use the horse (even more enjoyable!) for this same girl stumbled several times on landing and also didn’t leap very high. Oh how Gilbert loved those bounding leaps! The young limbs splayed wide, the rounded breasts joggling.

‘That’s the girl I’m going to deal with,’ announced Miss Conway, pointing to the blonde who had stumbled yet again. So Gilbert’s judgement had been proved correct. ‘Her name’s Christine.’

Gilbert was glad to note that this 16-year-old was not one of the skinnier ones. Rather to the contrary. Miss Conway was also glad to note that Christine was doing an excellent job of ‘slacking’. Normally she was one of the better performers in the gym. Money had persuaded her that it would be worthwhile going through the ordeal the Head had proposed. ‘If you’re doubtful, have a word with Amanda. She earned herself a nice little present… and didn’t come to a great deal of harm.’

This Christine had done and, having a wise head on young shoulders, had demanded, not £30, but £50 from Miss Conway. ‘Oh, my dear, that really is too much!’ had come the startled reply.

‘But you only slippered her; you told me you were going to cane me. That will hurt far more,’ Christine had protested.

‘True…’ agreed Miss Conway. ‘But you will not be getting so many strokes.’

In the end they had agreed on £40. Enough, the girl reckoned, to buy her a nice summer outfit. Not bad for just a few cuts. For her part, Miss Conway was content. Now that she could rely on her patron for regular contributions to ‘mother’s welfare’, the cash side of things didn’t matter too much!

‘Yes…’ said Gilbert musingly, after a while. ‘She doesn’t seem to be making a great deal of effort.’

‘As lazy as they come,’ snapped Miss Conway. ‘I’m going to give her a really sharp reminder!’

----//----

A quarter of an hour later Gilbert was in his position behind the door of the small ante-room, having once again a good view of the horse through a wide crack. As he looked upon it, heart beating faster, he recalled how Amanda had bounced and squirmed all over it, with her bottom getting redder and redder under repeated whacks from the slipper. It had been a marvellous experience for him and now he was going to get a repeat. He wondered how many whacks this younger girl would get. He hoped the same. Still, whatever it was, he would be satisfied.

Thus, understandably, Gilbert was taken aback when Miss Conway came in with the girl — carrying a cane in her hand! His stomach turned a somersault, it seemed. Never had he imagined he would be privileged to see a young girl caned! His pulse rate increased instantly and he noted that this Christine was even prettier than Amanda, even if her figure was not quite so sumptuous. All the same, she was most beautifully proportioned. Apple breasts, melon buttocks. She was looking both nervous and despondent, which was very understandable under the circumstances.

And now, it must be said, young Christine was not play acting. The actual sight of the cane had scared her no end. Near naked as she was, it made her feel so vulnerable. It made her flesh creep. Oh how much was it going to hurt? Surely the Head would not be too severe with her! On the way to the room, she almost chickened out. Then she fixed her mind firmly on the forty quid — and gathered some resolve.

‘Now, Christine,’ said Miss Conway, having closed the outer door, ‘as you know, at Milward’s we have a long history for inducing improved standards of education — particularly physical education — by means of corporal punishment. You will have heard about that, from other girls?’

‘Y-yes… miss… but I’m not sure…’

‘Christine! It is not for you to be sure. This is my decision. Your performance at P.E. for the past few sessions has been atrocious. Therefore you will be punished for it. That, I am sure, will guarantee a quick improvement.’

‘Miss… please… I’m not sure…’ repeated Christine. Miss Conway glared. She would have been really furious if the girl backed out at this late stage. All the same, she intended to go on as she had originally planned.

‘Quiet, girl!’ rapped the Head. ‘Now, just listen to me. This school has been established for well over a hundred years. During that time, countless girls have been caned on these premises. Admittedly, most of them during the earlier days. Nevertheless, tradition is tradition. It goes on. Now, let me tell you something else. When a girl is caned at Milward’s she is always caned naked. That’s another tradition…’

There was a dismayed gasp from the girl. Gilbert felt an added surge of excitement. This was really something! ‘Oh no… that’s awful…’ said Christine.

‘Awful?’ Miss Conway looked disdainful. ‘What’s awful about it? We’re here alone. This, my girl, is a matter of principle.’

Christine’s eyes widened and a sharp look came into them. Back to Gilbert, she held her hands up in front of her, fingers and thumbs splayed. Ten. Here’s another girl who would go far, thought Miss Conway as she nodded. The ‘ante’ was up to £50.

If… if I must then…’ half sobbed Christine.

‘It’s tradition… ’

Christine peeled off the leotard and stood naked. Gilbert found himself sweating. My word, what a superb young body! Unbelievably beautiful in its outline and texture. He knew, in that moment, he would go on supporting Miss Conway indefinitely if he could continue to observe such treasures. Yes… he would go on to the point of ruin.

‘I am going to give you six strokes, Christine. Bend over the horse. You deserve more but, since this is the first time you have had the cane, I intend to go easy on you.’

Apprehension was making the youngster’s lips quiver. The moment of truth was at hand. The moment of shame, too. She was going to have to bend her with her naked rear facing that unknown voyeur she knew was behind the door. Ghastly! Still, the thought of pain was an even more urgent matter. It was coming. Any moment now. She couldn’t help shivering. Gilbert was quite enchanted.

Even more so when Christine actually bent over the leather horse. As with Amanda, her shapely young bottom was fully presented to him. As well as other desirable intimacies. He wiped his brow. Was this good for his health? He could feel his heart pounding. To hell, what a lovely way to die anyway!

Miss Conway tapped the curving bottom with her slim cane. The flesh twitched and quivered. ‘Oh… p-please, Miss Conway…’ Christine was about to beg the Head not to be too hard on her when the first stroke whistled down. It was not the hardest of strokes but it was quite adequately painful for Christine… who instantly leapt up off the horse and twisted left… right… left… right with her hands pressed to the searing weal. ‘O-oh… that was… too much…’

‘That’s what you think, Christine. But it is for me to decide. Bend over again.’ The fact that the girl had extorted a further £10 out of her had not put Miss Conway in an altogether good mood. Moreover, it had already been understood between them that, unless the girl took the whole of her punishment, she wouldn’t get a single penny!

Nervously flinching, Christine bent again. That first stroke had hurt far more than she had expected. She had hoped it was going to be easy, but now she knew there was no chance of that. What had she got herself into?

Again that sound… again that burning streak of pain across her flesh. Oh… it was intolerable! She was up again… waltzing around with hands pressed urgently to the two streaks of fire. Gilbert saw the apple-breasts jobbling… and a lot more besides. Sheer heaven! ‘Mmfff… uuurrf…’ sobbed Christine, ‘I… I… can’t stand it…’

‘Really?’ Miss Conway’s eyebrows went up. ‘What a foolish girl you are. We’re almost halfway. You don’t want me to take drastic measures, do you?’

Christine, enduring the pain, weighed things up. Yes. One more. And it would be halfway. Come on… you can do it… she told herself. Then, nates clenching she once more bent over the horse. The cane cracked down and, with a series of gasping howls, she writhed down on to the floor, limbs splaying and kicking.

Gilbert had glimpses of young delights he never thought he’d have an opportunity of glimpsing again!

‘Halfway, Christine,’ announced Miss Conway. ‘Come along, be a brave girl. It will soon be over now.’

Sobbing unrestrainedly Christine hauled herself back over the horse. Was it worth it? Was it… oh was it? The fourth cut decided her that it wasn’t. Yet, to stop now, after all she had endured, would be absurd.

She must go on to the end.

It need hardly be said, Gilbert Hoskins was delighted the girl did!

‘Thank you, Miss Conway, a most instructive afternoon…’

‘My pleasure, Mr Hoskins. It is only right that a benefactor such as yourself should see how we run things here. Frequently.’

‘How kind.’ He saw a wan smile on those barren features.

‘I am afraid, Mr Hoskins,’ said the Head of Milward’s, ‘they have just put up the fees at Mother’s Nursing Home.’

‘Oh indeed, I’m sorry to hear that.’ And sorry indeed, he was. All the same, out came his cheque book.

The word frequently had definitely roused him.

----//----

Meanwhile, with cold cream soothing her weals, Christine was already beginning to reckon it had all been worthwhile. Maybe she’d even have another go sometime!

For her part, Amanda was positively anxious for a summons…