Gentlemen at Pleasure (AI enhanced)

Here is an enhanced version of the Guardians Club story Gentlemen at Pleasure from Blushes 21. I had to give up on one picture in this set as I couldn’t get it to be anything but weird.

‘It was on the train down to Truro, a lovely run as you know on a nice day and this was a real beauty, blue skies all the way. Anyway as it happened I was travelling second class, don’t know why, I rarely do, but if I hadn’t…’

‘George!’ said Max sharply. George stopped, eyes querying.

‘You’re going on a bit, George. Could you come to the point?’

‘Sorry,’ said George who knew he did go on a bit at times. ‘Well, it was the girl of course.’

At the word ‘girl’ the others immediately gave their full attention, because girls were a major interest of this little group assembled. An all-consuming, all-embracing interest it would not be too much to say. Young and softly nubile ones. Budding. George notwithstanding his rambling conversational manner was very much a member of the group with the same interests. So if he mentioned a girl…

The committee of the Guardians’ Club, although this was not a proper committee meeting, just an informal gathering, at Max’s place in a leafy and salubrious part of Sussex. No, not a committee meeting and not a girl in sight. There were a couple on the premises somewhere though. A Jane and was it a Samantha? Brought along by Alec and Algernon, but for general, er, consumption.

‘Let’s hear about the girl, George. Forget the incidentals,’ said Algy.

‘Oh really scrumptious. Absolutely mouth-watering. Blonde curls and a really divine sort of pouting mouth. Lips like ripe strawberries.’ George could be lyrical as well as long winded. ‘Just a little on the plump side I would say but that’s how I like ‘em. Oh yes, a real stunner.’

‘On the train?’ asked Max. ‘By herself?’ Oh yes indeed, George had their attention now.

‘With this chap. Quite a pleasant fellow, very keen on stamps. He was telling me about his…’ George stopped, aware of glaring eyes. ‘Sorry. Yes, well, this chap. He had charge of her but the thing was he didn’t seem at all keen on this. Quite remarkable when you consider what she was like. It seemed she belonged to a cousin or something and they had gone off to Australia or somewhere and so this chap had been left with her. Annabel her name was. And he wasn’t keen. Having trouble with discipline, keeping control, that sort of thing. When as I gathered what he really wanted to do was get on with his stamps.’

George stopped for a breather. It was a remarkable tale and there was no doubt of their rapt attention. ‘You should have got his name, George. We could have helped that chap.’

George smiled; the smug smile of a man who has a bombshell to deliver. A bombshell but a very pleasant one.

‘I’ve got more than that,’ he announced with a smirk of triumph. ‘I’ve got the girl. Annabel. We can have her.’

A bombshell indeed. A moment’s shocked silence, moments more of silent wonderment.

‘George old boy,’ breathed Algy finally. ‘You really are quite a fellow you know.’

A little giggle from Alec. ‘Have her? In the biblical sense maybe? Or is it old English?’ Alec had not actually read the Holy Book recently.

‘Why not!’ enthused the hero of the hour. ‘I mean that’s all part of a girl’s growing-up process, isn’t it? And she’s that age all right. Sixteen, just turned.’

‘Do you know that, George?’

‘Yes he told me. “Now she’s sixteen she’s worse than ever. Thinks she’s grown up.” The young madam sitting next to him gave me a really delicious pout. It was all I could do to stop myself grabbing her and grabbing her knickers down there and then.’

‘To smack her bottom,’ said Max.

‘Well yes. Or… well anything.’

‘Is she, I wonder…?’ mused Max. ‘I mean this chap, could he have… er… sampled? Or anyone else? Do you suppose?’

‘George doesn’t know that,’ said Algy firmly. ‘I mean there’s a limit to what you can find out on a train to Truro. Not unless you can take her into the loo or something and you can’t do that when she’s with this chap. We’ll find that out soon enough. But George — when? And where? Because I for one can hardly wait.’

George said, ‘He wouldn’t have, not this chap. It’s only stamps with him from what I could see.’ And then he told them what he’d arranged with the chap on the Truro train. At some length and with George’s usual asides and interpolations. But in the context the others were prepared to let him have more latitude than usual.

George’s sister’s place, not too far from Truro. For one thing this chap who had Annabel, lived in that general area, over the border in Devon, and there was also George’s sister. Miss Emily Maidment. Who until not too long ago had been Deputy Mistress at quite a good girls’ public school and although you might not necessarily think it to look at her Emily Maidment could be awfully hard on a teenage girl. Harder indeed than many men might wish to be.

It had been Alec’s idea. ‘If we let George’s sister loose on her and tell Emily she’s got a completely free rein, she can cane this Annabel just as hard as she likes… well, a day or two of that and the young person will be desperate to agree to anything.’

It certainly seemed an excellent scheme — although George himself had reservations about telling Emily she could cane ‘just as hard as she likes’, thinking as he was of Annabel’s prettily pouting mouth and knowing what his sister was capable of. Max wanted to know exactly what Alec meant by ‘agree to anything.’ Alec of course had earlier that summer spent a fortnight in France, a small and select establishment in Normandy, and had subsequently spoken in awed terms of the amazingly knowing and willing sixteen-year-old daughter of that household. Alec grinned at Max without answering.

----//----

George had the honour of fetching the young lady. The other three were naturally on tenterhooks. George’s sister had professed unhappiness at her role and had tried to appear indignant — being used to break in an innocent young girl for four unscrupulous rogues who really should know better — and having her house used for this purpose into the bargain. But she had agreed to it without too much need of persuasion and they had not much doubt that in reality the idea appealed to her. For would not Emily herself be getting very much into the act?

Yes Max and Alec and Algy were on tenterhooks all right. George was quite a long time although he had warned them that he might be, it was after all a longish drive and this chap might keep him a while chatting or might even force George to admire his stamps. And if the chap was giving you his girl, or loaning her to you, clearly you had to show a bit of courtesy. Yes. But there was inevitably the thought that George might take advantage of the situation and go in for a spot of dalliance, of stopping by the wayside, in some leafy woods of similar pleasant venue and indulge in a spot of unscheduled preliminary handling, viewing. George had stoutly denied any such intentions but one could see that nonetheless George would be subject to very great temptation. That was why they had suggested that someone might go with George but he had vigorously refused the offer.

There were unfortunately no other girls in residence at George’s sister’s. Partly out of respect for Emily they had thought it proper not to bring any others along and also of course to be able to concentrate their whole attentions on this new Annabel. So there was quite a bit of sitting down and standing up again and walking to and fro and muttering about old George.

But eventually mid afternoon, here it was, George’s Rover crunching up the driveway. A bit of a stampede for the front door. Yes here was George and here also this Annabel. A rush to open the car door — and not the one on George’s side. Oh yes indeed. George had not exaggerated. She was exactly as he had painted, a truly delicious specimen of budding girlhood, attired in a smart school uniform. White shirt, red tie, plum-coloured jersey, a grey pleated skirt. The plum jersey showing the most darling bumps at the front and she did have the most gorgeous pouting crushed-strawberry lips.

Helped out of the car, with a no doubt innocent show of thigh, Annabel looked from one to the other. Had she been informed she would be staying with four gentlemen? Three in addition to this one, Uncle George as he was to be called, who had met them a week ago on the train and who had now driven her here. Who had also…

George seemed a bit pink in the face. ‘A lot of traffic,’ he observed. ‘And of course one can’t rush away from a fellow. I mean not just a quick in-and-out.’

They looked at George and then at Annabel. Could it possibly be what was known as a Freudian slip? George saw the ambiguity of his remark. ‘I mean a fellow’s house, you can’t just go in and then come out again.’

‘Oh quite,’ said Max. Anyway there was no point worrying about Freudian slips, George was here and more to the point so was Annabel. The cynosure of all eyes, all thoughts.

She gave a shy smile and nodded that yes she had had a nice trip. The big blue eyes quite made your knees tremble. They showed no flicker at the fact that Uncle George hadn’t quite told the truth. They had stopped, but Uncle George had said it would be their little secret, his and hers, and they would not tell the others. Uncle George hadn’t stayed very long at all at her other uncle’s, like he had said, and he had stopped on the way. In those woods.

He simply hadn’t been able to resist if George had really meant to come straight back but… it was rather like a boy left alone in a sweet shop and promising not to touch anything. Sooner or later there is nothing for it, he has to stick his finger in. The sweet jar. And so… ‘Better have a rest,’ George had said. ‘Very tiring business, driving.’

A nice peaceful spot in some woods, a nice sunny clearing and with that sun shining down George had thought it the most natural, sensible thing to suggest that Annabel do a bit of sunbathing. The big blue eyes had looked, questioning… and then she had obediently taken things off. Jersey and skirt. Shoes and socks. Tie and shirt. Quite devastating, almost impossibly so. George had felt quite faint for a moment. A thin tight white sleeveless vest with clearly nothing underneath except Annabel herself, and down below equally thin and tight white knickers. Oh yes, George had been quite overcome as he made her lie back on the car rug. The way the skin-tight knickers enclosed the young lady’s person, especially that part of her person at the confluence of her thighs… George had not been able to take his eyes off it. You could see just about everything, at least in outline and then being so… well why not? Take them off,’ he had said. ‘Let the sun get properly at you. And the vest…’

Oh no George had certainly not told the whole and absolute truth to his fellow Clubmates. But then as they say all’s fair in love and war and matters regarding delicious young girls.

‘Where’s Emily?’ Max now inquired, eyeing the delicious morsel somewhat hungrily. George was getting her bag out of the boot, relieved that Annabel had not blurted anything out. You could never really tell with young persons, they were not always completely reliable. ‘She’s got to meet Emily,’ added Max, looking around.

She had indeed. It was Emily who was going to cane the daylights out of Annabel, so that she would come pleading for help and sanctuary. Which, at a price, they would provide. ‘Emily!’ called George. ‘We’ve arrived you know.’

Shortly that good lady appeared, smiling and welcoming. Not at all a frightening prospect, for Emily Maidment could be most charming when she felt so inclined. But on the other hand… She took Annabel’s arm and led her in. Upstairs to show her her cosy room and then down again. ‘We’ll have some tea now, I expect you’re feeling thirsty. Some nice home-made cake? And then of course we’ve got to get down to business.’

Business. Had the young lady been appraised of that aspect of her visit? It rather seemed not. Her uncle had been preoccupied, as usual, with his stamps and Uncle George, well, Uncle George had been preoccupied with other things. Both en route and on the car rug in the woods. So it did come as something of a shock when after tea Emily — Miss Maidment to Annabel — appeared in her academic gown and in her hand a long and lissom cane. A sight that had struck terror into many a one such as Annabel at that well-known school whose name is perhaps best not repeated here.

Annabel, fortified with cake and lemonade, looked with alarmed eyes. What was going on here? Emily Maidment’s voice when she spoke was scarcely recognisable as that of the friendly hostess at the tea table.

‘Right, young lady, let’s have some action, shall we? A little dose of what you’ve apparently been needing for some time.’

No, Annabel could not believe her eyes — or her ears. ‘What… what?’

‘My name is Miss Maidment, Annabel. Kindly use it when you address me.’

To stress this point the cane whipped in and sliced across Annabel’s calf. Sock-encased but nonetheless a telling stroke. A shocked and outraged yelp. Annabel did a little hopping dance.

‘Get your knickers off, Annabel. Pull your skirt up and then get up on that stool. And do it immediately or I shall get one of the gentlemen to take your knickers off for you.’

They were none of them far away as this drama began to unfold in the old panelled hall. Keeping a distance, letting Emily take control but certainly not far away. Watching, listening, intently.

‘Ple…please,’ protested the exquisite young thing. ‘I haven’t done anything.’

‘You have done a considerable amount, you defiant, unruly creature. Your uncle has listed a whole catalogue of offences and is at his wits end with you. Well I, young lady, am certainly not at my wits end. Oh dear me no. Now get those knickers off!’

Annabel looked desperately round, for Uncle George chiefly who when he had wanted something earlier had been so nice and friendly. George, though, had slunk away and was not now immediately in evidence. He was not far away, he certainly wanted to see Emily cane Annabel’s bare bottom but he did not want to be the object of her pleading — when she might get the idea of threatening disclosure. Annabel could see Max though. ‘Please!’ she cried in that direction. For to be ordered to take her knickers off. To get the cane… was just about the most sick-making thing.

‘I’m sorry but Miss Maidment is in charge here, my dear. She had great experience in girls’ schools so I think we can safely leave matters in her hands.’

‘Off!’ barked Emily once more.

Awfully reluctant hands went up under the skirt. ’Right off!!’ commanded that authoritarian voice.

‘And now lift your skirt right up. I have some pins here.’

Oh dear, could this be possible? Annabel’s knickers were off and her skirt was being pinned high up above her waist.

Oh my, oh my! Four pairs of hot male eyes absolutely feasting. Hands had come across in front to protect her privacy but undue modesty was surely not called for at this juncture.

‘Take those hands away; place them on your head,’ ordered Emily who in spite of what she had said was not a spoil sport.

Oh dear, oh dear! Just look. At that. Face red and hands on blonde head now but it was not the prettily blushing face they were all gazing at. George of course not for the first time but that had been more than an hour ago and he was as eager as the rest.

Just look! You could actually see… well, in girls that age of course you not infrequently could. The central fissure peeping in its bushy grove. They looked… and looked.

‘Turn round,’ commanded Emily when she felt they’d spent enough time looking at that. Turn and get up on the stool.’

Was this any better Annabel’s front view not now on show but of course her bottom was. Her bare bottom and all those men… Not to mention the fact that the stool hurt her legs.

‘Just stay there like that and don’t move. Think of the error of your ways, my girl. I shall be back in 10 minutes and if I find you have moved an inch I shall cane you three times as hard.’

Emily strode up the broad staircase. Max quickly signalled the others over, out of earshot of the kneeling girl. ‘Right, let’s get this organised. George, you go and tell Emily to make that 20 minutes. That’ll give us five minutes each. Five minutes of, er, friendly private chat with the girl, get her settled down etc before Emily starts on her. Ok? The rest of us go into the drawing room. I’ll keep time. OK? Who’s first then?’

Alec went first. What a supreme delight! A consoling, reassuring chat with the young person who is kneeling bare-bottomed on the stool with her hands on her head and who knows she’s about to be caned — in this case for the very first time. Naturally when a fellow is having this chat his hand will be doing its bit to reassure that part of her that is about to be dealt with. And what a part this Annabel has! She is a little plump perhaps as George has observed, just a little. Especially this darling bottom. Firmly resilient. Trembling slightly as you handle it. As you give each cheek a little jiggle.

‘Is she going to hurt me?’ whispered Annabel, that thought pressing even more heavily on her mind than what Alec’s hand was doing. ‘I’m rather afraid she is.’ Alec experienced a sharp thrill of pleasure — and dug two fingers in between the tops of Annabel’s thighs.

She gave a high-pitched squeak. At the prospect, of the fingers.

Twenty minutes of this and Annabel was already in something of a state. Because in fact rather than reassuring her they had made matters worse. The consoling hands at her bottom — not to mention elsewhere — had got her all hot and bothered. She was feeling almost sick with fright when once again there was the sound of Emily’s firm tread on the oak stairs.

‘Right, young lady. Had a good think about your behaviour, have you?’

It was all too much. Annabel began weeping.

‘Get down off there now. Stand facing the wall with your legs astride the stool. Keep your hands on your head.’

‘No!’ the desperate young thing blurted. ‘I can’t… you… can’t… Aaaoooouuhh!’

The cane without warning had sizzled in across that darling bum. Oh God! She stumbled down, almost falling, her legs stiff and clumsy. Struggling astride the stool. A really awful position to be in when you had no knickers on and your skirt was all pinned up. The four men, the four Guardians, all out in the hall now. Hovering, eager-eyed, just out of range of Emily’s cane arc. Almost unable to contain themselves.

Emily gave them a quick look. A schoolmistressy look which possibly spoke of overgrown schoolboys. And then was turning her attention to the quivering Annabel.

Crack!…

‘Aaaaaiieeeeee!’

Sharp intakes of breath from the watchers. Emily could really lay it on. It fairly made one wince. Poor Annabel clearly in a frantic state, her mind, her stricken bum, seemingly unable to comprehend what had happened. The bum dancing and clenching, with a nice red stripe coming up.

‘Keep still, Annabel!’ Emily’s voice sharply cutting through the tense still air.

Crackk!…

‘Aaaaaaaeeeeeoooowwww!’

----//----

‘Oh dear me. It quite made a chap shudder. That Emily!’ Max’s voice contained both awe and admiration; also the clear feeling that he himself would not have wanted to be in young Annabel’s position. He took a sip of his g-and-t.

There were the three of them in the drawing room: Max and Alec and Algernon. Emily was busy in the kitchen or somewhere. George? George was with Annabel. Up in her room, that is. As regards anything else one would have to be a fly on the wall or something. George had insisted that it was his right to be first and in spite of being a long-winded blatherer George could be insistent. The others had wanted to draw lots.

‘That George,’ said Alec with a shake of his head. ‘And he was an awful long time getting her here. When I go up I’m going to have a jolly good talk to her about that.’

‘Doesn’t make much odds now, old boy,’ said Max. ‘Although of course I should like to know.’ He raised his gaze to the ceiling. ‘I wonder exactly what he’s at right now? With the state she was in after old Emily had done with her you could imagine she’d be pretty, uh, complaisant. Hmmm. And there’s old George getting first bite at the cherry. So to speak.’

Max looked at his watch. The other three of them had drawn lots and Max had won so he was next. They had agreed on an hour each this first day. George had had 35 minutes now.

Alec grinned. ‘He might be telling her a nice bedtime story.’

They all laughed. Somewhat frustrated laughs though. It was frustrating sitting there waiting. But still, you know it would be worth it.