From New Blushes Uniform Girls 2.03. A continuation to Tutoring Gillian, which is an adapted version of Taking Her Medicine from Blushes Supplement 24.
Gillian mused about her popularity, yes, there was no doubt about it, now that Mandy Noble had left she felt sure she was the most popular girl in the school. Mandy had left so suddenly, not even a goodbye to her best friend Fiona Wilkes who was also very quiet and sullen lately, strange. Mandy had certainly been very popular with the masters using her rather oversized boobs to attract attention wherever possible. There was also the hot gossip Mandy had showered with two of the PT instructors but Gillian had always thought this to be untrue, after all those shower cubicles really were too small for three people to have a proper shower at the same time.
It was true however that Mandy had left her PT kit behind on purpose in the hope of being let off doing early morning exercise. The PT instructor was having none of it though and made her and Fiona Wilkes do the whole session naked, and in a mixed class as well, Gillian shuddered at the thought but felt a little excited as well. What she really couldn’t understand was that the whole episode had made Mandy even more popular, the little tart!
Paul, Gillian’s ex, had seen it all, everything. He said there was a queue of boys wanting to visit the toilet.
Yes, Gillian was secretly pleased Mandy had gone, it had left her the centre of attraction and certainly the masters’ favourite now. It did have its drawbacks though, masters were always insisting on after-school tutoring, to keep Gillian ‘on top’ as they put it, but most of it was ‘on bottom’ she thought. Like here at the moment with Richard Mason the senior school governor who had always taken an interest in Gillian’s further education. He had insisted that these little weekend trips were to broaden Gillian’s horizons and give her a greater interest in the world. Gillian had become more of an expert on the inside of hotel rooms where they seemed to spend most of the time. This weekend at Brighton was no different.
It was a large and luxurious hotel, living up to its name: the Grand. But then money was no real object for Mr Mason, he could well afford to indulge himself. Having no money problems of course may not be everything — a man in that position can easily become bored with life without the central interest that making money provides for the rest of us. But Richard Mason was fortunately not in that situation. He had his young companion, Gillian. His niece as he sometimes referred to her. ‘Mr Mason and niece,’ he said at the lobby. ‘We have two adjoining rooms booked.’
He might call her his niece and Gillian at 18 was young enough to be that but she was not any blood relation. She was more or less his ward one could say though not strictly legally that either. But certainly Richard Mason felt all the responsibility of a guardian; not onerous but a serious matter. Especially in these days when one can see all around the results of modern, less structured life. A complete abrogation of responsibility in other words, no sense of purpose, or discipline. This was the last thing he wanted to see in his Gillian. Mr Mason guarded constantly against it.
At his home in Wiltshire and also when, as now, they were on a weekend trip. One had perhaps to be even more careful on holiday when the regime he had ordered at home could easily be replaced by the sybaritic cosseting of hotel staff.
But on the other hand the different more cosmopolitan surroundings of a well-appointed hotel did offer extra opportunities for shall we say testing one’s very attractive young companion.
‘This seems pleasant enough,’ he observed when the bellboy had disappeared after showing them their quarters, two pleasantly furnished rooms facing the sea on the second floor, with bathrooms en-suite and of course the inter-connecting door.
‘Yes, Uncle Richard,’ Gillian delicately testing her double bed with her most attractive bottom. She was a very attractive girl all over, from the top of her head of thick ash-blonde hair cut medium short to the tips of her toes, at present in white high-heeled courts. The distance between these two ends was some 5’6” in her stockinged feet. They were — the stockings — just that. Mr Mason abhorred the abominable tights which for some years had been almost ubiquitous. Even if stockings had not made something of a come-back he would certainly have had Gillian in them, with a nice suspender belt. That or simply bare-legged. The 5’6” was composed of all the usual bits and pieces that 18-year-old girls have except that with Gillian one could say they were Jaguar components rather than run-of-the-mill Ford. A pert-nosed, full-lipped face and the rest slim but nonetheless well-rounded wherever it should be. As was of course especially evident when Gillian had no clothes on.
Perhaps Richard Mason had this in mind, to be refreshed by this sight after the mildly tiring drive down. ‘I should take a shower,’ he observed. Meaning, as his young companion knew, Gillian rather than himself. She smiled and stood up. ‘Yes, should I unpack first perhaps?’
Mr Mason didn’t feel there was need for unpacking at this moment. No. He wanted to see Gillian. In the shower and out. Before and after. And not only see her. There was something else. One needed to get into a routine right away in strange surroundings.
Gillian, standing, was already unfastening, unbuttoning. Obediently. ‘And perhaps we can walk on the front afterwards. Before dinner.’ Her big blue eyes with a shine to them. Excitement. And also apprehension. A girl may in a way be used to something but that does not mean... that it doesn’t cause... a little shiver. The thought. Because taking her clothes off... usually means...
Discipline for one thing. A disciplinary session. The sight of Gillian unclothed seemed to send Mr Mason — Uncle Richard — reaching for... his cane. Or a similar item. Gillian tried not to look at Mr Mason who had sat down in the armchair and was undoubtedly looking at her. As blouse and skirt came off and the rest, slip and bra and knickers. Suspender belt and stockings last of all. Sometimes he would make her keep them on. While he went to get the cane. Her peripheral vision said that Uncle Richard was getting up. Coming towards...
Standing with her knickers in her hand and the stockings still on. Mr Mason patting her bare bottom. ‘Not putting on any little extra ounces, are we Gillian dear?’ His hand smacked a meaty splat. ‘Second helpings of pudding perhaps?’
Gillian said a sharp ‘No!’ her weight was a constant nine stone, give or take a few ounces.
The hand splatted again, causing a heavy judder of the undeniably firm flesh. Richard Mason didn’t really think there was any extra weight on this splendid shape but it paid to keep a girl on her toes. His other hand came up and rubbed across Gillian’s pert breasts, taking in the soft pink nipples. Her breath hissed out in a sibilant. ‘Ooooh.’
‘I don’t know, Gillian. I don’t know. I wonder if you are putting on just a little. And with rich hotel food... should we perhaps have you on a diet whilst you’re here? Bread and water. And some nice big spoonfuls of healthy cod-liver oil for vitamins.’
‘No! Please...’ she squealed. The trouble with Uncle Richard was that you never knew when he was joking or not. The most outrageously awful things could turn out to be for real. Like the first time he said she was going to get the cane across her bare bottom. He couldn’t mean that. So she had thought.
‘We’ll see,’ Mr Mason said. He rubbed her nipples again. They were firmer now, beginning to stick out. ‘Actually I rather like the idea of cod-liver oil. It is good for you. Perhaps we could get someone to bring some up...’
‘No.... oooo...’ she breathed. But Mr Mason had that look in his eye. He gave the pretty tits a final fondle — Gillian’s nipples were right up now — and slapped her bottom. ‘Get your stockings off and have your shower.’ He was sitting down. Picking up the phone.
‘Get in the shower, Gillian!’
Gillian obeyed. Shoes and stockings and suspender belt off and walking with that lovely sway of her bare bottom to the bathroom. Behind her Mr Mason was talking to the desk. She tried to close her ears. But he was asking...
A polite knock at the door. ‘Nooo… ‘ Gillian breathed again. ‘I’ll be sick,’ she had said a few minutes earlier. ‘No you won’t be sick,’ was the answer. ‘I’ll hold your nose. A person can’t be sick if someone is holding their nose.’
Gillian was in her dressing gown, sea-green silk, knee length and fastened with a sash. Nothing underneath. She had had her shower and she hadn’t been caned. Because Mr Mason had got this other diabolical idea. Cod-liver oil.
It was a waiter. In a short white jacket; middle-aged, sort of Italian looking and carrying... a bottle... and a big metal spoon. Mr Mason let him in and closed the door and began explaining. Gillian tried not to listen but of course she was listening.
‘My niece may have some trouble taking it. So... if I hold her while you...’
The waiter was going to give it to her. He was grinning and nodding. Gillian felt herself sweating, her face scarlet. She shook her head. ‘No... I can do it.’ Although she doubted if she could actually take a spoonful of that awful stuff. But anyway Mr Mason didn’t want that. He was going to hold her, he repeated.
‘Put your hands in your pockets and keep them there.’ It was happening. Mr Mason behind her pushing Gillian’s hands down into the hip-high pockets of the dressing gown. The sash almost immediately came loose, undone, and the dressing gown slid apart. ‘No!’ she squealed seeing the gown opening, but it was quite possible that Mr Mason wanted it to happen. He was in that mood. Making her show her tits to the waiter while he fed her this awful stuff. She tried to close her arms together in the pockets. Mr Mason grabbed them. Pulled her arms — and the gown apart. Her tits... and everything else... her pussy. The waiter’s eyes were almost coming out of his head. Mr Mason let go of her arms and grabbed Gillian’s head. Her nose and her mouth forcing it open ‘come on,’ he rasped to the waiter. ‘Two good spoonfuls.’
It made her gag. The dreadful oily fishy sensation filling her mouth. She spluttered... but Mr Mason held Gillian’s head back with a firm grip on her nose and forced open her mouth. She had no option but to swallow. There was no thought now for the fact that her gown was gaping wide, exposing her tits, her pussy, to the eager-eyed waiter. ‘And another one,’ dear Uncle Richard said.
The big brimming spoon came up again. Tipping into Gillian’s open mouth. Some of it was spat out, onto the waiter’s nice white jacket, but most of it had to go down. Uncle Richard let go of her. Gillian grabbed at her mouth. She was gasping, tears in her eyes. A strangled cry and then a stumbling, half-blind dash to the bathroom, the dressing gown trailing out behind her.
‘You really didn’t take that very well. Gillian. A rather undisciplined performance. Do you agree with that?’
Gillian swallowed and bit her lip. They were in the dining room. A table for two over in the corner with a view out onto the front. Mr Mason had ordered. Gillian had half expected he might continue what he had started with the castor-oil. Order bread and water for her, to continue her humiliation. To make her cringe as she sat here. It was the same waiter, the one a little while ago in the room obligingly spooning that gagging stuff between her lips. But Mr Mason hadn’t done that, he had let her choose.
‘Don’t you agree, Gillian?’
‘I couldn’t... help it. I just couldn’t.’ She could still feel it in her mouth. ‘I was going to be sick.’
‘But you should have done better. It’s no answer to say you couldn’t help it. It is simply weakness, isn’t it?’
Gillian mumbled something. But there was no point in showing dissent; that would simply make it worse.
‘I think we’re going to need a little taste of the cane, my dear.’
Gillian rolled her big blue eyes. But it was no more or less than she could have expected. Mr Mason — Uncle Richard — had caned and strapped her for less than this. At times for nothing at all. She squirmed her bottom on the chair.
‘And I’m going to ask the waiter to do it.’
Gillian blinked. She wanted to scream out. That Uncle Richard just couldn’t humiliate her in that way. But screaming in public, in a hotel dining room would be a terrible offence. Her cheeks had gone bright red. A hissed, whispered, ‘Please…’
Mr Mason said. ‘I shall ask him to take your knickers down and make sure you really feel it. Right after dinner I think.’
The waiter was coming over with the soup. Gillian fixed her eyes on the patch of dazzling white table cloth immediately in front of her. Seconds later the soup plate was placed there. That hand holding it had spooned caster-oil into her mouth... and was now going to be wielding Uncle Richard’s cane. Because he meant it, it wasn’t a joke. Uncle Richard was in one of those awful moods when he would do impossibly awful things to her. Things that were done in the name of discipline. He meant it. He was saying it to the waiter.
‘After dinner if you’re free I’d like you to come up to the room again.’ Gillian glanced up, face scarlet. Her eyes met the waiter’s. He smiled. He was no doubt remembering her bare tits and pussy and the strangled cries she made as that stuff was poured between her forced-open lips. And he was no doubt wondering if there was going to be something else like that.
Mr Mason didn’t beat about the bush. As soon as the man was in the room he told him. ‘I want you to cane my niece for me. She did not behave at all well earlier. All that struggling and spluttering. Getting it on your jacket in fact. She needs a caning. And I don’t really like caning her myself.’
That wasn’t true; Mr Mason was quite happy caning her and he did it often enough. He simply wanted the extra humiliation of her being caned by the waiter. ‘Can you do that?’ Mr Mason asked.
The waiter looked confused but as the meaning sunk in his expression changed to one of excitement — as well it might. ‘Yes, of course.’ He had a slight Italian accent. He was wearing an informal sweater now, not the white jacket. ‘Yes, of course,’ he repeated looking hotly at Gillian.
She was wearing the same dress as in the dining room; form-fitting pale green jersey-knit material. But Mr Mason had made her take off the slip and bra she had had underneath. Now Gillian had only a brief pair of bikini knickers under the dress. Their outline showed through; as did the outline of her bare nipples.
‘I want her to really feel it. Can you cane her really hard?’ Uncle Richard’s voice was dispassionate, as if he were discussing how he wanted his steak done. The steak, though, was Gillian’s bottom.
The waiter nodded, eager-eyed. ‘Whatever you say. Young girls these days need some discipline, yes?’
‘Yes they do, Gillian, lift your dress. Right up. Over your head.’
She was standing by her bed still not fully able to believe Uncle Richard would go through with it. But disbelief or not he was handing the cane to this man. ‘Lift it, Gillian.’
The stretchy material came up, rather like skinning an animal. Inside-out and up over her head and raised arms. Her body trembling, nude except for the tiny bikini pants. Her bare tits sticking out. ‘Now lie over the bed,’ Mr Mason’s voice heard from inside the green-lit tent of the dress. ‘Lie over the bottom of the bed.’
She was down on the bed and someone was pulling her knickers down. It was the waiter. Mr Mason has gone to sit in the armchair, she could tell that from his voice. It was the waiter’s hands on her, tugging her knickers down across her knees. Her bottom was bare and she could sense the waiter drinking it in with his hot eyes. And relishing the thought of the cane.
‘Give it to her then. I want you to hurt her.’
Uncle Richard from across the room, his voice dispassionate as ever. A little pause... Gillian readied herself...
Her cry was muffled in the bed cover. The man had done as instructed, it was as bad as any Mr Mason himself had ever given her. Like a knife slicing into the ripe crests of her buttocks.
Almost on top of the first one, and just as bad Gillian opened her mouth to bite into the bedspread. Her face was wet. She was dribbling, or crying. Or both.
After four of them Gillian felt her dress being pulled down. Not right down, just to her waist. Her bottom was still bare; her now red-striped quivering nates. But she could see now. The man. As Mr Mason turned her face sideways. His hand came on her burning bottom.
‘All right, Gillian dear? You’re all right, aren’t you?’
She made a sobbing sound, yes she was crying.
‘It’s not finished yet, my dear. You’ve got to have some more. But I have to go out. I’ve an appointment to see a gentleman. I shall leave you here with Mr Carmine. You’re to do exactly what he says. Agree to whatever he tells you. Is that clear?’
What? What…? Gillian made another sobbing, choking sound. Her bottom felt red hot. And she was to have some more. Was that what Mr Mason was saying. More of the cane.
‘What....?’ she managed. But he was going out. The door closing behind him. She was here alone with this man, the waiter. Mr Carmine, Uncle Richard had said. As if to bring this home to Gillian, he now sat down next to her on the bed, where Mr Mason had sat. His hand came onto her bottom; like Mr Mason’s had.
‘Your Mr Mason says you are to have some more Gillian. You heard him say it.’ His voice was nervous, excited. As if he could scarcely believe this. The hand was fondling her bare bottom. His fingers sliding down in underneath.
Gillian gave a yelp... and the fingers pushed firmly in. Hard in between her warm thighs. ‘I think you need something else as well as the cane, Gillian. Mr Mason told me he thought you needed it.’
‘No…!’ she yelped at once aware that he wasn’t only talking about the cane.
The fingers came away. He smacked her still-hot bottom. ‘Yes Gillian. First some more cane. And then something else that a young girl needs, eh?’ He was all at once grabbing at Gillian’s lowered knickers. Pulling them on down. Off over her struggling feet.
‘Yes, first the cane,’ he repeated. ‘And then that other thing!’
Mr Mason was away about an hour. When he got back Gillian was still lying on the bed, sprawled on her front. The light was off and the curtains closed. Without switching the lights on he went to sit on the bed next to her. Gillian’s skirt was halfway down her thighs. Her knickers were lying on the carpet still. Mr Mason’s hand slid up under the skirt, to her warm bare bottom.
‘Come on,’ he said softly. ‘Time for bed.’ His hand gently caressed. ‘You can come in my bed tonight.’
We will follow the further adventures of Gillian in Gillian’s Further Education.